naphthoquinones and lawsone

Bacterial resistance development represents a serious threat to human health across the globe and has become a very serious clinical problem for many classes of antibiotics. Hence, there is a constant and urgent need for the discovery and development of new effective antibacterial agents to stem the emergence of resistant bacteria. 1,4-naphthoquinones are an important class of natural products and have been known for decades as a privileged scaffold in medicinal chemistry regarding their many biological properties. The significant biological properties of specific 1,4-naphthoquinones hydroxyderivatives have drawn the attention of researchers in order to find new derivatives with an optimized activity, mainly as antibacterial agents. Based on juglone, naphthazarin, plumbagin and lawsone moieties, structural optimization was realized with the purpose of improving the antibacterial activity. Thereupon, relevant antibacterial activities have been observed on different panels of bacterial strains including resistant ones. In this review, we highlight the interest of developing new 1,4-naphthoquinones hydroxyderivatives and some metal complexes as promising antibacterial agents alternatives. Here, we thoroughly report for the first time both the antibacterial activity and the chemical synthesis of four different 1,4-naphthoquinones (juglone, naphthazarin, plumbagin and lawsone) from 2002 to 2022 with an emphasis on the structure-activity relationship, when applicable.

Topics: Anti-Bacterial Agents; Bacteria; Coordination Complexes; Humans; Naphthoquinones

The second article in this continuing medical education series discusses cosmetic practices associated with cultural dermatoses, including hair care, traditional clothing, and skin decorations. Often, the steps individuals take to enhance their physical appearance are determined by cultural perceptions of beauty. Without awareness of cultural practices, a multitude of cutaneous dermatoses may be missed by the dermatologist. Recognition and understanding of patients' cultural backgrounds and habits will allow the practicing dermatologist to offer better counseling and treatment options while providing a more meaningful and understanding physician-patient relationship.

Topics: Beauty; Cosmetic Techniques; Cosmetics; Cultural Characteristics; Dermatitis, Allergic Contact; Education, Medical, Continuing; Ethnicity; Female; Humans; Incidence; Male; Naphthoquinones; Prognosis; Risk Assessment; Skin Diseases

The use of Lawsonia inermis L. (henna) for medicinal and cosmetic purposes is inextricably linked to ancient and modern cultures of North Africa and Asia. Literature and artwork indicates that Lawsonia inermis played an important holistic role in the daily lives of some ancient cultures, providing psychological and medicinal benefits, as well as being used for personal adornment. Although henna was historically applied to the hands and feet to protect against fungal pathogens and to hair to combat lice and dandruff, other traditional uses include the treatment of liver and digestive disorders, reduction of tissue loss in leprosy, diabetic foot disorders and ulcers.. Almost 70 phenolic compounds have been isolated from various parts of the plant. Naphthaquinones, which include the dyeing principle lawsone, have been linked to many of the pharmacological activities. The terpene, β-ionone is largely responsible for the pungent odour of the essential oil isolated from the flowers. In addition to other volatile terpenes, some non-volatile terpenoids, a single sterol, two alkaloids and two dioxin derivatives have also been isolated from the plant.. Henna is a pharmacologically important plant with significant in vitro and in vivo biological activities. Although a myriad of pharmacological activities have been documented, the antioxidant and antimicrobial activities are the most thoroughly investigated. Some incidents of adverse reactions following application to the skin have been reported, but these are mainly confined to cases involving individuals with glucose-6-phosphate dehydrogenase deficiency and reactions to adulterants added to henna products.. Adulteration of henna is very common and may have resulted in unwarranted scientific findings. Phytochemical profiling studies of the plant, which are crucial for the establishment of proper quality control protocols, are lacking and hamper the development of medicinal products. Although many in vitro studies have been conducted to evaluate the pharmacological activities and many in vivo studies have focussed on the toxicity of extracts, more in vivo studies to validate pharmacological activities are needed. The roles of specific compounds and their synergies have not been comprehensively investigated.

Topics: Animals; Coloring Agents; Ethnopharmacology; Humans; Lawsonia Plant; Medicine, Traditional; Naphthoquinones; Norisoprenoids; Plant Extracts

Although Asian cultural practices, such as acupuncture and threading, are widely used, there is limited medical literature describing their cutaneous effects and complications. This review briefly describes therapeutic cultural practices (traditional Chinese medicine, acupuncture, cupping, moxibustion, coining, Ayurveda, and aromatherapy) and cosmetic cultural practices (hair oils, henna, bindis, saris, and threading), with particular attention to dermatoses secondary to these practices. Traditional Chinese medicine and Ayurveda may cause heavy metal toxicity, severe cutaneous adverse reactions, and contact dermatitis. Cupping, moxibustion, and coining lead to dermatoses that may be mistaken for abuse by people unfamiliar with the practices. Hair oils may cause contact dermatitis and folliculitis. Paraphenylenediamine in black henna and bindi dyes and adhesives can cause severe allergic contact dermatitis. The drawstring in saris causes frictional irritation, which can lead to tinea corporis, koebnerization, and even squamous cell carcinoma. Threading may cause folliculitis, impetigo, and verrucae. The increasing prevalence of Asian cultural practices, which are performed inside and outside of Asia in this era of globalization, demands that dermatologists be familiar with the secondary dermatoses that may develop.

Topics: Acupuncture Therapy; Aromatherapy; Asian People; Clothing; Complementary Therapies; Cosmetic Techniques; Cosmetics; Humans; Medicine, Ayurvedic; Medicine, Chinese Traditional; Naphthoquinones; Skin Diseases

Nature has been a rich source of therapeutic agents for thousands of years and an impressive number of modern drugs have been isolated from natural sources based on the uses of these plants in traditional medicine. Henna is one such plant commonly known as Persian Henna or Lawsonia inermis, a bushy, flowering tree, commonly found in Australia, Asia and along the Mediterranean coasts of Africa. Paste made from the leaves of Henna plant has been used since the Bronze Age to dye skin, hairs and fingernails especially at the times of festivals. In recent times henna paste has been used for body art paintings and designs in western countries. Despite such widespread use in dyeing and body art painting, Henna extracts and constituents possess numerous biological activities including antioxidant, anti-inflammatory, antibacterial and anticancer activities. The active coloring and biologically active principle of Henna is found to be Lawsone (2- hydroxy-1, 4-naphthoquinone) which can serve as a starting building block for synthesizing large number of therapeutically useful compounds including Atovaquone, Lapachol and Dichloroallyl lawsone which have been shown to possess potent anticancer activities. Some other analogs of Lawsone have been found to exhibit other beneficial biological properties such as antioxidant, anti-inflammatory, antitubercular and antimalarial. The ability of Lawsone to undergo the redox cycling and chelation of trace metal ions has been thought to be partially responsible for some of its biological activities. Despite such diverse biological properties and potent anticancer activities the compound has remained largely unexplored and hence in the present review we have summarized the chemistry and biological activities of Lawsone along with its analogs and metal complexes.

Topics: Animals; Antimalarials; Antineoplastic Agents, Phytogenic; Antioxidants; Humans; Lawsonia Plant; Naphthoquinones; Plant Extracts; Plants, Medicinal; Tattooing

Contact urticaria (CU) defines the weal-and-flare reaction that occurs after external cutaneous contact with a causative agent. These reactions often cause discomfort for patients, affect their quality of life, and in severe cases may be life-threatening. Some dyes are known to be urticariogens. Many people have daily exposure to these urticariogens, because of the widespread use of dyes, for example in textiles, cosmetics and foods. We reviewed industrial and cosmetic dyes such as hair dyes, basic blue 99 dye, patent blue dyes, henna, red dyes, curcumin and reactive dyes, which can potentially cause CU. Overall, the reported cases of CU lacked appropriate controls. Hair-dye constituents such as preservatives and intensifiers may play an important role as causative agents of CU. We recommend appropriate protection guidelines to reduce the incidence of CU in high-risk groups such as hairdressers, dye-factory workers or workers in dye-related industries.

Topics: Coloring Agents; Cosmetics; Curcumin; Dermatitis, Contact; Humans; Naphthoquinones; Patch Tests; Quaternary Ammonium Compounds; Time Factors; Urticaria

Temporary henna-based tattoos, particularly popular among western tourists holidaying in exotic places, can expose to the risk to develop allergic reactions. Although hypersensitivity to henna is extremely rare, para-phenylenediamine, which is sometimes added to henna to obtain a dark, blackish color, is a frequent contact sensitizer. The purpose of this article is to review the literature about allergic reactions to temporary henna tattoos and outline the causes, clinical aspects and complications of this practice that should not be regarded as innocuous and risk-free.

Topics: Dermatitis, Allergic Contact; Humans; Naphthoquinones; Phenylenediamines; Tattooing

The introduction of ninhydrin treatment as a chemical technique for the visualisation of latent fingermarks on porous surfaces revolutionised approaches to forensic fingermark examination. Since then, a range of amino acid sensitive reagents has been developed and such compounds are in widespread use by law enforcement agencies worldwide. This paper reviews the development and use of these reagents for the detection of latent fingermarks on porous surfaces. A brief overview is provided, including an historical background, forensic significance, and a general approach to the development of latent fingermarks on porous surfaces. This is followed by a discussion of specific amino acid sensitive treatments.

Topics: Amino Acids; Aza Compounds; Forensic Sciences; Indans; Iridoid Glycosides; Iridoids; Naphthoquinones; Ninhydrin; Surface Properties

Topics: Adolescent; Child; Dermatitis, Allergic Contact; Female; Health Policy; Humans; Male; Naphthoquinones; Needs Assessment; Phenylenediamines; Policy Making; Tattooing; United States

Topics: Animals; Cosmetics; Female; Germany; Government Agencies; Hair Color; Hair Dyes; Humans; Male; Naphthoquinones; Neoplasms; Radiation Injuries; Risk Assessment; Risk Factors; Sunscreening Agents; Tattooing; Vitamin A; Zinc Oxide

Topics: Adult; Burns, Chemical; Female; Hand Dermatoses; Hand Injuries; Humans; Naphthoquinones; Tattooing

Topics: Acute Disease; Adult; Coloring Agents; Dermatitis, Contact; Emergency Nursing; Female; Hair Dyes; Humans; Hypersensitivity; Male; Naphthoquinones; Phenylenediamines; Tattooing

To test the effectiveness of henna in the management of palmar-plantar erythrodysesthesia (PPE) in patients receiving treatment with capecitabine or pegylated liposomal doxorubicin (PLD).. This was a randomized controlled feasibility study in three specialized tertiary cancer centers with 56 patients with a PPE grade 1 or above and various cancer diagnoses. The intervention included the local application of henna to the affected areas. The control group followed the same process with a henna inert. Primary outcome was PPE grade and secondary outcomes were the EORTC QLQ-C30, PPE-related QoL (HFS-14), activities of daily living (ECOG) and pain. Patients in both groups were assessed at baseline and then weekly at four follow-ups.. PPE grade in the intervention group (1-3.8%) was lower compared to the control group (4-13.38%) and also lower levels of pain were reported by the patients in the intervention group (2.46 ± 1.17) compared to the control (5.57 ± 2.01). ECOG status in the intervention group was improved compared to the control (p = 0.039). The intervention group, experienced higher Global Health Status (p ≤ 0.008), Physical function (p ≤ 0.001), Emotional Function (p = 0.029), Social function (p ≤ 0.001) and lower Fatigue (p ≤ 0.001) and Pain (p ≤ 0.001) compared to the Control group. A statistically significant interaction was found between Group and Time over the weekly measurements of HFS-14 scores (F = 5,009, p ≤ 0.002) indicating the significant effect of the intervention throughout the weekly assessments.. The trial provided preliminary evidence on henna's effectiveness for treating PPE during treatment with capecitabine or PLD, with lower PPE grades, better performance status and better HRQoL observed in the henna group. CLINICALTRIALS.. NCT01751893.

Topics: Adult; Aged; Capecitabine; Doxorubicin; Drug Interactions; Feasibility Studies; Female; Hand-Foot Syndrome; Humans; Male; Middle Aged; Naphthoquinones; Polyethylene Glycols; Treatment Outcome

Impatiens capensis (jewelweed) is native to the Eastern and Midwestern US and Canada. Many Native American tribes used I. capensis and its close relatives to treat/prevent rash from plant sources particularly Toxicodendron radicans and Urtica dioica. I. balsamina (garden balsam) a native of China was used by the indigenous people of Asia for similar purposes.. This study aims to validate ethnopharmacological use of jewelweed in poison ivy (PI) dermatitis prevention and to refute scientific papers denying this efficacy. Additionally, the content of lawsone, the purported effective agent in jewelweed preparations, was measured to see if its concentration correlated with jewelweed preparation efficacy.. Poison ivy was brushed onto forearms of volunteers in 6 locations and exposed areas were treated with jewelweed extracts, fresh plant mashes, soaps made of plant extracts, water and Dawn® dish soap. Rash development was scored on a scale of 0-14.. Jewelweed mash was effective in reducing poison ivy dermatitis, supporting ethnobotanical use. However, jewelweed extracts were not effective; and soaps made of these extracts were effective but no more so than jewelweed-free soaps. Lawsone content varied with harvest season and did not appear to affect rash development.. Jewelweed is an efficacious plant for preventing development of dermatitis following poison ivy contact, but soap is more effective. Lawsone content does not correlate with PI rash prevention. Perhaps saponins, the soapy component of jewelweed are the effective agents.

Topics: Adolescent; Adult; Aged; Dermatitis, Toxicodendron; Humans; Impatiens; Middle Aged; Naphthoquinones; Plant Preparations; Seasons; Soaps; Species Specificity; Toxicodendron; Treatment Outcome; Young Adult

Over a 10-year period, 15 glucose-6-phosphate dehydrogenase (G6PD)-deficient male newborns were admitted to Al-Jahra Hospital with acute haemolysis a few days after applying henna dye over the body, which is a unique Bedouin tribal practice to celebrate the arrival of the first-born boy. Laboratory investigations revealed significant anaemia, reticulocytosis and indirect hyperbilirubinaemia among the index newborns as compared with controls (p < 0.001). The mean (SD) haemoglobin concentration in index patients was 113.4 (13.4) g/l vs 171.2 (11.2) g/l in controls, reticulocytic count 13.8% (4.2%) vs 1.4% (0.74%), and indirect bilirubin 382.8 (58.7) mumol/l vs 63.7 (61.4) mumol/l. G6PD-deficient newborns with haemolysis linked to henna application had delayed age at presentation and a higher reticulocytic count and hyperbilirubinaemia compared with non-henna-induced haemolysis (p < 0.05). Percutaneous henna absorption is well recognized and clinical findings support the harmful effect of henna on G6PD-deficient red blood cells. A local health education programme has been established to prevent the use of henna dye in infancy.

Topics: Administration, Topical; Antifungal Agents; Glucosephosphate Dehydrogenase Deficiency; Hemolysis; Humans; Infant, Newborn; Male; Medicine, Ayurvedic; Naphthoquinones; Skin Absorption

Dihydroxyacetone (DHA) chemically induces long ultraviolet (UV) and/or visible photoprotection into the stratum corneum as demonstrated by (a) long UV protection of albino rats which were psoralen-photosensitized to black fluorescent light and (b) sunlight protection of five patients with long UV and/or visible photosensitivity. Previously, DHA treatment of skin was considered to provide no protection against UV. For clinical use, the combination of DHA and lawsone (2-hydroxy-1,4-naphthoquinone) is preferred to DHA alone, because it provides rapid, positive protection over a range extending from short UV into the visible region of sunlight.

Topics: Administration, Topical; Adolescent; Adult; Animals; Child; Dihydroxyacetone; Disease Models, Animal; Drug Combinations; Female; Humans; Light; Male; Middle Aged; Naphthoquinones; Photosensitivity Disorders; Rats; Sunscreening Agents; Trioses; Ultraviolet Rays

Hydrophilic, untethered 1,4-naphthoquinones (1,4-NQs) are plant secondary metabolites that are often excreted into the environment and play a role in various plant-microbial, plant-fungal, plant-insect and plant-plant interactions. The biological activity of 1,4-NQs is mainly related to their redox properties, i.e. the ability to undergo redox cycling in cells. These compounds may also undergo electrophilic addition to thiol-containing compounds. The aim of this study was to compare the impact of juglone, plumbagin, lawsone and 2-methoxy-1,4-naphthoquinone (2-met-NQ) on the antioxidant response of the green microalga Chlamydomonas reinhardtii. The algae were incubated with the examined compounds under low light for 6 h and the content of photosynthetic pigments, prenyllipid antioxidants, ascorbate, soluble thiols, proline, and superoxide dismutase activity was assessed. To examine the interaction between photosynthetic activity and naphthoquinone toxicity, we carried out the second experiment, in which C. reinhardtii was incubated with 1,4-NQs for 1 h under high light or in darkness. The pro-oxidant action of the examined 1,4-NQs depended on their reduction potentials, which decrease in order: juglone > plumbagin > 2-met-NQ > lawsone. Lawsone did not display pro-oxidant properties. Exposure to high light strongly enhanced the pro-oxidant effect of juglone, plumbagin, and 2-met-NQ, which is thought to result from the interception of the electrons from photosynthetic electron transfer chain. Only juglone was able to cause a fast depletion of plastoquinol, which may be an important mode of action of this allelochemical, responsible for its high toxicity to plants.

Topics: Antioxidants; Chlamydomonas reinhardtii; Naphthoquinones; Plants; Reactive Oxygen Species

Naphthoquinones are a valuable source of secondary metabolites that are well known for their dye properties since ancient times. A wide range of biological activities have been described highlighting their cytotoxic activity, gaining the attention of researchers in recent years. In addition, it is also worth mentioning that many anticancer drugs possess a naphthoquinone backbone in their structure. Considering this background, the work described herein reports the evaluation of the cytotoxicity of different acyl and alkyl derivatives from juglone and lawsone that showed the best activity results from a etiolated wheat coleoptile bioassay. This bioassay is rapid, highly sensitive to a wide spectrum of activities, and is a powerful tool for detecting biologically active natural products. A preliminary cell viability bioassay was performed on cervix carcinoma (HeLa) cells for 24 h. The most promising compounds were further tested for apoptosis on different tumoral (IGROV-1 and SK-MEL-28) and non-tumoral (HEK-293) cell lines by flow cytometry. Results reveal that derivatives from lawsone (particularly derivative

Topics: Antineoplastic Agents; Cell Line, Tumor; Etoposide; Female; HEK293 Cells; Humans; Naphthoquinones

Topics: Coloring Agents; Dermatitis, Allergic Contact; Humans; Naphthoquinones; Tattooing

The subclass naphthoquinone represents a substance group containing several compounds with important activities against various pathogenic microorganisms. Accordingly, we evaluated O-allyl-lawsone (OAL) antiparasitic and antifungal activity free and encapsulated in 2-hydroxypropyl-β-cyclodextrin (OAL MKN) against Trypanosoma cruzi and Sporothrix spp. OAL and OAL MKN were synthesized and characterized by physicochemical methods. The IC

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Animals; Antifungal Agents; Antiparasitic Agents; Chagas Disease; Mammals; Naphthoquinones; Trypanosoma cruzi

Candida albicans (C. albicans) and Streptococcus mutans (S. mutans) biofilms involve in denture stomatitis. This study compared compound 1 to 2% chlorhexidine gluconate (CHX), Polident, and distilled water (DW) in biofilms reduction and effect on polymethylmethacrylate acrylic (PMMA) properties. The structure of lawsone (naphthoquinone derivative) was modified by the addition of an alkylnyloxy group to yield compound 1. Dual-species biofilms of C. albicans and S. mutans were developed on PMMA discs. The colony-forming unit count measured the number of residual biofilm cells after exposure to the test agents. PMMA discs were examined for color stability, surface roughness, hardness, and chemical structure after 28 days. At 3 min, compound 1 was less effective than CHX in reducing C. albicans (p = 0.004) and S. mutans (p = 0.034) but more effective than Polident in reducing C. albicans (p = 0.001). At 15 min, no viable cells were detectable for compound 1 and its effectiveness was comparable to CHX (p = 0.365). SEM showed fungal cell surface damages in CHX, compound 1 and Polident groups. Only color change was affected by time (p < 0.001) and type of test agent (p = 0.008), and only CHX reached a clinical perception level. Compound 1 is a promising agent for removing biofilm from the PMMA surface without substantially degrading surface properties.

Topics: Biofilms; Candida albicans; Dentures; Disinfectants; Naphthoquinones; Polymethyl Methacrylate; Streptococcus mutans; Surface Properties

Diabetes is one of the major health issues globally. Type 1 diabetes mellitus develops due to the destruction of pancreatic β cells. Mesenchymal stem cells (MSCs) having remarkable self-renewal and differentiation potential, can regenerate β cells. MSCs preconditioned with bioactive small molecules possess enhanced biological features and therapeutic potential under in vivo environment. Interestingly, compounds of naphthoquinone class possess antidiabetic and anti-inflammatory properties, and can be explored as potential candidates for preconditioning MSCs. This study analyzed the effect of lawsone-preconditioned human umbilical cord MSCs (hUMSCs) on the regeneration of β cells in the streptozotocin (STZ)-induced Type 1 diabetes (T1D) rats. hUMSCs were isolated and characterized for the presence of surface markers. MSCs were preconditioned with optimized concentration of lawsone. T1D rat model was established by injecting 50 mg/kg of STZ intraperitoneally. Untreated and lawsone-preconditioned hUMSCs were transplanted into the diabetic rats via tail vein. Fasting blood sugar and body weight were monitored regularly for 4 weeks. Pancreas was harvested and β cell regeneration was evaluated by hematoxylin and eosin staining, and gene expression analysis. Immunohistochemistry was also done to assess the insulin expression. Lawsone-preconditioned hUMSCs showed better anti-hyperglycemic effect in comparison with untreated hUMSCs. Histological analysis presented the regeneration of islets of Langerhans with upregulated expression of βcell genes and reduced expression of inflammatory markers. Immunohistochemistry revealed strong insulin expression in the preconditioned hUMSCs compared with the untreated hUMSCs. It is concluded from the present study that lawsone-preconditioned hMSCs were able to exhibit pronounced anti-hyperglycemic effect in vivo compared with hUMSCs alone.

Topics: Animals; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 1; Humans; Hypoglycemic Agents; Insulin; Insulin-Secreting Cells; Mesenchymal Stem Cell Transplantation; Mesenchymal Stem Cells; Naphthoquinones; Rats

Topics: Coloring Agents; Dermatitis, Allergic Contact; Hair Color; Humans; Naphthoquinones; Tattooing

Schistosomiasis is the second most prevalent parasitic infectious disease after malaria, which affects millions of people worldwide and causes health and socioeconomic problems. The snail Biomphalaria glabrata is an intermediate host for the helminth, which is the causative agent of schistosomiasis: Schistosoma mansoni. One crucial strategy for controlling the disease is the eradication of the snail host. Niclosamide is the unique molluskicide applied in large-scale control programs, but its selectivity to other species is not adequate. Therefore, there is an urgent need to develop new molluskicides that are inexpensive, safe, and selective. Quinones are ubiquitous, playing important biological roles in fungi, plants, and others. Many synthetic molecules with relevant biological activities that contain the quinone nucleus in their structure are on the market in the therapy of cancer, malaria, or toxoplasmosis, for example. Derivatives of quinones are tools in the development of new molluskicides for Abbott laboratories. In the present work, 3-aryl-2‑hydroxy-1,4-naphthoquinones (ANs) were tested for molluskicide activity against Biomphalaria glabrata. The lethal concentration was determined for 48 h of continuous exposure. The naphthoquinones were found to have molluskicide properties. AN-15 was recorded as the highest mortality. Additionally, this analog exhibited in silico reduced ambient toxicity when compared to niclosamide. The findings of this study demonstrate that 3-aryl-2‑hydroxy-1,4-naphthoquinones are effective for the management of Biomphalaria glabrata under laboratory conditions.

Topics: Animals; Biomphalaria; Humans; Naphthoquinones; Niclosamide; Schistosoma mansoni; Schistosomiasis; Schistosomiasis mansoni

Malaria is a disease caused by a parasite that affects millions of people each year and results in many deaths. In 1948, 300 structurally related compounds were made and tested for antimalarial activity with the goal of finding a drug to treat the disease. From this work, promising compounds were identified and this work has served as a starting point for further investigations. Based on recent discoveries, this study made variations of promising 1948 compounds to investigate whether antimalarial activity could be improved. These compounds were made using two different methods. One derivative was found to be more potent than the original compound but was not the one expected based on the 1948 work.

Topics: Antimalarials; Humans; Naphthoquinones; Plasmodium falciparum

This research presents a green synthetic pathway for the preparation of a new biosorbent and eco-friendly extraction process of three phthalate esters: dimethyl phthalate, di-butyl phthalate and benzyl butyl phthalate, from cosmetics and baby care products. Dispersive solid-phase extraction was used based on a new core-shell biomass/sorbent; chitosan-loaded lawsone. The proposed method provides fortunate trapping of phthalate esters in a one-step extraction. Under the optimized extraction conditions, the current work was presented low detection limits (0.03-0.15 ng. g-1), limits of quantification (0.1-0.5 ng·g-1) and reasonable linearity (0.1-10 000 ng. g-1). The applicability of the method was estimated by recovery experiments at different spiking levels (n = 5) for phthalate esters in the real samples.

Topics: Chitosan; Chromatography, High Pressure Liquid; Chromatography, Liquid; Cosmetics; Esters; Naphthoquinones; Phthalic Acids; Solid Phase Extraction

Aedes aegypti is the primary vector of dengue, a significant public health problem in many countries. Controlling of Ae. aegypti is the biggest challenge in the mosquito control programe, and there is a need for finding bioactive molecules to control Ae. aegypti in order to prevent dengue virus transmission.. To assess the mosquitocidal property of lawsone and its 3-methyl-4H-chromen-3-yl-1- phenylbenzo[6,7]chromeno[2,3,c]pyrazole-dione derivatives (6a-6h) against various life stages of Ae. aegypti. Besides, to study the mode of action of the active compound by molecular docking and histopathological analysis.. All derivatives were synthesized from the reaction between 2-hydroxy-1,4-naphthoquinone, chromene-3-carbaldehyde, and 1-phenyl-3-methyl-pyrazol-5-one by using one pot sequential multicomponent reaction. The mosquito life stages were subjected to diverse concentrations ranging from 1.25, 2.5, 5.0, and 10 ppm for lawsone and its derivatives. The structure of all synthesized compounds was characterized by spectroscopic analysis. Docking analysis was performed using autodock tools. Midgut sections of Ae. aegypti larvae were analyzed for histopathological effects.. The derivative 6e is highly effective in the life stages of Ae. aegypti mosquito and it could be used in the integrated mosquito management programe.

Topics: Acetylcholinesterase; Aedes; Animals; Dengue; Molecular Docking Simulation; Mosquito Vectors; Naphthoquinones

We synthesized ten enamine naphthoquinones with yields ranging from 43 to 76%. These compounds were screened for their in vitro antiproliferative activities by MTT assay against four types of human cancer cell lines: HCT116, PC3, HL60 and SNB19. The naphthoquinones bearing the picolylamine (7) and quinoline (12) moieties were the most actives (IC

Topics: Amines; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Cell Survival; Cytotoxins; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Naphthoquinones; Picolinic Acids; Quinolines; Structure-Activity Relationship

Complexes are currently synthesized from plant origin because of their therapeutic effect against certain diseases with toxicity. Hence, in this work, four new transition metal(II) mixed ligand complexes have been synthesized using a curcumin Schiff base (primary ligand) and lawsone (as co-ligand). The geometry of these complexes was explored by elemental analyses, molar conductance, thermal analysis, magnetic moment values, IR, NMR, Mass, electronic and EPR spectral studies. Electronic absorption titrations, viscosity measurements and molecular docking studies reveal that all the metal complexes interact with the CT DNA by groove binding. Among all the complexes, the copper(II) complex (complex 1) exhibits a higher K

Topics: Chemistry Techniques, Synthetic; Coordination Complexes; Curcumin; DNA; Ligands; Models, Molecular; Naphthoquinones; Nucleic Acid Conformation; Schiff Bases; Temperature

We developed a novel method for the synthesis of bis-naphthoquinones (BNQ), which are hybrids of lawsone (2-hydroxy-1,4-naphthoquinone) and 3-hydroxy-juglone (3,5-dihydroxy-1,4-naphthoquinone). The anticancer activity of three synthesized compounds, named 4 (RC10), 5 (RCDFC), and 6 (RCDOH) was evaluated in vitro against two metastatic prostate cancer (PCa) cell lines, DU145 and PC3, using MTT assays. We found that 4 (RC10) and 5 (RCDFC) induced cytotoxicity against DU145 and PC3 cells. Flow cytometry analysis revealed that these two compounds promoted cell cycle arrest in G1/S and G2/M phases, increased Sub-G1 peak and induced inhibition in cell viability. We also showed that these effects are cell-type context dependent and more selective for these tested PCa cells than for HUVEC non-tumor cells. The two BNQ compounds 4 (RC10) and 5 (RCDFC) displayed promising anticancer activity against the two tested metastatic PCa cell lines, DU145 and PC3. Their effects are mainly associated with inhibition of cell viability, possibly through apoptotic cell death, besides altering the SubG1, G1/S and G2/M phases of cell cycle. 5 (RCDFC) compound was found to be more selective than 4 (RC10), when comparing their cytotoxic effects in relation to HUVEC non-tumoral cells. Future work should also test these compounds in combination with other chemotherapeutic drugs to evaluate their effects on further sensitizing drug-resistant metastatic PCa cells.

Topics: Antineoplastic Agents; Apoptosis; Cell Cycle; Cell Cycle Checkpoints; Cell Line, Tumor; Cell Proliferation; Cell Survival; Drug Screening Assays, Antitumor; Humans; Male; Naphthoquinones; PC-3 Cells; Prostatic Neoplasms

Melanoma is a malignant cancer that affects melanocytes and is considered the most aggressive skin-type cancer. The prevalence for melanoma cancer for the last five year is about one million cases. The impact caused of this and other types of cancer, revel the importance of research into potential active compounds. The natural products are an important source of compounds with biological activity and research with natural products may enable the discovery of compounds with potential activity in tumor cells.. The Sulforhodamine B was used to determine cell density after treatment with lawsone derivatives. Apoptosis and necrosis were analyzed by flow cytometer. Morphological changes were observed by fluorescence using the Phalloidin/FITC and DAPI stains. The clonogenic and wound healing assays were used to analyze reduction of colonies formation and migratory capacity of melanoma cells, respectability.. In pharmacological screening, seven compounds derived from lawsone were considered to have high cytotoxic activity (GI > 75%). Three compounds were selected to assess the inhibitory concentration for 50% of cells (IC. The results of this study showed that the evaluated lawsone derivatives have potential activity on tumor cells. The compound 9 is capable of inducing cell death by apoptosis in melanoma cells (B16F10).

Topics: Animals; Apoptosis; Cell Line, Tumor; Cell Proliferation; Cell Survival; Drug Screening Assays, Antitumor; Glycosides; Humans; Melanoma; Mice; Naphthoquinones; Skin Neoplasms; Tumor Stem Cell Assay

Herein, we have evaluated the in vivo therapeutic efficacy and systemic toxicity profile of a synthetic anticancer compound [3,3'-((4-(trifluoromethyl)phenyl)methylene)bis(2-hydroxynaphthalene-1,4-dione)]. A multifunctional mesoporous silica nanoparticle (MSN) based drug delivery network was also fabricated which specifically showed targeting nature towards the cancer cell. The mesopores of silica nanoparticles were tagged with phenyl boronic acid (PBA) for targeted drug delivery into tumor tissue. 1j was then loaded inside the nanocarriers followed by pore blocking with gold nanoparticles (GN) to attain a redox-responsive controlled drug delivery pattern. The synthesized nanocarriers (1j@-MSN-PBA-GN) having mean diameter of ~86 nm exhibited a moderate 1j loading content of 13.68% with overall negative surface charge. Both the targeted and non-targeted nanoformulations were tested for their anticancer activities both in vitro and in vivo models, and found more effective as compared with free 1j treatment. However, the targeted nanoformulations showed higher therapeutic effect due to increased cellular internalization and caused mitochondria-dependent apoptosis in MCF-7 cells via oxidative stress. Besides, the targeted nanoformulation significantly inhibited in the development of solid tumor in comparison to non-targeted nanoformulations and free 1j as a consequence of increased internalization of the drug-candidate in tumor tissue. Therefore, this study proposes that 1j can be considered as a potent anti-carcinogenic compound in vivo and its therapeutic potential is further increased by using PBA functionalized and GN gated MSN-based controlled drug delivery system without showing any significant systemic toxicity.

Topics: Doxorubicin; Drug Carriers; Drug Delivery Systems; Gold; Humans; Metal Nanoparticles; Nanoparticles; Naphthoquinones; Oxidation-Reduction; Porosity; Silicon Dioxide

Topics: Acetylcholinesterase; Butyrylcholinesterase; Carbonic Anhydrase I; Carbonic Anhydrase II; Cholinesterase Inhibitors; Dose-Response Relationship, Drug; Glycoside Hydrolase Inhibitors; Humans; Molecular Docking Simulation; Molecular Structure; Naphthoquinones; Structure-Activity Relationship

Henna is a herb that is used in traditional medicine for medical purposes as well as in the field of cosmetic. It is one of the agents that can trigger hemolytic crisis in G6PD deficient patients but it is considered safe in patients with normal G6PD enzyme. Here we present a case of non-immune hemolytic anemia occurred after ingestion of a homemade solution containing henna powder. Therapeutic plasma exchange was performed daily for 3 subsequent days and the hemoglobin levels and hemolytic markers were improved dramatically. Laboratory test revealed a normal G6PD enzyme level six weeks after recovery. We would like to emphasize the possibility of unexpected adverse effects and undefined ingredients of herbal products. Therapeutic plasma exchange can be a promising treatment option in such cases.

