curcumin has been researched along with betadex* in 30 studies
1 trial(s) available for curcumin and betadex
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Pharmacokinetic study of rhizoma Curcumae oil and rhizoma Curcumae oil-β-cyclodextrin inclusion complex in pigs after oral administration.
Pharmacokinetics of rhizoma Curcumae oil-pure drug (RCO-PD) and its β-cyclodextrin inclusion complex (RCO-βCD) were studied in a randomized two-way crossover design following a single oral administration of the two formulations. Germacrone concentrations in plasma were determined by high-performance liquid chromatography with UV detector. The concentrations vs. time data were analyzed by a noncompartmental pharmacokinetic method. The result showed that germacrone in both groups was rapidly absorbed followed by a slow elimination. The main parameters in RCO-PD group were as follows: t(1/2λz) 6.63±1.08 h, C(max) 2.50±0.34 μg/mL, MRT 7.19±0.93 h, and AUC(0-∞) 13.92±2.75 mg/L·h, while in RCO-βCD group, t(1/2λz) 6.77 ± 0.67 h, C(max) 2.98±0.24 μg/mL, MRT 8.87±0.76 h, and AUC(0-∞) 21.60 ± 1.95 mg/L·h, respectively. The above results indicated that C(max), T(max), AUC(0-t), AUC(0-∞), and MRT in RCO-βCD group were significantly different from RCO-PD group, and the relative bioavailability of RCO-βCD group is significantly higher while compared to RCO-PD group (F=156%, with its 90% confidence interval of 145-169%). Topics: Animals; Area Under Curve; beta-Cyclodextrins; Cross-Over Studies; Curcuma; Female; Half-Life; Male; Plant Oils; Rhizome; Swine | 2012 |
29 other study(ies) available for curcumin and betadex
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Comprehensive properties of photodynamic antibacterial film based on κ-Carrageenan and curcumin-β-cyclodextrin complex.
In this study, a biodegradable photodynamic antibacterial film (Car-Cur) was prepared using casting method with κ-Carrageenan (κ-Car) as film-forming substrate and curcumin-β-cyclodextrin (Cur-β-CD) complex as photosensitizer. The comprehensive performance of this Car-Cur film was investigated. The obtained results showed that the concentration of Cur-β-CD was an important factor determining the properties of film including tensile strength (TS) elongation at break (EB), water vapor permeability (WVP), water content (WC) and thermal stability. When the concentration of Cur-β-CD is 1%, the film demonstrated the maximum TS and EB, increased thermal stability, with desirable WVP and WC. Furthermore, this film also showed good photodynamic antibacterial potential against Staphylococcus aureus and Escherichia coli upon irradiation of blue LED light. Moreover, the film can be degraded in the soil in one week. In conclusion, our results suggested Car-Cur photodynamic film could be developed as biodegradable antimicrobial packaging material for food preservation. Topics: Anti-Bacterial Agents; beta-Cyclodextrins; Carrageenan; Curcumin; Escherichia coli; Food Packaging; Hot Temperature; Light; Photosensitizing Agents; Staphylococcus aureus; Steam; Tensile Strength | 2022 |
Preparation, Characterization and Evaluation of the Anti-Inflammatory Activity of Epichlorohydrin-β-Cyclodextrin/Curcumin Binary Systems Embedded in a Pluronic
Topics: Anti-Inflammatory Agents, Non-Steroidal; beta-Cyclodextrins; Cell Line; Curcumin; Drug Carriers; Drug Liberation; Epichlorohydrin; Humans; Psoriasis; Solubility | 2021 |
Preparation and photodynamic bactericidal effects of curcumin-β-cyclodextrin complex.
To overcome the poor water solubility of curcumin, a curcumin-β-cyclodextrin (Cur-β-CD) complex was prepared as a novel photosensitizer. Fourier-transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), and X-ray diffraction (XRD) were used to verify the formation of Cur-β-CD. Furthermore, the ROS generation capacity and photodynamic bactericidal effect were measured to confirm this Cur-β-CD complex kept photodynamic activity of curcumin. The result showed Cur-β-CD could effectively generate ROS upon blue-light irradiation. The plate count assay demonstrated Cur-β-CD complex possess desirable photodynamic antibacterial effect against food-borne pathogens including Staphylococcus aureus, Listeria monocytogenes and Escherichia coli. The cell morphology determined by scanning electron microscope (SEM) and transmission electron microscope (TEM) showed Cur-β-CD could cause cell deformation, surface collapse and cell structure damage of the bacteria, resulting in the leakage of cytoplasmic; while agarose gel electrophoresis and SDS-PAGE further illustrated the inactivation mechanisms by Cur-β-CD involve bacterial DNA damage and protein degradation. Topics: Anti-Bacterial Agents; beta-Cyclodextrins; Calorimetry, Differential Scanning; Curcumin; Escherichia coli; Light; Listeria monocytogenes; Photosensitizing Agents; Spectroscopy, Fourier Transform Infrared; Staphylococcus aureus; X-Ray Diffraction | 2021 |
A Novel Folic Acid Receptor-Targeted Drug Delivery System Based on Curcumin-Loaded β-Cyclodextrin Nanoparticles for Cancer Treatment.
