stilbenes and betadex

Trans-resveratrol, a polyphenol extracted from Vitis vinifera, has different beneficial effects following its administration on the skin. Here the potential use of binary systems to enhance in vitro and in vivo activity of trans-resveratrol was investigated. Thus the aqueous solubility of trans-resveratrol was investigated in the presence of growing concentrations of polyethylene glycol (PEG) or β-cyclodextrin (βCD) as solubilizing excipients. Then, the solid dispersion of trans-resveratrol with PEG or inclusion complexes trans-resveratrol/βCD were prepared and characterised by different methods. Cytotoxicity and inhibition of reactive oxygen species (ROS) following H2O2 challenge in the presence of trans-resveratrol, alone or associated to the excipients, was evaluated on human keratinocyte HaCaT cell line. Both the trans-resveratrol-containing binary systems induced significant reduction of H2O2-induced ROS production, especially in the case of βCD that was selected for the following phase of the study. Thus, the effect of a cream containing trans-resveratrol, alone or associated to βCD, on different skin parameters such as corneometry, colorimetry and elastometry, was evaluated on human volunteers. All patients showed a visible improvement of clinical conditions with a remarkable decrease of aging signs, but this effect was higher of the hemi face treated with the βCD-containing formulation versus formulation containing trans-resveratrol alone.

Topics: Aged; Antioxidants; beta-Cyclodextrins; Cell Line; Chemistry, Pharmaceutical; Colorimetry; Excipients; Female; Humans; Hydrogen Peroxide; Keratinocytes; Middle Aged; Polyethylene Glycols; Reactive Oxygen Species; Resveratrol; Single-Blind Method; Skin Aging; Solubility; Stilbenes

The delivery of protein into mammalian cells enables the dissection and manipulation of biological processes; however, this potency is challenged by the lack of an efficient protein delivery tool and a means to monitor its intracellular trafficking. Herein, we report that the hierarchical self-assembly of tetraphenylethylene (TPE)-featured metal-organic cages (MOCs) and β-cyclodextrin-conjugated polyethylenimine can generate fluorescent supramolecular nanoparticles (FSNPs) to deliver protein into neural cells, a cell line that is hard to transfect using conventional strategy. Further, the aggregation-induced emission (AIE) of TPE enabled the fluorescent monitoring of cytosolic protein release. It is found that FSNPs can deliver and release protein into cytosol for subcellular targeting as fast as 18 h post-delivery. Moreover, the delivery of molecular chaperone DJ-1 using FSNPs activates MAPK/ERK signaling of neural cells to protect cells from oxidative stress.

Topics: beta-Cyclodextrins; Cell Line, Tumor; Fluorescent Dyes; Humans; Macromolecular Substances; Nanoparticles; Neural Stem Cells; Oxidative Stress; Polyethyleneimine; Stilbenes

Plants encounter diverse stressors simultaneously with changing environmental factors. The combined effect of different types of stresses can have a wide range of effects on plants. The present study demonstrated that various stress factors such as the combination of chemical elicitors, namely paraquat (PQ), methyl jasmonate (MeJA) and methyl-β-cyclodextrin (CD), light exposure versus darkness, and mechanical shearing stress affected the defence response in peanut hairy root culture. The antioxidant activities were dramatically increased at all time points after hairy roots were subjected to elicitation with PQ + MeJA + CD under root cutting in both light and dark conditions. The stilbene compounds were highly increased in the culture medium after elicitor treatment of uncut hairy roots under dark conditions. In contrast to the high stilbene contents detected in culture medium under dark conditions, the transcription of the stilbene biosynthesis genes PAL, RS and RS3 was enhanced by the effect of light in uncut hairy root tissues. The antioxidant enzyme genes APX, GPX and CuZn-SOD of uncut and cut hairy roots were more highly expressed in light conditions than in dark conditions. The pathogenesis-related protein (PR)-encoding genes chitinase, PR4A, PR5 and PR10 of uncut hairy roots were highly expressed in response to light conditions compared to dark conditions at all time points. Recent evidence of the production of antioxidant stilbene compounds and defence response genes has implicated plant protective functions through defence responses under different stress challenges. Plant responses might therefore be regulated by the coordination of different signal responses through dynamic pathways.