Topics: Adult; Anemia, Hemolytic; Humans; Male; Naphthoquinones; Plasma Exchange

Topics: A549 Cells; Antineoplastic Agents; Cell Cycle Checkpoints; Cell Death; Cell Survival; Drug Carriers; Drug Liberation; Gene Expression Regulation, Neoplastic; Humans; Kinetics; Liposomes; Nanoparticles; Naphthoquinones; Particle Size

Cutaneous wounds accompanied by massive bleeding, bacterial infections might be lethal and cause fundamental therapeutic impediments in clinical fields. As part of the push for a solution, biomaterial having hemostatic-antibacterial features is highly desirable. Inspired by this concept, freeze dried sponges were developed followed by combining tempo-oxidized nanocellulose (TOCN), chitosan using EDC/NHS cross-linker with antibacterial lawsone loading for controlled delivery of this compound during wound healing. The pore diameter decreased upon increasing chitosan (2.5, 3.5, 4.5, 5.5% w/v) while TOCN ensured scaffold's mechanical stability. The in vitro degradation, lawsone release from fibroblast cell-compatible sponge was faster in acidic pH 5.5 than physiologic pH 7.4 indicating adaptability to physiological skin milieu of wounds. The rat tail amputation model, 14 days rat full-thickness cutaneous-wound model ensured hemostasis, dramatic wound closure after TLC4.5 (optimized scaffold) treatment suggesting its potential as functional wound healing substitute showing obvious avenue for hemostatis and skin tissue reconstruction arena.

Topics: Animals; Anti-Bacterial Agents; Bandages; Chitosan; Hemostasis; Naphthoquinones; Rats; Wound Healing

The proposed work, aims to provide a "green" and cutting-edge technique for the mordanting and dyeing of polyester fabric with natural henna dye using the advanced technology of micro waves. For providing a complete "green" and ecofriendly dyeing process, lemon was used as a natural bio mordant with micro waves and results were compared with conventional mordanting method followed by the natural henna dyeing of polyester fabric with microwave. Color properties were analyzed in detail. Scanning electron microscope (SEM), WIDE ANGLE X-RAY DIFFRACTION (WAXD) and Fourier transform infrared spectrometer (ATR-FTIR) studies provide the details of surface and structural changes induced by microwave lemon mordanting and henna dyeing of polyester. Microwave technique clearly reduced the mordanting and dyeing time upto 60-65% with improved fixation and color characteristics.

Topics: Color; Coloring Agents; Green Chemistry Technology; Microscopy, Electron, Scanning; Microwaves; Naphthoquinones; Polyesters; Spectroscopy, Fourier Transform Infrared; Textiles; X-Ray Diffraction

Topics: Adult; Asthma, Occupational; Cassia; Female; Hair Dyes; Humans; Immunoglobulin E; Inhalation Exposure; Lawsonia Plant; Naphthoquinones; Occupational Exposure; Rhinitis

Structural and optoelectronic properties of lawsone (L), lawsone ether (LE) and bilawsone (BL) were studied theoretically using the DFT and time-dependent DFT methods with hybrid functional B3LYP5 and 6-311G (2d,p) basis set. For the monomer lawsone molecule, isomerization reaction between two rotational isomers was analyzed based on a thermodynamic approach. The electronic spectra of the dyes molecules in a vacuum and solvents (DMSO and CH

Topics: Coloring Agents; Electrons; Ether; Ethers; Isomerism; Models, Molecular; Naphthoquinones; Solar Energy

Electrofermentation actively regulates the bacterial redox state, which is essential for bioconversion and has been highlighted as an effective method for further improvements of the productivity of either reduced or oxidized platform chemicals. 1,3-Propanediol (1,3-PDO) is an industrial value-added chemical that can be produced from glycerol fermentation. The bioconversion of 1,3-PDO from glycerol requires additional reducing energy under anoxic conditions. The cathode-based conversion of glycerol to 1,3-PDO with various electron shuttles (2-hydroxy-1,4-naphthoquinone, neutral red, and hydroquinone) using Klebsiella pneumoniae L17 was investigated. The externally poised potential of -0.9 V vs. Ag/AgCl to the cathode increased 1,3-PDO (35.5±3.1 mm) production if 100 μm neutral red was used compared with non-bioelectrochemical system fermentation (23.7±2.4 mm). Stoichiometric metabolic flux and transcriptional analysis indicated a shift in the carbon flux toward the glycerol reductive pathway. The homologous overexpression of glycerol dehydratase (DhaB) and 1,3-PDO oxidoreductase (DhaT) enzymes synergistically enhanced 1,3-PDO conversion (39.3±0.8 mm) under cathode-driven fermentation. Interestingly, a small current uptake (0.23 mmol of electrons) caused significant metabolic flux changes with a concomitant increase in 1,3-PDO production. This suggests that both an increase in 1,3-PDO production and regulation of the cellular metabolic pathway are feasible by electrode-driven control in cathodic electrofermentation.

Topics: Electrochemical Techniques; Electrodes; Electron Transport; Fermentation; Glycerol; Hydro-Lyases; Hydroquinones; Klebsiella pneumoniae; Naphthoquinones; Neutral Red; Oxidation-Reduction; Oxidoreductases; Propylene Glycols; Signal Transduction

Breast cancer is the most incident and mortal cancer type in women, with an estimated 2 million new cases expected by 2020 worldwide, with 600,000 deaths. As not all breast cancer types respond to the anti-hormonal therapy, the development of new antineoplastic drugs is necessary. Lawsone (2-hydroxy-1,4-naphtoquinone) is a natural bioactive naphtoquinone displaying a range of activities, with dozens of derivatives described in the literature, including some glycosides possessing antitumor activity. Here, a series of glycosides of lawsone are reported for the first time and all compounds displayed good activity against the SKBR-3 cell line, with IC

Topics: Breast Neoplasms; Female; Glycosides; Humans; Molecular Structure; Naphthoquinones; Structure-Activity Relationship

Lawsone is a natural naphthoquinone present in the henna leaf extract with several cytotoxic activities and used as precursor for synthesis of various pharmaceutical compounds. Its biological activities are thought to be the result of oxidative stress generated, although the hydroxy group at position C-2 in its structure tends to reduce its electrophilic potential. In view of lack of knowledge on its activity, the present work aimed to elucidate the biological effect of lawsone using the yeast Saccharomyces cerevisiae. In the model strain BY4741 it was defined 229 mmol/L as the minimal inhibitory concentration (MIC). Using 172 mmol/L as sub-MIC value it was observed that yap1 deletion mutant was sensitive to lawsone independent the presence of oxygen. Lawsone affected yeast growth in glycerol, indicating interference in the respiratory metabolism. Intracellular content of thiol groups did not indicate intensive oxidative stress and the presence of the anti-oxidant N-acetylcysteine (NAC) exacerbated lawsone toxicity. By analysing the sensitivity of atg mutant strains and the localization of GFP-Atg8 fusion protein, it was concluded that lawsone primarily produces mitochondrial malfunctioning, leading to indirect oxidative stress. It triggers the autophagic response that ultimately induces mitophagy.

Topics: Dose-Response Relationship, Drug; Gene Expression; Genes, Reporter; Lawsonia Plant; Microbial Sensitivity Tests; Mitochondria; Mitophagy; Molecular Structure; Naphthoquinones; Oxidative Stress; Plant Extracts; Saccharomyces cerevisiae

In general, fungal species are characterized by their opportunistic character and can trigger various infections in immunocompromised hosts. The emergence of infections associated with high mortality rates is due to the resistance mechanisms that these species develop.. This phenomenon of resistance denotes the need for the development of new and effective therapeutic approaches. In this paper, we report the investigation of the antioxidant and antifungal behavior of dimeric naphthoquinones derived from lawsone whose antimicrobial and antioxidant potential has been reported in the literature.. Seven fungal strains were tested, and the antioxidant potential was tested using the combination of the methodologies: reducing power, total antioxidant capacity and cyclic voltammetry. Molecular docking studies (PDB ID 5V5Z and 1EA1) were conducted which allowed the derivation of structureactivity relationships (SAR). Compound 1-i, derived from 3-methylfuran-2-carbaldehyde showed the highest antifungal potential with an emphasis on the inhibition of Candida albicans species (MIC = 0.5 µg/mL) and the highest antioxidant potential.. A combination of molecular modeling data and in vitro assays can help to find new solutions to this major public health problem.

Topics: Antifungal Agents; Antioxidants; Candida albicans; Dimerization; DNA Repair; Dose-Response Relationship, Drug; Microbial Sensitivity Tests; Molecular Docking Simulation; Molecular Structure; Naphthoquinones; Quantum Theory; Reactive Oxygen Species; Structure-Activity Relationship

Topics: Aminopyridines; Anthraquinones; Azo Compounds; Coloring Agents; Cresols; Dimethyl Sulfoxide; Dinitrochlorobenzene; Eugenol; Gene Expression; HaCaT Cells; Hair Dyes; Heme Oxygenase-1; Humans; Hydroquinones; In Vitro Techniques; Keratinocytes; Naphthoquinones; NF-E2-Related Factor 2; Phenylenediamines; Proto-Oncogene Proteins c-fos; Pyrogallol; Resorcinols; RNA, Messenger; Sodium Dodecyl Sulfate

Cells of the facultative photosynthetic bacterium Rhodobacter capsulatus exploit the simultaneous presence in the cultural medium of the toxic oxyanion tellurite (TeO

Topics: Crystallization; Nanoparticles; Naphthoquinones; Oxidation-Reduction; Rhodobacter capsulatus; Tellurium

Topics: Coloring Agents; Female; Humans; Lichenoid Eruptions; Naphthoquinones; Tattooing; Young Adult

Staining, as a valuable method for sperm morphological assessment, has been used to determine sperm abnormalities, fertilization capability and sperm suitability during freezing-thawing process. Synthetic dyes have been used for sperm viability and morphological evaluation. However, most of them have been made from chemical substances and have a perilous effect on the environment. In the current study, we evaluated three different natural dyes as the natural sources of dye for sperm staining. Bull frozen semen was used and prepared on slides for staining. Aqueous extract dye of black mulberry (BM), henna (HA), safflower (SA) and eosin-nigrosine (control group) were used for sperm staining. Additionally, the effect of staining dyes on viability and some morphological parameters (head area: HR, head abnormality: HB and tail abnormality: TA) were evaluated. Although none of the natural dyes could detect viability of the sperm cells, safflower stain (HR: 26.55 µm, HB: 0% TA: 28%) and black mulberry stain (HR: 25.07 µm, HB: 2% TA: 3%) compared to control group (HR: 34.29 µm, HB: 4%, TA: 4%) provoked a strong reaction in the sperm cells, so that the sperms were observed yellow and red respectively. The reaction of sperm cells to the henna dye was very poor and it did not stain the sperm cells. Thus, the present study demonstrated that SA and BM dyes are able to stain the spermatozoa and with further modification could be used as alternative dyes for sperm staining in the study of sperm morphology, but not viability. Staining with these dyes can be an alternative to current costly chemical staining methods.

Topics: Animals; Carthamus tinctorius; Cattle; Coloring Agents; Male; Morus; Naphthoquinones; Plant Preparations; Semen Analysis; Spermatozoa; Staining and Labeling

Topics: Blister; Coloring Agents; Dermatitis, Allergic Contact; Female; Glucocorticoids; Humans; Methylprednisolone; Middle Aged; Naphthoquinones; Phenylenediamines

Denitrification in mixed culture system has been extensively researched to date, but few studies have focused on accelerating the process using redox mediators to promote electron transfer. Strain L2, an iron-reducing bacteria, can remove 75.44% of nitrate under temperature of 30.60 °C, pH of 6.75 and Fe

Topics: Denitrification; Naphthoquinones; Nitrates; Oxidation-Reduction; Zoogloea

A previous analysis of undesirable events (UEvs), reported to four major companies following the use of hair-colouring products in Europe, showed that the reporting rates were stable for both oxidative and direct hair-colouring products over the period 2003-2006.. In order to verify the impact of risk management measures implemented since 2006, as well as the impact of a new Commission Regulation (No 1223/2009), the same four companies analysed cosmetovigilance data collected over an additional four-year period (2014-2017). The objective was to determine whether there was any time effect, country effect, or product type effect, as well as identify risk factors.. Each company collected reports of alleged UEvs, undesirable effects (UEfs) and serious undesirable effects (SUEs) for their products in their key European markets, and calculated the respective reporting rates (number of events/million units sold). A detailed analysis was performed on allergic contact dermatitis-type events.. The reporting rates for alleged UEvs and allergic-type UEfs associated with hair-colouring products remained stable over the four-year period, although a statistically significant decrease was observed for some companies. No time effect on SUEs was observed for three companies but a statistically significant decrease in SUEs was observed for one company. Black henna tattoos remained a major risk factor regarding SUEs due to hair dyes.. The reporting rates of undesirable events, including contact allergy-type events, were stable over time. This was true for oxidative and direct hair dyes, for both home use and professional exposure scenarios.

Topics: Dermatitis, Allergic Contact; Europe; Follow-Up Studies; Hair Dyes; Humans; Naphthoquinones; Product Surveillance, Postmarketing; Risk Factors; Scalp Dermatoses; Tattooing

The treatment of Staphylococcus aureus (S. aureus) infections has become more difficult due to the emergence of multidrug resistance in the bacteria. Here, we report the synthesis of a lawsone (2-hydroxy-1,4-naphthoquinone)-based compound as an antimicrobial agent against methicillin-resistant S. aureus (MRSA). A series of lawsone-derivative compounds were synthesized by means of tuning the lipophilicity of lawsone and screened for minimum inhibitory concentrations against MRSA to identify a candidate compound that possesses a potent antibacterial activity. The identified lawsone-derivative compound exhibited significantly improved drug resistance profiles against MRSA compared to conventional antibiotics. The therapeutic efficacy of the compound was validated using murine models of wound infection as well as non-lethal systemic infection induced by MRSA. Our study further revealed the multifaceted modes of action of the compound, mediated by three distinctive mechanisms: (1) cell membrane damage, (2) chelation of intracellular iron ions, and (3) generation of intracellular reactive oxygen species.

Topics: Animals; Anti-Bacterial Agents; Bacterial Outer Membrane; Male; Methicillin-Resistant Staphylococcus aureus; Mice; Mice, Inbred C57BL; Microbial Sensitivity Tests; Naphthoquinones; Staphylococcal Infections

Impatiens balsamina L. is a tropical ornamental and traditional medicinal herb rich in natural compounds, especially 2-methoxy-1,4-naphthoquinone (MNQ) which is a bioactive compound with tested anticancer activities. Characterization of key genes involved in the shikimate and 1,4-dihydroxy-2-naphthoate (DHNA) pathways responsible for MNQ biosynthesis and their expression profiles in I. balsamina will facilitate adoption of genetic/metabolic engineering or synthetic biology approaches to further increase production for pre-commercialization. In this study, HPLC analysis showed that MNQ was present in significantly higher quantities in the capsule pericarps throughout three developmental stages (early-, mature- and postbreaker stages) whilst its immediate precursor, 2-hydroxy-1,4-naphthoquinone (lawsone) was mainly detected in mature leaves. Transcriptomes of I. balsamina derived from leaf, flower, and three capsule developmental stages were generated, totalling 59.643 Gb of raw reads that were assembled into 94,659 unigenes (595,828 transcripts). A total of 73.96% of unigenes were functionally annotated against seven public databases and 50,786 differentially expressed genes (DEGs) were identified. Expression profiles of 20 selected genes from four major secondary metabolism pathways were studied and validated using qRT-PCR method. Majority of the DHNA pathway genes were found to be significantly upregulated in early stage capsule compared to flower and leaf, suggesting tissue-specific synthesis of MNQ. Correlation analysis identified 11 candidate unigenes related to three enzymes (NADH-quinone oxidoreductase, UDP-glycosyltransferases and S-adenosylmethionine-dependent O-methyltransferase) important in the final steps of MNQ biosynthesis based on genes expression profiles consistent with MNQ content. This study provides the first molecular insight into the dynamics of MNQ biosynthesis and accumulation across different tissues of I. balsamina and serves as a valuable resource to facilitate further manipulation to increase production of MNQ.

Topics: Flowers; Gene Expression Profiling; Gene Expression Regulation, Plant; Gene Ontology; Impatiens; Molecular Sequence Annotation; Naphthoquinones; Plant Leaves; Plants, Medicinal; Transcriptome

This study was carried out to investigate the biomedicinal potential of aqueous extract (1.25 and 2.5%) of three henna ecotypes (Shahdad, Roodbar and Bam) against Two types of Gram positive and negative bacteria,

Topics: Anti-Bacterial Agents; Antioxidants; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Ecotype; Gram-Negative Bacteria; Gram-Positive Bacteria; Lawsonia Plant; Microbial Sensitivity Tests; Naphthoquinones; Plant Extracts; Plant Leaves

Structurally diverse benzo[g]chromenes were conveniently synthesized by one-pot, multi-component reaction of N-alkyl-1-(methylthio)-2-nitroethenamine (derived from the reaction of nitroketene dithioacetal with various amines), aromatic aldehydes and 2-hydroxy-1,4-naphthoquinone in CH

Topics: Aldehydes; Amines; Benzopyrans; Naphthoquinones

Three natural naphthoquinones were screened to find new anti-virulence agents as inhibitors against sortase A from Staphylococcus aureus (SaSrtA) by quantifying the increase in fluorescence intensity upon substrate cleavage at various concentrations. The 5-hydroxy-1,4-naphthalenedione derivatives, juglone and plumbagin, demonstrated a potent inhibitory effect, with IC

Topics: Aminoacyltransferases; Anti-Bacterial Agents; Bacterial Proteins; Biofilms; Catalytic Domain; Cysteine Endopeptidases; Cysteine Proteinase Inhibitors; Enterococcus faecalis; Inhibitory Concentration 50; Models, Molecular; Molecular Docking Simulation; Naphthoquinones; Protein Binding; Staphylococcus aureus; Staphylococcus epidermidis

A series of new lawsone Mannich bases derived from salicylaldehydes or nitrofurfural were prepared and tested for their activities against Leishmania major, Toxoplasma gondii, and Trypanosoma brucei brucei parasites. The hydrochloride salts 5a and 6a of the Mannich bases 2a and 3a, derived from unsubstituted salicylaldehyde and long-chained alkyl amines, were selectively and strongly active against T. gondii cells and appear to be new promising drug candidates against this parasite. Compound 6a showed an even higher activity against T. gondii than the known lawsone Mannich base 1b. Compound 4a, derived from salicylaldehyde and 2-methylaminopyridine, was also distinctly active against T. gondii cells. The derivatives 3a (salicyl derivative), 3b (3,5-dichloro-2-hydroxyphenyl derivative), and 3d (5-nitrofuranyl derivative) as well as the hydrochlorides 6a and 6b were also efficacious against T. b. brucei cells with compounds 3a and 3b being more selective for T. b. brucei over Vero cells when compared with the known control compound 1b. The derivatives 5a, 5c, 6a, and 6c proved to be up to five times more active than 1b against L. major promastigotes and up to four times more efficacious against L. major amastigotes.

Topics: Antiparasitic Agents; Dose-Response Relationship, Drug; Leishmania major; Mannich Bases; Molecular Structure; Naphthoquinones; Parasitic Sensitivity Tests; Structure-Activity Relationship; Toxoplasma; Trypanosoma brucei brucei

Topics: Albumins; Algorithms; Coordination Complexes; Ligands; Mannich Bases; Metals; Molecular Docking Simulation; Molecular Dynamics Simulation; Molecular Structure; Naphthoquinones; Protein Binding; Spectrum Analysis; Thermodynamics

An efficient, mild and environmentally benign protocol has been developed for the synthesis of aminouracil-tethered tri-substituted methane derivatives. The three-component reaction of 2-hydroxy-1,4-naphthaquinone, 6-amino-1,3-dimethyluracil and aldehydes in the presence of molecular iodine as catalyst under reflux conditions resulted in aminouracil-tethered tri-substituted methane derivatives 4 in aqueous medium. Similarly, the four-component reaction of 2-hydroxy-1,4-naphthaquinone, o-phenylenediamine, aldehydes and aminouracil derivatives resulted in aminouracil-tethered tri-substituted methane derivatives 6 under the same reaction conditions. The notable features of this protocol are simple experimental procedure, cheap catalyst, readily available starting materials, moderate-to-good yields of the products having biologically active important moieties such as aminouracil, hydroxy-naphthaquinone/benzophenazine.

Topics: Aldehydes; Catalysis; Iodine; Methane; Naphthoquinones; Uracil; Water

In this study, we aimed to evaluate the role of electrospun nanofibers containing lawsone (2-hydroxy-1,4-naphthoquinone) in wound healing. Different concentrations of lawsone (0.5%, 1%, 1.5%) were electrospun in polycaprolactone-gelatin (PCL/Gel) polymers in core-shell architecture. Nanofibers were characterized using scanning electron microscopy (SEM), Transmission electron microscopy (TEM). Coaxial electrospinning of PCL/Gel/lawsone (PCL/Gel/Law) scaffolds prolonged the release of lawsone over a period of 20 days. In vitro bioactivity of fibers on human gingiva fibroblast cells (HGF) was evaluated by MTT assay. The PCL/Gel/Law 1% increased cell attachment and proliferation significantly. Additionally, the in vitro gene expression of transforming growth factor β (TGF-B1), collagen (COL1) and epidermal growth factor (EGF) was monitored using RT-qPCR technique, which there was significant increase in TGF-B1 and COL1 gene expression in PCL/Gel/Law 0.5% and 1% mats. In vivo wound healing activity of lawsone loaded scaffolds in rat wound model revealed that the PCL/Gel/Law 1% had the highest impact on healing by increasing re-epithelialization of the wound after 14 days. It can be inferred that lawsone 1% incorporation in the core of PCL/Gel electrospun nanofibers has excellent characteristics and can be used as wound dressing patch in medicine.

Topics: Animals; Anti-Infective Agents; Bandages; Cell Line; Cell Proliferation; Cell Survival; Collagen Type I; Delayed-Action Preparations; Electrochemical Techniques; Epidermal Growth Factor; Fibroblasts; Gelatin; Gene Expression Regulation; Humans; Male; Nanofibers; Naphthoquinones; Polyesters; Pseudomonas aeruginosa; Rats; Rats, Wistar; Skin; Staphylococcus aureus; Surgical Wound; Tissue Scaffolds; Transforming Growth Factor beta1; Wound Healing

Topics: Adult; Alopecia; Artifacts; Culture; Dermoscopy; Female; Hair Dyes; Hair Follicle; Humans; India; Male; Naphthoquinones

Topics: Adult; Allergens; Cymbopogon; Dermatitis, Allergic Contact; False Negative Reactions; Female; Humans; Naphthoquinones; Oils, Volatile; Patch Tests; Phenylenediamines; Pruritus; Skin; Tattooing

Topics: Animals; Antineoplastic Agents; Apoptosis; Cattle; Cell Line, Tumor; Cell Movement; Coordination Complexes; DNA; Humans; Intercalating Agents; Male; Naphthoquinones; Prostatic Neoplasms; Reactive Oxygen Species; Ruthenium; Spheroids, Cellular

Hair analysis plays an important role in abstinence control in forensic toxicology. However, hair coloration affects the concentrations of xenobiotics and may lead to false negative results. For instance, henna has been shown to decrease ethyl glucuronide concentrations in hair. For analysis of the main henna ingredient lawsone (2-hydroxy-1,4-naphthoquinone), hair samples were washed, cut into small pieces (less than 5 mm), incubated (20 mg) in water and with internal standard (theophylline) for 24 h at 37 °C. Lawsone was analyzed in the supernatant using liquid chromatography with diode array detection. For quantitative assay, the absorption at 280 nm was found to be linear up to 250 ng/mg hair. The detection limit of lawsone was 2.2 ng/mg, precision and accuracy were better than 6%. Lawsone was only detectable in 12 henna-colored hair samples in concentrations from 27.3 to 253.7 (median 92.6) ng/mg. The analysis of lawsone is recommended in cases of suspected hair coloration where assessment of oxidative treatment was negative (e.g. no increase of 1H-pyrrole-2,3,5-tricarboxylic acid (PTCA) and unobtrusive fluorescence microscopy).

Topics: Chromatography, Liquid; Forensic Toxicology; Hair; Hair Dyes; Humans; Microscopy, Fluorescence; Naphthoquinones

Topics: Adolescent; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Skin Diseases, Vesiculobullous; Tattooing

Naphthoquinones, plants secondary metabolites are known for their antibacterial, antifungal, anti-inflammatory, anti-cancer and anti-parasitic properties. The biological activity of naphthoquinones is connected with their ability to generate reactive oxygen species and to modify biological molecules at their nucleophilic sites. In our research, the effect of naphthazarin (DHNQ) combined with 2-hydroxy-1,4-naphthoquinone (NQ-2-OH) or 1,4-naphthoquinone (1,4-NQ) on the elongation growth, pH changes of the incubation medium, oxidative stress and redox activity of maize coleoptile cells were investigated. This paper describes experiments performed with maize (

Topics: Cotyledon; Indoleacetic Acids; Naphthoquinones; Oxidative Stress; Plant Growth Regulators; Zea mays

Allergic contact dermatitis caused by henna-based hair-colouring products has been associated with adulteration of henna with p-phenylenediamine (PPD).. To develop a testing approach based on in vitro techniques that address key events within the skin sensitization adverse outcome pathway in order to evaluate the allergenic potential of hair-colouring products.. The following in vitro assays were used to test the sensitizing capacity of hair dye ingredients: the micro-direct peptide reactivity assay (mDPRA); the HaCaT keratinocyte-associated interleukin (IL)-18 assay; the U937 cell line activation test (U-SENS)/IL-8 levels; the blood monocyte-derived dendritic cell test; and genomic allergen rapid detection (GARD skin). Those techniques with better human concordance were selected to evaluate the allergenic potential of 10 hair-colouring products.. In contrast to the information on the label, chromatographic analyses identified PPD in all products. The main henna biomarker, lawsone, was not detected in one of the 10 products. Among the techniques evaluated by testing hair dye ingredients, the mDPRA, the IL-18 assay, GARD skin and the U-SENS correlated better with human classification (concordances of 91.7%-100%) and were superior to the animal testing (concordance of 78.5%). Thus, these assays were used to evaluate hair-colouring products, which were classified as skin sensitizers by the use of different two-of-three approaches.. Our findings highlight the toxicological consequences of, and risks associated with, the undisclosed use of PPD in henna-based "natural" "real-life" products.

Topics: B7-2 Antigen; Biological Assay; Cell Line, Tumor; Chromatography, High Pressure Liquid; Dendritic Cells; Dermatitis, Allergic Contact; Hair Dyes; Humans; In Vitro Techniques; Interleukin-18; Interleukin-8; Keratinocytes; Naphthoquinones; Phenylenediamines

Quinones are becoming an essential tool for refractory organics treatment, while their quantification may be not well-considered. In this paper, two kinds of potential errors in quantification were evaluated in multiple pH conditions. They were derived from the coexistence of oxidized/reduced quinone species (Type I) and pH-sensitive feature (Type II), respectively. These errors would remarkably influence the accuracy of quantification while they haven't been emphasized. Thus, to elaborate the relationship between the two types of errors and the absorbance or pH conditions, three typical quinones [Anthraquinone-1-sulfonate (α-AQS), anthraquinone-2,6-disulfonate (AQDS) and lawsone] were selected and their acid dissociation coefficients (pKa) as well as UV-Vis spectra were determined. Results revealed that, for Type I, the relative error (RE) of α-AQS concentration would exceed the limit (5%) when reduced α-AQS was below 48% of total α-AQS. Similar results were found for lawsone. However, the RE can be eliminated by the equation established in this paper. For Type II, the pH-sensitive feature was related to the pKa values of quinones. Absorbances of α-AQS and lawsone would change remarkably with pH variation. Therefore, a model for correction was established. Analog data showed high consistency with experimental data [r = 0.995 (n = 25, p < 0.01) and r = 0.997 (n = 36, p < 0.01), for lawsone and α-AQS respectively]. Especially, the determination of AQDS concentrations was noticed to be pH-independent at 437 nm under pH 4.00 to 9.18 conditions. Based on these features, a comprehensive data solution was proposed for handling these errors.

Topics: Anthraquinones; Calibration; Hydrogen-Ion Concentration; Naphthoquinones; Oxidation-Reduction; Quinones; Scientific Experimental Error; Wastewater; Water Purification

1,4-naphthoquinones, especially juglone, are known for their anticancer activity. However, plumbagin, lawsone, and menadione have been less investigated for these properties. Therefore, we aimed to determine the effects of plumbagin, lawsone, and menadione on C6 glioblastoma cell viability, ROS production, and mitochondrial function.. Cell viability was assessed spectrophotometrically using metabolic activity method, and by fluorescent Hoechst/propidium iodide nuclear staining. ROS generation was measured fluorometrically using DCFH-DA. Oxygen uptake rates were recorded by the high-resolution respirometer Oxygraph-2k.. Plumbagin and menadione displayed highly cytotoxic activity on C6 cells (IC. Plumbagin and menadione exhibit strong prooxidant, mitochondrial oxidative phosphorylation uncoupling and cytotoxic activity. In contrast, lawsone demonstrates a moderate effect on C6 cell viability and mitochondrial functions, and possesses strong antioxidant properties.

Topics: Animals; Antineoplastic Agents; Antioxidants; Apoptosis; Cell Line, Tumor; Cell Survival; Glioblastoma; Mitochondria; Naphthoquinones; Oxidants; Oxidation-Reduction; Oxidative Stress; Phosphorylation; Phytotherapy; Plant Extracts; Rats; Reactive Oxygen Species; Uncoupling Agents; Vitamin K 3

Anaerobic fermentation of waste activated sludge (WAS) for recycling valuable volatile fatty acids (VFAs) is economically valuable. However, the fermentation of protein is the rate-limiting step of VFA production with WAS as a substrate. In this study, the effect of redox mediators (RMs, i.e., riboflavin and lawsone) on the enhanced production of VFAs from WAS was investigated. The results indicate that both RMs can promote protein-dependent fermentation, increasing maximum VFA accumulation by 43.9% and 42.5% respectively. In cultures supplemented with riboflavin and lawsone, VFA production was highly correlated with protease activities, but not with α-glucosidase activities. This implies that RMs affected the redox reaction of amino acids degradation, resulting in an increased release of ammonia. Sequencing results showed that RMs significantly increased the abundance of bacteria related to VFA fermentation and protein/amino acid degradation at the levels of phylum, class, order, family, and even genus.

Topics: alpha-Glucosidases; Bacteria; Carbohydrate Metabolism; Fatty Acids, Volatile; Fermentation; Naphthoquinones; Oxidation-Reduction; Proteins; Riboflavin; Sewage; Waste Disposal, Fluid

As a first host barrier, the skin is constantly exposed to environmental insults that perturb its integrity. Tight regulation of skin homeostasis is largely controlled by the aryl hydrocarbon receptor (AhR). Here, we demonstrate that Henna and its major pigment, the naphthoquinone Lawsone activate AhR, both in vitro and in vivo. In human keratinocytes and epidermis equivalents, Lawsone exposure enhances the production of late epidermal proteins, impacts keratinocyte differentiation and proliferation, and regulates skin inflammation. To determine the potential use of Lawsone for therapeutic application, we harnessed human, murine and zebrafish models. In skin regeneration models, Lawsone interferes with physiological tissue regeneration and inhibits wound healing. Conversely, in a human acute dermatitis model, topical application of a Lawsone-containing cream ameliorates skin irritation. Altogether, our study reveals how a widely used natural plant pigment is sensed by the host receptor AhR, and how the physiopathological context determines beneficial and detrimental outcomes.

Topics: Animals; Cells, Cultured; Dermatitis; Guided Tissue Regeneration; Homeostasis; Humans; Keratinocytes; Lawsonia Plant; Mice; Models, Animal; Naphthoquinones; Receptors, Aryl Hydrocarbon; Skin; Wound Healing; Zebrafish

Naphthoquinones are known for their broad range of biological activities. Given the increasing demands of consumers in relation to food quality and growing concerns about the impact of synthetic herbicides, it is necessary to search for new agrochemicals. Natural products and allelopathy provide new alternatives for the development of pesticides with lower toxicity and greater environmental compatibility.. A structure-activity relationship to evaluate the effect of bioavailability was performed. A total of 44 O-acyl and O-alkyl derivatives of juglone and lawsone with different linear chain lengths were prepared. These compounds were tested on etiolated wheat coleoptiles, standard target species (STS) and four weeds, Echinochloa crus-galli L., Lolium rigidum Gaud., Lolium perenne L. and Avena fatua L. The results showed a strong influence of lipophilicity and, in most cases, the data fitted a logP-dependent quadratic mathematical model.. The effects produced were mostly stunting and necrosis caused by growth inhibition. The potential structure and activity behaviour is described. © 2017 Society of Chemical Industry.

Topics: Avena; Echinochloa; Herbicides; Lolium; Naphthoquinones; Plant Weeds; Structure-Activity Relationship

Lawsone redox (LQ) mediator was covalently bound to granular activated carbon (GAC) by Fischer esterification. A high LQ adsorption capacity on GAC was achieved (∼230 mg/g), and desorption studies showed strong chemical stability. Furthermore, kinetic experiments with solid-phase redox mediator (RM) and their controls (soluble RM, GAC and anaerobic sludge) were tested for decolorization of congo red dye at initial concentration of 175 mg/L. Benzidine, a by-product of complete congo red reduction, was also measured by HPLC analysis along the kinetic experiments. The highest percentage of decolorization after 24 h of incubation was achieved in cultures with soluble (77%) and immobilized (70%) LQ. In contrast, low decolorization efficiency was reached in anaerobic bio-reduction assays with unmodified GAC (47%) and anaerobic sludge (28%) after 24 h. Removal of congo red by adsorption onto LQ-GAC was negligible. The rate of benzidine production was slower than decolorization rate, suggesting that one azo bond of congo red is selectively broke and followed by a slower breaking of the second azo bond, consequently, appearance of benzidine in solution. These issues could be attributed to the steric rearrangement and the inhibitory effects of the produced aromatic amines in the biotransformation process.