A novel folate receptor-targeted β-cyclodextrin (β-CD) drug delivery vehicle was constructed to improve the bioavailability, biosafety, and drug loading capacity of curcumin. Controlled release and targeted delivery was achieved by modifying the nanoparticles with folic acid (FA).. Folate-conjugated β-CD-polycaprolactone block copolymers were synthesized and characterized. Curcumin-loaded nanoparticles (FA-Cur-NPs) were structured by self-assembly. The physicochemical properties, stability, release behavior and tumor-targeting ability of the fabricated nanoparticles were studied.. The average particle size and drug loading of FA-Cur-NPs was 151.8 nm and 20.27%, respectively. Moreover, the FA-Cur-NPs exhibited good stability in vitro for 72 h. The drug release profiles showed that curcumin from FA-Cur-NPs was released significantly faster in a pH 6.4 phosphate buffered solution (PBS) than in pH 7.4, indicating that curcumin can be enriched around the tumor site compared with normal cells. Additionally, the internalization of FA-Cur-NPs was aided by FA receptor-mediated endocytosis, and its cytotoxicity was proportional to the cellular uptake efficiency. Furthermore, in vivo studies confirmed that FA-Cur-NPs exhibited marked accumulation in the tumor site and excellent antitumor activity.. These findings suggest that FA-Cur-NPs are a promising approach for improving cancer therapy through active targeting and controllable release. Topics: Animals; Antineoplastic Agents; beta-Cyclodextrins; Curcumin; Drug Carriers; Drug Delivery Systems; Drug Liberation; Female; Folate Receptors, GPI-Anchored; Folic Acid; HeLa Cells; Humans; Mice; Mice, Inbred BALB C; Mice, Nude; Nanoparticles; Neoplasms; Particle Size; Polyesters; Tissue Distribution; Xenograft Model Antitumor Assays | 2021 |
Encapsulating curcumin in ethylene diamine-β-cyclodextrin nanoparticle improves topical cornea delivery.
Curcumin is a powerful scavenger of reactive oxygen species and could prevent the corneal cells from oxidative damage. However, the clinical efficacy of curcumin is limited by its low aqueous solubility and stability, leading to poor bioavailability. β-cyclodextrin, with a hydrophilic surface and a hydrophobic cavity and self-assembling properties, can form inclusion complexes with lipophilic drugs such as curcumin for ocular delivery. We synthesized ethylene diamine (EDA)-modified β-cyclodextrin and prepared the curcumin complexation using the solvent evaporation method. The EDA-β-cyclodextrin provided a better thermodynamic stability and higher complex yield for curcumin complexes, compared to β-cyclodextrin, which were demonstrated on the analysis of their van't Hoff plots and phase solubility diagrams. We characterized EDA-β-cyclodextrin curcumin nanoparticles and determined that the EDA modified β-cyclodextrin is a more suitable carrier than parental β-cyclodextrin, using FT-IR, XRD, TEM, and analyses of solubility and storage stability. In addition, the curcumin-EDA-β-cyclodextrin nanoparticles had better in vitro corneal penetration and 3 -h cumulative flux in a porcine cornea experiment, and displayed an improved biocompatibility, confirmed by the histological examination of porcine corneas and cell viability of bovine corneal epithelial cells. These results together revealed a role of EDA modification in the β-cyclodextrin carrier, including the improvement of curcumin complex formation, thermodynamic properties, cytotoxicity, and the in vitro corneal penetration. The EDA-β-cyclodextrin inclusion can provide curcumin a higher degree of aqueous solubility and corneal permeability. Topics: Animals; beta-Cyclodextrins; Cornea; Curcumin; Drug Delivery Systems; Ethylenediamines; Nanoparticles; Particle Size; Solubility; Surface Properties; Swine | 2020 |
A Cyclodextrin-Based Controlled Release System in the Simulation of In Vitro Small Intestine.
A novel cyclodextrin (CD)-based controlled release system was developed in the small intestine to control the rate of drug release, on the premise of enteric-coated tablets. The system was designed based on the enzymes exogenous β-cyclodextrin glycosyltransferase (β-CGTase) and endogenous maltase-glucoamylase (MG), wherein MG is secreted in the small intestine and substituted by a congenerous amyloglucosidase (AG). The vanillin-/curcumin-β-CD complexes were prepared and detected by Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC), and host CD degradation was measured based on the glucose yield. The combination of β-CGTase and AG was also functional in the CD complex system. The variations in the concentrations of added β-CGTase, with AG constantly in excess, could effectively alter the rate of host CD degradation and guest release by monitoring glucose production and color disappearance, thus, demonstrating that guest release in the CD complex system could be precisely controlled by changing the amount of β-CGTase used. Thus, the in vitro simulation of the system indicated that a novel controlled release system, based on endogenous MG, could be established in the small intestine. The CD-based controlled release system can be potentially applied in drug delivery and absorption in the small intestine. Topics: alpha-Glucosidases; Benzaldehydes; beta-Cyclodextrins; Calorimetry, Differential Scanning; Curcumin; Delayed-Action Preparations; Drug Delivery Systems; Drug Liberation; Glucan 1,4-alpha-Glucosidase; Glucosyltransferases; Intestine, Small; Kinetics; Spectroscopy, Fourier Transform Infrared; Substrate Specificity; Thermogravimetry | 2020 |
Design & development of nanosponge loaded topical gel of curcumin and caffeine mixture for augmented treatment of psoriasis.