Topics: Acetates; Arachis; beta-Cyclodextrins; Cyclopentanes; Darkness; Gene Expression Regulation, Plant; Light; Oxylipins; Paraquat; Plant Roots; Stilbenes; Stress, Mechanical; Tissue Culture Techniques

On the basis of BSA stabilized tetraphenylethylene nanocrystals (BSA-TPE NCs) as aggregation-induced enhanced electrochemiluminescence (ECL) emitters with high ECL efficiency and good biocompatibility, as well as molecular recognition between β-CD and ferrocene, an ultrasensitive and versatile ECL biosensing platform was constructed to achieve microRNA detection in cancer cells.

Topics: Animals; beta-Cyclodextrins; Biocompatible Materials; Biosensing Techniques; Cattle; Cell Line, Tumor; Electrochemical Techniques; Ferrous Compounds; Fluorescent Dyes; Humans; Limit of Detection; Luminescent Measurements; Metallocenes; MicroRNAs; Nanoparticles; Sensitivity and Specificity; Serum Albumin, Bovine; Stilbenes

The present investigation was designed to explore the effectiveness of pterostilbene (PT) on insulin resistance, metabolic syndrome and oxidative stress in fructose-fed insulin resistant rats.. Age-matched, male Sprague-Dawley rats (330±30g body weight) were allocated into five groups (n=10). Control (C) group received 65% cornstarch, and the diabetic (D) group received 65% fructose for eight weeks. The third group (D+PT20) received 65% fructose and PT 20mg/kg/day for eight weeks. The fourth group (D+PT40) received 65% fructose and PT 40mg/kg/day for eight weeks. The fifth group (D+M) received 65% fructose and metformin (M) 100mg/kg/day for eight weeks. PT was dissolved in 10% β-cyclodextrin and given orally to rats. Several biochemical parameters were determined to assess the PT efficacy against insulin resistance, metabolic complications, and hepatic oxidative stress.. Significantly high HOMA-IR (p<0.001) values in D group compared to C group indicate the presence of insulin resistance. Significantly high levels of TBARS (p<0.001) and decreased levels of SOD (p<0.001) and GSH (p<0.001) in hepatic tissues of D group indicate oxidative stress associated with insulin resistance. Pterostilbene treatment to fructose-fed diabetic rats significantly decreased HOMA-IR (p<0.001) values. Furthermore, PT treatment significantly decreased hepatic TBARS (p<0.001) and increased SOD (p<0.001) and GSH (p<0.001) levels in fructose-fed diabetic rats.. Current study reveals that PT is successful in ameliorating glycemic control, insulin sensitivity while diminishing metabolic disturbances and hepatic oxidative stress in a fructose-induced T2DM rat model.

Topics: Animals; beta-Cyclodextrins; Blood Glucose; Diabetes Mellitus, Experimental; Diabetes Mellitus, Type 2; Fructose; Insulin Resistance; Male; Metabolic Syndrome; Metformin; Oxidative Stress; Rats; Rats, Sprague-Dawley; Stilbenes; Superoxide Dismutase; Thiobarbituric Acid Reactive Substances

The supramolecular inclusion properties of beta-cyclodextrin (beta-CD) and resveratrol (Res) were investigated using drug-protein interaction spectroscopy method. The differences between the results of interaction spectroscopy method and the results of classical method were compared. The total energy of the stable inclusion of cyclodextrin-resveratrol was calculated by Gaussian theory calculation. The stable inclusions in the process of interaction between resveratrol/inclusion complex and bovine lactgoferrin (BLF) were studied by molecular modeling. The results showed that the interaction spectroscopy method could explain the property of the inclusion in a more sensitive manner, it also interpreted the conveying mechanism of BLF binding with inclusion complex. The molecular modeling result showed consistent results with Gaussian theory calculation; both of the two methods obtained the stable configuration of beta-CD-Res inclusion. The relevant result provided an experimental consequence for the pharmacology research of beta-cyclodextrin-resveratrol inclusion complex as well as offering a new reference to the future research of supramolecular inclusion compound.