Topics: Anaerobiosis; Biotransformation; Carbon; Coloring Agents; Congo Red; Naphthoquinones; Oxidation-Reduction; Sewage; Water Pollutants, Chemical

Morita-Baylis-Hillman acetates and α-bromonitroalkenes have been employed in cascade reactions with lawsone and 2-aminonaphthoquinone for the one-pot synthesis of heterocycle fused quinonoid compounds. The reactions reported here utilized the 1,3-binucleophilic potential of hydroxy- and aminonaphthoquinones and the 1,2/1,3-bielectrophilic potential of bromonitroalkenes and Morita-Baylis-Hillman acetates for the synthesis of pyrrole and furan fused naphthoquinones. The synthesized compounds were evaluated against HCT-116 (human colon carcinoma cells), PC3 (human prostate cancer cells), HL-60 (human promyelocytic leukemia cells), SF295 (human glioblastoma cells) and NCI-H460 (human lung cancer cells) and exhibited antitumor activity with IC

Topics: Acetates; Alkenes; Amination; Antineoplastic Agents; Cell Line, Tumor; Chemistry Techniques, Synthetic; Furans; Halogenation; Humans; Models, Molecular; Naphthoquinones; Neoplasms; Pyrroles; Quinones; Structure-Activity Relationship

Lawsonia inermis L. (Lythraceae) is cultivated in many countries, including Japan, China, India and Egypt. Its leaves are well known as hair dye and exhibit antibacterial, anticancer, antifungal and anticonvulsant activities. However, there are few reports on its branches. 2-Hydroxy-1,4-naphthoquinone (lawsone) is a characteristic compound in its leaves. However, it remains to be clarified whether lawsone is present in other plant parts or not. In this study, we measured lawsone contents in the extracts of L. inermis flowers, leaves and branches by HPLC with tandem mass spectrometry. The extracts of L. inermis flowers, leaves and branches contained 116.9, 486.2 and 5.4 μg/g lawsone, respectively. Lawsone content was much lower in branches than the other plant parts. Next, in order to identify the biological constituents in the branches, we isolated nine known compounds and examined their effects on neurite outgrowth in PC12 cells. Among the constituents isolated, 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and quercetin 7-O-β-D-glucopyranoside (8) showed accelerative effects on neurite outgrowth in PC12 cells.

Topics: Animals; Antifungal Agents; Lawsonia Plant; Naphthoquinones; Neuronal Outgrowth; Plant Extracts; Plant Leaves; Rats

The Drug-induced liver injury is one of the common unfavourable impacts, which seriously affects any drug therapy. This study documented the hepatoprotective efficacy of lawsone, the major bioactive naphthoquinone present in Lawsonia inermis L. (Lythraceae) using in vitro and in vivo models. Lawsone was isolated from the leaves of L. inermis and its structure was confirmed using spectroscopic data. In-vitro antioxidant effect of lawsone was evaluated using ABTS assay. Hepatoprotective effect of lawsone was determined with RIF-INH treated HepG2 cells and Wistar rats. Administration of RIF-INH reduced the viability of the HepG2 cells and the treatment with lawsone significantly restored the viability of the cells even at lower concentration (7.5 μM). The other parameters such as the leakage of transaminases and MDA levels were also significantly reduced by the treatment with lawsone. Oral administration of lawsone to the animals did not show any toxicity up to 2 g/kg b.w. concentration. Treatment with lawsone to the RIF-INH administered animals significantly lowered the serum transaminases levels. The ratio of albumin to globulin was improved and the level of bilirubin was lowered. This study indicated the hepatoprotective effect of lawsone; detailed investigations will give deeper understanding of the application of lawsone for hepatoprotection.

Topics: Alanine Transaminase; Alkaline Phosphatase; Animals; Aspartate Aminotransferases; Bilirubin; Cell Survival; Chemical and Drug Induced Liver Injury; Hep G2 Cells; Humans; Isoniazid; L-Lactate Dehydrogenase; Liver; Male; Naphthoquinones; Protective Agents; Rats, Wistar; Rifampin; Serum Albumin; Serum Globulins

Naphthoquinones are among the most active natural products obtained from plants and microorganisms. Naphthoquinones exert their biological activities through pleiotropic mechanisms that include reactivity against cell nucleophiles, generation of reactive oxygen species (ROS), and inhibition of proteins. Here, we report a mechanistic antiproliferative study performed in the yeast Saccharomyces cerevisiae for several derivatives of three important natural naphthoquinones: lawsone, juglone, and β-lapachone. We have found that (i) the free hydroxyl group of lawsone and juglone modulates toxicity; (ii) lawsone and juglone derivatives differ in their mechanisms of action, with ROS generation being more important for the former; and (iii) a subset of derivatives possess the capability to disrupt mitochondrial function, with β-lapachones being the most potent compounds in this respect. In addition, we have cross-compared yeast results with antibacterial and antitumor activities. We discuss the relationship between the mechanistic findings, the antiproliferative activities, and the physicochemical properties of the naphthoquinones.

Topics: Anti-Bacterial Agents; Antifungal Agents; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Humans; Mitochondria; Molecular Structure; Naphthoquinones; Oxidative Stress; Saccharomyces cerevisiae; Staphylococcus aureus; Structure-Activity Relationship

An efficient reaction utilizing propargyl carbonates through Claisen rearrangement to synthesize furanonaphthoquinones is described. The remarkable transformation exhibits excellent functional group tolerance, affording the target furanonaphthoquinones in moderate to good yields (41-85%) under mild reaction conditions. Scaled-up preparation of the model product can make this reaction a method of choice for synthesis of furanonaphthoquinone derivatives. The resulting furanonaphthoquinones were evaluated as potential indoleamine 2,3-dioxygenase inhibitors in vitro.

Topics: Carbonates; Catalysis; Enzyme Inhibitors; HeLa Cells; Humans; Indoleamine-Pyrrole 2,3,-Dioxygenase; Naphthoquinones; Palladium; Quinones; Stereoisomerism

Phytochemicals like Lawsone have some drawbacks that stem from their poor solubility. Low solubility in aqueous mediums results in low bioavailability, poor permeability and instability of phytochemical compounds in biological environments. The aim of this study was to design nanoniosomes containing Lawsone (Law) using non-ionic surfactants and cholesterol. Niosomes were prepared by thin film hydration method (TFH). Then, they were loaded with Henna extract (HLaw) and standard Lawsone (SLaw), and two resulted formulations were compared. The henna extract was analyzed by mass gas chromatography. Size, zeta potential, polydispersity index (PDI) and morphology of the loaded formulations were evaluated by dynamic light scattering (DLS) and scanning electron spectroscopy (SEM). The incorporation and release rate of Law from niosome bilayers were evaluated by UV-Vis spectroscopy. In vitro experiments were carried out to evaluate antitumor activity in MCF-7 cell line. The results showed distinct spherical shapes and particle sizes were about 250 nm in diameter and have negative zeta potentials. Niosomes were stable at 4 °C for 2 months. Entrapment efficiently of both formulations was about 70% and showed a sustained release profile. In vitro study exhibited that using of niosome to encapsulating Law can significantly increase antitumor activity of formulation in MCF-7 cell line compared to Law solution (free Law). Thus, niosomes are a promising carrier system for delivery of phytochemical compounds that have poor solubility in biological fluids. Graphical abstract ᅟ.

Topics: Cell Line, Tumor; Cell Survival; Cholesterol; Drug Compounding; Drug Liberation; Drug Stability; Humans; Lawsonia Plant; Liposomes; Naphthoquinones; Neoplasms; Particle Size; Plant Extracts; Surface Properties; Surface-Active Agents

In this study, chitosan/bioactive glass (BG)/lawsone coatings were deposited by electrophoretic deposition (EPD) on polyetheretherketone (PEEK)/BG layers (previously deposited by EPD on 316-L stainless steel) to produce bioactive and antibacterial coatings. First, the EPD of chitosan/BG/lawsone was optimized on stainless steel in terms of suspension stability, homogeneity and thickness of coatings. Subsequently, the optimized EPD parameters were used to produce bioresorbable chitosan/bioactive glass (BG)/lawsone coatings on PEEK/BG layers. The produced layered coatings were characterized in terms of composition, microstructure, corrosion resistance, in vitro bioactivity, drug release kinetics and antibacterial activity. Ultraviolet/Visible (UV/VIS) spectroscopic analyses confirmed the release of lawsone from the coatings. Moreover, the deposition of chitosan/BG coatings was confirmed by Scanning Electron Microscopy (SEM) and Fourier Transform Infrared spectroscopy (FTIR). The coated specimens presented higher corrosion resistance (10 times) in comparison to that of bare 316-L stainless steel and showed convenient wettability for initial protein attachment. The presence of lawsone in the top layer provided antibacterial effects against Staphylococcus carnosus. Moreover, the developed coatings formed apatite-like crystals upon immersion in simulated body fluid, indicating the possibility of achieving close interaction between the coating surface and bone. © 2018 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 106A: 3111-3122, 2018.

Topics: Anti-Bacterial Agents; Benzophenones; Chitosan; Coated Materials, Biocompatible; Drug Delivery Systems; Drug Liberation; Humans; Ketones; Naphthoquinones; Polyethylene Glycols; Polymers; Staphylococcal Infections; Staphylococcus; Wettability

Angioedema is a type-1 hypersensitivity reaction that can be life threatening. It affects the skin airways and the gastrointestinal tract. Henna is a green powder used to dye skin and nails. We report a 29 year old patient who presented with angioedema Her patch test was positive to paraphenynlenediamine. She was discharged after successful treatment with intravenous steroids and later topical steroids.

Topics: Adult; Angioedema; Coloring Agents; Female; Glucocorticoids; Hair Dyes; Humans; Naphthoquinones; Patch Tests; Phenylenediamines

Henna is a vegetable hair dye that can be used by individuals who are sensitized to oxidative dyes due to low allergenicity. The reported incidence of slate-grey facial dyspigmentation following the use of henna hair dye is extremely rare. This study aimed to identify the clinical, dermoscopic, and histopathological features of slate-grey facial dyspigmentation following the use of henna hair dye in Korean patients. We identified all patients who presented with slate-grey facial dyspigmentation following usage of henna hair dye. Patients were further evaluated for clinical, dermoscopic, and histopathological findings along with their patch test results. All 11 patients were females with Fitzpatrick's skin phototype III or IV. Prominent slate-grey-coloured dyspigmentation on the lateral side of the face and neck was most common in eight (72%) patients. Under dermoscopic examination, a pseudo-network with grey dots was observed in all patients. Histopathological examination revealed liquefaction degeneration of the epidermal basal layer and pigmentary incontinence in the papillary dermis in all patients. The diagnosis of pigmented contact dermatitis following usage of henna was made based on the clinical, dermoscopic, and histopathological findings in all patients. Pigmented contact dermatitis associated with henna occurs mostly in middle-aged women and requires long-term treatment. Therefore, careful attention should be paid when henna is used to dye hair in this age group.

Topics: Aged; Biopsy, Needle; Cohort Studies; Dermatitis, Allergic Contact; Dermoscopy; Female; Humans; Immunohistochemistry; Korea; Middle Aged; Naphthoquinones; Patch Tests; Pigmentation Disorders; Rare Diseases; Retrospective Studies; Risk Assessment

Lawsone (2-hydroxy-1, 4-napthoquinone), also known as hennotannic acid, is an orange red dye used as a popular skin and hair colorant. The dye is produced in the leaves of Lawsonia inermis L, often referred to as the "henna" tree. In this study, we report the production of lawsone by an endophytic fungus, Gibberella moniliformis isolated from the leaf tissues of Lawsonia inermis. The fungus produced the orange-red dye in potato dextrose agar and broth, independent of the host tissue. Presence of lawsone was confirmed spectrometrically using HPLC and ESI-MS/MS analysis. The fragmentation pattern of lawsone was identical to both standard lawsone and that extracted from plant tissue. This is a first report of lawsone being produced by an endophytic fungus, independent of the host tissue. The study opens up interesting questions on the possible biosynthetic pathway through which lawsone is produced by the fungus.

Topics: Animals; Citrus sinensis; Fungi; Gibberella; Lawsonia Plant; Naphthoquinones; Plant Extracts; Tandem Mass Spectrometry

Malaria persists as a major public health problem. Atovaquone is a drug that inhibits the respiratory chain of Plasmodium falciparum, but with serious limitations like known resistance, low bioavailability and high plasma protein binding.. The aim of this work was to perform molecular modelling studies of 2-hydroxy-1,4-naphthoquinones analogues of atovaquone on the Qo site of P. falciparum cytochrome bc1 complex (Pfbc1) to suggest structural modifications that could improve their antimalarial activity.. We have built the homology model of the cytochrome b (CYB) and Rieske iron-sulfur protein (ISP) subunits from Pfbc1 and performed the molecular docking of 41 2-hydroxy-1,4-naphthoquinones with known in vitro antimalarial activity and predicted to act on this target.. Results suggest that large hydrophobic R2 substituents may be important for filling the deep hydrophobic Qo site pocket. Moreover, our analysis indicates that the H-donor 2-hydroxyl group may not be crucial for efficient binding and inhibition of Pfbc1 by these atovaquone analogues. The C1 carbonyl group (H-acceptor) is more frequently involved in the important hydrogen bonding interaction with His152 of the Rieske ISP subunit.. Additional interactions involving residues such as Ile258 and residues required for efficient catalysis (e.g., Glu261) could be explored in drug design to avoid development of drug resistance by the parasite.

Topics: Antimalarials; Electron Transport Complex III; Naphthoquinones; Plasmodium falciparum; Sequence Analysis, Protein

Topics: Bone and Bones; Coloring Agents; Fracture Healing; Fractures, Bone; Humans; Naphthoquinones; Tattooing; Time Factors; Ultrasonography

Fusarium oxysporum is an ascomycete facultative fungus which generally affects to plants. However, it is recently known as a serious emerging opportunistic pathogen of human and other animals. F. oxysporum shows broad resistance to commonly used antifungal agents and therefore development of alternative therapeutic agents is required. In this study, we investigated the antifungal efficacy of plant based natural lawsone against pathogenic F. oxysporum. Antifungal susceptibility test determined the concentration dependent growth inhibition of lawsone against F. oxysporum with minimum inhibitory concentration (MIC) at 100μg/mL. Ultra-structural analysis indicates the prominent damage on cell wall of the mycelium after lawsone treatment, and suggests that it could increase the membrane permeability and disintegration of cells leading to cellular death. Propidium iodide (PI) uptake assay results showed the higher level of cell death in lawsone treated F. oxysporum which further confirms the loss of plasma membrane integrity. Also, detection of reactive oxygen species (ROS) using DCFH-DA has clearly indicated that lawsone (100μg/mL) can induce the ROS level in the filaments of F. oxysporum. MTT assay results showed the loss of viability and germination capacity of F. oxysporum spores by lawsone in concentration dependent manner. Moreover, lawsone treatment induced the mRNA expression of two autophagy related genes (ATG1 and ATG8) indicating that lawsone may activate the autophagy related pathways in F. oxysporum due to the oxidative stress generated by ROS. F. oxysporum infected zebrafish has recovered after lawsone therapy as a topical treatment suggesting that lawsone is a potential natural antifusariosis agent.

Topics: Animals; Antifungal Agents; Autophagy; Cell Membrane; Cell Membrane Permeability; Cell Wall; Disease Models, Animal; Fish Diseases; Fluoresceins; Fusarium; Gene Expression Regulation, Fungal; Genes, Fungal; Hyphae; In Vitro Techniques; Microbial Sensitivity Tests; Microbial Viability; Microscopy, Confocal; Microscopy, Electron, Scanning; Muscles; Naphthoquinones; Pest Control, Biological; Plant Diseases; Plant Extracts; Propidium; Reactive Oxygen Species; RNA, Messenger; Spores, Fungal; Zebrafish

Cosmetic products are subject to the European Cosmetics Regulation: They shall not harm human health when used under "normal or reasonably foreseeable conditions". Hazardous cosmetic products are reported by the EU Member States to the EU Commission and are listed in the database of the European Rapid Alert System RAPEX.. The reports from Germany on dangerous cosmetic products from the years 2005-3/2017 in the European RAPEX database were systematically analyzed.. During the study period, 157 dangerous cosmetic products were reported from Germany. The most common product categories were bleaching creams (24.2%) because of the content of hydroquinone, mercury or corticosteroids, creams/lotions/gels (10.8%) mainly due to microbiological contamination, henna products (10.2%) because of sensitizing concentrations of paraphenylene diamine, and nail adhesives (8.9%) because of high levels of methyl methacrylate.. Hazardous cosmetic products appear to be rare in view of the high market volume of cosmetics, even though the total number of official investigations the RAPEX reports based on is not known. Dermatologists should inform the competent monitoring authorities in case of a suspected harm to health caused by dangerous cosmetic products so that the products can be examined and, if necessary, withdrawn from the market.

Topics: Adhesives; Bleaching Agents; Cosmetics; Databases, Factual; Germany; Glucocorticoids; Humans; Hydroquinones; Mercury; Methylmethacrylate; Naphthoquinones; Phenylenediamines; Skin Cream

We report in vitro and in vivo anti-inflammatory activities of a series of copper(II)-lawsone complexes of the general composition [Cu(Law)2(LN)x(H2O)(2-x)]·yH2O; where HLaw = 2-hydroxy-1,4-naphthoquinone, x = 1 when LN = pyridine (1) and 2-aminopyridine (3) and x = 2 when LN = imidazole (2), 3-aminopyridine (4), 4-aminopyridine (5), 3-hydroxypyridine (6), and 3,5-dimethylpyrazole (7). The compounds were thoroughly characterized by physical techniques, including single crystal X-ray analysis of complex 2. Some of the complexes showed the ability to suppress significantly the activation of nuclear factor κB (NF-κB) both by lipopolysaccharide (LPS) and TNF-alpha (complexes 3-7 at 100 nM level) in the similar manner as the reference drug prednisone (at 1 μM level). On the other hand, all the complexes 1-7 decreased significantly the levels of the secreted TNF-alpha after the LPS activation of THP-1 cells, thus showing the anti-inflammatory potential via both NF-κB moderation and by other mechanisms, such as influence on TNF-alpha transcription and/or translation and/or secretion. In addition, a strong intracellular pro-oxidative effect of all the complexes has been found at 100 nM dose in vitro. The ability to suppress the inflammatory response, caused by the subcutaneous application of λ-carrageenan, has been determined by in vivo testing in hind-paw edema model on rats. The most active complexes 1-3 (applied in a dose corresponding to 40 μmol Cu/kg), diminished the formation of edema simalarly as the reference drug indomethacine (applied in 10 mg/kg dose). The overall effect of the complexes, dominantly 1-3, shows similarity to anti-inflammatory drug benoxaprofen, known to induce intracellular pro-oxidative effects.

Topics: Animals; Anti-Inflammatory Agents; Cell Line, Tumor; Copper; Crystallography, X-Ray; Dose-Response Relationship, Drug; Edema; Humans; Inflammation; Male; Naphthoquinones; NF-kappa B; Rats; Rats, Wistar; Spectrometry, Mass, Electrospray Ionization

Topics: Biodegradation, Environmental; Catechols; Chromans; Industrial Microbiology; Naphthoquinones; Pseudomonas; Salicylic Acid

New Ru(II) complexes with lawsone (law) characterized as trans-[Ru(law)(PPh

Topics: A549 Cells; Antineoplastic Agents; Coordination Complexes; G1 Phase; Humans; Naphthoquinones; Neoplasms; Ruthenium; S Phase

Chagas disease is an endemic parasitic infection that occurs in 21 Latin American countries. New therapies for this disease are urgently needed, as the only two drugs available (nifurtimox and benznidazol) have high toxicity and variable efficacy in the disease's chronic phase. Recently, a new chemical entity (NCE) named Pyranaphthoquinone (IVS320) was synthesized from lawsone. We report herein, a detailed study of the physicochemical properties and in vitro trypanocidal activity of IVS320. A series of assays were performed for characterization, where thermal, diffractometric, and morphological analysis were performed. In addition, the solubility, permeability, and hygroscopicity of IVS320 were determined. The results show that its poor solubility and low permeability may be due to its high degree of crystallinity (99.19%), which might require the use of proper techniques to increase the IVS320's aqueous solubility and permeability. The trypanocidal activity study demonstrated that IVS320 is more potent than the reference drug benznidazole, with IC50/24 h of 1.49 ± 0.1 μM, which indicates that IVS320 has potential as a new drug candidate for the treatment of Chagas disease.

Topics: Binding Sites; Chagas Disease; Humans; Models, Molecular; Molecular Structure; Naphthoquinones; Permeability; Protein Binding; Solubility; Trypanocidal Agents; Trypanosoma

Multidrug resistance (MDR) represents a serious problem in cancer treatment. One strategy to overcome this obstacle is to identify agents that are selectively lethal to MDR cells. The aim of this study was to discover novel compounds against MDR leukemia and to determine the molecular mechanisms behind collateral sensitivity. A library of 1162 compounds was tested against parental, drug-sensitive CCRF-CEM cells using the resazurin assay. A total of 302 compounds showed reasonable activity (less than 50% cell viability). Eleven out of 30 lawsone derivatives revealed considerable collateral sensitivity in MDR P-glycoprotein (Pgp)-overexpressing CEM/ADR5000 cells. They reduced β-catenin activity in a Wnt/β-catenin reporter cell line. Their activities significantly correlated with apolar desolvation (R = 0.819). Compound (1) (3-hydroxy-1,4-dioxo-N-phenyl-naphthalene-2-carboxamide) was the most active compound and dose-dependently down-regulated protein expression of β-catenin, c-MYC, Pgp and Frizzled 7. By molecular docking, we predicted that compound (1) bound to the palmitoyl-binding groove of the cysteine-rich domain of Frizzled-7 and Frizzled-8. Compound (1) neither stimulated ATPase activity of Pgp nor reactive oxygen species generation, both of which have been previously described as possible mechanisms of collateral sensitivity. Instead, we found that Wnt/β-catenin signaling was selectively inhibited in CEM/ADR5000 cells, but not in CCRF-CEM cells. In conclusion, we found for the first time that the inhibition of Wnt/β-catenin signaling may represent a novel molecular mechanism of collateral sensitivity in MDR cells. Wnt/β-catenin signaling, therefore, represents a potential therapeutic target for the selective killing of Pgp-mediated MDR.

Topics: Antineoplastic Agents; beta Catenin; Cell Line, Tumor; Dose-Response Relationship, Drug; Drug Resistance, Neoplasm; Humans; Molecular Structure; Naphthoquinones; Precursor Cell Lymphoblastic Leukemia-Lymphoma; Reactive Oxygen Species; Signal Transduction; Wnt Proteins

The development of an optimal microemulsion of lawsone for transdermal delivery was the core objective of the study. Effects of formulation variable including oils, surfactants and co-surfactants on the per- cutaneous delivery of lawsone microemulsion have also been inspected. Pseudotemary phase diagrams with oil, cosurfactant-surfactant mixtures (Smix) were constructed to recognize the microemulsion areas. Microemulsion prepared was of 5%. The in vitro transdermal penetration of microemulsion of lawsone was determined by Franz diffusion cell. These profiles indicated that the absorption and rate of penetration of lawsone microemul- sion was far better than the saturated solution of lawsone. The formulation was characterized for pH, conduc- tivity, viscosity and passed stability tests. A non-irritant formulation to skin was prepared in this way. The out- comes specify that the transdermal drug delivery ability and phase behavior of microemulsion is affected by the type of cosurfactant and surfactant.

Topics: Administration, Cutaneous; Adult; Drug Carriers; Drug Compounding; Drug Liberation; Drug Stability; Electric Conductivity; Emulsions; Excipients; Female; Humans; Hydrogen-Ion Concentration; Lawsonia Plant; Male; Naphthoquinones; Permeability; Phytotherapy; Plant Extracts; Plants, Medicinal; Skin; Skin Absorption; Solubility; Surface-Active Agents; Viscosity; Young Adult

Henna has a very low allergic potential, and severe allergenic contact dermatitis is mainly caused by p-phenylenediamine (PPD), which is added to temporary black 'henna tattoos', and potentially also by some heavy metals.. To determine the presence of, and quantify, Lawsone, PPD and heavy metal contaminants (cobalt, nickel, lead, and chromium) in commercial temporary black henna tattoo mixtures (n = 25) sold in Turkey.. Lawsone and PPD concentrations were analysed with high-performance liquid chromatography, and heavy metal quantification was performed with inductively coupled plasma mass spectrometry.. PPD was found in all 25 black henna tattoo samples purchased from tattoo shops; levels varied between 3.37% and 51.6%. Lawsone was detected (0.002-88.2%) in 21 of the 25 temporary black henna tattoo samples analysed. Heavy metal contaminant levels were 0.44-3.11 ppm for Co, 1.13-2.20 ppm for Ni, 1.59-17.7 ppm for Pb, and 35.0-76.9 ppm for Cr.. Our results suggest that commercial temporary black henna mixtures containing PPD levels up to 51.6% pose a risk of contact sensitization and severe allergic contact dermatitis among users. It is important to identify both the additives and metallic contaminants of black henna tattoo products; the significance of metal contaminants has still to be assessed.

Topics: Chromatography, High Pressure Liquid; Chromium; Cobalt; Coloring Agents; Cosmetics; Dermatitis, Allergic Contact; Humans; Lead; Metals, Heavy; Naphthoquinones; Nickel; Phenylenediamines; Tattooing; Turkey

Substituted lawsone Mannich bases 2a-e, 3a-e and 4a-e were prepared and tested for their biological activities. The new fatty alkyl substituted compounds 2a-c exhibited strong and selective growth inhibitory activities in the low one-digit micromolar and sub-micromolar range against a panel of human cancer cell lines associated with ROS formation. In addition, compounds 2a-c revealed sub-micromolar anti-trypanosomal activities against parasitic Trypanosoma brucei brucei cells via deformation of the microtubule cytoskeleton. The N-hexadecyl compound 2c was also highly active against locally isolated Entamoeba histolytica parasite samples exceeding the activity of metronidazole.

Topics: Antineoplastic Agents; Cell Line, Tumor; Cytoskeleton; Drug Design; Entamoeba histolytica; Humans; Inhibitory Concentration 50; Mannich Bases; Naphthoquinones; Structure-Activity Relationship; Trypanocidal Agents; Trypanosoma brucei brucei

Para-phenylenediamine is widely used as a chemical in hair dyes and in combination with henna. This dye is used to paint the body for decorative reasons, to speed the processing time of henna and to intensify the results. Para-phenylenediamine is widely used in the Middle East, North Africa and India. Several reports have been published of the fatal ingestion of hair dye containing para-phenylenediamine. Here, we describe the case of a 14-year-old girl who ingested the compound but whose prompt treatment prevented her death. Ingestion of para-phenylenediamine produces a typical triad of angioneurotic oedema, rhabdomyolysis and acute tubular necrosis. Awareness of signs of these associated conditions in our patient, together with a comprehensive history, facilitated appropriate treatment to be instituted. We document the steps we took to enable her complete physical recovery.

Topics: Acute Kidney Injury; Adolescent; Angioedema; Chlorpheniramine; Female; Fluid Therapy; Furosemide; Hair Dyes; Humans; Hydrocortisone; Naphthoquinones; Phenylenediamines; Respiration, Artificial; Rhabdomyolysis; Suicide, Attempted; Tracheostomy

Topics: Antineoplastic Agents; Cell Proliferation; DNA Topoisomerases, Type II; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Molecular Structure; Naphthoquinones; Structure-Activity Relationship; Topoisomerase II Inhibitors; Tumor Cells, Cultured

Lawsone (LS) a colored napthoquinone compound obtained from the plant Lawsonia inermis L. (Lythraceae) is known for its usefulness of being a precursor for synthesis of some anticancer compounds. Literatures support potent anticancer activity of napthoquinone derivatives in human colon cancer, present study evaluates the effect and mechanism of LS on chemical induced colon cancerous rats and human colon cancer DLD-1 cells, the study was supported by endoscopy, histological and immunohistochemistry analysis. KAD rats were subjected to colon cancer mediated by Azoxymethane (AOM) injections followed Dextran sodium sulfate (DSS) orally in drinking water. After endoscopic confirmation the rats were given LS (200mg/ml) orally for 8 weeks. Presence of aberrant foci, types of tumors and the proliferative effect on tumor lesions was studied by macroscopic, histological and immunohistochemical analysis. To establish the mechanism, human colon DLD-1 cancer cells were exposed to LS and its effect on proliferation were studied. LS reduced aberrant crypt without affecting tumor pathology. Histological study of colon suggested decrease in numbers of adenomas and lesions. Immunohistochemistry confirmed the antiproliferative activity in adenocarcinomas without affecting the cells of normal colon mucosa. Results on human DLD-1 cells showed LS delayed progression of cell cycle by decreasing expression of cyclin B1 as well as cdk1 by inactivating NF-κB without inducing apoptosis. The study concluded role of LS in suppressing cell proliferation of colon tumors. The suppressive activity on DLD-1 cells was not by apoptosis but by decreased NF-κB activity resulting in suppression of expression levels of cyclin B1 and cdk1.

Topics: Adenocarcinoma; Animals; Antineoplastic Agents, Phytogenic; Azo Compounds; Carcinogens; Cell Cycle; Cell Line, Tumor; Cell Proliferation; Colonic Neoplasms; Dextran Sulfate; Endoscopy; Humans; Intestinal Mucosa; Naphthoquinones; NF-kappa B; Rats; Signal Transduction

Topics: Child; Drug Hypersensitivity; Glucosephosphate Dehydrogenase Deficiency; Hemolysis; Humans; Male; Naphthoquinones; Treatment Outcome

Suicide messages on the skin are rare. Until now, in all reported cases, the writing tool used by the victims has been a pen. We report a suicide case by hanging in which the victim had written a note on her palm in mehndi, or henna, at a wedding ceremony three days before the fatal act. The note was discovered at autopsy.

Topics: Adult; Female; Forensic Medicine; Humans; Naphthoquinones; Skin; Suicide; Writing

A 64-year-old female presented with facial hyperpigmentation. She had dyed her hair monthly with pure henna powder for the past seven months. After patch tests, the patient was diagnosed as post-inflammatory hyperpigmentastion due to allergic contact dermatitis to pure henna that has rarely been reported. The patient underwent Q-switched Nd:YAG laser treatment and was treated with oral tranexamic acid for 10 weeks. The hyperpigmentation on her forehead demonstrated substantial improvement.

Topics: Antifibrinolytic Agents; Coloring Agents; Combined Modality Therapy; Cosmetic Techniques; Dermatitis, Allergic Contact; Female; Hair Dyes; Humans; Hyperpigmentation; Lasers, Solid-State; Low-Level Light Therapy; Middle Aged; Naphthoquinones; Tranexamic Acid

This research focuses on the microbial recovery of elemental tellurium (Te(0)) from aqueous streams containing soluble tellurium oxyanions, tellurate (Te(VI)), and tellurite (Te(IV)). An anaerobic mixed microbial culture occurring in methanogenic granular sludge was able to biocatalyze the reduction of both Te oxyanions to produce Te(0) nanoparticles (NPs) in sulfur-free medium. Te(IV) reduction was seven times faster than that of Te(VI), such that Te(IV) did not accumulate to a great extent during Te(VI) reduction. Endogenous substrates in the granular sludge provided the electron equivalents required to reduce Te oxyanions; however, the reduction rates were modestly increased with an exogenous electron donor such as H2. The effect of four redox mediators (anthraquinone-2,6-disulfonate, hydroxocobalamin, riboflavin, and lawsone) was also tested. Riboflavin increased the rate of Te(IV) reduction eleven-fold and also enhanced the fraction Te recovered as extracellular Te(0) NPs from 21% to 64%. Lawsone increased the rate of Te(VI) reduction five-fold, and the fraction of Te recovered as extracellular material increased from 49% to 83%. The redox mediators and electron donors also impacted the morphologies and localization of Te(0) NPs, suggesting that NP production can be tailored for a particular application.

Topics: Anthraquinones; Biocatalysis; Hydroxocobalamin; Metal Nanoparticles; Methane; Microbial Consortia; Naphthoquinones; Oxidation-Reduction; Riboflavin; Sewage; Tellurium

Topics: Cell Line; Dose-Response Relationship, Drug; Enzyme Activation; Fibroblasts; Humans; Keratinocytes; Naphthoquinones; NIMA-Interacting Peptidylprolyl Isomerase; Resveratrol; Signal Transduction; Sirtuin 1; Skin; Stilbenes; Ultraviolet Rays; Up-Regulation

Topics: Angioedema; Female; Hair Dyes; Humans; Hypersensitivity; Naphthoquinones; Young Adult

A transition-metal-free asymmetric supercapacitor (ASC) is successfully fabricated based on an earth-abundant biomass derived redox-active biomolecule, named lawsone. Such an ASC exhibits comparable or even higher energy densities than most of the recently reported transition-metal-based ASCs, and this green ASC generation from renewable resources is promising for addressing current issues of electronic hazard processing, high cost, and unsustainability.

Topics: Electric Capacitance; Electrochemistry; Naphthoquinones; Polymers; Positron-Emission Tomography; Pyrroles; Transition Elements

The toxic oxyanion tellurite (TeO3(2-)) is acquired by cells of Rhodobacter capsulatus grown anaerobically in the light, via acetate permease ActP2 and then reduced to Te(0) in the cytoplasm as needle-like black precipitates. Interestingly, photosynthetic cultures of R. capsulatus can also generate Te(0) nanoprecipitates (TeNPs) outside the cells upon addition of the redox mediator lawsone (2-hydroxy-1,4-naphtoquinone). TeNPs generation kinetics were monitored to define the optimal conditions to produce TeNPs as a function of various carbon sources and lawsone concentration. We report that growing cultures over a 10 days period with daily additions of 1mM tellurite led to the accumulation in the growth medium of TeNPs with dimensions from 200 up to 600-700 nm in length as determined by atomic force microscopy (AFM). This result suggests that nucleation of TeNPs takes place over the entire cell growth period although the addition of new tellurium Te(0) to pre-formed TeNPs is the main strategy used by R. capsulatus to generate TeNPs outside the cells. Finally, X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared (FT-IR) analysis of TeNPs indicate they are coated with an organic material which keeps the particles in solution in aqueous solvents.

Topics: Fructose; Lactic Acid; Malates; Nanoparticles; Naphthoquinones; Photosynthesis; Pyruvic Acid; Rhodobacter capsulatus; Tellurium

Topics: Art; Asia; Ceremonial Behavior; Drug Eruptions; Female; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Allergens; Child; Coloring Agents; Cosmetics; Dermatitis, Contact; Exanthema; Humans; Hypersensitivity, Delayed; Male; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Adult; Ceremonial Behavior; Female; Humans; Hypersensitivity; Naphthoquinones; Paintings

The concentrations of lead, nickel and cadmium in various hennas and synthetic hair dyes were determined by high-resolution continuum source graphite furnace atomic absorption spectrometry (HR-CS GFAAS). For this purpose, 1 g of sample was digested using 4 mL of hydrogen peroxide (30%) and 8 mL of nitric acid (65%). The digests were diluted to 15 mL and the analytes were determined by HR-CS GFAAS. All determinations of Pb and Cd were performed using NH4H2PO4 as a modifier. The analytes in hair certified reference materials (CRMs) were found within the uncertainty limits of the certified values. In addition, the analyte concentrations added to hair dye were recovered between 95 and 110%. The limits of detection of the method were 48.90, 3.90 and 12.15 ng g(-1) for Pb, Cd and Ni, respectively and the characteristic concentrations were 8.70, 1.42 and 6.30 ng g(-1), respectively. Finally, the concentrations of the three analytes in various synthetic hair dyes with different brands, shades and formulae as well as in two henna varieties were determined using aqueous standards for calibration. The concentrations of Pb, Cd and Ni in hair dyes were in the ranges of LOD-0.56 μg g(-1), LOD-0.011 ng g(-1) and 0.030-0.37 μg g(-1), respectively, whereas those in the two hennas were 0.60-0.93 μg g(-1), 0.033-0.065 ng g(-1) and 0.49-1.06 μg g(-1), respectively.