Combination of curcumin with anti-inflammatory drug like caffeine shows augmented antipsoriatic action compared to curcumin alone and reduce the time taken for treatment of Psoriasis.. The objective of the present study was to develop nanosponge (NS) based topical gel of curcumin (CUR) and caffeine (CFN) combination that acts as a potential system for the treatment of psoriasis.. NS composed of dimethyl carbonate (DMC) as crosslinker and beta-cyclodextrin (β-CD) as polymer were prepared by hot melt method and incorporated in topical gels. Factorial design (3. The physical and chemical characteristics exhibited by the prepared NS and gels (F1-F9) were found to be optimal. The optimization resulted in achieving formulation N10 with 69.72% in vitro drug release and 12,329.78cp viscosity. Histopathology studies revealed that prepared nanogel has promising anti-psoriatic activity. The results concluded that CUR and CFN combination has reduced the time required for showing anti-psoriatic activity to 10 days when compared to CUR alone that took around 20 days. Moreover, the nanogel has depicted sustained drug release till 12 h.. From the experimental findings it has been concluded that CUR and CFN combination significantly augmented the anti-psoriatic efficacy with respect to individual components and also reduced the time required for onset of effect. Thus, the proposed nanogel would be an imperative drug delivery system for more effective anti-psoriatic therapy. Graphical abstract. Topics: Administration, Topical; Animals; beta-Cyclodextrins; Caffeine; Curcumin; Delayed-Action Preparations; Disease Models, Animal; Drug Combinations; Drug Compounding; Female; Formates; Imiquimod; Male; Mice; Nanostructures; Particle Size; Psoriasis | 2020 |
β-Cyclodextrin-modified hyaluronic acid-based supramolecular self-assemblies for pH- and esterase- dual-responsive drug delivery.
Although some drug-based supramolecular systems have been constructed to overcome multidrug resistance and enhance the bioavailability of chemical drugs, strengthening the specific stimuli-responsive and active targeting ability of these systems is still a major challenge. In this paper, the synthesis and self-assembly behaviour of supramolecular self-assemblies with active targeting β-cyclodextrin-modified hyaluronic acid (HA-CD) and drug-drug conjugates (curcumin-oxoplatin, Cur-Pt) as building moieties were carefully investigated. Notably, the curcumin was chosen not only as the chemical anti-cancer drug, but also acted as the guest molecule which could be included into CD cavity to form host-guest interaction-based supramolecular assemblies. The obtained self-assemblies exhibited pH- and esterase-responsive drug release behaviours. Furthermore, basic cell experiments were performed to prove their effective cellular toxicity based on A549 cells and PC3 cells with high expression of CD44 receptor but they showed no toxicity to normal LO-2 cells with low expression of CD44 receptor, which suggests their potential application in the targeted drug release field. Topics: A549 Cells; Antineoplastic Agents; beta-Cyclodextrins; Biomarkers, Tumor; Cell Line; Cell Survival; Cisplatin; Curcumin; Delayed-Action Preparations; Drug Carriers; Drug Liberation; Esterases; Gene Expression; Glycoconjugates; Hepatocytes; Humans; Hyaluronan Receptors; Hyaluronic Acid; Hydrogen-Ion Concentration; Kinetics; Organ Specificity; PC-3 Cells | 2020 |
The potential use of curcumin-β-cyclodextrin inclusion complex/chitosan-loaded cellulose sponges for the treatment of chronic wound.
In this research, the cellulose sponges with curcumin-β-cyclodextrin inclusion complex (CMx) and chitosan (CS) were fabricated for use as wound dressings. 1-Allyl-3-methylimidazolium chloride (AMIMCl) ionic liquid as a green solvent was used for the fabrication of cellulose sponges. Due to the low aqueous solubility and low bioavailability of curcumin, cyclodextrins (CDs) were applied and complexed with curcumin to obtain CMx. In addition, CS was incorporated in the cellulose sponges to improve the antibacterial activity of sponges. Attenuated total reflection-Fourier transform infrared (ATR-FTIR) analysis, morphological appearances, mechanical properties, water retention and weight loss, release behaviors, antibacterial activity, indirect cytotoxicity, cell attachment, and cell proliferation of the CMx/CS-loaded cellulose sponges were investigated. From the results, the cellulose sponges showed a porous structure. The incorporation of CMx and CS improved the mechanical properties when compared to the neat cellulose sponges. Moreover, the addition of CS into the cellulose sponges exhibited antibacterial activity against E. coli and S. aureus. Furthermore, the indirect cytotoxicity of the CMx/CS-loaded cellulose sponges was non-toxic and compatible with NCTC L929 and NHDF cells. Consequently, the CMx/CS-loaded cellulose sponges might be good candidates for use as wound dressing materials for the treatment of wound, especially chronic wound. Topics: Anti-Bacterial Agents; Bandages; beta-Cyclodextrins; Cellulose; Chitosan; Curcumin; Cyclodextrins; Drug Liberation; Escherichia coli; Humans; Porosity; Spectroscopy, Fourier Transform Infrared; Staphylococcus aureus; Water; Wound Healing | 2020 |
Preservative effects of fish gelatin coating enriched with CUR/βCD emulsion on grass carp (Ctenopharyngodon idellus) fillets during storage at 4 °C.
Topics: Amino Acids; Animals; beta-Cyclodextrins; Carps; Curcumin; Emulsions; Food Storage; Gelatin; Hydrogen-Ion Concentration; Protective Agents; Pseudomonas; Seafood; Temperature; Thiobarbiturates | 2019 |
Modulation of aggregation of silk fibroin by synergistic effect of the complex of curcumin and β-cyclodextrin.
Amyloid aggregation has been associated with numerous human pathological diseases. A recent study has demonstrated that silk fibroin intermittently endorses amyloidogenesis in vivo. In the current study, we explored the propensity of silk fibroin to undergo amyloid-like aggregation and its prevention using an optimized concoction of curcumin with β-cyclodextrin. Aggregation of silk fibroin resulted in the formation of fibrils with a diameter of ~3.2 nm. However, addition of the optimized concentration of curcumin and β-cyclodextrin to silk fibroin inhibited aggregation and preserved the random coil conformation even under aggregation inducing conditions, as demonstrated by CD and FTIR spectroscopy. Benzene rings of curcumin interact with the aromatic residues of fibroin via hydrophobic interactions. However, β-cyclodextrin preferentially interacts with the non-polar residues, which are the core components for nucleation dependent protein aggregation. The present study demonstrates the ability of the concoction of curcumin and β-cyclodextrin in tuning the self assembly process of fibroin. It also provides a platform to explore the assembly process of nano-fibril and hierarchical structures in vitro along with a novel insight for designing clinically relevant silk-based functional biomaterials. Topics: beta-Cyclodextrins; Curcumin; Ethanol; Fibroins; Hydrogen Bonding; Molecular Docking Simulation; Protein Conformation | 2019 |
Thermo-responsive molecularly imprinted polymer containing magnetic nanoparticles: Synthesis, characterization and adsorption properties for curcumin.
A novel intelligent thermoresponsive-magnetic molecularly imprinted polymer (TMMIP) nanocomposite based on N-isopropylacrylamide (NIPAM) & Fe Topics: Acrylamides; Adsorption; beta-Cyclodextrins; Biosensing Techniques; Curcumin; Drug Liberation; Ferrosoferric Oxide; Kinetics; Magnetic Fields; Magnetite Nanoparticles; Molecular Imprinting; Nanocomposites; Phase Transition; Polymerization; Solutions; Temperature | 2018 |
Antimicrobial coatings on polyethylene terephthalate based on curcumin/cyclodextrin complex embedded in a multilayer polyelectrolyte architecture.
Bacterial contamination is a growing concern worldwide. The aim of this work was to develop an antimicrobial coating based on curcumin-cyclodextrin inclusion complex and using polyethylene terephthalate (PET) film as a support matrix. After a pre-treatment aimed to provide sufficient electric charge to the PET surface, it was electrostatically coated with repeated multilayers comprising alternately deposited positively-charged poly-l-lysine (PLL) and negatively-charged poly-l-glutamic acid (PLGA) and carboxymethyl-β-cyclodextrin (CMBCD). The coatings had an architecture (PLL-PLGA) Topics: Anti-Infective Agents; beta-Cyclodextrins; Coated Materials, Biocompatible; Curcumin; Drug Liberation; Microbial Sensitivity Tests; Polyelectrolytes; Polyethylene Terephthalates; Polymers; Spectrometry, X-Ray Emission; Static Electricity | 2018 |
Water-soluble Complex of Curcumin with Cyclodextrins: Enhanced Physical Properties For Ocular Drug Delivery.
Curcumin, a natural hydrophobic polyphenol, has been reported to have diverse pharmacological activities. Previous studies have evaluated its efficacy using both oral and transdermal dosage forms. However, two major obstacles-poor aqueous solubility and low stability-severely limited its pharmaceutical use.. The main objective of this study was to prepare curcumin eye drops that provided sustained release to allow for once daily application in retinitis pigmentosa.. To achieve our goal, curcumin was complexed with β -cyclodextrin and hydroxypropyl-β- cyclodextrin in two molar ratios (1:1 and 1:2) using co-solvent, co-solvent with sonication and freezedrying filtration methods. A total of 12 complexes were prepared, then characterized using differential scanning calorimetry, powder X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, solubility assessment and in vitro release studies.. An improvement in curcumin aqueous solubility relative to pure curcumin was achieved for all 12 complexes. However, the freeze-drying filtration method was superior to all other methods because it produced highly water-soluble drug-CD complexes. Based on our stability analyses, pH 6.8 phosphate buffer containing 1% Tween 80 was selected as the release medium for in vitro release studies because curcumin exhibited high stability in this medium. Our F11 formulation provided sustained release of the drug for more than 96 h with a maximum amount released of drug (21.77±0.26 μg/ml). Our in vitro release data also showed that release of drug from curcumin-CDs inclusion complexes followed a Higuchi non-Fickian diffusion mechanism.. Based on these results, F11 was formulated as eye drops, which provide a promising once daily novel topical delivery of this naturally derived phytochemical. Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Calorimetry, Differential Scanning; Chemistry, Pharmaceutical; Curcumin; Cyclodextrins; Delayed-Action Preparations; Drug Delivery Systems; Eye; Freeze Drying; Microscopy, Electron, Scanning; Ophthalmic Solutions; Solubility; Solvents; Spectroscopy, Fourier Transform Infrared; Water; X-Ray Diffraction | 2017 |
Polyphenols in combination with β-cyclodextrin can inhibit and disaggregate α-synuclein amyloids under cell mimicking conditions: A promising therapeutic alternative.