Topics: Cadmium; Calibration; Consumer Product Safety; Hair Dyes; Humans; Lead; Limit of Detection; Naphthoquinones; Nickel; Reference Standards; Risk Assessment; Spectrophotometry, Atomic; Turkey

Denture stomatitis is a very common disease affecting the oral mucosa of denture wearers. The aim of this study was to measure the antifungal effect of henna against Candida albicans adhered to acrylic resin as a possible method for prevention of denture stomatitis. One-hundred-eighty acrylic plates were prepared of heat-cured acrylic denture resin. The specimens were divided into six groups of 30 samples each. The first group was only polymer and monomer following the conventional manufacturer instruction for processing complete dentures. The other five groups were processed by adding different concentration of Yamani henna powder (Harazi) to the polymer in a concentration of henna: polymer 1%, 2.5%, 5%, 7.5% and 10%, respectively. Samples were incubated in artificial saliva rich with Candida albicans at 37 °C, and the effect of henna on Candida albicans was evaluated in two different methods: semi-quantitative slide count and a culture-based quantitative assay (quantitative). Variation in the number of live Candida was observed with the increase in the concentration of Yamani henna powder. It was observed that the variation in live Candida, between control group and group B (concentration of Yamani henna powder was 1%), was statistically significant with a p-value of 0.0001. Similarly, variations in live Candida were significant, when the concentration of powder was 7.5% or 10% in contrast with control group and p-values were 0.0001 and 0.001 respectively. Adding henna to acrylic resin denture could be effective in controlling Candida albicans proliferation on the denture surface; however, its effects on the physical properties of acrylic resin denture need further studies.

Topics: Acrylic Resins; Antifungal Agents; Candida albicans; Candidiasis, Oral; Colony Count, Microbial; Denture Bases; Humans; Naphthoquinones; Stomatitis, Denture

Henna (Lawsonia inermis) is applied to stain keratin, present in hair, skin and fingernails, a red-orange or rust colour. Producers of temporary tattoos mix the aromatic amine compound, para-phenylenediamine (PPD) into natural henna to create 'black henna' that rapidly stains the skin black. However, PPD may cause severe delayed hypersensitivity reactions following skin contact. This study proposes a rapid direct-analysis method to detect and identify PPD using an atmospheric solids analysis probe (ASAP) coupled to a Q-ToF mass spectrometer (MS). Since laborious, multistep methods of analysis to determine PPD are undesirable, due to the instability of the compound in solution, a screening method involving no sample preparation steps was developed. Experiments were carried out to optimise the corona current, sample cone voltage, source temperature, and desolvation gas temperature to determine ideal ASAP-Q-ToF-MS analysing conditions. Eleven of the 109 henna samples, originating from various countries, tested positive for PPD when henna products were screened using ASAP-MS, without any form of sample preparation other than grinding. Ultra-performance liquid chromatography electrospray ionisation-mass spectrometry (UPLC-Q-ToF-MS) was subsequently used to confirm the results from ASAP and to determine the concentrations of PPD in henna products. The allergen was detected in the same eleven samples, with concentrations ranging from 0.05-4.21% (w/w). It can be concluded that the sensitivity of the ASAP-MS technique is sufficient (limit of detection=0.025% w/w) to allow screening of henna samples for the presence of PPD. This relatively new technique can be applied to commercial products without extraction, sample treatment or chromatographic separation.

Topics: Allergens; Chromatography, High Pressure Liquid; Coloring Agents; Irritants; Mass Spectrometry; Naphthoquinones; Phenylenediamines; Skin

Topics: Child; Diagnosis, Differential; Exanthema; Humans; Male; Naphthoquinones; Tattooing

Topics: Adolescent; Coloring Agents; Dermatitis, Allergic Contact; Facial Dermatoses; Female; Hand Dermatoses; Humans; Naphthoquinones; Neck

Topics: Coloring Agents; Diagnosis, Differential; Exanthema; Humans; Hypersensitivity, Delayed; Male; Naphthoquinones; Pain

Temporary henna tattoos have become increasingly widespread among children and young people, especially in holiday spots in recent years. Although reactions to henna tattoo are becoming progressively more common, only few cases of a henna pseudo-tattoo resulting in temporary hypertrichosis have been reported so far. Here, we have reported a 5-year-old girl who developed allergic contact dermatitis and localized hypertrichosis on her right arm after application of temporary henna tattoo during summer holiday.

Topics: Child, Preschool; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Hypertrichosis; Naphthoquinones; Tattooing; Time Factors

It is widely accepted that the addition of redox mediators increases the decolorization rates of azo dyes by bacterial strains under anaerobic conditions. However, little information exists about whether quinoid redox mediators can enhance the performance of aerobic azo dye decolorization. In the present study, quinone-mediated decolorization of different azo dyes by whole cells and cell extracts from the Escherichia coli strain CD-2 under aerobic conditions were investigated. The results demonstrated that reduction rates of different azo dyes were greatly increased when quinone compounds were used as redox mediators. Compared with menadione, 2-hydroxy-1,4-naphthoquinone (lawsone) was more effective at aiding azo dye degradation and the optimum concentration for lawsone is 0.1 mM. Strain CD-2 and the anthraquinone were co-immobilized by entrapment in different polymeric matrices. The co-immobilized beads exhibited good catalytic activity for azo dye degradation and kept stable during successive repeated experiments. The mechanism of the quinone-mediated reduction showed that although whole cells incubated with quinones could significantly increase the rate of decolorization of azo dyes, the quinone compounds did not directly promote azoreductase activity. According to the survey, this is the first report to confirm that the addition of quinoid redox mediators to bacteria increased decolorization under aerobic conditions.

Topics: Aerobiosis; Azo Compounds; Escherichia coli; Molecular Structure; Naphthoquinones; Oxidation-Reduction; Quinones; Sewage; Vitamin K 3; Waste Disposal, Fluid; Water Pollutants, Chemical

To evaluate the effects of henna on the results of pulse oximetry in healthy women.. 100 young women (20-60 years of age) were recruited. The Iranian original red henna was used to colour the index finger of THE non-dominant hand; the middle finger of the same hand was the control. Blood oxygen saturation was simultaneously measured by two calibrated pulse oximeters.. Henna did not affect pulse oximetry measurement of oxygen saturation. There was no statistically significant difference between the control and the henna dyed fingers.. Henna is not likely to change the accuracy of oxygen saturation measured by pulse oximeter.. 20120906159N20.

Topics: Adult; Coloring Agents; Cosmetics; Female; Humans; Middle Aged; Naphthoquinones; Oximetry; Oxygen; Young Adult

Hair coloring products are one of the most important cosmetics for modern people; there are three major types of hair dyes, including the temporary, semi-permanent and permanent hair dyes. The selected hair dyes (such as ammonium persulfate, sodium persulfate, resorcinol and lawsone) are the important components for hair coloring products. Therefore, we analyzed the effects of these compounds on melanogenesis in B16-F10 melanoma cells. The results proved that hair dyes resorcinol and lawsone can reduce the production of melanin. The results also confirmed that resorcinol and lawsone inhibit mushroom and cellular tyrosinase activities in vitro. Resorcinol and lawsone can also downregulate the protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16-F10 cells. Thus, we suggest that frequent use of hair dyes may have the risk of reducing natural melanin production in hair follicles. Moreover, resorcinol and lawsone may also be used as hypopigmenting agents to food, agricultural and cosmetic industry in the future.

Topics: Ammonium Sulfate; Animals; Cell Line, Tumor; Cell Survival; Coloring Agents; Down-Regulation; Melanins; Melanoma, Experimental; Mice; Microphthalmia-Associated Transcription Factor; Monophenol Monooxygenase; Naphthoquinones; Resorcinols; Sodium Compounds; Sulfates

Human adipose-derived stem cells (hASCs) are an attractive cell source for therapeutic applicability in diverse fields for the repair and regeneration of damaged or malfunctioning tissues and organs. There is a growing number of cell therapies using stem cells due to their characteristics of modulation of immune system and reduction of acute rejection. So a challenge in stem cells therapy is the delivery of cells to the organ of interest, a specific site. The aim of this paper was to investigate the effects of a supramolecular assembly composed of single-walled carbon nanotubes (SWCNT), molecular magnets (lawsone-Co-phenanthroline), and a synthetic peptide (FWYANHYWFHNAFWYANHYWFHNA) in the hASCs cultures. The hASCs were isolated, characterized, expanded, and cultured with the SWCNT supramolecular assembly (SWCNT-MA). The assembly developed did not impair the cell characteristics, viability, or proliferation. During growth, the cells were strongly attached to the assembly and they could be dragged by an applied magnetic field of less than 0.3 T. These assemblies were narrower than their related allotropic forms, that is, multiwalled carbon nanotubes, and they could therefore be used to guide cells through thin blood capillaries within the human body. This strategy seems to be useful as noninvasive and nontoxic stem cells delivery/guidance and tracking during cell therapy.

Topics: Adipose Tissue; Cell Separation; Cell Survival; Cells, Cultured; Humans; Magnets; Mesenchymal Stem Cell Transplantation; Mesenchymal Stem Cells; Nanotubes, Carbon; Naphthoquinones; Peptides; Phenanthrolines

This study focuses on two main aspects: developing a novel cost-effective electrode material and power production from domestic wastewater using three different mediators. Methylene blue (MB), neutral red (NR) and 2-hydroxy-1,4-naphthoquinone (HNQ) were selected as electrode mediators with different concentrations. A tin-coated copper mesh electrode was tested as anode electrode. Maximum power density of the microbial fuel cell (MFC) with 300 μM MB was 636 mW/m². Optimal mediator concentrations with respect to the achieved maximum power output for MB, NR and HNQ were 300 μM, 200 μM and 50 μM, respectively. The results demonstrate that tin-coated copper mesh showed a higher biocompatibility and electrical conductivity.

Topics: Bioelectric Energy Sources; Electrodes; Methylene Blue; Naphthoquinones

Unprotected sunlight exposure is a risk factor for a variety of cutaneous cancers. Topically used dihydroxyacetone (DHA) creates, via Maillard reaction, chemically fixed keratin sunscreen in the stratum corneum with significant protection against UVA/Soret radiation. When used in conjunction with naphthoquinones a naphthoquinone-modified DHA Maillard reaction is produced that provides protection across the UVB/UVA/Soret spectra lasting up to 1 week, resisting sweating and contact removal. The aim of this study was to examine a simplified version of this formulation for effect on UV transmission and to determine if penetration levels merit toxicity concerns. Permeability was demonstrated for freshly prepared DHA (30 mg/mL) and lawsone (0.035 mg/mL) alone and in combination using a side-by-side diffusion apparatus at 37°C over 48 h across shed snake skin and dermatomed pig skin. These samples were then examined for effectiveness and safety. Concentrations were determined by HPLC and UPLC monitored from 250-500 nm. Lawsone flux significantly decreased across pig skin (20.8 (± 4.8) and 0.09 (± 0.1) mg/cm(2) h without and with DHA, respectively) but did not change across shed snake skin in the presence of DHA. Significantly reduced lawsone concentration was noted in donor chambers of combined solutions. Damage was not observed in any skins. Darker coloration with greater UV absorbance was observed in skins exposed to the combined solution versus individual solutions. This study confirmed that combined DHA and lawsone provided effective blocking of ultraviolet light through products bound in keratinized tissue. DHA permeation levels in pig skin suggest further in vitro and in vivo study is required to determine the safety of this system.

Topics: Animals; Boidae; Diffusion; Dihydroxyacetone; Naphthoquinones; Skin; Sunscreening Agents; Swine; Ultraviolet Rays

The use of natural, nontoxic, convenient and eco-friendly dyes for histopathological diagnosis avoids some of the synthetic dyes' hazards. I used an aqueous extract of henna at a concentration of 20 g/ml and acidified with acetic acid to stain mycetoma grains. Henna stained mycetoma grains orange-red to brown. The engulfed mycetoma grains within inflammatory cells stained well with henna extract compared to hematoxylin and eosin (H & E) and hexamine silver.

Topics: Coloring Agents; Humans; Mycetoma; Naphthoquinones; Staining and Labeling

Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.

Topics: Alkenes; Antineoplastic Agents; Cell Proliferation; Crystallography, X-Ray; Dimerization; Glutathione; HL-60 Cells; Humans; Molecular Conformation; Naphthoquinones; Structure-Activity Relationship

The inhibitory effect of azo dyes and quinoid compounds on an anaerobic consortium was evaluated during a decolorization process and biogas production. In addition, the impact of quinoid compounds such as lawsone (LAW) and anthraquinone-2,6-disulfonate (AQDS) on the rate of decolorization of Direct Blue 71 (DB71) was assessed. The anaerobic consortium was not completely inhibited under all tested dye concentrations (0.1-2 mmol l(-1)), evidenced by an active decolorization process and biogas production. The presence of quinoid compounds at different concentrations (4, 8, and 12 mmol l(-1)) also inhibited biogas production compared to the control incubated without the quinoid compounds. In summary, the anaerobic consortium was affected to a greater extent by increasing the quantity of azo dyes or quinoid compounds. Nevertheless, at a lower concentration (1 mmol l(-1)) of quinoid compounds, the anaerobic consortium effectively decolorized 2 mmol l(-1) of DB71, increasing up to 5.2- and 20.4-fold the rate of decolorization with AQDS and LAW, respectively, compared to the control lacking quinoid compounds.

Topics: Anaerobiosis; Anthraquinones; Azo Compounds; Biofuels; Catalysis; Coloring Agents; Microbial Consortia; Naphthoquinones; Oxidation-Reduction

2-Acetyl-1-hydroxynaphthalene was converted into 1,4-dimethoxy-2-naphthoxyacetic acid in seven steps (methylation, Bayer-Villiger oxidation, hydrolysis, bromination, methylation, alkylation and hydrolysis). 2-Hydroxy-1,4-naphthoquinone on acetylation, aromatization, methylation and hydrolysis, respectively, also yielded the title compound.

Topics: Naphthaleneacetic Acids; Naphthoquinones

Topics: Administration, Topical; Adult; Coloring Agents; Dermatitis, Contact; Diagnosis, Differential; Glucocorticoids; Humans; Male; Naphthoquinones; Phenylenediamines; Skin Cream; Tattooing; Treatment Outcome

Naturally occurring 2-hydroxy-1,4-naphthoquinones are well known to form readily stable complexes with transition metals. In this short communication we describe for the first time the synthesis and preliminary data about structural characterization of complexes between two naturally widespread 2-hydroxy-1,4-naphthoquinones, namely lapachol (1) and lawsone (2), with selected lanthanides like lanthanum, gadolinium, and ytterbium. When tested as cytotoxic compounds, such complexes exhibited an activity that was either higher or equal to that of the parent naphthoquinone.

Topics: Lanthanoid Series Elements; Naphthoquinones

Topics: Administration, Cutaneous; Adult; Coloring Agents; Dermatitis, Allergic Contact; Diagnosis, Differential; Glucocorticoids; Humans; Male; Naphthoquinones; Tattooing; Torso; Treatment Outcome

For the development of potent novel antileishmanial agents, 3,3'-(arylmethylene)bis(2-hydroxynaphthalene-1,4 dione) derivatives were synthesized from lawsone and evaluated for cytotoxicity on Leishmania donovani promastigotes as well as on leishmanial DNA topoisomerase-I. Enzyme inhibition studies were conducted with simultaneous and preincubation conditions. Total inhibition is compared to camptothecin (CPT), which was taken as positive control on both the systems of enzyme inhibition. The range of activity varied from 37.5 to 70 µM in simultaneous assay and 13-16 µM in preincubation assay. Furthermore, when evaluated against L. donovani promastigotes, the synthesized compounds exhibited the activity ranging from 2 to 14 µM. The results revealed that all the compounds exhibit promising antileishmanial activity.

Topics: Antiprotozoal Agents; DNA Topoisomerases, Type I; DNA, Superhelical; Electrophoresis, Agar Gel; Inhibitory Concentration 50; Leishmania donovani; Molecular Structure; Naphthoquinones; Parasitic Sensitivity Tests; Plasmids; Topoisomerase I Inhibitors

Hand-foot syndrome (HFS) is the most frequently reported side effect of oral capecitabine therapy. In addition to treatment interruption and dose reduction, supportive treatments can help alleviate symptoms. Although its efficacy has not been proven in clinical studies, certain authors report on the use of prophylactic or therapeutic pyridoxine supplementation for the prevention of minimization to be useful in preventing worsening of HFS but are no substitute for dose modifications.. We report a case of an interesting observation in a patient with pancreatic cancer receiving capecitabine whose HFS was improved with the use of "henna".. Henna has been used for histories as a medicine, preservative, and cosmetic. Our case underlines the basis to further evaluate the anti-inflammatory, antipyretic, and analgesic effects of henna. We encourage other investigators to publish any similar cases or any other herbal or non-drug therapies. HFS is a common side effect of many drugs, including capecitabine, sorafinib and regorafenib. HFS is bothersome for patients even in low grades and impacts quality of life of patients. HFS cannot be prevented and currently the treatments aimed at controlling syndrome are not very effective. Exploring other potential treatment or management options such as henna is of high value.

Topics: Adenocarcinoma; Antimetabolites, Antineoplastic; Capecitabine; Deoxycytidine; Female; Fluorouracil; Hand-Foot Syndrome; Humans; Middle Aged; Naphthoquinones; Pancreatic Neoplasms

Tattooing with henna is a routine practice in the Arab world. To the best of our knowledge, no previous studies have evaluated the adverse histological effects following henna tattooing on the ultrastructure of the skin. The objectives of this study were to diagnose the cytopathological alterations induced by commercial henna and to investigate the adverse role of henna when combined with sun ray on the skin. The skin of albino rats was tattooed with natural and black henna for three months, skin samples were examined by transmission electron microscope. In addition, the concentration of lead in henna samples was estimated by using atomic absorption spectrophotometry. The results expanded the understanding of the pathogenesis of henna-induced phytophotodermatitis. We hypothesized that henna-associated additives penetrated the epidermal barrier to gain access to the vascular dermis where the harmful ingredients became concentrated, leading to skin pathology through a dual mechanism. First, these ingredients became re-transported into the epidermis through vesicular trafficking leading to dermo-epidermal blistering and cytoplasmic vacuolization of the stratum basal cells. Following this, cytoplasmic vacuoles poured their content into the nuclei through continuities with the perinuclear cisterna, possibly leading to genetic mutation. The progression of keratinocytes into the next layers became associated with nuclear and cytoplasmic signs of apoptosis with subsequent phagocytosis in other epidermal cells, most probably keratinocytes. The second mechanism of injury was mediated through accumulation of inflammatory cells around capillaries in the dermis with the release of angiogenic and mitogenic mediators resulting in vasculopathy.

Topics: Animals; Coloring Agents; Keratinocytes; Microscopy, Electron, Transmission; Naphthoquinones; Rats; Skin; Spectrophotometry, Atomic; Sunlight; Tattooing

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Edema; Humans; Male; Naphthoquinones; Tattooing

The effect of naturally occurring quinones including lawsone (LQ), ubiquinone (UQ), juglone (JQ), and 1,4-naphthoquinone (NQ) on the biotransformation of carbon tetrachloride (CT) in the presence of Geobacter sulfurreducens and ferrihydrite was investigated. AQDS was used as the model compound for comparison. The reductive dissolution of ferrihydrite by G. sulfurreducens was enhanced by AQDS, NQ, and LQ. However, addition of UQ and JQ had little enhancement effect on Fe(II) production. The bioreduction efficiency and rate of ferrihydrite was highly dependent on the natural property and concentration of quinone compounds and the addition of low concentrations of LQ and NQ significantly accelerated the biotransformation rate of CT. The pseudo-first-order rate constants for CT dechlorination (kobsCT) in AQDS-, LQ- and NQ-amended batches were 5.4-5.8, 4.6-7.4 and 2.4-5.8 times, respectively, higher than those in the absence of quinone. A good relationship between kobsCT for CT dechlorination and bioreduction ratio of ferrihydrite was observed, indicating the important role of biogenic Fe(II) in dechlorination of CT under iron-reducing conditions. Spectroscopic analysis showed that AQDS and NQ could be reduced to semiquinones and hydroquinones, while only hydroquinones were generated in LQ-amended batches.

Topics: Biodegradation, Environmental; Carbon Tetrachloride; Ferric Compounds; Ferrous Compounds; Geobacter; Hazardous Substances; Naphthoquinones; Oxidation-Reduction; Quinones; Solvents

The facultative photosynthetic bacterium Rhodobacter capsulatus is characterized in its interaction with the toxic oxyanions tellurite (Te(IV)) and selenite (Se(IV)) by a highly variable level of resistance that is dependent on the growth mode making this bacterium an ideal organism for the study of the microbial interaction with chalcogens. As we have reported in the past, while the oxyanion tellurite is taken up by R. capsulatus cells via acetate permease and it is reduced to Te(0) in the cytoplasm in the form of splinter-like black intracellular deposits no clear mechanism was described for Se(0) precipitation. Here, we present the first report on the biotransformation of tellurium and selenium oxyanions into extracellular Te(0) and Se(0)nanoprecipitates (NPs) by anaerobic photosynthetically growing cultures of R. capsulatus as a function of exogenously added redox-mediator lawsone, i.e. 2-hydroxy-1,4-naphthoquinone. The NPs formation was dependent on the carbon source used for the bacterial growth and the rate of chalcogen reduction was constant at different lawsone concentrations, in line with a catalytic role for the redox mediator. X-ray diffraction (XRD) analysis demonstrated the Te(0) and Se(0) nature of the nanoparticles.

Topics: Anaerobiosis; Anions; Bacterial Proteins; Chalcogens; Microscopy, Electron, Transmission; Nanoparticles; Naphthoquinones; Oxidation-Reduction; Photosynthesis; Rhodobacter capsulatus; Selenium Compounds; Tellurium; X-Ray Diffraction

The hydroxyl radical ((●)OH)-induced oxidation reactions of isomeric hydroxy naphthoquinones (generally having anti-tumor activities) namely, lawsone and juglone, were carried out and the reaction mechanism was elucidated.. The degradation products from the reaction of (●)OH (produced by H(2)O(2)/UV) with lawsone and juglone were analyzed using a liquid chromatography quadrupole-time-of-flight mass spectrometer (LC-Q-TOF-MS). The transient intermediate studies were investigated using picosecond pulse radiolysis technique.. Mono hydroxylated and dihydroxylated adducts of both lawsone and juglone were identified from the product analysis. The isomeric mono-hydroxylated adducts of lawsone were confirmed using survival yield (SY) analysis. The hydroxylated adducts of lawsone also underwent dimerization reaction. The transient spectral analysis using pulse radiolysis studies revealed the formation of hydroxycyclohexadienyl type radical of both lawsone and juglone as the initially formed intermediate.. The (●)OH-induced reactions of both lawsone and juglone result in the mono and di-hydoxylated derivatives. The demonstration of the various isomeric products using mass spectrometry is a clear proof of the addition probability of (●)OH at different positions of lawsone and juglone, which is generally a difficult task using other analytical techniques.

Topics: Chromatography, Liquid; Hydroxyl Radical; Models, Chemical; Molecular Structure; Naphthoquinones; Oxidation-Reduction; Pulse Radiolysis; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry; Ultraviolet Rays

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Drug Eruptions; Erythema Multiforme; Female; Humans; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

Allergic contact dermatitis related to para-phenylendiamine (PPD) from temporary black henna tattoos and hair dyes has become an epidemic in recent years. Several cases of adverse skin reactions to PPD have been reported in the literature. Herein, we present a case of angioedema-like allergic contact dermatitis related to hair coloring with henna.

Topics: Adult; Angioedema; Dermatitis, Allergic Contact; Face; Hair Dyes; Humans; Male; Naphthoquinones; Scalp Dermatoses; Tongue

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Diagnosis, Differential; Humans; Impetigo; Male; Naphthoquinones; Staphylococcus aureus; Tattooing

The powder of henna is extensively used as decorative skin paint for nail coloring and as a popular hair dye in Asian countries. Its human health risk is extensive, and it is frequently released as waste into the aquatic environment raising the concerns. Zebrafish (Danio rerio) embryos were employed to study the developmental effects of henna. Normal fertilized zebrafish embryos under standard water were selected for the control and test chambers. Three predetermined sublethal concentrations (100, 200, and 275 μM) of henna in 24-well cell culture plates were tested on 1-h postfertilized embryo (pfe) for 96 h. Observation for rates of survival and mortality was recorded; digital camera was used to image morphological anomalies of embryos with a stereomicroscope; and functional abnormalities at 24, 48, 72, and 96 h were performed. The hatching rates of embryos were reduced significantly when treated with 200 and 275 μM or higher concentrations of henna. Slow blood circulation in the whole body was observed with a median effect on hatching exposed to 200 and 275 μM of henna at 48-h pfe. At 72- and 96-h pfe, blood circulation was ceased in the whole body but still had a heartbeat. At 96-h pfe, pericardial sac edema, yolk sac edema, head deformation, spine crooked malformation, and tail malformation (bent tails or hook-like tails) were observed in the surviving larvae at 100 μM. In summary, exposure to henna at 100, 200, and 275 μM causes some altered morphological and physiological abnormalities including increased mortality, hatching delay, slow blood circulation, pericardial sac edema, yolk sac edema, abnormal body axes, twisted notochord, tail deformation, weak heartbeat, and growth retardation and was also detected in some treated embryos and groups having adverse effects on embryonic development of zebrafish provoking potential human developmental risk studies.

Topics: Animals; Embryo, Nonmammalian; Embryonic Development; Hair Dyes; Heart Rate; Naphthoquinones; Zebrafish

A series of lawsone derivatives are synthesized. The structures of the synthesized compounds are analyzed by FT-IR, Mass, Elemental analysis, (1)H, (13)C, HSQC, HMBC and theoretical studies.

Topics: Green Chemistry Technology; Magnetic Resonance Spectroscopy; Molecular Conformation; Naphthoquinones; Spectroscopy, Fourier Transform Infrared

Topics: Acute Kidney Injury; Administration, Cutaneous; Coloring Agents; Female; Hair Dyes; Humans; Middle Aged; Naphthoquinones; Phenylenediamines; Renal Dialysis

Naphthoquinones represent the group of plant secondary metabolites with cytotoxic properties based on their ability to generate reactive oxygen species and interfere with the processes of cell respiration. Due to this fact, the possible cytotoxic mechanisms on cellular and subcellular levels are investigated intensively. There are many targets of cytotoxic action on the cellular level; however, DNA is a critical target of many cytotoxic compounds. Due to the cytotoxic properties of naphthoquinones, it is necessary to study the processes of naphthoquinones, DNA interactions (1,4-naphthoquinone, binapthoquinone, juglone, lawsone, plumbagin), especially by using modern analytical techniques. In our work, the Raman spectroscopy was used to determine the possible binding sites of the naphthoquinones on the DNA and to characterize the bond of naphthoquinone to DNA. Experimental data reveals the relationships between the perturbations of structure-sensitive Raman bands and the types of the naphthoquinones involved. The modification of DNA by the studied naphthoquinones leads to the nonspecific interaction, which causes the transition of B-DNA into A-DNA conformation. The change of the B-conformation of DNA for all measured DNA modified by naphthoquinones except plumbagin is obvious.

Topics: DNA; DNA, B-Form; Naphthoquinones; Plants; Reactive Oxygen Species; Secondary Metabolism; Spectrum Analysis, Raman

Topics: Abdomen; Abdominal Wall; Coloring Agents; Fiducial Markers; Humans; Naphthoquinones; Preoperative Care

Topics: Adult; Female; Humans; Laser Therapy; Lasers, Solid-State; Naphthoquinones; Skin; Tattooing

Although there have been many studies on bacterial removal of soluble azo dyes, much less information is available for biological treatment of water-insoluble azo dyes. The few bacterial species capable of removing Sudan dye generally require a long time to remove low concentrations of insoluble dye particles. The present work examined the efficient removal of Sudan I by Shewanella oneidensis MR-1 in the presence of redox mediator. It was found that the microbially reduced anthraquinone-2,6-disulfonate (AQDS) could abiotically reduce Sudan I, indicating the feasibility of microbially-mediated reduction. The addition of 100 μM AQDS and other different quinone compounds led to 4.3-54.7 % increase in removal efficiencies in 22 h. However, adding 5-hydroxy-1,4-naphthoquinone into the system inhibited Sudan I removal. The presence of 10, 50 and 100 μM AQDS stimulated the removal efficiency in 10 h from 26.4 to 42.8, 54.9 and 64.0 %, respectively. The presence of 300 μM AQDS resulted in an eightfold increase in initial removal rate from 0.19 to 1.52 mg h⁻¹ g⁻¹ cell biomass. A linear relationship was observed between the initial removal rates and AQDS concentrations (0-100 μM). Comparison of Michaelis-Menten kinetic constants revealed the advantage of AQDS-mediated removal over direct reduction. Different species of humic acid could also stimulate the removal of Sudan I. Scanning electronic microscopy analysis confirmed the accelerated removal performance in the presence of AQDS. These results provide a potential method for the efficient removal of insoluble Sudan dye.

Topics: Aerobiosis; Anthraquinones; Coloring Agents; Humic Substances; Microscopy, Electron, Scanning; Naphthols; Naphthoquinones; Oxidation-Reduction; Shewanella; Solubility

In the present study, a series of metallic complexes of the 1,4-naphthoquinone lawsone (2-6) were synthesized and evaluated for potential cytotoxicity in a mouse leukemic macrophagic RAW 264.7 cell line. Cell viability was determined by the MTT assay. Significant growth inhibition was observed for the copper complex (4) with an IC(50) value of 2.5 μM. This compound was selected for further evaluation of cytotoxic activity on several human cancer cells including HT-29 (human colorectal adenocarcinoma), HepG2 (human hepatocellular carcinoma) and HeLa, (human cervical adenocarcinoma cells). Significant cell viability decrease was also observed in HepG2 cells. The apoptotic potential of this complex was evaluated in these cells. Compound 4 induced apoptosis by a mechanism that involves the activation of caspases 3, 8 and 9 and modulation of apoptotic-related proteins such as Bax, Bad, and p53. These results indicate that metal complexes of lawsone derivatives, in particular compound 4, might be used for the design of new antitumoral agents.

Topics: Antineoplastic Agents; Apoptosis; Cell Proliferation; Cell Survival; Crystallography, X-Ray; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HeLa Cells; Hep G2 Cells; HT29 Cells; Humans; Macrophages; Models, Molecular; Molecular Structure; Naphthoquinones; Organometallic Compounds; Structure-Activity Relationship; Tumor Cells, Cultured

Topics: Adolescent; Anti-Bacterial Agents; Coloring Agents; Dermatitis, Allergic Contact; Drug Therapy, Combination; Forearm; Glucocorticoids; Histamine Antagonists; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing; Treatment Outcome

The efficacy of lawsone against L-arginine induced acute pancreatitis was determined at 24 h by determination of serum levels of amylase, lipase and proinflammatory cytokines [tumor necrosis factor (TNF)-alpha, C-reactive proteins and interleukin (IL)], pancreatic myeloperoxidase (MPO) activity, lipid peroxidation (thiobarbituric acid reactive substances (TBARS)], nitrate/nitrite levels, and the wet weight/body weight ratio. Lawsone and methylprednisolone treatments significantly attenuated the L-arginine- induced increases in pancreatic wet weight/body weight ratio, and decreased the serum levels of amylase and lipase, and TNF-alpha and IL-6 and significantly lowered pancreatic levels of MPO, TBARS, and nitrate/nitrite. The histoimmunological findings further proved the amelioration of pancreatic injury by lawsone and further proved anti-inflammatory and antioxidant agent property of lawsone.

Topics: Acute Disease; Animals; Anti-Inflammatory Agents; Antioxidants; Arginine; C-Reactive Protein; Cytokines; Enzyme Inhibitors; Interleukin-6; Interleukins; Male; Naphthoquinones; Neutrophils; Oxidative Stress; Pancreas; Pancreatitis; Rats; Rats, Wistar; Thiobarbituric Acid Reactive Substances; Tumor Necrosis Factor-alpha

Allergic contact dermatitis from nonpermanent black henna tattoos has been frequently reported, particularly in children. Contamination or adulteration of the dyes with para-phenylendiamine has been identified as major cause of active sensitization and elicitation of severe allergic contact dermatitis. Sequelae include permanent sensitization, hyper- or hypopigmentation, scarring, keloids, and hypertrichosis. We report a rare case of irritant dermatitis to an unknown ingredient in a black henna tattoo with consecutive hypopigmentation. Sensitization to para-phenylendiamine and other para-compounds was excluded by patch test evaluation. This is relevant for future exposure to consumer products such as hair dyes or in occupational settings. Generally, black henna tattoos, particularly if done with dyes of unknown composition, should be strongly discouraged.