Parkinson's disease is characterized by the presence of insoluble and neurotoxic aggregates (amyloid fibrils) of an intrinsically disordered protein α-synuclein. In this study we have examined the effects of four naturally occurring polyphenols in combination with β-cyclodextrin (β-CD) on the aggregation of α-synuclein in the presence of macromolecular crowding agents. Our results reveal that even at sub-stoichiometric concentrations of the individual components, the polyphenol-β-CD combination(s) not only inhibited the aggregation of the proteins but was also effective in disaggregating preformed fibrils. Curcumin was found to be the most efficient, followed by baicalein with (-)-epigallocatechin gallate and resveratrol coming in next, the latter two exhibiting very similar effects. Our results suggest that the efficiency of curcumin results from a balanced composition of the phenolic OH groups, benzene rings and flexibility. The latter ensures proper positioning of the functional groups to maximize the underlying interactions with both the monomeric form of α-synuclein and its aggregates. The uniqueness of β-CD was reinforced by the observation that none of the other cyclodextrin variants [α-CD and HP-β-CD] used was as effective, in spite of these possessing better water solubility. Moreover, the fact that the combinations remained effective under conditions of macromolecular crowding suggests that these have the potential to be developed into viable drug compositions in the near future. MTT assays on cell viability independently confirmed this hypothesis wherein these combinations (and the polyphenols alone too) appreciably impeded the toxicity of the prefibrillar α-synuclein aggregates on the mouse neuroblastoma cell lines (N2a cells). Topics: alpha-Synuclein; Amyloid; Amyloidogenic Proteins; Animals; beta-Cyclodextrins; Catechin; Cell Line; Cell Survival; Circular Dichroism; Curcumin; Humans; Mice; Parkinson Disease; Polyphenols; Protein Aggregation, Pathological | 2017 |
Development of curcumin-cyclodextrin/cellulose nanocrystals complexes: New anticancer drug delivery systems.
The synthesis of curcumin-cyclodextrin/cellulose nanocrystals (CNCx) nano complexes was performed. CNCx were functionalized by ionic association with cationic β-cyclodextrin (CD) and CD/CNCx complexes were used to encapsulate curcumin. Preliminary in vitro results showed that the resulting curcumin-CD/CNCx complexes exerted antiproliferative effect on colorectal and prostatic cancer cell lines, with IC50s lower than that of curcumin alone. Topics: beta-Cyclodextrins; Cell Line, Tumor; Cell Proliferation; Cellulose; Curcumin; Drug Carriers; HT29 Cells; Humans; Microscopy, Confocal; Nanoparticles | 2016 |
Curcumin-cyclodextrin complexes enhanced the anti-cancer effects of curcumin.
Curcumin (CUR), as a yellow pigment in the spice turmeric (Curcuma longa), possessed a pleiotropic application containing cancer therapy. Due to its poor oral bioavailability, the objective of this study was to investigate the use of curcumin-cyclodextrin complexes (CD15) as an approach to cancer chemoprevention. In this study, CUR encapsulation into the β-cyclodextrin (CD) cavity was achieved by the saturated aqueous solution method. CD15 was characterized by Fourier transform infrared (FTIR) and UV spectra analyses. An optimized CD15 was evaluated by cellular uptake and anti-cancer activity. As a result, CD15 enhanced curcumin delivery and improved its therapeutic efficacy compared with free curcumin in vivo and in vitro. Therefore, through regulation of MAPK/NF-κB pathway, CD15 up-regulated p53/p21 pathway, down-regulated CyclinE-CDK2 combination and increased Bax/caspase 3 expression to induce cellar apoptosis and G1-phase arrest. In conclusion, these results suggested that CD15 formulation should be used as a system for improving curcumin delivery and its therapeutic efficacy in lung cancer. Topics: A549 Cells; Animals; Anticarcinogenic Agents; Apoptosis; beta-Cyclodextrins; Cell Line, Tumor; Cell Survival; Curcumin; Dose-Response Relationship, Drug; Drug Carriers; Drug Compounding; Drug Liberation; Humans; Mice; Mice, Inbred Strains; Neoplasms, Experimental; Solubility; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Surface Properties; Tissue Distribution | 2016 |
Sustaining guest molecules on bio-surfaces by grafting the surfaces with cyclodextrins.
Grafting cyclodextrins (CDs) onto materials is an interesting approach to provide the remarkable ability of CDs to form an inclusion complex with various guest molecules onto other (bio)materials. Here we show the design, synthesis and characterization of "a ready to graft β-CD", which is a cyclodextrinyl methacrylate (M-β-CD), which will easily attach covalently to thiol-containing materials via a simple Michael thiol-ene click reaction under a biologically mild condition. Reacting M-β-CD with soluble keratin, human hair and a mucin layer as model biomaterials, in the presence of either tris (2-carboxyethyl) phosphine or vitamin C, resulted in β-CD-grafted keratin that displayed a controlled release of 8-anilino-1-naphthalenesulfonic acid, and both β-CD-grafted-hair strands and β-CD-grafted-mucin layers that effectively retained curcumin. Although this was demonstrated with β-CD on these three biomaterials, this platform could theoretically equally be used with other CDs to give a different range of guest material complexation, and be able to be applied to other thiol-containing materials. Topics: beta-Cyclodextrins; Biocompatible Materials; Curcumin; Female; Humans; Keratins; Microscopy, Fluorescence; Mucins; Solubility; Spectrometry, Fluorescence; Surface Properties | 2015 |
Characterization of the host-guest complex of a curcumin analog with β-cyclodextrin and β-cyclodextrin-gemini surfactant and evaluation of its anticancer activity.
Curcumin analogs, including the novel compound NC 2067, are potent cytotoxic agents that suffer from poor solubility, and hence, low bioavailability. Cyclodextrin-based carriers can be used to encapsulate such agents. In order to understand the interaction between the two molecules, the physicochemical properties of the host-guest complexes of NC 2067 with β-cyclodextrin (CD) or β-cyclodextrin-gemini surfactant (CDgemini surfactant) were investigated for the first time. Moreover, possible supramolecular structures were examined in order to aid the development of new drug delivery systems. Furthermore, the in vitro anticancer activity of the complex of NC 2067 with CDgemini surfactant nanoparticles was demonstrated in the A375 melanoma cell line.. Physicochemical properties of the complexes formed of NC 2067 with CD or CDgemini surfactant were investigated by synchrotron-based powder X-ray diffraction, Fourier-transform infrared spectroscopy, and thermogravimetric analysis. Synchrotron-based small- and wide-angle X-ray scattering and size measurements were employed to assess the supramolecular morphology of the complex formed by NC 2067 with CDgemini surfactant. Lastly, the in vitro cell toxicity of the formulations toward A375 melanoma cells at various drug-to-carrier mole ratios were measured by cell viability assay.. Physical mixtures of NC 2067 and CD or CDgemini surfactant showed characteristics of the individual components, whereas the complex of NC 2067 and CD or CDgemini surfactant presented new structural features, supporting the formation of the host-guest complexes. Complexes of NC 2067 with CDgemini surfactants formed nanoparticles having sizes of 100-200 nm. NC 2067 retained its anticancer activity in the complex with CDgemini surfactant for different drug-to-carrier mole ratios, with an IC50 (half-maximal inhibitory concentration) value comparable to that for NC 2067 without the carrier.. The formation of host-guest complexes of NC 2067 with CD or CDgemini surfactant has been confirmed and hence the CDgemini surfactant shows good potential to be used as a delivery system for anticancer agents. Topics: Antineoplastic Agents; beta-Cyclodextrins; Cell Line, Tumor; Cell Survival; Curcumin; Drug Carriers; Humans; Surface-Active Agents | 2015 |
A 1H NMR Study of Host/Guest Supramolecular Complexes of a Curcumin Analogue with β-Cyclodextrin and a β-Cyclodextrin-Conjugated Gemini Surfactant.
Host systems based on β-cyclodextrin (βCD) were employed as pharmaceutical carriers to encapsulate a poorly soluble drug, curcumin analogue (NC 2067), in order to increase its water solubility. βCD was chemically conjugated with an amphiphilic gemini surfactant with the ability to self-assemble and to form nanoscale supramolecular structures. The conjugated molecule, βCDgemini surfactant (βCDg), was shown to be a promising drug delivery agent. In this report, its physicochemical properties were assessed in aqueous solution using 1D and 2D 1H NMR spectroscopy. The results showed that the apolar hydrocarbon domain of the gemini surfactant was self-included within the βCD internal cavity. The host/guest complexes composed of native βCD or βCDg with NC 2067 were examined using 1D/2D ROESY NMR methods. The stoichiometry of βCD/NC 2067 complex was estimated using Job's method via 1H NMR spectroscopy. The binding geometry of NC 2067 within βCD was proposed using molecular docking and further supported by 1D and 2D ROESY NMR results. Addition of NC 2067 to βCDg revealed minimal changes to the overall structure of the βCDg system, in agreement with the formation of a βCDg/NC 2067 ternary complex. Topics: Alkenes; Antineoplastic Agents; beta-Cyclodextrins; Chemistry, Pharmaceutical; Curcumin; Cyclodextrins; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Structure; Quaternary Ammonium Compounds; Solubility | 2015 |
Curcumin-β-cyclodextrin inclusion complex: stability, solubility, characterisation by FT-IR, FT-Raman, X-ray diffraction and photoacoustic spectroscopy, and food application.
Curcumin was complexed with β-CD using co-precipitation, freeze-drying and solvent evaporation methods. Co-precipitation enabled complex formation, as indicated by the FT-IR and FT-Raman techniques via the shifts in the peaks that were assigned to the aromatic rings of curcumin. In addition, photoacoustic spectroscopy and X-ray diffraction, with the disappearance of the band related to aromatic rings, by Gaussian fitting, and modifications in the spectral lines, respectively, also suggested complex formation. The possible complexation had an efficiency of 74% and increased the solubility of the pure colourant 31-fold. Curcumin-β-CD complex exhibited a sunlight stability 18% higher than the pure colourant. This material was stable to pH variations and storage at -15 and 4°C. With an isothermal heating at 100 and 150°C for 2h, the material exhibited a colour retention of approximately 99%. The application of curcumin-β-CD complex in vanilla ice creams intensified the colour of the products and produced a great sensorial acceptance. Topics: beta-Cyclodextrins; Curcumin; Hydrogen-Ion Concentration; Polymers; Solubility; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis; Spectrum Analysis, Raman; X-Ray Diffraction | 2014 |
β-cyclodextrin and curcumin, a potent cocktail for disaggregating and/or inhibiting amyloids: a case study with α-synuclein.
Aggregation of α-synuclein has been implicated in Parkinson's disease (PD). While many compounds are known to inhibit α-synuclein aggregation, dissolution of aggregates into their constituent monomers cannot be readily achieved. In this study, using a range of techniques, we have shown that an optimized cocktail of curcumin and β-cyclodextrin, at appreciably low concentrations, not only inhibited aggregation but also broke up the preformed aggregates almost completely. We propose that these compounds exhibit synergy in their action and thus provide us with the exciting prospect of working toward the development of a suitable drug candidate for prevention and treatment of PD. Topics: alpha-Synuclein; Amyloid; Benzothiazoles; beta-Cyclodextrins; Circular Dichroism; Curcumin; Drug Synergism; Fluorescent Dyes; Thiazoles | 2014 |
NMR (¹H, ROESY) spectroscopic and molecular modelling investigations of supramolecular complex of β-cyclodextrin and curcumin.