Topics: Child; Coloring Agents; Dermatitis, Contact; Humans; Hypopigmentation; Immunization; Male; Naphthoquinones; Phenylenediamines; Tattooing

Topics: 2-Naphthylamine; Allergens; Coloring Agents; Dermatitis, Allergic Contact; Dermatitis, Occupational; Humans; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing; Young Adult

Topics: Adolescent; Dermatitis, Contact; Female; Humans; Naphthoquinones; Tattooing

In continuation of our studies with chemoprevention potential of plant-derived naphthoquinone derivatives, leaf powder of the medicinal plant Lawsonia inermis L, commonly known as 'henna', was evaluated by its inhibition of the Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Lawsone (2-hydroxy- 1,4-naphthoquinone), the reddish orange pigment artifact formed during the extraction or preparation of the dye from henna leaves and believed to be the active component, was also assessed in this in vitro assay. Both showed a profound inhibition (>88%) of EBV-EA activation. In the in vivo two-stage mouse skin carcinogenesis study using UV-B radiation for initiation and TPA for tumor promotion, oral feeding of henna (0.0025%) in drinking water ad libitum decreased tumor incidence by 66% and multiplicity by 40% when compared to the positive control at 10 weeks of treatment. Similarly, in the above mouse model, orally fed lawsone (0.0025%) decreased tumor incidence by 72% and multiplicity by 50%. The tumor inhibitory trend continued throughout the 20-week test period. Similar antitumor activities were observed when henna (0.5 mg/ml) was applied topically on the back skin in the UV-B initiated, TPA promoted and peroxynitrite initiated, TPA promoted mouse skin carcinogenesis models. Topically applied lawsone (0.015 mg/ml) also exhibited similar protection against tumor formation in the 7,12-dimtehylbenz(a)anthracene induced and TPA promoted skin cancer in mice. Also, there was a delay of 1 to 2 weeks in tumor appearance in both henna and lawsone treated groups compared to control in all three test models. This study ascertains the skin cancer chemopreventive activity of henna leaf powder and lawsone when administered by either oral (through drinking water) or topical (by application on the back skin) routes. Further, it emphasizes the need for the evaluation of these henna-derived green chemopreventive candidates in combination with currently used sunscreen agents for complementary anticancer potential against UV-induced skin carcinogenesis.

Topics: 9,10-Dimethyl-1,2-benzanthracene; Administration, Cutaneous; Administration, Oral; Animals; Antigens, Viral; Antineoplastic Agents, Phytogenic; B-Lymphocytes; Carcinogenesis; Cell Line, Tumor; Female; Herpesvirus 4, Human; Humans; Lawsonia Plant; Male; Naphthoquinones; Papilloma; Plant Extracts; Plant Leaves; Skin Neoplasms; Tetradecanoylphorbol Acetate; Ultraviolet Rays

The abilities of two natural products, genipin and lawsone, to enhance blood contaminated fingermarks on papers of various porosities and colour were investigated and compared to the routinely used amino acid reagents, ninhydrin and 1,8-diazafluoren-9-one (DFO). Fingermarks in blood were deposited as a split depletion series on various paper types and colours for ageing periods of 6 weeks, 4 weeks, 2 weeks and 1 week before enhancement. The developed marks were observed under different lighting conditions, recorded and graded by way of attributing quantitative data to each series. Results indicated that while genipin showed some potential as a reagent for the enhancement of latent fingermarks, it displayed no suitability for the enhancement of fingermarks in blood on paper. Lawsone also failed to successfully enhance either type of fingermark. Upon comparison of the results with those of ninhydrin and DFO it was found that ninhydrin displayed the highest success rate of development of these marks.

Topics: Aza Compounds; Blood; Coloring Agents; Dermatoglyphics; Humans; Indicators and Reagents; Iridoids; Naphthoquinones; Ninhydrin; Paper

Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure-activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.

Topics: Enzyme Inhibitors; Models, Molecular; Naphthoquinones; Nuclear Magnetic Resonance, Biomolecular; Oxidoreductases; Structure-Activity Relationship; Wolinella

Topics: Dermatitis, Contact; Female; Humans; Naphthoquinones; Skin Diseases, Vesiculobullous; Tattooing; Young Adult

Topics: Child; Dermatitis, Allergic Contact; Humans; Naphthoquinones; Phenylenediamines; Tattooing

Lawsonia inermis Linn. (Lythraceae) or henna has been used since the earliest times as a medicine, preservative, and cosmetic. It has long been recommended in traditional medicine as an astringent, purgative, and abortifacient.. Lawsone and six extracts of L. inermis plant, used by Algerian traditional healers to treat infectious diseases, were screened for their antifungal activity against filamentous fungi.. Water and five organic extracts - DMSO, ethanol, chloroform, ethyl acetate, and di-ethyl ether - of L. inermis leaves, collected in the area of Adrar (Algeria), were prepared by soaking 25 g of powdered plant in 100 mL of solvent. The extracts were screened for antifungal activity using the poisoned food technique against five filamentous fungi.. Results demonstrated that the best yield (8.03%) was obtained with the ethanol extract. The commercial lawsone showed potentially interesting MICs against the strains Fusarium oxysporum (12 µg/mL) and Aspergillus flavus (50 µg/mL). The ethanol extract showed the only interesting MIC (230 µg/mL of crude extract) against the strain F. oxysporum compared with other extracts.. These results suggest that the Algerian L. inermis plant has antifungal activity that can be related to the presence of lawsone in the leaves plant. The results can be exploited largely in research of new antifungal drugs.

Topics: Algeria; Antifungal Agents; Fungi; Lawsonia Plant; Medicine, Traditional; Microbial Sensitivity Tests; Naphthoquinones; Plant Extracts; Plant Leaves; Solvents

A series of 36 new phenylsulfanylmethyl[1,4]naphthoquinones (7-42) were synthesized by a three-component reaction that involves lawsone, the appropriate aldehyde and thiols with variable substitution patterns. These reactions involve the in situ generation of o-quinone methides (o-QM) via Knoevenagel condensation and 1,4-nucleophilic addition under conventional heating or microwave irradiation. The new naphthoquinones obtained by this methodology were shown to have moderate to good in vitro antimalarial activity against Plasmodium falciparum (3D7).

Topics: Antimalarials; Cells, Cultured; Flow Cytometry; Humans; Indolequinones; Malaria, Falciparum; Molecular Structure; Naphthoquinones; Plasmodium falciparum; Sulfhydryl Compounds

Dimerization of lawsone occurs upon reaction with Co(BF(4))(2)·6H(2)O and N,N'-bis(pyridin-2-ylmethyl)ethylenediamine (py(2)en) to produce the mononuclear complex [Co(III)(bhnq)(py(2)en)]BF(4)·H(2)O (1). This complex has been investigated as a prototype of a bioreductive prodrug, where the bhnq(2-) ligand acts as a model for cytotoxic naphthoquinones. Cyclic voltammetry data in aqueous solution have shown a quasi-reversible Co(III)/Co(II) process at E(1/2) = -0.26 V vs Fc/Fc(+). Reactivity studies revealed the dissociation of bhnq(2-) from the complex upon reduction of 1 with ascorbic acid, and a dependence of the reaction rate on the oxygen concentration suggests the occurrence of redox cycling.

Topics: Cell Proliferation; Cobalt; Crystallography, X-Ray; Dimerization; Models, Molecular; Molecular Structure; Naphthoquinones; Organometallic Compounds; Oxidation-Reduction; Prodrugs; Saccharomyces cerevisiae; Structure-Activity Relationship

Very few studies are available in which the components of henna products used by tattoo artists have been analysed.. The aim of this study was to quantify the amounts of lawsone (2-hydroxy-1,4-naphthoquinone, the active ingredient in henna) and p-phenylenediamine (PPD) in products used by tattoo artists and in commercial henna preparations used as hair dyes or to create temporary tattoos.. We used high-performance liquid chromatography to detect and quantify lawsone and PPD concentrations in three products used by henna tattoo artists, 11 commercially available henna preparations, and a batch of henna leaves (Lawsonia inermis).. The henna leaves contained 1.85-1.87% lawsone. Only one of the three preparations used by tattoo artists contained lawsone (0.21-0.35%), and all three were adulterated with PPD (1-64%). Of the 11 commercial henna preparations analysed, nine contained lawsone (1-2%) and two contained PPD (2% and 12%).. Products purporting to be henna, but that in fact contain no henna, are being offered. Moreover, these products may contain PPD, which is associated with health risks, especially severe allergic reactions.

Topics: Chromatography, High Pressure Liquid; Coloring Agents; Consumer Product Safety; Dermatitis, Allergic Contact; Hair Dyes; Humans; Lawsonia Plant; Naphthoquinones; Phenylenediamines; Plant Leaves; Spain; Tattooing; Thorax

Three relatively new reagents for developing latent fingermarks on porous substrates, 1,2-indandione (IND), 5-methylthioninhydrin (5-MTN), and lawsone, are compared with the more widely used ninhydrin and 1,8-diazofluoren (DFO). Developed latent fingermark visualization on 10 different substrates comprising colored papers, cardboard, and cellophane rather than conventional printer and writing/notepad paper is assessed using latent fingermark deposits from 48 donors. Results show improved fluorescent fingermark visualization using IND compared with DFO on a range of colored cardboards and thick white paper, thus extending the range of substrates known to yield improved visualization with IND. Adding zinc chloride to IND failed to yield any further improvement in fluorescent fingermark visualization. 5-MTN (with and without zinc chloride posttreatment) showed no improvement in visualization compared with ninhydrin and DFO although visible fingermarks were developed. Lawsone produced fluorescent visible fingermarks only with white substrates, which were inferior to those produced with DFO.

Topics: Adolescent; Adult; Aza Compounds; Dermatoglyphics; Female; Humans; Indans; Indicators and Reagents; Male; Middle Aged; Naphthoquinones; Ninhydrin; Porosity; Surface Properties; Young Adult

The increased frequency of case reports of allergic contact dermatitis from non-permanent black henna tattoos in recent years shows the popularity of this form of body painting.. Seven patients presented with allergic contact dermatitis after initial hair or eyelash dyeing. They all had a history of a previous reaction from a black henna tattoo. All were patch tested with the European standard patch test series and the standard supplemental series, as well as special series for dyes and hairdressers.. All seven patients showed a positive reaction in patch testing with para-phenylenediamine (PPD) (0.3 % and/or 1.0 % in pet.). Five patients also had positive reactions to other dyes such as aminophenol, para-toluene diamine, disperse orange and yellow and four patients reacted to benzocaine. These were interpreted as cross-reactions. The time from sensitization by the black henna tattoo to the onset of allergic contact dermatitis after hair dyeing was an average of 6.2 years.. The most common cause of allergic contact dermatitis after black henna tattoos is PPD. Both the long skin contact and the high concentrations of PPD increase the risk of sensitization. Allergic contact dermatitis may be followed by post-inflammatory hyper- or hypopigmentation, scarring and lifelong sensitization, which can have occupational impact, especially for hair dressers and cosmeticians.

Topics: Adolescent; Adult; Dermatitis, Allergic Contact; Female; Hair Dyes; Humans; Male; Middle Aged; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Adult; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones

Para-phenylenediamine (PPD) can induce immediate or - more often - delayed hypersensitivity. We report the case of 48-year old female admitted to the out-patient allergy clinic a day after her visit in a beauty parlour, where she had her eyelashes and eyebrows dyed with henna. Physical examination revealed prominent edema of the upper part of the face including forehead, cheeks and eyes causing severe narrowing of the palpebral chink. Skin prick tests (SPT) with common allergens were positive for Dermatophagoides pteronyssinus, Dermatophagoides farinae and moulds, while the SPT with PPD was negative. Patch test to PPD was positive. Further investigations revealed eosinophilia in the tear fluid. To our knowledge, this is the first case of PPD-induced contact blepharoconjunctivitis (CB) with concomitant increased eosinophilia in the tear fluid.

Topics: Blepharitis; Conjunctivitis, Allergic; Eosinophilia; Eyebrows; Eyelashes; Female; Hair Dyes; Humans; Middle Aged; Naphthoquinones; Tears

Zinc(II) and copper(II) complexes of a tridentate Mannich base L1 derived from 2-hydroxy-1,4-naphthoquinone, pyridinecarboxyaldehyde and 2-aminomethylpyridine, [ZnL1Cl(2)]·H(2)O 1 and [CuL1Cl(2)]·2H(2)O 2, have been synthesized and fully characterized. The structure of complex 1 has been elucidated by a single crystal X-ray diffraction study: the zinc atom is pentacoordinate and the coordination geometry is a distorted square base pyramid, with a geometric structural parameter τ equal to 0.149. Vibrational spectroscopy and ab initio DFT calculations of both compounds have confirmed that the two complexes exhibit similar structures. Full assignment of the vibrational spectra was also supported by careful analysis of the distorted geometries generated by the normal modes.

Topics: Coordination Complexes; Copper; Crystallography, X-Ray; Electron Spin Resonance Spectroscopy; Electrons; Hydrogen Bonding; Magnetic Resonance Spectroscopy; Mannich Bases; Models, Molecular; Molecular Conformation; Naphthoquinones; Quantum Theory; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis, Raman; Thermodynamics; Vibration; Zinc

Topics: Coloring Agents; Hazardous Substances; Humans; Laser Therapy; Naphthoquinones; Tattooing

Naphthoquinone derivatives are under investigation as potential therapeutic agents. The antibacterial and antifungal activity of lawsone and of some novel naphthoquinone derivatives was assessed in vitro.. The antimicrobial activity was determined using diffusion disk and the broth microdilution methods against seven bacteria and three Candida species, according to recommendations of the Clinical and Laboratory Standards Institute.. Two compounds (P05 et P06) presented a good antibacterial effectiveness against two gram-positive bacteria. No antifungal potency was observed against the three Candida albicans strains used in the test.. Our results prove that the introduction of substituents on ketone function position 4 decreased the antimicrobial properties of the synthetized compounds.

Topics: Anti-Bacterial Agents; Antifungal Agents; Bacteria; Candida albicans; Disk Diffusion Antimicrobial Tests; Naphthoquinones

A new class of pentacyclic diquinoid compounds has been synthesized with a facile one-pot reaction of two molecules of 2-hydroxynaphthoquinone and 1-bromoalkanes in the presence of ferrocene. These molecules were isolated as enol tautomers that exhibit intramolecular hydrogen bond and extended electronic conjugation as proved by the intense absorption spectrum with a broad band between 400 and 600 nm. The spectroscopic and electrochemical characterization of this new class of compounds has been performed. One of the synthesized diquinoid derivatives showed a significant cytotoxicity with IC(50) values of 25-50 μM against Cisplatin-Resistant SKOV3 and colon carcinoma SW480 cell lines. The results of our study provide a valuable tool to a one-pot synthesis of highly conjugated polyquinones, analogous to important biological systems, with significant antitumoral activity.

Topics: Alkanes; Antineoplastic Agents; Cell Line, Tumor; Cell Survival; Cisplatin; Ferrous Compounds; Fibroblasts; Humans; Hydrogen Bonding; Metallocenes; Naphthoquinones; Stereoisomerism; Structure-Activity Relationship

Topics: Erythema Multiforme; Female; Humans; Naphthoquinones; Tattooing; Young Adult

The purpose of this study was to determine the effect of different colour nail polishes and henna on the measurement of oxygen saturation and the differences among the measurements of three pulse oximetry devices.. 33 healthy females with a mean age of 19±1.0 years and no complaints or known disease were included into the study. All the participants applied henna to one of their fingers a day before the study. Just before the study, one finger was left empty as control and the other fingers were dyed using various colours of nail polish (red, blue, beige, purple, brown, white, pink, green, colourless polish, light blue, light green and yellow). There were more than eight colour nail polishes and some fingers were used for the other colours after being completely cleaned. The same brand nail polishes were used for the study. Oxygen saturation measurements were done using three different pulse oximetry devices (device I, II, III) from the control, different colour nail polished and henna applied fingers. The measurements of different devices, different colour nail polishes, henna and control were statistically compared.. The mean saturations obtained from blue, beige, purple and white nail polished fingers were significantly lower than those of control and the other coloured fingers. In addition, the mean measurement of device II was significantly lower than those of other devices.. The results suggest that blue, beige, purple and white nail polished fingers might cause pulse oximetry devices to make incorrect measurements.

Topics: Adult; Color; Coloring Agents; Cosmetics; Female; Fingers; Humans; Nails; Naphthoquinones; Oximetry; Oxygen; Young Adult

For many surgical procedures skin marking is required well before surgery and induction of anesthesia. In some cases, the patient may need to be standing or sitting while the skin area is marked. Marking of perforators and varicosities in chronic venous diseases, marking of stoma sites for urinary or fecal diversions are some examples. The side of surgery should ideally be marked preoperatively to avoid wrong side surgery. Marks made with conventional marking pens fade or disappear with preoperative skin preparation, whereas marks made with henna paste, which is orange to dark brown in color, last for up to 3 weeks in spite of regular showers and skin cleansing, even with ethanol. This property of henna encouraged us to use it as a preoperative skin marker.. Henna paste was used as a preoperative skin marker in 250 patients. In 154 patients with chronic venous diseases, perforators and varicosities were marked during duplex scanning. Henna was used to mark the colostomy site in 28 patients with carcinoma of the rectum prior to abdominoperineal resection of the rectum (APR) (four of them laparoscopic APR) and the aspiration site in 11 patients with liver abscesses and 4 patients with pleural empyemas, under ultrasonographic (USG) guidance. In addition, henna was used to mark the correct side of surgery in 47 patients undergoing unilateral inguinal hernia surgery. Marking was done from 1 to 8 days before surgery.. The marking with henna was clearly visible in all the cases even after preoperative skin preparation with ethanol up to 8 days after application. There were no complications associated with the marking. All marks disappeared 4 weeks after application. In terms of successful execution of the desired procedure, the use of henna marking was successful in all the cases.. Henna is an ideal substance for use as a preoperative skin marker. It can be safely and effectively used as a marker for varicose vein surgery, ultrasound-guided identification of lesions, establishing the ideal site for stomas on the abdominal wall, and to identify the correct side of surgery. Markings made with henna are durable and do not fade with routine bathing or preoperative skin preparation. In most cases there are no associated complications. Henna is cheap, safe, and convenient, and indications for its use can be ubiquitous.

Topics: Coloring Agents; Female; Humans; Male; Naphthoquinones; Preoperative Care; Skin; Surgical Procedures, Operative; Time Factors

Topics: Coloring Agents; Humans; Naphthoquinones; Preoperative Care; Skin; Surgical Procedures, Operative; Time Factors

Topics: Adolescent; Adult; Aged; Aging; Child; Coloring Agents; Dermatitis, Allergic Contact; Dermatitis, Occupational; Humans; Middle Aged; Naphthoquinones; Patch Tests; Phenylenediamines; Prevalence; Young Adult

Henna, or Lawsonia inermis, has been used since antiquity by women in the Orient for dyeing the hair, hands, and feet. Contact dermatitis to pure henna is very rare, most often caused by additives such as perfume oils or paraphenylenediamine (PPD). We report the case of a girl who presented contact dermatitis to henna associated with eczema to draw attention to the dangers related to its use.. A 12-year-old girl developed erythematovesicular and edematous lesions with very itchy burning, suggestive of contact dermatitis, 48 hours after application of black henna. Lesions were located at the tattooing site exactly following the original design. The patient also had eczema lesions on the left cheek after contact with the tattooed hand. The lesions were improved by treatment with level II corticosteroids.. Today, henna has become very popular in Western countries. PPD is added to reduce the fixation time or to obtain a darker color. It can cause severe systemic reactions. The most common allergic reaction is contact dermatitis. Treatment is based on topical steroids. Better legislation on temporary tattooing practices and control preparations as well as regular annual information aimed at the general public are essential.. This observation raises awareness of the importance of information on the serious risks of a labile tattoo, most particularly for the young.

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Tattooing

A rapid method for the determination of para-phenylenediamine (PPD) in cosmetic products, such as henna tattoos has been developed and evaluated. This analytical procedure involved extracting a 10mg test portion of cosmetic product in 10 mL of ethyl acetate, followed by determination by gas chromatography-mass spectrometry in the selected ion monitoring mode (GC/MS-SIM). 1,4-Phenylenediamine-2,3,5,6-d(4) was selected as an internal standard that was added at the beginning of the extraction procedure and used to correct for recovery and matrix effects. The linearity ranged from 1.0 to 1275 μg/mL with a coefficient of determination (r(2)) greater than 0.999. LOQ and LOD were 1.0 and 0.10 μg/mL, respectively. The recovery in a tattoo product containing PPD was 94% and that for a tattoo product containing no PPD reached 105%. Extraction efficiency of 98% was obtained. This method has been successfully applied to henna temporary tattoo and other henna-related cosmetic products for the determination and quantitation of PPD.

Topics: Cosmetics; Drug Stability; Gas Chromatography-Mass Spectrometry; Least-Squares Analysis; Naphthoquinones; Phenylenediamines; Reproducibility of Results; Sensitivity and Specificity

Temporary tattooing with black henna is known to cause contact dermatitis; however, this adverse effect is not considered to be life threatening. We report a female adolescent who used black henna as a hair dye and developed severe contact dermatitis with scalp, facial, and neck swelling causing hoarseness and stridor. A flexible bronchoscopy showed a normal epiglottis, and the patient was intubated, ventilated, and eventually recovered. We conclude that the use of black henna hair dye in sensitized patients can be life threatening.

Topics: Adolescent; Dermatitis, Allergic Contact; Edema; Female; Hair Dyes; Hoarseness; Humans; Naphthoquinones; Respiratory Sounds; Scalp Dermatoses

A drug-inorganic nanostructured material involving pharmaceutically active compound lawsone intercalated Zn-Al layered double hydroxides (Law-LDHs) with Zn/AI = 4 has been assembled by co-precipitation and ion exchange methods. Powder X-ray diffraction (XRD) and Fourier transform infrared spectra (FTIR) analysis indicate a successful intercalation of lawsone between the layers of layered double hydroxides. It suggests that layered double hydroxides may have application as the basis of a drug delivery system.

Topics: Aluminum; Hydroxides; Intercalating Agents; Naphthoquinones; Spectroscopy, Fourier Transform Infrared; Surface Properties; X-Ray Diffraction; Zinc

The surface-enhanced Raman spectrum of lawsone, a well known natural dye, has been investigated. Activation with KNO(3) or Na(2)SO(4) solution was necessary to enhance the Raman signal, whereas addition of NaCl solution depletes the effects. In the enhanced Raman spectrum, the strong double-bond stretching bands are most distinctive and show large red shifts from those in the infrared and FT-Raman spectra. The observed strong double-bond stretching bands reflect lawsone coordinated perpendicular to the Ag surface. DFT computations have been carried out for the plausible configurations of lawsone coordinated to an adatom on the Ag surface. Lawsone coordinated to an Ag(+) adatom with H(+) released best reproduces the observed vibrational characteristics.

Topics: Models, Molecular; Naphthoquinones; Silver; Spectrum Analysis, Raman; Surface Properties

Topics: Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Phenylenediamines; Young Adult

An 11-year-old boy got a temporary black henna tattoo while on vacation. After 3 days he developed an itching rash at the site of the tattoo, that spread to the rest of the body. This was most likely an allergic contact dermatitis and erythema exsudativum multiforme minor caused by the often high concentrations of the strong sensitizer para-phenylenediamine (PPD) in the henna.

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Tattooing

Topics: Catheterization, Peripheral; Coloring Agents; Female; Humans; Naphthoquinones; Tattooing

The aim of this study was elucidation of the difference in inhibition influence of 5-hydroxy-1,4-naphthoquinone (juglone) and 2-hydroxy-1,4-naphthoquinone (lawsone) on jack bean urease activity. It was found that juglone acted as a strong, time and concentration dependent inactivator of urease. On the contrary, lawsone showed an inconsiderable inhibition influence. The reactivation of juglone modified urease showed the participation of reversible and irreversible contribution in the inactivation. In the presence of an excess of DTT, urease inactivated by juglone regained 70% of its activity. The reversible inactivation was attributed to oxidation of the essential urease thiols by reactive oxygen species (ROS) realizing during reduction of juglone to seminaphthoquinone. Presence of hydrogen peroxide in the incubation system was proved by direct determination and by application of catalase. The irreversible contribution in the inhibition was assumed as an arylation of urease thiol groups by juglone. The insignificant urease inhibition by lawsone was concluded as an effect of a low hydrogen peroxide generation and lawsone resistance for reaction with protein thiols. It was found that lawsone well reacted with l-cysteine, poorly with glutathione and hardly with urease thiols. The observed sequence was arranged according the rule the more complex thiol the less susceptible for reaction with lawsone. On the other hand, juglone displayed an excellent reactivity towards both thiols and urease. Thus, this indicated a significance of a steric hindrance which appeared when the hydroxyl group changing position from 5 in juglone (5-hydroxy-1,4-naphthoquinone) to 2 in lawsone (2-hydroxy-1,4-naphthoquinone).

Topics: Canavalia; Catalase; Dithiothreitol; Enzyme Inhibitors; Hydrogen Peroxide; Kinetics; Naphthoquinones; Urease

Topics: Dihydroxyacetone; Humans; Maillard Reaction; Naphthoquinones; Photosensitivity Disorders; Radiation Protection; Sunlight; Urticaria

Topics: Child; Coloring Agents; Eczema; Humans; Hypertrichosis; Male; Naphthoquinones; Tattooing

The reduction of Cr(VI) by resting Escherichia coli cells was significantly enhanced by the quinone redox mediators, lawsone, menadione, anthraquinone-2-sulfonate and anthraquinone-2,6-disulfonate. In the presence of 0.2 mM lawsone, over 97.5% Cr(VI) (100 mg l(-1)) was reduced in 4h. The mediated reduction occurred at initial Cr(VI) concentrations of 50-250 mg l(-1), and increased with increasing initial biomass concentrations from 0.05 to 1.2 g l(-1). The addition of glucose as electron donor promoted the reduction process. Cu(2+), Ni(2+) and Co(2+) inhibited, whereas Mn(2+) and Pb(2+) stimulated reduction. Four rounds of mediated reduction were completed in 19 h, suggesting its stability and persistence. The efficient mediated microbial reduction of Cr(VI) is promising for rapid anaerobic removal of chromate.

Topics: Biodegradation, Environmental; Biomass; Chromates; Escherichia coli; Glucose; Metals; Naphthoquinones; Oxidation-Reduction; Quinones

Topics: Australia; Child; Humans; Hypersensitivity; Male; Naphthoquinones; Tattooing

Temporary 'black henna' tattoos, an increasingly popular body decoration in pediatric population, are associated with a growing incidence of adverse events. Black henna does not exist naturally, it is obtained from original henna after the addition of other compounds, among them paraphenilendiamine (PPD), which serves to darken the tattoo and allows greater precision to the design. PPD is known to be a strong sensitizer and increases the risk of allergic contact dermatitis. They may present as long lasting local reactions, and pigmentary sequels apart from problems with the future use of many products present in the daily life, as a result of sensitization by PPD. We report the case of an eleven-year old girl with an allergic contact dermatitis to black henna tattoo with a positive patch test to PPD, in order to warn against these types of temporary tattoos.

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Tattooing; Time Factors

The protein glycation inhibitory activity of ethanolic extract of Lawsonia inermis (henna) plant tissues was evaluated in vitro using the model system of bovine serum albumin and glucose. Protein oxidation and glycation are posttranslational modifications that are implicated in the pathological development of many age-related disease processes. This study investigated the effects of Lawsonia inermis ethanolic extract and its components, on protein damage induced by a free radical generator in in vitro assay system. We found that alcoholic extract of Lawsonia inermis can effectively protect against protein damage and showed that its action is mainly due to Lawsone. In addition, the presence of gallic acid also plays an important role in the protective activity against protein oxidation and glycation. Two known compounds, namely, Lawsone and gallic acid previously isolated from this plant were subjected to glycation bioassay for the first time. It was found that the alcoholic extract, lawsone (1) and gallic acid (2) showed significant inhibition of Advanced Glycated End Products (AGEs) formation and exhibit 77.95%, 79.10% and 66.98% inhibition at a concentration of 1500 microg/mL, 1000 microg/mL and 1000 microM respectively. Lawsonia inermis, compounds 1 and 2 were found to be glycation inhibitors with IC(50) 82.06 +/- 0.13 microg/mL, 67.42 +/- 1.46 microM and 401.7 +/- 6. 23 microM respectively. This is the first report on the glycation activity of these compounds and alcoholic extract of Lawsonia inermis.

Topics: Ethanol; Gallic Acid; Glucose; Glycation End Products, Advanced; Glycosylation; Lawsonia Plant; Naphthoquinones; Plant Extracts; Protein Processing, Post-Translational; Serum Albumin, Bovine

Temporary henna tattooing has been very popular during recent years. Henna (Lawsonia inermis) is a plant from the Lythraceae family. For henna tattooing, henna dye is used. It is a dark green powder, made from the leaves of the plant, used for hair dyeing and body tattooing. Very often, para-phenylenediamine (PPD) is added to henna dye to make color blacker and to speed up dyeing. PPD may be a very potent contact sensitizer. We report a 9-year-old boy with allergic contact dermatitis due to temporary henna tattooing. Patch testing showed a positive reaction to PPD. After the treatment with topical corticosteroid and oral antihistamines, the lesion cleared with discrete residual hypopigmentation.

Topics: Allergens; Child; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

Topics: Adult; Cicatrix; Coloring Agents; Drug Hypersensitivity; Humans; Hypopigmentation; Male; Naphthoquinones; Tattooing

Henna is a very popular plant in many countries, including Tunisia. Henna leaves have been used for thousands of years as a medicine, as a cosmetic and also for dyeing textile fabrics. This paper investigates the color modification of cotton, which has been colored by henna, due to gamma-ray irradiation. A cotton fabric tinted by means of a henna solution is irradiated using a (60)Co source at doses ranging from 0 to 25 kGy with a dose rate of 146.53 Gy/min. Decoloration of the henna dye in cotton fabrics was observed by studying variation of the L* and the h degrees as a function of the irradiation dose. This work reveals that cotton colored by henna can be used as a new indicator to differentiate between an unirradiated and irradiated product.

Topics: Color; Colorimetry; Cotton Fiber; Dose-Response Relationship, Radiation; Gamma Rays; Gossypium; Naphthoquinones; Radiation Dosage

Topics: Child; Coloring Agents; Drug Eruptions; Humans; Male; Naphthoquinones; Tattooing

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from beta-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the beta-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.

Topics: Alkylation; Alkynes; Esters; Isoquinolines; Ketones; Molecular Structure; Naphthoquinones; Stereoisomerism

Temporary henna tattoos have become increasingly widespread. Although reactions to henna tattoo are becoming progressively more common, only one case of a henna pseudotattoo resulting in temporary hypertrichosis has been reported so far. We report three patients who received paint-on henna tattoos on their right upper arm. Approximately 1 week later, localized hypertrichosis was observed over the same area as the tattoo, which resolved spontaneously within 3-4 months. Clinicians should be aware of this complication and it should be noted that treatment is not necessary as hypertrichosis resolves spontaneously.

Topics: Adolescent; Adult; Arm; Child; Coloring Agents; Female; Humans; Hypertrichosis; Male; Naphthoquinones; Remission, Spontaneous; Tattooing

We describe a case of a 10 year old boy who developed an contact dermatitis to black henna tattoo. Sixteen days later he was brought to the emergency department because of an presumed superinfection by S. aureus. The infection was successfully treated with dicloxacillin and the allergic reaction with bethametasone ointment and tablets. The use of pure henna is legal but has been proven to be harmful in animal experiments. Para-phenylendiamine (PPD) has been mixed with henna to achieve a darker colour and to decrease the treatment time and is well known to cause allergic reactions.

Topics: Administration, Cutaneous; Administration, Oral; Anti-Allergic Agents; Anti-Bacterial Agents; Betamethasone; Child; Coloring Agents; Dermatitis, Allergic Contact; Dicloxacillin; Humans; Male; Naphthoquinones; Ointments; Phenylenediamines; Staphylococcal Skin Infections; Staphylococcus aureus; Tablets; Tattooing; Treatment Outcome

Topics: Administration, Topical; Antifungal Agents; Diabetic Foot; Foot Ulcer; Humans; Naphthoquinones; Risk Factors

Topics: Adolescent; Coloring Agents; Cross Reactions; Dermatitis, Allergic Contact; Female; Hair Dyes; Humans; Naphthoquinones; Tattooing

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Tattooing

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Female; Hand Dermatoses; Humans; Naphthoquinones; Phenylenediamines; Tattooing

A novel and simple spectrophotometric method for the determination of Captopril with sodium 1,2-naphthoquinone-4-sulfonate is established in this paper. The detailed reaction mechanism is proposed and discussed. It is based on the fact that captopril can catalyze the reaction between sodium 1,2-naphthoquinone-4-sulfonate and hydroxyl ion to form 2-hydroxy-1,4-naphthoquinone in buffer solution of pH 13.00. Beer's law is obeyed in a range of 0.64-80 mugmL(-1) at the maximal absorption wavelength of 442 nm. The equation of linear regression is A=0.05815+0.00589C (mugmL(-1)), with a linear regression correlation coefficient of 0.9981. The detection limit is 0.3 mugmL(-1), R.S.D. is 0.77% and the recovery rate is in range of 96.0-103.8%. Furthermore, the method has been validated and successfully applied to the determination of captopril in pharmaceutical samples.

Topics: Angiotensin-Converting Enzyme Inhibitors; Captopril; Catalysis; Hydrogen-Ion Concentration; Hydroxides; Mass Spectrometry; Naphthoquinones; Spectrophotometry; Spectrophotometry, Infrared

Capecitabine is a chemotherapeutic drug for use in cancers. Hand-foot syndrome (HFS) is side effect of capecitabine which can lead the cessation of the therapy or dose reduction. Henna (Lawsonia inermis) is a traditionally used plant of Middle-East that is applied on hands and feet. Some of cancer patients in capecitabine treatment who developed HFS, we recommended to apply henna. In these patients, six patients were grade 3 HFS and four were grade 2 HFS. Complete response (CR) were seen in four of grade 3 HFS and all of grade 2; two grade 3 HFS improved to grade 1. So far, in the chemotherapy, there was no need of dose reduction and also no side effect of henna seen. Clinical improvement in these patients may relate to anti-inflammatory, antipyretic and analgesic effects of henna. Prospective studies are needed to show this therapeutic effect of henna.

Topics: Administration, Cutaneous; Adult; Aged; Antimetabolites, Antineoplastic; Capecitabine; Deoxycytidine; Female; Fluorouracil; Foot Dermatoses; Hand Dermatoses; Humans; Middle Aged; Naphthoquinones; Neoplasms; Paresthesia; Severity of Illness Index; Syndrome; Treatment Outcome

Topics: Adult; Coloring Agents; Drug Hypersensitivity; Female; Humans; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Allergens; Dermatitis, Allergic Contact; Diagnosis, Differential; Female; Hair Dyes; Humans; Middle Aged; Naphthoquinones; Patch Tests; Scalp Dermatoses

A gas chromatography-mass spectrometry (GC-MS) method has been proposed for the determination of carcinogenic and toxic aromatic amines in hair dye, henna and dyed hair samples. The method includes ion-pair extraction of aromatic amines from aqueous samples with bis-2-ethylhexylphosphate (BEHPA) released after solving the samples in acidic solution followed by sonication, derivatisation of compounds with isobutyl chloroformate (IBCF) and their GC-MS analysis in both electron impact (EI) and positive and negative ion chemical ionisation (PNICI) mode as their isobutyloxycarbonyl (isoBOC) derivatives. The obtained recoveries of aromatic amines ranged from 92.2 to 98.4% and the precision of this method, as indicated by the relative standard deviations (RSDs) was within the range of 0.7-4.2%. The detection limits obtained from calculations by using GC-MS results based on signal-to-noise ratio (S/N)=3 were within the range from 0.02 to 0.20 ng/g. In the present study, the commercially available 54 permanent hair dye, 35 modified or natural henna and 15 dyed hair samples were analysed for the aromatic amines by the proposed method and the method was shown to be suitable to determine the aromatic amine ingredients and metabolites of these commercial products.

Topics: Amines; Gas Chromatography-Mass Spectrometry; Hair Dyes; Naphthoquinones

We report on a 14-year-old boy who was presented to the emergency department with an acute swelling of the face and scalp 3 days after using a new hair dye. The patient had applied a black henna tattoo 1 year earlier. Patch testing revealed an allergy to the potent skin sensitizer paraphenylenediamine, a common ingredient of hair dyes and also found in black henna tattoo. It is important for emergency physicians to be aware of the possibility of a delayed type-IV hypersensitivity reaction from black henna tattoos manifesting as an acute contact dermatitis. These patients may have gross facial swelling but should not be treated for angioedema.

Topics: Adolescent; Coloring Agents; Edema; Face; Hair Dyes; Humans; Hypersensitivity, Delayed; Male; Naphthoquinones; Phenylenediamines

The toxic profile of lawsone (2-hydroxy-[1,4]naphthoquinone) and a series of [1,4]naphthoquinone derivatives was evaluated against the brine shrimp Artemia salina and against the mollusk Biomphalaria glabrata, the main transmitting vector of schistosomiasis in Brazil. Of the seventeen compounds tested nine fell below the threshold of 100 microg/mL set for potential molluscicidal activity by the World Health Organization. As a general rule derivatives with non-polar substituents presented the highest molluscicidal activities. These substances showed significant toxicity in A. salina lethality bioassay.

Topics: Animals; Artemia; Biomphalaria; Molluscacides; Naphthoquinones

In vivo genotoxicity tests play a pivotal role in genotoxicity testing batteries. They are used both to determine if potential genotoxicity observed in vitro is realised in vivo and to detect any genotoxic carcinogens that are poorly detected in vitro. It is recognised that individual in vivo genotoxicity tests have limited sensitivity but good specificity. Thus, a positive result from the established in vivo assays is taken as strong evidence for genotoxic carcinogenicity of the compound tested. However, there is a growing body of evidence that compound-related disturbances in the physiology of the rodents used in these assays can result in increases in micronucleated cells in the bone marrow that are not related to the intrinsic genotoxicity of the compound under test. For rodent bone marrow or peripheral blood micronucleus tests, these disturbances include changes in core body temperature (hypothermia and hyperthermia) and increases in erythropoiesis following prior toxicity to erythroblasts or by direct stimulation of cell division in these cells. This paper reviews relevant data from the literature and also previously unpublished data obtained from a questionnaire devised by the IWGT working group. Regulatory implications of these findings are discussed and flow diagrams have been provided to aid in interpretation and decision-making when such changes in physiology are suspected.

Topics: Aniline Compounds; Animals; Body Temperature; Bone Marrow Cells; Erythropoietin; Guidelines as Topic; Hyperthermia, Induced; Micronucleus Tests; Mutagenicity Tests; Mutagens; Naphthoquinones; Phenol; Phenylhydrazines; Pyridines; Reserpine; Rodentia; Sensitivity and Specificity; Triazoles

The highly reactive indanedioneketene 5, resulting from the thermal decomposition of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone (lawsone, 4), in the absence of nucleophiles dimerizes to the corresponding tetraoxo spiro oxetanone 6 in quantitative yield. This oxetanone exhibits an interesting reactivity toward amines.

Topics: Amines; Crystallography, X-Ray; Dimerization; Hydrogen Bonding; Indans; Ketones; Models, Molecular; Molecular Structure; Naphthoquinones; Stereoisomerism; Temperature

Topics: Adolescent; Adult; Canada; Cohort Studies; Dermatitis, Allergic Contact; Female; Hair Dyes; Humans; Immunization; Incidence; Naphthoquinones; Patch Tests; Phenylenediamines; Risk Assessment; Tattooing

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Bilirubin; Blood Transfusion; Coloring Agents; Glucosephosphate Dehydrogenase Deficiency; Humans; Hyperbilirubinemia; Infant, Newborn; Male; Naphthoquinones; Phototherapy; Treatment Outcome

Topics: Agar; Candida albicans; Cryptococcus neoformans; Culture Media; Naphthoquinones

Lawsone (2-hydroxy-1,4-naphthoquinone) is the active ingredient of Lawsonia alba, whose crushed leaves are known as henna, used as a hair and skin dye in many parts of the world. Accidental or deliberate ingestion of Lawsone has a high mortality rate (up to 31%) owing to rhabdomyolysis and renal failure. The authors report the first successful use of plasmapheresis as an adjunct to the treatment of these symptoms in a 69-year-old man who suffered severe symptoms of Lawsone poisoning due to inadvertent ingestion. Although most cases reported in the literature have been treated using supportive techniques, including hemodialysis, the high mortality despite these measures suggests that prompt plasma exchange may be a lifesaving technique for this syndrome.

Topics: Aged; Hair Dyes; Humans; Male; Naphthoquinones; Plasma Exchange; Plasmapheresis; Treatment Outcome

Topics: Alopecia; History, 19th Century; Humans; Inflammation; Naphthoquinones; Phenylenediamines; Plant Extracts; Skin

In the last years there have been increasing reports of adverse cutaneous reactions to temporary black henna tattoos. Black henna does not exist naturally, it is obtained from original henna after the addition of other compounds, among them paraphenylenediamine (PPD), that darken it and facilitate the process of tattoing. Paraphenylenediamine is an aromatic compound that presents cross reactions with other components that have a benzene ring in their molecular structure. Many of these products may be present in the daily life of any person.. We reviewed patients that have shown erythema, inflammation and/or vesiculation in a previously tattooed area. The patients have undergone a temporary tattoo in street stalls during the summer period (2004-2005). A total of five patients were included, there were four men and one woman with a mean age of 13 years (3-34) and a mean latency period of 9.4 days (5-14). Black ink and plastic stencils were used to perform the tattoo. None of the patients has had previous contact with hair dyes or tattoos and none of them referred a personal history of atopic dermatitis. Patch testing was carried out using the standard set of the Spanish Group for Research in Contact Dermatitis [GEIDC] (TRUE TEST, Pharmacia. Hillerod. Denmark), with readings at 48 and 96 hours.. Sensitization to PPD is confirmed in three patients, one of them was also sensitized to formaldehyde. Hypopigmented scars persist in three patients.. Black henna pseudotattoos are a source of sensitization to PPD with potential severe consequences in a medium to long term. Currently there is no specific legislation with respect to the practice of this type of tattoos in our country.

Topics: Adult; Benzoquinones; Biotransformation; Child; Child, Preschool; Dermatitis, Allergic Contact; Female; Humans; Hypopigmentation; Ink; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Prodrugs; Tattooing

Temporary henna tattoos have become increasingly popular as a safe alternative to permanent tattoos among American and European children and teenagers during the summer holidays. Currently, temporary henna tattoos contain not only henna, but also other additives such as para-phemylenediamine (PPD), which is considered to be the chemical agent that most frequently causes skin reactions associated with the use of commercial black henna. In this report, we describe an 11-year-old boy who applied a temporary black henna tattoo on his right arm during the summer holidays in Greece and developed a severe contact dermatitis at the tattoo site with residual hypopigmentation. He had no previous history of contact dermatitis, however he did suffer from seasonal allergic rhinitis and atopic dermatitis. Patch testing revealed a strong reaction to PPD, a substance commonly contained in temporary henna tattoo preparations.. Henna tattoos are an increasing problem worldwide since they carry an increased risk of severe skin reactions; therefore we suggest that the use of temporary henna tattoos in children be discouraged.

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Dermatitis, Atopic; Humans; Male; Naphthoquinones; Tattooing

Lawsone is an active naphthoquinone derivative isolated from henna (Lawsonia inermis L.), a widely used hair dye. Previous study on the toxicity of lawsone remains unclear since the involvement of oxidative stress and the kind of ROS (reactive oxygen species) involved have not been fully resolved yet. This present study reports the cytotoxic effects of lawsone and henna. We carried out CAT assay (a zone of inhibition test of bacterial growth and colony-forming efficiency test of transformant Escherichia coli strains that express mammalian catalase gene derived from normal catalase mice (Cs(a)) and catalase-deficient mutant mice (Cs(b))), Ames mutagenicity assay and H(2)O(2) generation assay. Lawsone generated H(2)O(2) slightly in phosphate buffer system and was not mutagenic in Ames assay using TA 98, TA 100 and TA 102, both in the absence and presence of metabolic activation. Lawsone exposure inhibited the growth of both Cs(a) and Cs(b) strains in a dose-dependent manner. Mean zone diameter for Cs(a) was 9.75+/-0.96 mm and 12.75+/-1.5 mm for Cs(b). Natural henna leaves did not show toxic effects, whereas two out of four samples of marketed henna products were shown toxicity effects. Catalase abolished zone of inhibition (ZOI) of marketed henna products, eliminated ZOI of lawsone in a dose-dependent manner and low concentration of exogenous MnSOD and Cu/ZnSOD eliminated the toxicity. Histidine and DTPA, the metal chelator; BHA and low concentration of capsaicin, the inducer of NADH-quinone reductase, effectively protected Cs(a) and Cs(b) against lawsone in this study. We suggest that lawsone cytotoxicity is probably mediated, at least in part, by the release of O(2)(-), H(2)O(2) and OH(-).

Topics: Animals; Antioxidants; Ascorbic Acid; Butylated Hydroxyanisole; Capsaicin; Catalase; Cytoprotection; Dose-Response Relationship, Drug; Escherichia coli; Hair Dyes; Histidine; Hydrogen Peroxide; Hydroxyl Radical; Lawsonia Plant; Mice; Microbial Sensitivity Tests; Mutation; Naphthoquinones; Oxidative Stress; Pentetic Acid; Plant Extracts; Reactive Oxygen Species; Superoxide Dismutase; Superoxides

Topics: Asthma; Child; Humans; Latex Hypersensitivity; Male; Naphthoquinones

Lawsone (2-hydroxy-1,4-naphthoquinone) is the principal color ingredient in henna, a color additive approved with limitations for coloring hair by the Food and Drug Administration (FDA) under 21 CFR 73.2190. In 2002, the scientific committee on cosmetics and non-food products (SCCNFP), now known as the scientific committee for consumer products (SCCP), evaluated the safety of lawsone as a coloring agent in hair dye products of the European Union (EU). The SCCNFP concluded that lawsone was mutagenic and not suitable for use as a hair coloring agent. As a result, studies were conducted to measure the extent of lawsone absorption through human skin. Lawsone skin absorption was determined from two hair coloring products and two shampoo products, all containing henna. [(14)C]-Lawsone (sp. act. 22.9 mCi/mmol) was added to each commercial product and the products were applied to dermatomed, nonviable human skin mounted in flow-through diffusion cells perfused with a physiological buffer (HEPES-buffered Hanks' balanced salt solution, pH 7.4). Products remained on the skin for 5 minutes (shampoos) and 1 hour (hair color paste). For the henna hair paste products, 0.3 and 1.3% of the applied dose was absorbed into the receptor fluid in 24 hours while 2.2 and 4.0% remained in the skin. For both henna shampoo products, 0.3% of the applied dose was absorbed into the receptor fluid at 24 hours while 3.6 and 6.8% remained in the skin. For all products, most of the lawsone applied was washed from the surface of the skin (83-102%) at the end of the exposure period. Extended absorption studies were conducted for 72 hours to determine if skin levels of lawsone in the 24 hour studies might eventually be percutaneously absorbed. These studies determined that the majority of the lawsone remained in the skin with only a small but significant increase (for three out of four products) in receptor fluid values. Therefore, it appears that receptor fluid values would give a good estimate of lawsone absorption for an exposure estimate and that skin levels of lawsone need not be included.

Topics: Carbon Radioisotopes; Diffusion Chambers, Culture; Dose-Response Relationship, Drug; Hair Dyes; Humans; In Vitro Techniques; Naphthoquinones; Powders; Reproducibility of Results; Skin; Skin Absorption; Soaps; Solutions; Time Factors

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Tattooing

Topics: Adolescent; Arm; Coloring Agents; Drug Contamination; Granuloma, Foreign-Body; Humans; Male; Mercury; Naphthoquinones; Tattooing

Electrochemical oxidation of catechols (1a-c) has been studied in the presence of 2-hydroxy-1,4-naphtoquinone (3b) in aqueous solutions, using cyclic voltammetry and controlled-potential coulometry. The results indicated that the electrochemically generated o-benzoquinones (2a-c) participate in Michael addition reaction with 3b to the corresponding benzofuranoquinones (8a-c, 10a-c). The electrochemical synthesis of these compounds has been successfully preformed at a carbon rod electrode with good yields using an environmentally friendly method.

Topics: Benzofurans; Electrochemistry; Electrodes; Environmental Pollution; Hydrogen-Ion Concentration; Naphthoquinones; Oxidation-Reduction

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Humans; Latex Hypersensitivity; Male; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Adolescent; Coloring Agents; Drug Eruptions; Female; Hand; Humans; Naphthoquinones

The lawsone content has been evaluated quantitatively in eight commercial henna powders and two collected henna leaves. The phenolic, chloroform-soluble fraction of the majority of the examined samples showed the presence of lawsone and two other pigments. Here we aimed to optimize high performance thin layer chromatography for the determination of lawsone. Upon using the optimized method the examined samples showed considerable variation in lawsone concentration ranging from 0.004 up to 0.608 wt%, indicating that some samples were almost devoid of lawsone. Some of these products were subjected to preliminary in vivo toxicity studies.

Topics: Animals; Chromatography, Thin Layer; Lawsonia Plant; Male; Molecular Structure; Naphthoquinones; Powders; Rats; Sensitivity and Specificity; Toxicity Tests

Investigation on solvent-induced polymorphism in X-ray structures of 2-hydroxy-1,4-naphthoquinone (Lawsone) 1, is carried out. In protic methanol, 1 crystallizes in monoclinic space group P2(1)/c (1a) comprising of 2D hydrogen bonded network via cyclic dimers. In aprotic solvent such as acetone on the other hand, 1 exhibits orthorhombic space group Pna 2(1) (1b) and emerges with 1D catemeric chain. Solvent-induced topological isomerism of cyclic dimers and helical catemeric chains arising from (i) bifurcated intra- and inter molecular hydrogen bondings viz. O-H...O=C interactions between C(2) hydroxyl and C(1), C(4) carbonyls, (ii) C-H...O interactions viz. C(3)-H...O(1)C(1) have been discussed. A signal for radical in 1 at g = 2.0058 is signatured by EPR spectrum and it's oxime derivative viz. 2-hydroxy-4-naphthoquinone-1-oxime 2, in solid state shows biradical and monoradical formation with aggregation of dimer and monomer due to non-covalent hydrogen bonds. Zero field split parameters for 2 are estimated to be D = 215 G, Ex = 13 G, Ey = 47 G at 298 K. A half field signal at 77 K indicates triplet ground state. Frozen glass EPR of 2 resolves as regioregular dimeric-monomeric species showing hyperfine interactions with 1-oximino nitrogen in dimer A (14N) = 15.5 G].

Topics: Acetone; Crystallography, X-Ray; Electron Spin Resonance Spectroscopy; Methanol; Molecular Structure; Naphthoquinones; Oximes; Solvents

Topics: Adult; Coloring Agents; Female; Humans; Male; Naphthoquinones; Oximetry; Oxygen

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Patch Tests; Tattooing

Topics: Adult; Blister; Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing

Henna (Lawsonia inermis, family Lythraceae) is a shrub cultivated in India, Sri Lanka and North Africa and contains the active dye lawsone (2-hydroxy-1,4-naphthoquinone). Henna dye is obtained from the dried leaves, which are powdered and mixed with oil or water and are used to prepare hair and body dyes. Temporary henna tattoos are readily available worldwide, last on the skin for several weeks and offer a self-limited, convenient alternative to a permanent tattoo. The addition of para-phenylenediamine (PPD), which is widely recognised as a sensitizer, increases the risk of allergic contact dermatitis from henna tattoo mixtures, and a number of cases have been reported. We examined 15 henna samples available in Korea for the presence of PPD and heavy metals such as nickel, cobalt, chromium, lead and mercury using high-performance liquid chromatography (HPLC), atomic absorption spectroscopy (AAS), mercury analyser and inductively coupled plasma emission spectroscopy. PPD, nickel and cobalt were detected in 3, 11 and 4 samples, respectively.

Topics: Chromatography, High Pressure Liquid; Cobalt; Dermatitis, Contact; Humans; Naphthoquinones; Nickel; Phenylenediamines; Spectrophotometry, Atomic; Tattooing

Topics: Acute Disease; Allergens; Child; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing

Quinones are widely distributed in the environment, both as natural products and as pollutants. This paper reports that one of the simplest quinones, 2-methyl-1,4-naphthoquinone (menadione), effectively inhibited apoptosis in the presence of UVA. Menadione suppressed the apoptosis induced by serum depletion and cell detachment. This effect was significantly enhanced by UVA irradiation. An antioxidant, N-acetylcysteine, completely inhibited the antiapoptotic effects of both menadione itself and menadione plus UVA, and peroxidation of the cells after treatment was observed using a probe to detect the intracellular production of peroxides. By contrast, 2-hydroxy-1,4-naphtoquinone (lawsone) showed no antiapoptotic effect in the presence or absence of UVA. Lawsone is reported not to undergo the redox process that produces reactive oxygen species. These results indicated that intracellular peroxidation contributed to the antiapoptotic effects of both menadione itself and menadione plus UVA. Dysregulation of the apoptotic process is critical to carcinogenesis. The photosensitization of quinone compounds as it relates to the inhibition of apoptosis should be examined in the future.

Topics: Acetylcysteine; Animals; Apoptosis; Cell Survival; DNA Fragmentation; Mice; Naphthoquinones; NIH 3T3 Cells; Peroxides; Ultraviolet Rays; Vitamin K 3

Topics: Coloring Agents; Humans; Naphthoquinones; Surgical Flaps; Tissue and Organ Harvesting

Topics: Adolescent; Burns, Chemical; Child; Coloring Agents; Humans; Male; Naphthoquinones; Tattooing

Temporary henna tattoo, which has become popular among young people, is obtained from the mixture of the plants Lawsonia alba or Lawsonia inermis and paraphenylenediamine (PPD). In forming reactions frequent development of anti-PPD substance is noticed. A 13-year old boy who started itching, erythema, enduration on the application area, increasingly urticarial rash, conjunctivitis and swelling of the lips 48 h after being applied the temporary henna tattoo was hospitalized. He had a local reaction to henna tattoo when he was 5-year old. He was treated with parenteral corticosteroids and oral antihistaminic drugs. Skin reactions persisted for 18 days. The patient showed no early reaction to henna 10% and PPD 1% concentration in saline solution but did late reaction (after 48 h) to PPD in diameter of 12x13 mm in prick test in 3 weeks after the reaction. A case who developed angioneurotic edema and urticaria to temporary henna tattoo noticed that the henna tattoo is not an innocent application and young people need to be informed on this subject.

Topics: Administration, Oral; Adolescent; Adrenal Cortex Hormones; Angioedema; Coloring Agents; Drug Combinations; Female; Histamine Antagonists; Humans; Hypersensitivity, Delayed; Infusions, Parenteral; Male; Naphthoquinones; Skin Tests; Tattooing; Time Factors; Treatment Outcome; Tuberculin; Urticaria

A case of contact dermatitis resulting from temporary tattooing with henna is described. The skin was stained using a dye described as 'black' henna. This is produced by the addition of paraphenylenediamine (PPD) to traditional henna dye in order to make temporary skin tattoos appear darker. Sensitisation to PPD may also cause sensitivity to printers' inks, clothing dyes, hair dyes, local anaesthetics, sulphonamides, and para-aminosalicylic acid. The case of contact dermatitis described responded to application of topical steroid with no sequelae; however patients may be left with hypo- or hyper-pigmentation of the skin or even permanent scarring.

Topics: Anti-Inflammatory Agents; Betamethasone Valerate; Dermatitis, Contact; Humans; Male; Naphthoquinones; Tattooing

Henna is used as a hair dye and to make temporary tattoos on the skin. It is usually mixed with p-phenylendiamine (PPD) to increase colour intensity and to reduce the time of fixation on the skin proteins. PPD can cross react with azoic dyes which are used as textile dyes. We studied a patient with skin eczema in the area of a henna temporary tattoo. The epicutaneous tests performed with the standard Trolab and Chemotecnique hair dressing and textile batteries, showed positive results to PPD, p-toluendiamine, 5-4aminophenol, Yellow 3, Orange Red and Red 1, and negative results to three types of henna. The eczema in this patient was due to sensitisation to PPD on a henna tattoo with cross reaction to azoic dyes. The recent fashion of applying temporal tattoos in occidental countries may produce an increase in the frequency of contact dermatitis due to henna mixtures with cross- reaction to related compounds and possibly producing permanent skin changes.

Topics: Adult; Coloring Agents; Cross Reactions; Dermatitis, Contact; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing; Time Factors

Topics: Adolescent; Allergens; Dermatitis, Allergic Contact; Diagnosis, Differential; Facial Dermatoses; Female; Hair Dyes; Humans; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Severity of Illness Index; Tattooing

Topics: Child; Child, Preschool; Coloring Agents; Dermatitis, Contact; Humans; Male; Naphthoquinones; Tattooing

To investigate the antimicrobial activity of henna's fresh and dry leaves and seeds obtained from Oman.. This study was carried out at the College of Medicine and Health Sciences, Sultan Qaboos University, Muscat, Sultanate of Oman during the period January-June, 2004. Crude extracts of fresh and dry leaves and seeds were investigated for their antimicrobial activity against 3 standard bacterial strains namely: Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Eleven different bacterial strains were obtained from patients attending the Sultan Qaboos University Hospital, Muscat, Sultanate of Oman. In addition, one Candida albicans (C. albicans) species was used for testing the antifungal activity of the Omani henna sample.. All fresh and dry leaves and seeds of the Omani henna demonstrated antibacterial activity against all 3 standard strains and the 11 patients' isolated strains. Henna dry leaves demonstrated the best in-vitro antimicrobial activity and in particular against Shigella sonnei. However, henna fresh and dry seeds failed to show any activity against C. albicans.. Omani henna does possess, in-vitro antibacterial activity against a wide spectrum of bacterial strains and C. albicans.

Topics: Anti-Bacterial Agents; Antifungal Agents; Candida albicans; Escherichia coli; Humans; Lawsonia Plant; Naphthoquinones; Plant Preparations; Pseudomonas aeruginosa; Seeds; Shigella sonnei; Staphylococcus aureus

Decorative henna skin painting can provoke severe reactions in the skin. We report 3 cases of unusual and persistent hyperpigmentation following nonpermanent henna tattoo, which alerted us to identify an additional side effect.

Topics: Adult; Female; Humans; Hyperpigmentation; Naphthoquinones; Tattooing

Experiments were conducted to examine the role of humic acid and quinone model compounds in bromate reduction by Fe(0). The reactivity of Fe(0) toward bromate declined by a factor of 1.3-2.0 in the presence of humic acid. Evidence was obtained that the quick complexation of humic acid with iron species and its adsorption passivated the iron surface and decreased the rate of bromate reduction by Fe(0). On the other hand, in the long run, the reduced functional groups present in humic acid were observed to regenerate Fe(II) and reduce bromate abiotically. Compared with the case of humic acid only, the simultaneous presence of Fe(II) and humic acid significantly increased the bromate removal rate. Fe(III)/Fe(II) acted as a catalyst in the oxidation of humic acid by bromate. Anthraquinone-2,6-disulfonate (AQDS) and lawsone did not cause any significant effect on the bromate reduction rate by Fe(0). However, the redox reactivity of lawsone in the presence of Fe(III) was evident, while AQDS did not show any under the tested conditions. The difference was attributable to the presence/ absence of reducing functional groups in the model compounds. The electron spin resonance further demonstrated that the redox functional groups in humic acid are most likely quinone-phenol moieties. Although the bromate reduction rate by regenerated Fe(II) is a few times slower than that by Fe(0), the reactive Fe(II) can be, alternatively, reductively formed to maintain iron surface activation and bromate reduction to prolong the lifetime of the zerovalent iron.

Topics: Adsorption; Anthraquinones; Bromates; Catalysis; Electron Spin Resonance Spectroscopy; Ferric Compounds; Humic Substances; Iron; Kinetics; Models, Chemical; Naphthoquinones; Oxidation-Reduction; Quinones; Spectroscopy, Fourier Transform Infrared

Topics: Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Tattooing

Topics: Allergens; Arm; Child, Preschool; Coloring Agents; Dermatitis, Allergic Contact; Diagnosis, Differential; Female; Humans; Hypopigmentation; Naphthoquinones; Patch Tests

Henna (Lawsonia inermis) has been used for centuries as a herbal hair and skin dye, but very little is known about its additives and contaminants that could adversely affect human health. An analytical method was developed to determine organochlorine compounds in henna, as they are still widely used in the areas where henna is grown. Samples were sonicated with n-hexane, extracts cleansed on Florisil sorbent and analysed using gas chromatography with electron capture detection. The overall recoveries were 17-33 % with the extraction RSD 5-21%, while the levels of lindane (gamma-HCH), p,p'-DDT, and p,p'-DDE in henna samples were 7-157 microg kg(-1). The same procedure was successfully applied to analyse black tea samples for the same compounds, and which showed lower contamination.

Topics: Chromatography, Gas; Coloring Agents; Drug Contamination; Food Contamination; Hair Dyes; Hydrocarbons, Chlorinated; Insecticides; Naphthoquinones; Tea

Contact dermatitis following the application of temporary paint-on henna tattoos indicates a potentially serious problem of active sensitization. We describe 2 cases involving sisters who travelled to Bali together and acquired a temporary black henna tattoo to the lower back region. Both sisters subsequently developed a contact dermatitis at the tattoo site, the dermatitis disseminating in one sister. There was persistent hyperpigmentation at the tattoo site in both sisters several months after the application. Patch testing revealed a positive reaction to para-phenylenediamine (PPD) in both sisters. One sister also showed reactions to other hair dyes and to multiple organic dyes. Allergic contact dermatitis to PPD contained in temporary henna tattoos is an increasing problem worldwide, with cross-reaction to related compounds and permanent skin changes, a frequent consequence of sensitization to this significant allergen.

Topics: Adolescent; Clothing; Coloring Agents; Dermatitis, Allergic Contact; Female; Hair Preparations; Humans; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing; Time Factors

Temporary henna tattoos are a popular fashion accessory in recent years. The tattoo dye consists of henna extract from the plant Lawsonia, and p-phenylenediamine to create a darker shade to the tattoo. Increasingly, emergency departments are seeing children with atopic reactions to these tattoos. The p-phenylenediamine component can cause a spongiotic dermatitis with lympho-histiocytic infiltrates. I present two cases of reactions to temporary tattoos in children attending the emergency department. The acute management of these cases and the possible future consequences of sensitization to p-phenylenediamine are discussed.

Topics: Adolescent; Child; Coloring Agents; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing

We have operated a microbial fuel cell in which glucose was oxidized by Klebsiella pneumoniae in the anodic compartment, and biomineralized manganese oxides, deposited by Leptothrix discophora, were electrochemically reduced in the cathodic compartment. In the anodic compartment, to facilitate the electron transfer from glucose to the graphite electrode, we added a redox mediator, 2-hydroxy-1,4-naphthoquinone. We did not add any redox mediator to the cathodic compartment because the biomineralized manganese oxides were deposited on the surface of a graphite electrode and were reduced directly by electrons from the electrode. We have demonstrated that biomineralized manganese oxides are superiorto oxygen when used as cathodic reactants in microbial fuel cells. The current density delivered by using biomineralized manganese oxides as the cathodic reactant was almost 2 orders of magnitude higher than that delivered using oxygen. Several fuel cells were operated for 500 h, reaching anodic potentials of -441.5 +/- 31 mVscE and cathodic potentials of +384.5 +/- 64 mVscE. When the electrodes were connected by a 50 Ohms resistor, the fuel cell delivered the peak power density of 126.7 +/- 31.5 mW/m2.

Topics: Bioelectric Energy Sources; Bioreactors; Electrochemistry; Electrodes; Glucose; Graphite; Klebsiella pneumoniae; Leptothrix; Manganese Compounds; Naphthoquinones; Oxides

Topics: Coloring Agents; Humans; Hyperpigmentation; Naphthoquinones; Risk Factors; Tattooing

Topics: Administration, Topical; Adrenal Cortex Hormones; Child; Coloring Agents; Dermatitis, Allergic Contact; Follow-Up Studies; Humans; Hypersensitivity, Delayed; Male; Naphthoquinones; Patch Tests; Risk Assessment; Tattooing

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Glucocorticoids; Humans; Male; Naphthoquinones; Ointments; Tattooing; Time Factors

Topics: Adolescent; Coloring Agents; Female; Humans; Naphthoquinones; Suicide

Topics: Coloring Agents; Dermatitis, Allergic Contact; Humans; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

[reaction: see text] Thermal decomposition of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone (lawsone) in the presence of indole derivatives affords 3-acylated indoles existing in their enol forms, through a ring contraction and alpha,alpha'-dioxoketene formation reaction. The same reactants afford 3-(3-indolyl)-2-hydroxy-1,4-naphthoquinones in a copper-catalyzed reaction. Enamines, among other C-nucleophiles tested, give analogous results.

Topics: Indoles; Molecular Structure; Naphthoquinones; Onium Compounds

The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.

Topics: Amines; Catalysis; Heterocyclic Compounds; Models, Biological; Naphthoquinones; Onium Compounds

The fragment of tau containing the first and third tubulin-binding motifs, involved in self-assembly of tau, was phosphorylated by protein kinase A (PKA). In the presence of hydroxynonenal (HNE) or in the presence of quinones such as juglone, 2,3-dimethoxy-5-methyl-1,4-benzoquinone (coenzyme Q(0) or DMM), or menadione, the polymerization of this phosphorylated tau fragment is catalyzed, whereas polymerization of the unmodified fragment takes place in a lesser extent. The quinones coenzyme Q(0) and menadione are found in every cell, including neural cells, and may interact with tau protein to facilitate its assembly into filamentous structures. These tau filaments, assembled in the presence of quinones, have a fibrillar morphology very similar to that of paired helical filaments present in the brains of patients with Alzheimer's disease.

Topics: Amino Acid Motifs; Amino Acid Sequence; Benzoquinones; Cyclic AMP-Dependent Protein Kinases; Humans; Molecular Sequence Data; Naphthoquinones; Neurofibrillary Tangles; Peptide Fragments; Phosphorylation; Polymers; Protein Binding; Protein Processing, Post-Translational; Quinones; Recombinant Proteins; tau Proteins; Tubulin; Ubiquinone; Vitamin K 1; Vitamin K 3

2-Hydroxy-1,4-naphthoquinone (HNQ) has been found positive in a previous chromosome aberration test in Chinese hamster ovary (CHO) cells and in a mouse bone marrow micronucleus test at 72h after oral administration (vehicle: DMSO). However it was negative at 24 and 48h sampling times, and in subsequent micronucleus tests that used 0.5% aqueous methyl cellulose (MC) as vehicle. We performed a bone marrow micronucleus test in male and female NMRI BRL/BR mice at oral doses of 75, 150 and 300mg/kg in two vehicles (DMSO and 0.5% aqueous MC), evaluated micronuclei at 24, 48 and 72h, plasma levels of HNQ at 0.5, 1 and 4h, and haematology parameters at 72h after administration. The mechanism of in vitro clastogenic activity of HNQ was investigated by evaluation of the potential of HNQ to produce oxidative DNA damage after treatment of CHO with 10mM HNQ, followed by quantification of DNA fragments using the comet assay. In the micronucleus test, HNQ at 300mg/kg produced mortality and clinical signs at similar incidence and severity for both vehicles. Levels of HNQ in the plasma of treated mice were dose-related, of similar magnitude for both vehicles, but higher in females than in males. Maximum concentrations were found at 0.5 or 1h. At 300mg/kg, HNQ slightly affected RBC parameters suggesting haematotoxicity. No increase in the frequency of micronuclei was observed for any dose, vehicle or time point, whereas the positive control substance (CPA) produced a clear positive response. No evidence of HNQ-induced oxidative DNA damage was found at clastogenic concentrations in vitro, whereas the positive control substance (H(2)O(2)) produced a clear increase. In conclusion, HNQ was negative for induction of bone marrow micronuclei in mice up to 72h after administration in two different vehicles, and its in vitro clastogenicity was not due to oxidative damage. These results confirm that HNQ poses no or negligible genotoxic risk.

Topics: Animals; Bone Marrow; CHO Cells; Cricetinae; DNA Damage; Mice; Micronucleus Tests; Naphthoquinones; Oxidative Stress

Henna is a traditional cosmetic agent and is used worldwide. It is used worldwide not only as a cosmetic agent to stain the hair, skin and nails but also is applied to the body on lesions in the treatment of seborrheic dermatitis or fungal infections. Different pathologies have been described as caused by henna. The aim of this study is to draw attention to the adverse effects of henna, applied over the whole body, observed in glucose-6-phosphate dehydrogenase (G6PD) enzyme deficient siblings. In the present paper, we report on two siblings with G6PD deficiency who developed haemolytic anaemia following topical application of henna to their whole body to treat skin lesions. Their parents were also found to be G6PD deficient. Even though anti-inflammatory, analgesic and antipyretic effects of henna have been shown, it may cause severe side-effects in some cases. For this reason, especially, in the regions where G6PD enzyme deficiency is common, people should be informed about the side-effects of topical henna application and clinicians should be aware of these manifestations.