In this paper we have investigated the solubility enhancement of curcumin through inclusion complexation by β-cyclodextrin as well as the topology and geometry of interaction between curcumin and carrier. For this purpose, the phase solubility of curcumin was assessed using Higuchi and Connors method, and the inclusion complex was characterised by 1D (1)H and 2D ROESY NMR analysis, and finally confirmed by molecular modelling. The phase solubility diagram demonstrated the AL-type which confirms an increase in curcumin solubility by increasing the concentration of β-cyclodextrin. (1)H NMR and ROESY spectra results showed a cross-peak between H-3 proton of β-cyclodextrin and the aromatic rings group of curcumin. This revealed the hydrophobic interactions between aromatic rings of curcumin and the cavity of β-cyclodextrin. Finally, the enthalpy of formation was obtained from molecular modelling results which in turn indicated that the process is exothermic and low-energy interactions are involved in the inclusion complex formation. Topics: beta-Cyclodextrins; Curcumin; Magnetic Resonance Spectroscopy; Models, Molecular | 2014 |
(Copper-curcumin) β-cyclodextrin vaginal gel: delivering a novel metal-herbal approach for the development of topical contraception prophylaxis.
Delivering a safe and effective topical vaginal contraceptive is the need of present era. We explored the potential of a metal (copper) and herbal moiety (curcumin) for this topical contraceptive prophylaxis. Complex of copper and curcumin (Cu-Cur) was synthesized and the concerns regarding its aqueous solubility was resolved by including it into the hydrophobic cavity of β-cyclodextrin (β-CD) as (Cu-Cur)CD inclusion complex. Dose assessment was made on the basis of in-vitro spermicidal assays and cell cytotoxicity studies. Finally the (Cu-Cur)CD loaded vaginal gel was prepared, characterized and evaluated for in-vitro spermicidal activity and preclinical toxicity studies. Spectral and morphological characterizations confirmed the synthesis of (Cu-Cur) and (Cu-Cur)CD inclusion complex. Spermicidal assays and Hela cell cytotoxic data revealed an optimized 1.5% (Cu-Cur)CD for further studies. 1.5% w/w (Cu-Cur)CD loaded carbopol 974p gel provided 100% motility even at 2-fold dilution and preclinical toxicity studies in Rats and Rabbits revealed its highly safe profile. The hypothesis of considering metal-herbal complex and its cyclodextrin complex has worked and the well planned strategy of including it in (β-CD) cavity provided a preeminent platform for vaginal delivery. In-vitro assays and preclinical toxicity analysis confirmed its potential to be used as highly safe and effective prophylaxis. Topics: Animals; beta-Cyclodextrins; Cell Line, Tumor; Contraception; Copper; Curcumin; Female; HeLa Cells; Humans; Hydrophobic and Hydrophilic Interactions; Male; Rabbits; Rats; Solubility; Vaginal Creams, Foams, and Jellies | 2014 |
Inhibition of osteoclast differentiation by gold nanoparticles functionalized with cyclodextrin curcumin complexes.
Gold nanoparticles (GNPs) have been previously reported to inhibit osteoclast (OC) formation. However, previous research only confirmed the osteoclastogenesis inhibitory effect under in vitro conditions. The aim of this study was to develop a therapeutic agent for osteoporosis based on the utilization of GNPs and confirm their effect both in vitro and in vivo. We prepared β-cyclodextrin (CD) conjugated GNPs (CGNPs), which can form inclusion complexes with curcumin (CUR-CGNPs), and used these to investigate their inhibitory effects on receptor activator of nuclear factor-κb ligand (RANKL)-induced osteoclastogenesis in bone marrow-derived macrophages (BMMs). The CUR-CGNPs significantly inhibited the formation of tartrate-resistant acid phosphatase (TRAP)-positive multinuclear cells in BMMs without inducing cytotoxicity. The mRNA expressions of genetic markers of OC differentiation including c-Fos, nuclear factor of activated T cells 1 (NFATc1), TRAP, and osteoclast associated receptor (OSCAR) were significantly decreased in the presence of CUR-CGNPs. In addition, the CUR-CGNPs inhibited OC differentiation of BMMs through suppression of the RANKL-induced signaling pathway. Additionally, CUR-CGNPs caused a decrease in RANKL-induced actin ring formation, which is an essential morphological characteristic of OC formation allowing them to carry out bone resorption activity. Furthermore, the in vivo results of an ovariectomy (OVX)-induced osteoporosis model showed that CUR-CGNPs significantly improved bone density and prevented bone loss. Therefore, CUR-CGNPs may prove to be useful as therapeutic agents for preventing and treating osteoporosis. Topics: Actins; Animals; beta-Cyclodextrins; Bone Marrow Cells; Cell Differentiation; Cell Survival; Curcumin; Gene Expression Regulation; Gold; Intracellular Space; Macrophages; Metal Nanoparticles; Mice; Osteoclasts; RANK Ligand; Signal Transduction | 2014 |
Interaction of curcumin and bixin with β-cyclodextrin: complexation methods, stability, and applications in food.
This work aimed to compare methods for the formation of complexes of bixin and curcumin with β-cyclodextrin (β-CD) and to evaluate the stability of the complexes formed by these methods and their food applications. The stoichiometric relationship between curcumin and β-CD was 1:2 and that between bixin and β-CD was 1:1. Curcumin-β-CD and bixin-β-CD complexes formed by kneading, coprecipitation, and simple mixing were evaluated by differential scanning calorimetry (DSC), thermogravimetry analysis (TGA), or nuclear magnetic resonance (NMR-H). For both curcumin and bixin, the best method of complexation was coprecipitation. Complexation of colorants with β-CD promoted an intensification of color and increased water solubility; however, stabilization in the presence of light occurred only for bixin. Application of curcumin-β-CD in cheese and yogurt and bixin-β-CD in the curd did not alter the initial characteristics of the products, which were sensorialy well accepted. Therefore, the complexation of these natural colorants with β-CD favors their use in low-fat foods, broadening the field of industrial application. Topics: beta-Cyclodextrins; Carotenoids; Cheese; Chemical Precipitation; Curcumin; Drug Stability; Food Coloring Agents; Food Technology; Light; Yogurt | 2011 |
beta-Cyclodextrin-curcumin self-assembly enhances curcumin delivery in prostate cancer cells.