Topics: Administration, Topical; Anemia, Hemolytic; Child; Dermatologic Agents; Female; Glucosephosphate Dehydrogenase Deficiency; Humans; Ichthyosis Vulgaris; Male; Naphthoquinones; Pedigree; Siblings

Lawsone (2-hydroxy-1,4-naphthoquinone) is the active ingredient of henna (Lawsonia alba), the crushed leaves of which are used as a cosmetic dye. Application of henna can induce a severe hemolytic anemia, and lawsone is thought to be the causative agent. Administration of lawsone to rats has been shown to induce a hemolytic response that is associated with oxidative damage to erythrocytes. However, direct exposure of isolated erythrocytes to lawsone did not provoke oxidative damage, suggesting that lawsone must undergo extra-erythrocytic bioactivation in vivo. In the present study, the survival of rat 51Cr-labeled erythrocytes in vivo after in vitro exposure to lawsone and its hydroquinone form, 1,2,4-trihydroxynaphthalene (THN) has been examined. Neither lawsone nor THN were directly hemolytic or methemoglobinemic, even at high concentrations (>3 mM). Lawsone had no effect on erythrocytic GSH levels, whereas THN (3 mM) induced a modest depletion (approximately 30%). Cyclic voltammetry revealed that the lack of hemotoxicity of lawsone was associated with a poor capacity to undergo redox cycling. In contrast, ortho-substituted 1,4-naphthoquinones without a 2-hydroxy group, such as 2-methyl- and 2-methoxy-1,4-naphthoquinone, were redox active, were able to deplete GSH, and were direct-acting hemolytic agents. An oxidant stress-associated hemolytic response to lawsone could be provoked, however, if it was incubated with GSH-depleted erythrocytes. The data suggest that lawsone is a weak direct-acting hemolytic agent that does not require extra-erythrocytic metabolism to cause hemotoxicity. Thus, the hemolytic response to henna may be restricted to individuals with compromised antioxidant defenses.

Topics: Anemia, Hemolytic; Animals; Cell Survival; Chromium Radioisotopes; Coloring Agents; Cytoskeletal Proteins; Electrochemistry; Glucosephosphate Dehydrogenase Deficiency; Glutathione; Hemolysis; Magnetic Resonance Spectroscopy; Male; Methemoglobin; Naphthoquinones; Oxidation-Reduction; Oxidative Stress; Pentose Phosphate Pathway; Rats; Rats, Sprague-Dawley; Reactive Oxygen Species

Topics: Adolescent; Dermatitis, Allergic Contact; Hair Dyes; Humans; Male; Naphthoquinones; Tattooing

Topics: Adolescent; Adult; Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Male; Middle Aged; Naphthoquinones; Patch Tests; Phenylenediamines; Risk Factors; Tattooing; Time Factors

Topics: Back; Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Phenylenediamines; Tattooing; Thiram

Topics: Aged; Benzocaine; Coloring Agents; Cross Reactions; Dermatitis, Allergic Contact; Drug Hypersensitivity; Humans; Male; Naphthoquinones; Phenylenediamines; Sulfonamides; Tattooing

While allergic reactions to henna painting are extremely rare, we have witnessed an increasing number of reports of cutaneous reactions after henna tattooing, also called temporary tattooing. The reason for this lies in the contemporary composition of the paint, which contains paraphenylenediamine (PPD). We present six patients who developed allergic contact dermatitis after skin painting with "black henna", and who showed hypersensitivity to PPD. We discuss the issue of the short sensitization period of our patients and the reported ones.

Topics: Adolescent; Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Male; Naphthoquinones; Phenylenediamines; Skin Tests; Tattooing

Topics: Child; Coloring Agents; Dermatitis; Humans; Male; Naphthoquinones; Tattooing

Topics: Allergens; Dermatitis, Allergic Contact; Diagnosis, Differential; Eczema; Female; Hair Dyes; Humans; Middle Aged; Naphthoquinones; Patch Tests; Scalp Dermatoses

2-Hydroxy-1,4-naphthoquinone (HNQ; Lawsone; CAS 83-72-7) is the principal natural dye ingredient contained in the leaves of Henna (Lawsonia inermis). Published genotoxicity studies on HNQ suggested it was a weak bacterial mutagen for Salmonella typhimurium strain TA98 or was more clearly mutagenic for strain TA 2637, both in the presence of metabolic activation. HNQ was unable to induce sex-linked recessive lethal mutations in Drosophila melanogaster. However, a small increase in micronucleus frequency was reported in the bone marrow of mice at a single mid-range dose level, 24h after intraperitoneal injection. In view of the wide use of Henna hair dyes it was deemed necessary to conduct a thorough investigation, under Good Laboratory Practice conditions, of the genotoxicity of HNQ. HNQ was non-mutagenic in bacterial (Ames test) or mammalian (V79 hprt) assays. It was borderline positive in a mouse lymphoma tk mutation assay and a chromosome aberration test (CHO cells), results that may reflect a similar clastogenic mechanism. Negative in vivo genotoxicity results were noted in the rat hepatocyte in vivo/in vitro UDS test, in peripheral lymphocytes (chromosome aberrations) of rats receiving repeated oral doses of HNQ at the MTD for 28 days, and in mouse and hamster bone marrow chromosome aberration tests. However small, but statistically significant increases in the incidence of bone marrow micronuclei were observed in two out of five tests at 72 h after dosing, but not at 24 or 48 h. There was evidence of haematotoxicity at 72 h, which may have been enhanced by the vehicle (DMSO) used in the positive tests. As erythropoiesis and administration of haematotoxic agents are known to induce small increases in the frequency of bone marrow micronuclei, typically at delayed sampling times, the data suggest that the positive 72 h response produced by HNQ is consistent with stimulation of haematopoiesis subsequent to haematological toxicity of HNQ, and not due to a DNA-reactive mechanism. Overall, the weight of evidence suggests that Henna and HNQ pose no genotoxic risk to the consumer.

Topics: Animals; Bone Marrow Cells; Cell Transformation, Neoplastic; Coloring Agents; Cricetinae; DNA; Dose-Response Relationship, Drug; Female; Hepatocytes; Leukemia L5178; Male; Mesocricetus; Mice; Micronuclei, Chromosome-Defective; Mutagenicity Tests; Mutagens; Naphthoquinones; Rats; Rats, Inbred Strains; Salmonella typhimurium

Quinones can function as redox mediators in the unspecific anaerobic reduction of azo compounds by various bacterial species. These quinones are enzymatically reduced by the bacteria and the resulting hydroquinones then reduce in a purely chemical redox reaction the azo compounds outside of the cells. Recently, it has been demonstrated that the addition of lawsone (2-hydroxy-1,4-naphthoquinone) to anaerobically incubated cells of Escherichia coli resulted in a pronounced increase in the reduction rates of different sulfonated and polymeric azo compounds. In the present study it was attempted to identify the enzyme system(s) responsible for the reduction of lawsone by E. coli and thus for the lawsone-dependent anaerobic azo reductase activity. An NADH-dependent lawsone reductase activity was found in the cytosolic fraction of the cells. The enzyme was purified by column chromatography and the amino-terminal amino acid sequence of the protein was determined. The sequence obtained was identical to the sequence of an oxygen-insensitive nitroreductase (NfsB) described earlier from this organism. Subsequent biochemical tests with the purified lawsone reductase activity confirmed that the lawsone reductase activity detected was identical with NfsB. In addition it was proven that also a second oxygen-insensitive nitroreductase of E. coli (NfsA) is able to reduce lawsone and thus to function under adequate conditions as quinone-dependent azo reductase.

Topics: Amino Acid Sequence; Anaerobiosis; Azo Compounds; Drug Resistance, Bacterial; Drug Resistance, Neoplasm; Escherichia coli; Escherichia coli Proteins; Molecular Sequence Data; Naphthoquinones; Nitroreductases; Oxidoreductases; Oxygen; Substrate Specificity

Topics: Drug Eruptions; Humans; Naphthoquinones; Tattooing

Topics: Allergens; Child; Coloring Agents; Dermatitis, Allergic Contact; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Adolescent; Dermatitis, Allergic Contact; Hair Dyes; Humans; Male; Naphthoquinones

The use of temporary natural henna painting for body adornment and hair dyeing is very common in several countries of the Indian subcontinent, Middle East, and North Africa, and the fad is spreading in other parts of the world. Several cases of para-phenylenediamine (PPD) contaminated, temporary traditional/natural henna induced sensitization and acute allergic reaction have been reported, along with occasional serious long term and rare fatal consequences. We report here a 17-year-old girl with blisters over her hands of five-days duration that appeared within 72 hours of applying a temporary henna paint to her hands during a social occasion. Similar lesions were noted on her face. She had previously applied black henna only once, a year earlier without developing any lesions. Clinical diagnosis of acute allergic contact dermatitis (ACD) was made. After a short course of oral corticosteroids, topical mometasone furaote 1.0% cream, and oral antihistamines, the lesions healed completely over the next four weeks leaving post-inflammatory hypopigmentation. Patch testing done with standard European battery, PPD 1% in petrolatum, and commercially available natural henna powder revealed a 3+ reaction to PPD at 48 hours. No reaction was seen at the natural henna site. Awareness of the condition among physicians and the public and regulation regarding warnings of the risks of using such products is urgently warranted.

Topics: Adolescent; Allergens; Dermatitis, Allergic Contact; Diagnosis, Differential; Facial Dermatoses; Female; Hand Dermatoses; Humans; Naphthoquinones; Patch Tests; Phenylenediamines

A woman developed widespread contact dermatitis after temporary tattooing with henna, caused by paraphenylenediamine (PPD) which had been added to the henna as an enhancer. The patient recovered after treatment; a week later an acute generalized rebound occurred after she wore dark clothing (black chador). Patch tests revealed type-IV allergy to PPD, along with multiple sensitisations to other textile dyes (disperse orange 3, para-aminoazobenzole, Bismark brown R). Temporary henna tattoos are not always harmless holiday souvenirs. The addition of color enhancers such as PPD into henna may lead to multiple contact allergies to other textile dyes.

Topics: Adrenal Cortex Hormones; Adult; Coloring Agents; Cross Reactions; Dermatitis, Contact; Female; Humans; Naphthoquinones; Phenylenediamines; Recurrence; Skin Tests; Tattooing

Topics: Back; Child; Coloring Agents; Dermatitis, Contact; Humans; Male; Naphthoquinones

Skin tattooing with henna seems a safe alternative to permanent skin tattooing. Contact dermatitis due to henna is rare. Most of the reactions are due to additives, especially paraphenylenediamine, which is added to speed up the process of skin dyeing and to give a darker brown to black colour ('black' henna) instead of the otherwise reddish brown henna colour. Paraphenylenediamine is a well-known strong sensitizer, particularly due to its use as a hair dye. Three patients, two boys aged 8 and 10 years and a 30-year-old woman, developed allergic contact dermatitis after skin painting, after which hypopigmentation remained. Patch tests with paraphenylenediamine were strongly positive in all three patients. This positive reaction means that they will never be able to dye their hair and that they have an increased risk of cross-reactions with other dyes, but also with local anaesthetics, sulfonamides, para-aminoazobenzoic acid or para-aminosalicylic acid.

Topics: Adult; Child; Coloring Agents; Cross Reactions; Dermatitis, Allergic Contact; Female; Humans; Hypopigmentation; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

An electrochemical system consisted of Gluconobacter oxydans as a microorganism and 2-hydroxy-1,4-naphthoquinone (HNQ) as a mediator has been setup to examine the effect of initial carbon sources on the detection of glucose. Catalytic current due to the oxidation of glucose was observed only when both G. oxydans and HNQ were present. From amperometric measurements, it was found that the sensitivity strongly depended on the initial carbon sources. The sensitivity was highest for the cells cultured in a fructose-containing medium and decreased in the order, mannitol > sucrose > glucose > galactose > glycerol. The difference in sensitivity was explained by considering the current rising pattern at an initial stage of a microbial fuel cell constructed with the same components. The rising time, not the fuel cell efficiency, could directly be related to the sensitivity order. A sensor where G. oxydans was confined at the vicinity of the electrode by the semipermeable membrane was constructed. A linear response over a millimolar range of glucose concentration was observed with a cell grown in galactose-containing medium. This work demonstrates that the initial carbon source play an important role on glucose sensoring and should be considered in a real application.

Topics: Bioelectric Energy Sources; Biosensing Techniques; Carbon; Cells, Cultured; Electrochemistry; Gluconobacter oxydans; Glucose; Glycerol; Hexoses; Naphthoquinones; Oxidation-Reduction; Sensitivity and Specificity

The ethanolic extract of Lawsonia inermis leaves and lawsone tested for trypsin inhibitory activity showed an IC(50) value of 64.87 and 48.6 microg/ml, respectively.

Topics: Anti-Inflammatory Agents; Inhibitory Concentration 50; Lawsonia Plant; Naphthoquinones; Plant Extracts; Trypsin; Trypsin Inhibitors

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Female; Follow-Up Studies; Humans; Hypersensitivity, Delayed; Hypopigmentation; Immunization; Leg Dermatoses; Naphthoquinones; Patch Tests; Perfume; Tattooing

The effects of the redox mediator lawsone (2-hydroxy-1,4-naphthoquinone) on the ability of Escherichia coli to reduce anaerobically polymeric azo compounds were analysed. Two types of polymeric azo compounds were tested, that have been proposed as putative tools for the site-specific targeting of drugs to the colon. The first group of polymers consisted basically of linear chains of polymethacrylic acid or polymethylmethacrylate which were interrupted by subunits of 4,4'-bis(methacryloylamino)azobenzene. These polymers differed significantly in their hydrophilicity according to the relative proportion of polymethacrylic acid used for the polymerization procedure. The second group of polymers consisted of almost water-insoluble poly(ether-ester)azo polymers that were composed of 4-(6-hydroxyhexyl)oxy-phenylazobenzoate and 16-hydroxyhexadecanoate. The addition of lawsone to the anaerobically incubated cultures of E. coli resulted in a pronounced increase in the reduction rates of the water-soluble poly(methacrylate-co-4,4'-bis(methacryloylamino)azobenzene) and in a much smaller, but significant, increase in the reduction rates of the hydrophobic poly(ether-ester)azo polymers. An increase in the amount of azo groups resulted, for the hydrophobic poly(ether-ester)azo polymers, in an increased reduction rate in the presence of the redox mediator lawsone.

Topics: Azo Compounds; Biodegradation, Environmental; Escherichia coli; Hydrophobic and Hydrophilic Interactions; Methylmethacrylates; Molecular Weight; Naphthoquinones; Oxidation-Reduction; Palmitic Acids; Polymers; Polymethacrylic Acids; Time Factors; Water

Recently, temporary paint-on tattoos have become increasingly popular as a safe alternative to permanent tattoos in Asia and other regions. The most common dye for such temporary tattoos is henna, a vegetable dye. Henna is considered to possess low allergenicity because the incidence of allergic contact dermatitis to henna has rarely been reported. However, recently, allergic reactions to henna used in temporary tattoos have been reported frequently.. Ten patients developed inflamed skin eruptions after receiving temporary paint-on tattoos in either Thailand or Indonesia. The 6 patients who were patch tested all exhibited moderate to strong positive reactions to p-phenylenediamine (1% in petrolatum). Four of the 6 patients were then tested with commercial black henna obtained from Thailand, and all 4 had strong positive reactions. A skin biopsy specimen showed lichenoid dermatitis. Mass spectrometry analysis of commercial black henna for molecular weight revealed a major peak at the mass-charge ratio of 108.1, which corresponds to the molecular weight of p-phenylenediamine.. The most likely causative agent for the lichenoid reaction associated with use of commercial black henna for temporary tattooing, currently popular in Southeast Asia, is p-phenylenediamine. With the increased popularity of temporary paint-on tattoos, clinicians should be aware of the possible associated complications.

Topics: Adolescent; Adult; Age Distribution; Biopsy, Needle; Dermatitis, Allergic Contact; Female; Humans; Immunohistochemistry; Incidence; Male; Mass Spectrometry; Naphthoquinones; Patch Tests; Risk Assessment; Risk Factors; Sampling Studies; Sex Distribution; Taiwan; Tattooing

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Hypersensitivity, Delayed; Naphthoquinones; Tattooing

Temporary black henna tattoos are very popular as body adornment. Although contact allergy to natural henna is unusual, the inclusion of hair dye, p-phenylenediamine (PPD), increases the risk of contact sensitization.. This study was performed to identify the presence and concentration of PPD in a black henna tattoo mixture to which our patient developed contact allergy.. The presence of PPD in a black henna tattoo mixture, various samples of commercially available henna powders, and several hair dye products was qualitatively and quantitatively detected using high performance liquid chromatography (HPLC).. This study demonstrated that PPD was present in the black henna tattoo mixture at a concentration of 15.7%, which is significantly higher than commercial hair dye preparations.. The presence of PPD in black henna tattoo mixtures in high concentration poses a health hazard and a risk of allergic contact sensitization with potential long-term consequences.

Topics: Adult; Arm; Back; Chromatography, High Pressure Liquid; Coloring Agents; Dermatitis, Allergic Contact; Diagnosis, Differential; Female; Humans; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

The addition of quinoid redox mediators to anaerobically incubated cultures of various taxonomically different bacterial species resulted in significantly increased reduction rates for the azo dye amaranth. From different quinones tested, generally anthraquinone-2-sulfonate (AQS) and lawsone (2-hydroxy-1,4-naphthoquinone) caused the highest increase in the azoreductase activities. The effects of AQS and lawsone were studied in greater detail with Sphingomonas xenophaga BN6 and Escherichia coli K12. Both strains reduced the quinones under anaerobic conditions with significantly different relative activities. The chemically reduced forms of AQS, lawsone, and different other quinones were assayed for their ability to decolorize amaranth, and a good correlation between the redox potentials of the quinones and the reduction rates of the azo dyes was observed. The addition of AQS or lawsone also increased the ability of unacclimated sewage sludge to reduce azo dyes. Chemically pure lawsone could be replaced by the powdered leaves of the henna plant which contain significant amounts of lawsone.

Topics: Azo Compounds; Bacteria, Anaerobic; Coloring Agents; Naphthoquinones; Oxidation-Reduction; Quinones; Sewage

Topics: Adolescent; Child; Coloring Agents; Dermatitis, Contact; Female; Humans; Lichenoid Eruptions; Male; Naphthoquinones; Time Factors

Topics: Adult; Female; Humans; Hypersensitivity, Immediate; Naphthoquinones

To guarantee invariable skin markings in patients undergoing a course of external radiotherapy, especially using conformal techniques. Cutaneous markings with henna also increase patient comfort, because washing and showering are allowed.. Henna, a completely natural product, is a skin colorant with a history of 5,000 years. It is applied to the skin in the form of a paste. While drying, henna stains the superficial skin layers for several weeks, and the marked area can be exposed to water arbitrarily. In case of fading of the stain before the end of radiotherapy, the marking procedure can be repeated. From November 1998 until March 2000, we performed skin markings with henna in 158 patients with different tumor sites. The majority of patients received conformal radiotherapy techniques. All patients have been evaluated concerning durability of the markings, the. The median durability of henna staining is 23 days (range 12-48 days). On average, two marking procedures (range 1-4) are necessary for a patient treated with curative intent. Although washing and showering are freely permitted, no adverse cutaneous side effects (e.g., erythema, allergic reactions) have been observed.. Skin marking by temporary tattooing with henna increases the accuracy of external radiotherapy. It yields stable and invariable markings for the entire course of radiotherapy and also increases the comfort of patients.

Topics: Humans; Naphthoquinones; Radiotherapy, Conformal; Tattooing

Four patients developed contact dermatitis to black henna tattoos on holiday in the Middle East and Asia. Two to ten days after skin painting an itchy, reddish swelling developed at the site of the tattoo exactly following its sharply demarcated borders. Histological investigation of the lesions revealed spongiotic dermatitis with dense lymphohistiocytic infiltrates. Patch testing in all patients showed a strong reaction to p-phenylenediamine (PPD). The other tests, including standard series and henna powder, were all negative. Healing time after application of topical class III and IV steroids was prolonged. These reports show an impressive side effect of temporary tattoos with possible long-term damage. Rather than henna, the causative agent in the pastes used for temporary tattoos appears to be PPD, a widely used dye that is added to the pastes in high concentrations to produce a darker shade. The growing incidence of this complication requires close observation, while practitioners should be aware of this sensitisation and of possible subsequent allergic reactions, especially after hair colouring with dyes based on PPD.

Topics: Adult; Coloring Agents; Dermatitis, Contact; Female; Humans; Male; Naphthoquinones; Phenylenediamines; Tattooing

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Female; Hair Dyes; Humans; Naphthoquinones

We examined the effects of a 35% ethanol extract (IB) from the petals of Impatiens balsamina L. and the principal active compounds from IB on chronic and serious pruritus and the development of dermatitis using NC mice, a model of atopic dermatitis. IB at 100 mg/kg significantly inhibited serious scratching behaviour in the NC mouse with established dermatitis when administered i.v. 1 h before, or p.o. 24 h before the measurement. A 10 microg/kg dose of kaempferol 3-rutinoside and 2-hydroxy-1,4-naphthoquinone (lawsone) isolated from IB also inhibited scratching behaviour in the NC mouse with established dermatitis. When 4-week-old NC mice with no symptoms were administered orally 100 mg/kg/day of IB until 13 weeks of age, protection was also noted against scratching behaviour during the development of dermatitis. IB was effective for the prevention and treatment of atopic dermatitis.

Topics: Animals; Antipruritics; Behavior, Animal; China; Dermatitis, Atopic; Disease Models, Animal; Drugs, Chinese Herbal; Glucosides; Impatiens; Male; Mice; Mice, Inbred Strains; Naphthoquinones; Phytotherapy; Plant Extracts; Plant Structures; Plants, Medicinal; Pruritus; Quercetin

Topics: Allergens; Arm; Dermatitis, Allergic Contact; Diagnosis, Differential; Female; Humans; Naphthoquinones; Patch Tests; Tattooing

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Tattooing

Haemolytic crisis in glucose-6-phosphate dehydrogenase deficient individuals following topical application of henna occurred in four children: a female neonate (haemoglobin 50 g/l, serum bilirubin 700 micromol/l), who recovered after exchange transfusion; a male infant (haemoglobin 28 g/l) who died despite transfusion; and two preschool children (haemoglobin 40 and 41 g/l respectively).

Topics: Acute Disease; Child, Preschool; Coloring Agents; Fatal Outcome; Female; Glycogen Storage Disease Type I; Hemolysis; Humans; Infant; Infant, Newborn; Male; Naphthoquinones

Topics: Adolescent; Child; Coloring Agents; Dermatitis, Allergic Contact; Erythema Multiforme; Female; Humans; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Vitiligo

The growth of the white-rot basidiomycete Pleurotus sajor-caju in malt-agar plates was inhibited by three naturally occurring, plant-derived naphthoquinones: juglone, lawsone, and plumbagin. The latter two compounds exerted the most potent antifungal activity, and lawsone killed the mycelium at concentrations higher than 200 ppm. Plates containing juglone and lawsone presented large decolorized areas extending from area of fungal growth, suggesting an extracellular enzymatic degradation of these quinones. Screening of culture plates for extracellular enzymatic activities revealed the presence of both laccase and veratryl alcohol oxidase in most plates, the diffusion of both enzymes matching the decolorized area. In agitated cultures, the presence of juglone was found to stimulate the production of veratryl alcohol oxidase in a significant manner. This is the first time degradation of plant derived naphthoquinones by a white-rot fungus is reported.

Topics: Biodegradation, Environmental; Culture Media; Microbial Sensitivity Tests; Naphthoquinones; Plants; Pleurotus

Topics: Child; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

Two pentacyclic triterpenoids have been isolated from the aerial parts of Lawsonia alba. The structures of the new constituents, named as lawsonic acid and lawsonin have been elucidated as 3 alpha-E-ferulyloxy-lup-20(29)-en-28-oic acid and 3 alpha-E-ferulyloxy-urs-11-en-13 beta-ol respectively through spectroscopic studies.

Topics: Antifungal Agents; Lythraceae; Naphthoquinones; Triterpenes

The use of traditional cosmetics and remedies such as kohl and henna is very common in Morocco, especially among women, children and babies. Kohl is a dangerous eye cosmetic. It is usually mixed with other harmful substances, then applied on women's eyebrows and used in skin treatments for infants. Henna is another traditional product, with religious associations, which has been widely used over the centuries for cosmetic and medical purposes. Many people add various herbs or other substances to the henna in order to strengthen it or to give it a stronger colour. Our results were reassuring in that the concentrations of lead found in non-elaborate (henna only) samples of henna were low. However, when henna was mixed with other products (elaborate henna), these concentrations increased. Lead concentrations in kohl were very high however, unlike henna, were lower in mixed kohl as mixing with other products diluted the concentration of lead. Nevertheless, in both types of kohl, lead concentrations were very high and consequently constitute a risk for public health, particularly for children.

Topics: Adult; Coloring Agents; Cosmetics; Drug Contamination; Female; Humans; Infant, Newborn; Lead; Medicine, Traditional; Naphthoquinones; Sulfides; Trace Elements

A young girl presented with a hypopigmentation in the shape of the sun. During a holiday in Egypt 3 months before a non-permanent henna tattoo had been applied on her right upper arm. Three to 4 days later there was a severe cutaneous reaction followed by massive swelling of the arm. The lesion took 6 weeks to subside. Patch testing revealed positive reactions to para-phenylenediamine (PPD) but not to henna or any other standard allergen. Especially in Arabic countries PPD is a common additive in natural henna preparations to enhance the weak colouring properties of the natural henna dye. We conclude that henna preparations may contain 'hidden' allergens, such as PPD, which can provoke severe cutaneous reaction without any cosensitization to the henna dye itself.

Topics: Child; Female; Follow-Up Studies; Humans; Hypersensitivity, Delayed; Hypopigmentation; Naphthoquinones; Patch Tests; Risk Assessment; Tattooing

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Tattooing

Mitochondrially-bound dihydroorotate dehydrogenase (EC 1.3.99.11) catalyzes the fourth sequential step in the de novo synthesis of uridine monophosphate. The enzyme has been identified as or surmised to be the pharmacological target for isoxazol, triazine, cinchoninic acid and (naphtho)quinone derivatives, which exerted antiproliferative, immunosuppressive, and antiparasitic effects. Despite this broad spectrum of biological and clinical relevance, there have been no comparative studies on drug-dihydroorotate dehydrogenase interactions. Here, we describe a study of the inhibition of the purified recombinant human and rat dihydroorotate dehydrogenase by ten compounds. 1,4-Naphthoquinone, 5,8-hydroxy-naphthoquinone and the natural compounds juglon, plumbagin and polyporic acid (quinone derivative) were found to function as alternative electron acceptors with 10-30% of control enzyme activity. The human and rat enzyme activity was decreased by 50% by the natural compound lawsone ( > 500 and 49 microM, respectively) and by the derivatives dichloroally-lawsone (67 and 10 nM), lapachol (618 and 61 nM) and atovaquone (15 microM and 698 nM). With respect to the quinone co-substrate of the dihydroorotate dehydrogenase, atovaquone (Kic = 2.7 microM) and dichloroally-lawsone (Kic = 9.8 nM) were shown to be competitive inhibitors of human dihydroorotate dehydrogenase. Atovaquone (Kic = 60 nM) was also acompetitive inhibitor of the rat enzyme. Dichloroally]-lawsone was found to be a time-dependent inhibitor of the rat enzyme, with the lowest inhibition constant (Ki* = 0.77 nM) determined so far for mammalian dihydroorotate dehydrogenases. Another inhibitor, brequinar was previously reported to be a slow-binding inhibitor of the human dihydroorotate dehydrogenase [W. Knecht, M. Loffler, Species-related inhibition of human and rat dihyroorotate dehydrogenase by immunosuppressive isoxazol and cinchoninic acid derivatives, Biochem. Pharmacol. 56 (1998) 1259-1264]. The slow binding features of this potent inhibitor (Ki* = 1.8 nM) with the human enzyme, were verified and seen to be one of the reasons for the narrow therapeutic window (efficacy versus toxicity) reported from clinical trials on its antiproliferative and immunosuppressive action. With respect to the substrate dihydroorotate, atovaquone was an uncompetitive inhibitor of human dihydroorotate dehydrogenase (Kiu = 11.6 microM) and a non-competitive inhibitor of the rat enzyme (Kiu = 905/ Kic = 1,012 nM). 1.5 mM po

Topics: Animals; Atovaquone; Benzoquinones; Binding, Competitive; Biphenyl Compounds; Dihydroorotate Dehydrogenase; Enzyme Inhibitors; Humans; Inhibitory Concentration 50; Kinetics; Naphthoquinones; Oxidoreductases; Oxidoreductases Acting on CH-CH Group Donors; Quinones; Rats; Substrate Specificity

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Follow-Up Studies; Humans; Lichenoid Eruptions; Male; Naphthoquinones; Neck; Tattooing

Topics: Administration, Topical; Adult; Anti-Inflammatory Agents; Coloring Agents; Dermatitis, Allergic Contact; Female; Glucocorticoids; Humans; Middle Aged; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

Topics: Administration, Topical; Adult; Anti-Inflammatory Agents; Coloring Agents; Dermatitis, Allergic Contact; Humans; Hydrocortisone; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Pruritus; Tattooing

Skin painting (pseudotattooing) with henna is traditionally performed mainly in Muslim or Hindu persons. Recently, transient artists have begun using black henna mixtures to temporarily paint the skin. Emergence of allergic contact dermatitis after application indicates the presence of a skin sensitizer in such preparations and poses future risks.. Four patients developed allergic contact dermatitis after skin painting with black henna performed in France, Egypt, and the United States. The delay of symptoms suggested previous sensitization in 1 patient and active sensitization in 3 patients. Of 3 patients who underwent patch testing, the results were positive for p-phenylenediamine in 3 patients and for p-toluylenediamine in 1 patient. These sensitizers are found in hair dye preparations.. The mixtures used by the artists possibly contained natural henna, a rare and weak skin sensitizer, and likely contained chemical coloring agents, diaminobenzenes, such as p-phenylenediamine and/or diaminotoluenes. The long duration of skin contact, the high concentrations of sensitizing materials, and the lack of a neutralizing agent dramatically increase the risk of skin sensitization, which is why such substances are prohibited for direct skin application. Because of the worldwide vogue of skin painting, future cases of sensitization to p-phenylenediamine and diaminobenzenes or diaminotoluenes are expected.

Topics: Adult; Allergens; Child; Coloring Agents; Dermatitis, Allergic Contact; Diagnosis, Differential; Female; Humans; Male; Naphthoquinones; Patch Tests; Phenylenediamines; Tattooing

Contact dermatitis to henna are rarely reported. Most of the time, they are related to additives, especially scented oils or paraphenylene diamine. This latter substance is added to shorten the time of application and to enhance the darkness of the color. We report one case of an allergic contact dermatitis to henna skin tattoo, probably related to a paraphenylene diamine derivative.. A 25-year-old woman developed an allergic contact dermatitis at the site of application of two henna skin tattoos on her right arm. She never dyed her hair and wore dark clothing without problems. Epicutaneous tests were positive for henna paste, paraphenylene diamine, N-isopropyl-N'phenylparaphenylene diamine and five chemical dyes, probably related to cross- reactions between paraphenylene diamine and these dyes. Epicutaneous test with henna powder was negative, confirming the absence of allergy to henna. Fluorescence analysis detected the presence of a primary amine in henna paste but high performance liquid chromatography analysis did not reveal the presence of paraphenylene diamine or any suspect dye. An another allergen, related compound of paraphenylene diamine, was probably present but we failed to identify it with precision.. Labile henna skin tattoos are in fashion at the moment in western European countries. They can be a secrete source of paraphenylene diamine, or one of its related compounds, sensitization.

Topics: Adult; Coloring Agents; Dermatitis, Contact; Female; Humans; Naphthoquinones; Tattooing

Topics: Child, Preschool; Cicatrix; Coloring Agents; Dermatitis, Contact; Humans; Keloid; Male; Naphthoquinones; Tattooing

It has previously been shown that rats pre-treated with butylated hydroxyanisole (BHA), a well-known inducer of the enzyme DT-diaphorase, are protected against the harmful effects of 2-methyl-1,4-naphthoquinone. This is consistent with a role for diaphorase in the detoxification of this quinone, but it is not known if increased tissue levels of this enzyme give protection against other naphthoquinone derivatives. In the present study, rats were dosed with BHA and then challenged with a toxic dose of 2-hydroxy-1,4-naphthoquinone, a substance that causes haemolytic anaemia and renal damage in vivo. Pre-treatment with BHA had no effect upon the nephrotoxicity of 2-hydroxy-1,4-naphthoquinone, but the severity of the haemolysis induced by this compound was increased in the animals given BHA. DT-Diaphorase is known to promote the redox cycling of 2-hydroxy-1,4-naphthoquinone in vitro, with concomitant formation of 'active oxygen' species. The results of the present experiment suggest that activation of 2-hydroxy-1,4-naphthoquinone by DT-diaphorase may also occur in vivo and show that increased tissue levels of DT-diaphorase are not always associated with naphthoquinone detoxification.

Topics: Anemia, Hemolytic; Animals; Butylated Hydroxyanisole; Drug Interactions; Enzyme Induction; Female; Kidney; Liver; NAD(P)H Dehydrogenase (Quinone); Naphthoquinones; Rats; Rats, Sprague-Dawley; Spleen; Stomach

Topics: Adult; Coloring Agents; Cosmetics; Dermatitis, Contact; Drug Eruptions; Female; Hand Dermatoses; Humans; Middle Aged; Naphthoquinones

It has previously been shown that rats pre-treated with butylated hydroxyanisole (BHA), a well-known inducer of the enzyme DT-diaphorase, are protected against the toxic effects of 2-methyl-1,4-naphthoquinone but are made more susceptible to the harmful action of 2-hydroxy-1,4-naphthoquinone. In the present experiments, the effects of BHA have been compared with those of other inducers of DT-diaphorase. Rats were dosed with BHA, butylated hydroxytoluene (BHT), ethoxyquin (EQ), dimethyl fumarate (DMF) or disulfiram (DIS) and then challenged with a toxic dose of the naphthoquinones. All the inducers protected against the haemolytic anaemia induced by 2-methyl-1,4-naphthoquinone in rats, with BHA, BHT and EQ being somewhat more effective than DMF and DIS. A similar order of activity was recorded in the relative ability of these substances to increase hepatic activities of DT-diaphorase, consistent with a role for this enzyme in facilitating conjugation and excretion of this naphthoquinone. In contrast, all the compounds increased the haemolytic activity of 2-hydroxy-1,4-naphthoquinone. DMF and DIS were significantly more effective in this regard than BHA, BHT and EQ. DMF and DIS also caused a much greater increase in levels of DT-diaphorase in the intestine, suggesting that 2-hydroxy-1,4-naphthoquinone is activated by this enzyme in the gut. BHA, BHT and EQ had no effect on the nephrotoxicity of 2-hydroxy-1,4-naphthoquinone, but the severity of the renal lesions was decreased in rats pre-treated with DMF and DIS. The results of the present experiments show that modulation of tissue levels of DT-diaphorase may not only alter the severity of naphthoquinone toxicity in vivo, but may also change the relative toxicity of these substances to different target organs.

Topics: Animals; Butylated Hydroxyanisole; Butylated Hydroxytoluene; Dimethyl Fumarate; Disulfiram; Enzyme Induction; Ethoxyquin; Female; Fumarates; NAD(P)H Dehydrogenase (Quinone); Naphthoquinones; Rats; Vitamin K 3

Streptomyces coelicolor Müller contains two superoxide dismutases (SODs), nickel-containing (NiSOD) and iron- and zinc-containing SOD (FeZnSOD). The sodF gene encoding FeZnSOD was isolated by using PCR primers corresponding to the N-terminal peptide sequence of the purified FeZnSOD and a C-terminal region conserved among known FeSODs and MnSODs. The deduced amino acid sequence exhibited highest similarity to Mn- and FeSODs from Propionibacterium shermanii and Mycobacterium spp. The transcription start site of the sodF gene was determined by primer extension. When the sodF gene was cloned in pIJ702 and introduced into Streptomyces lividans TK24, it produced at least 30 times more FeZnSOD than the control cells. We disrupted the sodF gene in S. lividans TK24 and found that the disruptant did not produce any FeZnSOD enzyme activity but produced more NiSOD. The expression of the cloned sodF gene in TK24 cells was repressed significantly by Ni, consistent with the regulation pattern in nonoverproducing cells. This finding suggests that the cloned sodF gene contains the cis-acting elements necessary for Ni regulation. When the sodF mRNA in S. coelicolor Muller cells was analyzed by S1 mapping of both 5' and 3' ends, we found that Ni caused a reduction in the level of monocistronic sodF transcripts. Ni did not affect the stability of sodF mRNA, indicating that it regulates transcription. S. lividans TK24 cells overproducing FeZnSOD became more resistant to oxidants such as menadione and lawsone than the control cells, suggesting the protective role of FeZnSOD. However, the sodF disruptant survived as well as the wild-type strain in the presence of these oxidants, suggesting the complementing role of NiSOD increased in the disruptant.

Topics: Amino Acid Sequence; Base Sequence; Cloning, Molecular; Drug Resistance, Microbial; Escherichia coli; Gene Expression Regulation, Bacterial; Gene Expression Regulation, Enzymologic; Molecular Sequence Data; Mycobacterium; Naphthoquinones; Propionibacterium; Recombinant Proteins; Sequence Alignment; Sequence Homology, Amino Acid; Spores, Bacterial; Streptomyces; Superoxide Dismutase; Superoxides; Transcription, Genetic; Vitamin K

Quinones were studied for their growth inhibitory effect on cultured malignant cells. HCT-15 cells derived from human colon carcinoma were used for these experiments. Quinones used were arbutin in the benzoquinone group, juglone and lawsone in the naphthaquinone group, alizarin, emodin, 1,8-dihydroxyanthraquinone, and anthraquinone in the anthraquinone group, and xanthone. Cultured cells were incubated with various concentrations of the quinones for four days in a 5% CO2 incubator, after which cell numbers were counted and significance of differences was analyzed by Student's t test. Anthraquinones and naphthaquinones used in these experiments were more effective than the monocyclic quinone. The 50% suppression dose was less than 12.5 micrograms/ml for them. The number of OH groups seemed to play an important role in the degree of the cell growth inhibition: anthraquinones with 2 or 3 OH groups were more effective than those with no OH group like, 9,10-dioxoanthracene and xanthone. In fact, anthraquinones with no OH group and xanthone were not significantly effective. Flow cytometric histograms revealed a specific pattern; that is, lawsone and juglone in the naphthaquinone group and alizarin and 1,8-dihydroxy-anthraquinone in the anthraquinone group blocked mainly the S phase, and emodin in the anthraquinone group blocked the G1 to S phase of the cell cycle.

Topics: Anthraquinones; Antineoplastic Agents; Arbutin; Cell Division; Colonic Neoplasms; Humans; Naphthoquinones; Quinones; Tumor Cells, Cultured; Xanthenes; Xanthones

Continuing a program on the chemistry and biological activity of compounds from the Brazilian flora, the lytic activity against bloodstream forms of T. cruzi of nine new heterocyclic naphthooxazole and naphthoimidazole derivatives obtained from the reaction of naphtoquinones isolated from Tabebuia sp. (Tecoma) with amino-containing reagents has been studied. Also for the first time the biological activity of allyl derivatives of lawsone, a natural quinone from Lausonia alba inactive against T. cruzi, is reported. The introduction of an allyl group in lawsone gives rise to O-allyl-lawsone and C-allyl-lawsone that showed activity against the parasite, with ID50 values of 420.7 +/- 71.1 and 330.7 +/- 62.4 mumol/l, respectively. The trypanocidal activity of the naphtho heterocyclics synthesized from the original quinones showed no concordant behavior in relation to the parent compound. Six of nine of the synthesized compounds presented lower ID50 values than crystal violet, indicating a general trend of activity among naphthalenic heterocyclics of the oxazole/imidazole type. However, their chemical structures do not endow them with the capacity of free radical generation by biological reduction as the quinoidal moiety, nor do they have chemical reducible appendage like the nitro group of nifurtimox and benznidazole, responsible for such behaviour. As a hypothesis, the pattern of their biological actions should be focused in other aspects of their chemical structures. Because of their polycyclic planar topology, these derivatives are potential candidates for experimental tests as DNA intercalating agents.

Topics: Animals; Brazil; Chagas Disease; Heterocyclic Compounds; Intercalating Agents; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mice; Naphthoquinones; Plants, Medicinal; Quinones; Spectrophotometry, Infrared; Trypanocidal Agents; Trypanosoma cruzi

Vegetable dyes can be recommended to patients sensitized to oxidative dyes due to their low allergenic power. The most important of these is henna which is used as a reddishbrown hair dye in some parts of the world. Different pathologies have been described caused by henna but the incidence of contact dermatitis appears to be extremely rare. In the present paper, we describe the case of a 30-year-old woman who developed allergic contact dermatitis following application of henna, but who did not work with the dye professionally.

Topics: Adult; Coloring Agents; Dermatitis, Allergic Contact; Female; Humans; Naphthoquinones; Skin; Skin Tests

Topics: Adult; Coloring Agents; Dermatitis, Contact; Female; Humans; Nails; Naphthoquinones

To evaluate the in vitro oxidation potential of lawsone (2-hydroxy-1,4 naphthoquinone). Lawsone is a chemical present in henna, the crushed leaves of which are used worldwide as a cosmetic agent to stain the hair, skin, and nails.. Venous blood from glucose-6-phosphate dehydrogenase (G6PD)-normal and G6PD A- subjects were incubated with various amounts of lawsone for 2 hours at 37 degrees C. Reduced glutathione and methemoglobin (MHb) levels were measured before and after incubation.. Final molar concentrations of lawsone in normal blood of 1.4, 2.8, 5.7, and 8.6 x 10-3 mol/L increased MHb percentages from 0.5% to 2.2%, 8.3%, 9.5% and 12.5%, respectively. In a C6PD A- blood, MHb percentages were 19.8%, 32.2%, 44.9%, and 53.9%. At a lawsone concentration of 2.8 x 10-3 mol/L, blood from 15 healthy adults formed MHb percentages of 7.4% +/- 3.3% (+/- 1 SD); in blood from 4 G6PD A- adults, percentages were 44.5%, 40.6%, 41.3%, and 42.8%. Simultaneous measurements of reduced glutathione revealed preincubation values of greater than 40 mg/100 mL of red cells in blood of healthy and G6PD A- subjects. Postincubation values were greater than 40 in blood of healthy subjects and less than 40 in blood of G6PD A- subjects.. These in vitro observations indicate that lawsone is an agent capable of causing oxidative hemolysis. In regions of the world where there is a high incidence of G6PD deficiency and unexplained hyperbilirubinemia, oxidative hemolysis secondary to the cutaneous application of henna could be the initiating event.

Topics: Adult; Coloring Agents; Cosmetics; Erythrocytes; Glucosephosphate Dehydrogenase; Glucosephosphate Dehydrogenase Deficiency; Glutathione; Hemolysis; Humans; Infant, Newborn; Jaundice, Neonatal; Methemoglobin; Naphthoquinones; Oxidation-Reduction

Topics: Adult; Female; Foot; Hair Dyes; Humans; Naphthoquinones; Phenylenediamines; Poisoning; Pulmonary Edema; Saudi Arabia

A case of a hairdresser who developed an immediate-type hypersensitivity with urticaria, rhinitis, and bronchial asthma on exposure to henna is reported. Prick tests with henna 1% in aqua and in ethanol showed positive reactions. Both patch tests and prick tests performed with the dye in henna, lawsone, or 2-hydroxy-1, 4-naphtoquinone, which is supposed to be an allergen, had negative results. These results suggest that not only 2-hydroxy-1,4-naphtoquinone but also other still undetermined ingredients of the henna powder should be considered as possible allergen(s).

Topics: Adult; Beauty Culture; Dermatitis, Occupational; Female; Hair Preparations; Humans; Hypersensitivity, Immediate; Naphthoquinones; Patch Tests

Topics: Female; Foot; Glucosephosphate Dehydrogenase; Humans; Naphthoquinones; Poisoning

Studies were undertaken to evaluate the ability of various quinoneimines to induce micronuclei in bone marrow cells as a measure of their genotoxicity. Accordingly, 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (I), its 2-acetyl derivative (II) and 2-[(5-methyl-3-isoxazolyl)amino]-N-(5-methyl-3-isoxazolyl)-1 ,4- naphthoquinone-4-imine (III), as well as two of their precursors, 2-hydroxynaphthoquinone (NQ-2-OH) and 3,4-dimethyl-5-aminoisoxazole (DMAI) were given by intraperitoneal injection at 5, 50, 100 and 200 mg/Kg doses to S.J.L. Swiss mice with 24 h sampling time. Compounds I and II displayed highly significant differences at 50, 100 and 200 mg/kg doses (p < 0.01) and their mutagenic dose response curves correlated closely with an inverted U-shaped form whose interpretation is still the subject of controversy. NQ-2-OH only produced a significant increase in micronucleus frequency at 50 mg/kg, whereas no mutagenic activity was found for compound III and DMAI at the doses assayed. At 50 mg/kg the order of relative mutagenic potencies was I > II > NQ-2-OH. Mechanisms advanced to explain loss of drug activity at high doses include capture saturation, enzymatic induction during metabolism and participation of an independent defense system.

Topics: Animals; Bone Marrow; Dose-Response Relationship, Drug; Female; Isoxazoles; Male; Mice; Micronucleus Tests; Mutagens; Naphthoquinones; Sex Factors

2-Hydroxy-1,4-naphthoquinone has previously been shown to cause severe haemolytic anaemia and renal tubular necrosis in animals. In order to establish if such toxic effects are common to other 2-hydroxynaphthoquinone derivatives, the short-term toxicity of a number of 2-hydroxy-3-alkyl-1,4-naphthoquinones has been compared in rats. 2-Hydroxy-3-methyl, 2-hydroxy-3-ethyl- and 2-hydroxy-3-propyl-1,4-naphthoquinone were found to cause both haemolysis and renal damage, although the severity of the changes provoked by these substances was much lower than those induced by the parent compound at an equivalent dose-level. Furthermore, the toxicity of the hydroxy-alkylnaphthoquinones decreased with increasing size of the alkyl substituent and no toxic changes were recorded in animals dosed with 2-hydroxy-3-butyl- or 2-hydroxy-3-pentyl-1,4-naphthoquinone. The relationship between the in vivo effects of these substances and previously reported data on their in vitro cytotoxicity is discussed in relation to the mechanism of toxicity of these and other naphthoquinone derivatives.

Topics: Animals; Creatinine; Female; Heinz Bodies; Hematocrit; Hemoglobins; Kidney; Liver; Naphthoquinones; Organ Size; Rats; Rats, Sprague-Dawley; Spleen; Toxicity Tests; Urea

Crude ethanolic extract of Lawsonia inermis L. (0.25-2.0 g/kg) produced significant and dose-dependent anti-inflammatory, analgesic, and antipyretic effects in rats. The extract also produced significant increases in pentobarbitone-induced sleeping time. Using a liquid-liquid extraction procedure, the extract was fractionated into chloroform, butanol, and water fractions, and these were tested for the above activities. The butanol and chloroform fractions showed more potent anti-inflammatory, analgesic, and antipyretic effects than the crude extracts, while the aqueous extract showed significantly less effect. As compared with the other extracts, the butanolic extract (500 mg/kg) was the most effective in the analgesic test. From the chloroform extract, a pure compound was isolated and identified, using chromatographic and spectroscopic techniques, as 2-hydroxy-1,4-naphthaquinone (lawsone). The isolated compound was found to possess significant anti-inflammatory, analgesic, and antipyretic activity. It potentiated significantly the pentobarbitone-induced sleeping time. The anti-inflammatory effect of lawsone (500 mg/kg) was not significantly different from that of the reference drug phenylbutazone (100 mg/kg).

Topics: 1-Butanol; Administration, Oral; Analgesics, Non-Narcotic; Analysis of Variance; Animals; Anti-Inflammatory Agents; Antifungal Agents; Body Temperature; Butanols; Chemical Fractionation; Chloroform; Chromatography, Thin Layer; Dose-Response Relationship, Drug; Edema; Ethanol; Male; Naphthoquinones; Pain; Plant Extracts; Plants, Medicinal; Rats; Rats, Wistar; Sleep

A controlled study was designed to examine the effect of red and black henna on the measurement of oxygen saturation by pulse oximetry. Fifty adult normal female volunteers had their left thumb coloured with red henna (40) or black henna (10). The uncoloured right thumb was used as a control. All measurements were done under room temperature, and the same pulse oximeter was used in all volunteers. In the red henna group there was no difference on oximetry reading between right and left thumb. In contrast, the thumb coloured with black henna gave no reading when compared to the uncoloured right thumb. On the basis of this study, pulse oximetry is not limited by red henna while black henna has a potential of causing major error in the measurement of oxygen saturation by pulse oximetry. In these cases we recommend to use ear oximetry for accurate measurement of oxygen saturation.

Topics: Adult; Coloring Agents; Diagnostic Errors; Female; Humans; Naphthoquinones; Oximetry; Oxygen; Saudi Arabia; Thumb

Poisoning by a mixture of henna dye and para-phenylenediamine dyes led to the hospitalization of 31 Sudanese children between 1984 and 1989. There was a characteristic clinical presentation. All children presented with an acute and severe angioneurotic oedema and 15 of the cases required emergency tracheostomy for respiratory obstruction. Acute renal failure occurred in five children who recovered after peritoneal dialysis. Mortality was high, all 13 deaths occurring within 24 hours of presentation. Hypotensive shock gave a poor prognosis. It is possible that similar cases may be occurring unrecognized where henna is traditionally used. A programme of public education and restriction of para-phenylenediamine is urgently required in The Sudan and other affected nations. Ingestion was accidental in 12 children, deliberate in 10 and homicidal in three cases. Cutaneous absorption was likely in the remaining six.

Topics: Acute Kidney Injury; Adolescent; Angioedema; Child; Child, Preschool; Female; Hair Dyes; Humans; Lung Diseases, Obstructive; Male; Naphthoquinones; Phenylenediamines; Sudan

Topics: Aged; Azo Compounds; Cosmetics; Dermatitis, Allergic Contact; Humans; Male; Naphthols; Naphthoquinones; Sunscreening Agents

The effect of hydroxy substitution on 1,4-naphthoquinone toxicity to cultured rat hepatocytes was studied. Toxicity of the quinones decreased in the series 5,8-dihydroxy-1,4-naphthoquinone greater than 5-hydroxy-1,4-naphthoquinone greater than 1,4-naphthoquinone greater than 2-hydroxy-1,4-naphthoquinone, and intracellular GSSG formation decreased in the order 5,8-dihydroxy-1,4-naphthoquinone greater than 5-hydroxy-1,4-naphthoquinone much greater than 1,4-naphthoquinone much greater than 2-hydroxy-1,4-naphthoquinone. The electrophilicity of the quinones decreased in the order 1,4-naphthoquinone much greater than 5-hydroxy-1,4-naphthoquinone greater than 5,8-dihydroxy-1,4-naphthoquinone much greater than 2-hydroxy-1,4-naphthoquinone. Treatment of the hepatocytes with BSO (buthionine sulfoximine) or BCNU (1,3-bis-2-chloroethyl-1-nitrosourea) increased 5-hydroxy-1, 4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone toxicity, whereas neither BSO nor BCNU largely affected 1,4-naphthoquinone and 2-hydroxy-1, 4-naphthoquinone toxicity. Dicumarol increased the toxicity of 1,4-naphthoquinone dramatically and somewhat the toxicity of 2-hydroxy-1,4- naphthoquinone, whereas 5-hydroxy-1,4-naphthoquinone and 5,8-dihydroxy-1,4-naphthoquinone toxicity increased only slightly. The toxicity of 5,8-dihydroxy-1,4-naphthoquinone decreased dramatically in reduced O2 concentration, whereas 1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone, and 2-hydroxy-1,4-naphthoquinone toxicity was not largely affected. It was concluded that 5,8-dihydroxy-1,4-naphthoquinone toxicity is due to free radical formation, whereas the toxicity of 1,4-naphthoquinone and of 5-hydroxy-1,4-naphthoquinone also has an electrophilic addition component. The toxicity of 2-hydroxy-1,4-naphthoquinone could not be fully explained by either of these phenomena.

Topics: Animals; Buthionine Sulfoximine; Carmustine; Cell Survival; Dicumarol; Glutathione; Liver; Male; Methionine Sulfoximine; Mitochondria, Liver; Molecular Structure; Naphthoquinones; Oxidation-Reduction; Oxygen Consumption; Rats; Rats, Inbred Strains; Structure-Activity Relationship

The short-term toxicity of 2-hydroxy-1,4-naphthoquinone (lawsone) and 2-methyl-1,4-naphthoquinone (menadione) has been compared in rats. 2-Methyl-1,4-naphthoquinone has been shown previously to cause haemolytic anaemia in animals, and this was confirmed in the present experiment. 2-Hydroxyl-1,4-naphthoquinone was found also to cause haemolysis, in a dose-dependent manner, as reflected by decreased blood packed cell volumes and haemoglobin levels and by histopathological changes in spleen, liver and kidney. With both naphthoquinones, the haemolysis was of the oxidative type, characterized by the presence of Heinz bodies within erythrocytes. Haemolysis was the only toxic change identified in rats dosed with 2-methyl-1,4-naphthoquinone. In contrast, 2-hydroxyl-1,4-naphthoquinone was not only a haemolytic agent but also a nephrotoxin, causing renal enlargement, elevated plasma levels of urea and creatinine and histologically-identified tubular necrosis, largely confined to the distal segment of the proximal convoluted tubules. The relationship between the in vivo toxic effects of these naphthoquinones and previously-reported data on their in vitro cytotoxic action is discussed.

Topics: Animals; Female; Hemolysis; Kidney Diseases; Naphthoquinones; Rats; Rats, Inbred Strains; Time Factors; Vitamin K

The tuberculostatic activity of the herb henna (Lawsonia inermis Linn.) was tested in vitro and in vivo. On Lowenstein Jensen medium, the growth of tubercle bacilli from sputum and of Mycobacterium tuberculosis H37Rv was inhibited by 6 micrograms/ml of the herb. In vivo studies on guinea pigs and mice showed that the herb at a dose of 5 mg/kg body weight led to significant resolution of experimental tuberculosis following infection with M. tuberculosis H37Rv.

Topics: Animals; Guinea Pigs; In Vitro Techniques; Mice; Microbial Sensitivity Tests; Mycobacterium tuberculosis; Naphthoquinones; Tuberculosis

Degradation of 2-hydroxy-1,4-naphthoquinone (HNQ) by lignin peroxidase is discussed. Degradation rat was remarkably increased by an increase in veratryl alcohol concentration. Degradation is partly prevented by adding OH. scavenger (mannitol or DMSO) to the reaction mixture. Addition of O2-. scavenger (Mn2+) to the reaction mixture completely prevents the degradation. These results suggest that active oxygen species formed in the lignin peroxidase-H2O2-veratryl alcohol system play an important role in HNQ degradation.

Topics: Agaricales; Benzyl Alcohols; Free Radical Scavengers; Kinetics; Naphthoquinones; Peroxidases; Superoxides

The oxidation-reduction potential of p-hydroxybenzoate hydroxylase (4-hydroxybenzoate, NADPH: oxygen oxidoreductase (3-hydroxylating), EC 1.14.13.2) from Pseudomonas fluorescens has been measured in the presence and absence of p-hydroxybenzoate using spectrocoulometry. The native enzyme demonstrated a two-electron midpoint potential of -129 mV during the initial reductive titration. The midpoint potential observed during subsequent oxidative and reductive titrations was -152 mV. This marked hysteresis is proposed to arise from the oxidation and reduction of the known air-sensitive thiol group on the enzyme (Van Berkel, W.J.H. and Müller, F. (1987) Eur. J. Biochem. 167, 35-46). Redox titrations of the enzyme in the presence of substrate showed a two-electron midpoint potential of -177 mV. No spectral or electrochemical evidence for the thermodynamic stabilization of any flavin semiquinone was observed in the titrations performed. These data show that the affinity of the apoenzyme for the hydroquinone form of FAD is 150-fold greater than for the oxidized flavin and that the substrate is bound to the reduced enzyme with a 3-fold lower affinity than to the oxidized enzyme. These data are consistent with the view that the stimulatory effect of substrate binding on the rate of enzyme reduction by NADPH is due to the respective geometries of the bound FAD and NADPH rather than to a large perturbation of the oxidation-reduction potential of the bound flavin coenzyme.

Topics: 4-Hydroxybenzoate-3-Monooxygenase; Coloring Agents; Electrochemistry; Flavin-Adenine Dinucleotide; Hydroxybenzoates; Indigo Carmine; Mixed Function Oxygenases; Naphthoquinones; Oxidation-Reduction; Parabens; Paraquat; Pseudomonas fluorescens; Spectrum Analysis; Thermodynamics

Topics: Adult; Coloring Agents; Dermatitis, Contact; Humans; Male; Naphthoquinones

Several quinoid compounds mediated the reduction of ferrylmyoglobin (MbIV) to metmyoglobin (MbIII). The efficiency of the MbIV reduction to MbIII was accomplished by the quinones in the following order: p-benzoquinone greater than 1,4-naphthoquinone greater than 2-OH-1,4-naphthoquinone greater than 2,3-epoxy-1,4-naphthoquinone. The quinone-mediated reduction of MbIV to MbIII had the following characteristics: (a) it was stoichiometrically--rather than catalytically--related to the number of cycles of the MbIV----MbIII transition involving the reduction of H2O2. (b) It proceeded with similar efficiencies under aerobic and anaerobic conditions. (c) It did not require the free radical form of MbIV(.MbIV), thus excluding a two-electron oxidation of the quinone. (d) the nucleophilic addition of--NH2 groups of the apoprotein on the quinone seemed not to be involved through an alternative pathway in the reduction of MbIV, especially since 2-OH-1,4-naphthoquinone, a compound which cannot undergo nucleophilic addition, also facilitated the reduction of the ferryl compound. (e) No two-electron oxidation products of the unsubstituted quinones, such as quinone epoxides, were detected in the spent reaction mixture analyzed by HPLC with electrochemical detection. On the basis of these observations, it is suggested that the reduction of MbIV to MbIII by the above quinonoid compounds is a one-electron transfer process, with electron abstraction being probably accomplished at some site in the benzo ring of the quinone.

Topics: Benzoquinones; Chemical Phenomena; Chemistry; Chromatography, High Pressure Liquid; Hemeproteins; Hydrogen Peroxide; Kinetics; Metmyoglobin; Naphthoquinones; Oxidation-Reduction; Quinones; Spectrophotometry

The mechanisms of toxicity to isolated rat hepatocytes of two structurally related naphthoquinones have been studied. Both 5-OH-1,4-naphthoquinone (5-OH-1,4-NQ; juglone) and 2-OH-1,4-naphthoquinone (2-OH-1,4-NQ; lawsone) caused a concentration-dependent cytotoxicity to hepatocytes which was preceded by a depletion of intracellular glutathione. 5-OH-1,4-NQ caused a depletion of intracellular glutathione when incubated either at 4 degrees C or 37 degrees C whereas 2-OH-1,4-NQ caused a depletion of intracellular glutathione when the hepatocytes were incubated at 37 degrees C but not at 4 degrees C. 5-OH-1,4-NQ but not 2-OH-1,4-NQ reacted with glutathione in buffered solution. These results suggested that the depletion of intracellular glutathione by 2-OH-1,4-NQ is enzyme mediated whereas in the case of 5-OH-1,4-NQ the direct chemical reaction with gluathione may be largely responsible for the depletion. A critical role for depletion of protein thiols in menadione-induced cytotoxicity has been proposed. In agreement with earlier work, menadione caused a decrease in protein sulphydryls prior to cell death, however, at cytotoxic concentrations of both 2-OH-1,4-NQ and 5-OH-1,4-NQ this decrease only accompanied rather than preceeded cell death. The mechanism of toxicity of 5-OH-1,4-NQ is similar to that of other naphthoquinones and involves formation of its corresponding naphthosemiquinone, active oxygen species and redox cycling as it stimulated a disproportionate increase in both microsomal NADPH oxidation and oxygen consumption.(ABSTRACT TRUNCATED AT 250 WORDS)

Topics: Animals; Antifungal Agents; Glutathione; In Vitro Techniques; Liver; Male; Microsomes, Liver; NADP; Naphthoquinones; Oxidation-Reduction; Oxygen Consumption; Rats; Rats, Inbred Strains; Sulfhydryl Compounds

The cyanide-insensitive respiration of bloodstream trypomastigote forms of Trypanosoma brucei (75 +/- 8 nmol O2 min-1(mg protein)-1) is completely inhibited by the mitochondrial ubiquinone-like inhibitors 2-hydroxy-3-undecyl-1,4-naphthoquinone (UHNQ) and 5-n-undecyl-6-hydroxy-4,7-dioxobenzothiazole (UHDBT). The Ki values for UHDBT (30 nM) and UHNQ (2 microM) are much lower than the reported Ki for salicylhydroxamic acid (SHAM) (5 microM), a widely used inhibitor of the cyanide-insensitive oxidase. UHNQ also stimulated the glycerol-3-phosphate-dependent reduction of phenazine methosulfate, demonstrating that the site of UHNQ inhibition is on the terminal oxidase of the cyanide-insensitive respiration of T. brucei. These results suggest that a ubiquinone-like compound may act as an electron carrier between the two enzymatic components of the cyanide-insensitive glycerol-3-phosphate oxidase.

Topics: Animals; Cyanides; Cytochrome b Group; Cytochromes c1; Glycerolphosphate Dehydrogenase; Mitochondria; Naphthoquinones; Oxygen Consumption; Salicylamides; Thiazoles; Trypanosoma brucei brucei

Topics: Coloring Agents; Hair Dyes; Hair Preparations; Humans; Naphthoquinones

The ability of an anti-sickling drug lawsone, 2-OH-1,4-naphthoquinone, and two related compounds to inhibit the haematoporphyrin-sensitised photohaemolysis of normal and sickle cell erythrocytes has been investigated. The compounds appear to protect the erythrocyte membranes by reaction with transient oxidative species. Differential effects between normal and sickle cells are shown and these are attributed to the different membrane composition of irreversibly sickled erythrocytes. This report describes a possible basis for the decreased formation of irreversibly sickled cells in the presence of lawsone.

Topics: Erythrocyte Membrane; Hematoporphyrins; Hemolysis; Humans; Naphthoquinones; Photochemistry

Sodium lawsonate (SL: derivative of lawsone, hydroxy-1,4-naphthaquinone) was studied for its activity profile in mice and rats, with emphasis on actions on the central nervous system. The drug produced a cataleptic state, hypothermia and loss of active avoidance behaviour, but it did not augment barbiturate sleep. The catalepsy was prevented by hyoscine (mice) or by sodium salicylate (rats). SL did not affect apomorphine-sterotypy (a dopamine-mediated behaviour) but blocked the lithium-induced head twitches (a serotonin-mediated behavioural response). SL did not produce excitation, analgesia or exhibit anti-MES activity. All actions of SL were rapid in onset and brief in duration. In view of effective dose range (40-80 mg/kg, i.p.) and MLD 50 values (76 mg/kg, i.p., in mice; 122 mg/kg, i.p., in rats), safety index of SL appears to be low.

Topics: Analgesics; Animals; Avoidance Learning; Body Temperature; Catalepsy; Dopamine; Electroshock; Female; Male; Mice; Naphthoquinones; Pentobarbital; Rats; Serotonin; Sleep

Topics: Adolescent; Dermatitis, Contact; Female; Humans; Naphthoquinones

From humus obtained from Stuttgart, a bacterium was isolated with lawsone (2-hydroxy-1,4-naphthoquinone) as selective source of carbon. This bacterium is capable of utilizing lawsone as sole source of carbon and energy. Morphological and physiological characteristics of the bacterium were examined and it was identified as a strain of Pseudomonas putida. The organism is referred to as Pseudomonas putida L2. The degradation of lawsone by Pseudomonas putida L2 was investigated. Salicylic acid and catechol were isolated and identified as metabolites. In lawsone-induced cells of Pseudomonas putida L2, salicylic acid is converted to catechol by salicylate 1-monooxygenase. Catechol 1,2-dioxygenase catalyses ortho-fission of catechol which is then metabolized via the beta-ketoadipate pathway. Formation of cis,cis-muconate and beta-ketoadipate was demonstrated by enzyme assays. Salicylate 1-monooxygenase and catechol 1,2-dioxygenase are induced sequentially. The enzymes of the beta-ketoadipate pathway are also inducible. Naphthoquinone hydroxylase, however, was demonstrated in induced and non-induced cells. This constitutive enzyme enables Pseudomonas putida L2 to degrade various 1,4-naphthoquinones in experiments with resting cells.

Topics: Biotransformation; Cell-Free System; Chromatography, Thin Layer; Mixed Function Oxygenases; Naphthoquinones; Pseudomonas; Spectrophotometry, Ultraviolet

Topics: Adult; Asthma; Female; Hair Dyes; Hair Preparations; Humans; Hypersensitivity, Immediate; Immunoglobulin E; Naphthoquinones; Occupational Diseases; Peak Expiratory Flow Rate; Radioallergosorbent Test

Topics: Anemia, Sickle Cell; Animals; Electrophoresis, Cellulose Acetate; Erythrocytes, Abnormal; Humans; Mice; Naphthoquinones; Oxygen Consumption

Inhibition of cyclo-oxygenase reaction during prostaglandin formation in the renal medulla of the rat by 1,4-naphthoquinone derivatives is compared with the known enzyme inhibition properties of natural and synthetic flavonols. Structure-activity relationship study shows strong correlation between chemical properties (vicinal hydroxy-oxo structure of planar molecules) and physicochemical parameters (polarity and acidity). The most potent compounds are 2-ethyl-5-hydroxy-1,4-naphthoquinone (9) and 2-methyl-3-hydroxy-1,4-naphthoquinone (6).

Topics: Animals; Coloring Agents; In Vitro Techniques; Male; Naphthoquinones; Prostaglandin Antagonists; Prostaglandins; Rats; Rats, Inbred Strains; Structure-Activity Relationship

Hereditary polymorphic light eruption (HPLE) occurs in Indians of North and South America. Affected persons are sensitive to long ultraviolet radiation and therefore receive no substantial benefit from conventional sunscreens. We have treated 46 patients with HPLE at the Red Lake Reservation, Minn, with topically administered dihydroxyacetone and lawsone, orally given beta carotene, or both. Oral beta carotene afforded adequate photoprotection to 33 patients, and four additional patients were protected with the combined use of oral and topical agents. Epidemiologic studies support our proposals that HPLE is a causative factor in streptococcal pyoderma in the American Indian and may be associated with epidemics of streptococcal glomerulonephritis.

Topics: Adolescent; Adult; Aged; Carotenoids; Child; Child, Preschool; Coloring Agents; Dihydroxyacetone; Female; Glomerulonephritis; Humans; Indians, North American; Indians, South American; Male; Middle Aged; Naphthoquinones; Photosensitivity Disorders; Pyoderma; Streptococcal Infections

During antifungal screening of higher plants, the leaves of Lawsonia inermis were found to exhibit strong fungitoxicity. On chemical investigation, the antifungal factor was found to be 2-hydroxy-1,4-naphthoquinone (Lawsone). The minimum effective dose against test organism was found to be 1000 ppm. Lawsone was found to exhibit fungicidal activity, wide fungitoxic spectrum and nonphytotoxicity.

Topics: Antifungal Agents; Methods; Naphthoquinones; Plant Extracts

Topics: Analgesics; Animals; Anticonvulsants; Body Temperature; Ketones; Mice; Naphthoquinones; Sleep

Topics: Balsaminaceae; Biochemical Phenomena; Biochemistry; Chromatography; Impatiens; Infrared Rays; Naphthoquinones; Plants; Research; Spectrophotometry

Topics: Chemistry, Pharmaceutical; Cyanates; Hydrocarbons; Mustard Plant; Naphthoquinones; Pharmacy; Research

Topics: Coloring Agents; Cosmetics; Dermatomycoses; Humans; Lawsonia Plant; Naphthoquinones; Pharmacology

Topics: Amebicides; Dysentery, Amebic; Humans; Naphthoquinones; Plant Extracts; Quinones

Topics: Allergens; Flowers; Lawsonia Plant; Naphthoquinones; Oils, Volatile

Topics: Naphthoquinones

Topics: Humans; Lawsonia Plant; Naphthoquinones