Curcumin, a hydrophobic polyphenolic compound derived from the rhizome of the herb Curcuma longa, possesses a wide range of biological applications including cancer therapy. However, its prominent application in cancer treatment is limited due to sub-optimal pharmacokinetics and poor bioavailability at the tumor site. In order to improve its hydrophilic and drug delivery characteristics, we have developed a beta-cyclodextrin (CD) mediated curcumin drug delivery system via encapsulation technique. Curcumin encapsulation into the CD cavity was achieved by inclusion complex mechanism. Curcumin encapsulation efficiency was improved by increasing the ratio of curcumin to CD. The formations of CD-curcumin complexes were characterized by Fourier transform infrared (FTIR), differential scanning calorimetry (DSC), thermo-gravimetric analysis (TGA), scanning electron microscope (SEM), and transmission electron microscope (TEM) analyses. An optimized CD-curcumin complex (CD30) was evaluated for intracellular uptake and anti-cancer activity. Cell proliferation and clonogenic assays demonstrated that beta-cyclodextrin-curcumin self-assembly enhanced curcumin delivery and improved its therapeutic efficacy in prostate cancer cells compared to free curcumin. Topics: Antineoplastic Agents; beta-Cyclodextrins; Calorimetry, Differential Scanning; Cell Line, Tumor; Cell Proliferation; Cell Survival; Curcumin; Drug Compounding; Drug Delivery Systems; Humans; Male; Microscopy, Electron; Prostatic Neoplasms; Spectroscopy, Fourier Transform Infrared; Thermogravimetry; Tumor Stem Cell Assay; X-Ray Diffraction | 2010 |
New cyclodextrin bioconjugates for active tumour targeting.
A new cyclodextrin-based carrier for active targeting of low soluble and degradable drugs has been synthesized and characterized. Beta-cyclodextrins were first reacted with excess hexamethylene diisocyanate and the resulting CD-(C6-NCO)5 derivative was reacted with 700 Da diamino-PEG to yield CD-(C6-PEG-NH2)5. About one out of five free amino groups of PEG were functionalised with folic acid (FA) as a tumour targeting moiety. The chemical structures of the intermediates as well as the final product, CD-(C6-PEG)5-FA, were characterized by 1H and 13C NMR, reverse phase and gel permeation chromatography, and UV-Vis spectroscopy. After modification, the haemolytic activity of beta-cyclodextrins decreased by about 70%. In the presence of the new carrier, the beta-estradiol solubility increased by more than 300 fold and the chlorambucil degradation rate decreased by 50-60%. CD-(C6-PEG)5-FA formed an inclusion complex with curcumin displaying an association constant of 954,732 M(-1). The new carrier increased the curcumin solubility by about 3200 fold as compared to native beta-cyclodextrins and reduced its degradation rate at pH 6.5 and 7.2 by 10 and 45 fold, respectively. FA receptor-overexpressing human nasopharyngeal tumour KB cell lines and non-folic acid receptor-expressing human breast cancer MCF7 cells were used to evaluate the targeting properties of the new drug delivery system. The in vitro studies demonstrate that the new carrier possesses potential selectivity for the folate receptor-overexpressing tumour cells as ED50 values of 52 microM, 58 microM and 21 microM were obtained with curcumin-loaded CD-(C6-PEG-NH2)5, curcumin in foetal serum medium and CD-(C6-PEG)5-FA, respectively. Topics: Antineoplastic Agents; beta-Cyclodextrins; Carrier Proteins; Cell Line, Tumor; Chlorambucil; Curcumin; Drug Carriers; Drug Delivery Systems; Drug Stability; Estradiol; Folate Receptors, GPI-Anchored; Folic Acid; Humans; Hydrophobic and Hydrophilic Interactions; KB Cells; Polyethylene Glycols; Receptors, Cell Surface | 2007 |
Study on the supramolecular interaction of curcumin and beta-cyclodextrin by spectrophotometry and its analytical application.
The supramolecular interaction of curcumin and beta-cyclodextrin (beta-CD) has been studied by spectrophotometry. The mechanism of the inclusion was studied and discussed based on the variations of pK(a), absorption intensity, and infrared spectrograms. The results show that beta-CD reacts with curcumin to form a 2:1 host-guest complex with an apparent formation constant of 5.53 x 10(5) mol(-2) x L2. Based on the enhancement of the absorbance of curcumin produced through complex formation, a spectrophotometric method for the determination of curcumin in bulk aqueous solution in the presence of beta-CD was developed. The linear relationship between the absorbance and curcumin concentration was obtained in the range of 0-15 microg/mL, with a correlation coefficient (r) of 0.9991. The detection limit was 0.076 microg/mL. The proposed method was used to determine the curcumin in curry and mustard with satisfactory results. Topics: Acetonitriles; beta-Cyclodextrins; Curcumin; Cyclodextrins; Drug Interactions; Hydrogen-Ion Concentration; Solutions; Solvents; Spectrophotometry; Spectrophotometry, Infrared; Thermodynamics | 2002 |