Topics: Animals; beta-Cyclodextrins; Cattle; Lactoferrin; Magnetic Resonance Spectroscopy; Models, Molecular; Resveratrol; Stilbenes

Piceatannol is one of resveratrol derivatives having health promoting potential. However, its low water-solubility and bioavailability could limit its use in both food and pharmaceutical fields. The aim of this work is the study of piceatannol complexation by β-cyclodextrin (β-CD) in aqueous media. The complex formed could improve the bioavailability, the solubility and the stability of piceatannol. The method used was based on RP-HPLC in which, β-CD was added to methanol/water mixtures mobile phases. The apparent formation constant of piceatannol/β-cyclodextrin complex was determined. Within the concentration interval studied (0-4 mM), whenever the concentration of β-CD increased, retention time of piceatannol decreased; indicating an enhancement of solubility due to the formation of the piceatannol/β-CD complex. The formation constants (KF) of the piceatannol/β-CD complex varied significantly with both the methanol concentration in the water-methanol mixture and the temperature. Moreover, in all the physicochemical conditions tested, the stoichiometry of piceatannol/β-CD complex was 1:1. Finally, the thermodynamic parameters were determined: ΔG°=-13.123 kJ mol(-1), ΔH°=-33. 265 kJ mol(-1) and ΔS°=-67.559 J mol(-1) K(-1).

Topics: beta-Cyclodextrins; Chromatography, High Pressure Liquid; Resveratrol; Stilbenes; Thermodynamics

We report on the synthesis and the photophysical properties of a trans-nitroalkoxystilbene dimer (DPNS). The fluorescence quantum yield (Φ(f)), the Stokes shift, and the quantum yield for the trans-to-cis photoisomerization (Φ(t→c)) are strongly dependent on the nature of the solvent. Upon increasing solvent polarity, Φ(f) increases together with the decrease of Φ(t→c). This solvent-induced reverse behavior mainly stems from the progressive stabilization of a highly polar twisted internal charge transfer state (TICT) at excited singlet level which opens a competing channel to photoisomerization. In the presence of hydroxylic substrates (i.e., alcohols or water), fluorescence of DPNS is strongly quenched due to a hydrogen bonding interaction at excited state. The efficiency of the process is clearly correlated to the H-bond donor ability of the quencher. In aqueous solution, the major formation of a 2:1 host-guest complex with β-cyclodextrins (β-CD) prevents the quenching by H(2)O and leads to a 50-fold increase of the fluorescence signal together with a strong band blue-shift with respect to that of the free chromophore. This latter effect was rationalized in terms of a severe reduction of the solvent-induced stabilization of the TICT state. As a consequence, the trans-to-cis photoisomerization reaction is reactivated and leads to a paradoxical 14-fold increase of Φ(t→c) even though DPNS is sequestered in β-CD cavities.

Topics: beta-Cyclodextrins; Dimerization; Fluorescence; Hydrogen Bonding; Molecular Structure; Photochemical Processes; Spectrometry, Fluorescence; Stilbenes

The aim of this work was to increase the solubility, stability and permeation of resveratrol by complexation with cyclodextrin-based nanosponges (NS). Nanosponges are recently developed hyper-cross-linked cyclodextrin polymers nanostructured to form three-dimensional networks; they are obtained by reacting cyclodextrin with a cross-linker such as carbonyldiimidazole. They have been used to increase the solubility and stability of poorly soluble actives. This study aimed at formulating complexes of resveratrol with β-cyclodextrin nanosponges in different weight ratios. DSC, FTIR and X-ray powder diffraction (XRPD) studies confirmed the interaction of resveratrol with NS. XRPD showed that the crystallinity of resveratrol decrease after encapsulation. The particle sizes of resveratrol-loaded NS are in between 400 to 500 nm with low polydispersity indices. Zeta potential is sufficiently high to obtain a stable colloidal nanosuspension. TEM measurement also revealed a particle size around 400 nm for NS complexes. The in vitro release and stability of resveratrol complex were increased compared with plain drug. Cytotoxic studies on HCPC-I cell showed that resveratrol formulations were more cytotoxic than plain resveratrol. The permeation study indicates that the resveratrol NS formulation showed good permeation in pigskin. The accumulation study in rabbit mucosa showed better accumulation of resveratrol NS formulation than plain drug. These results signify that resveratrol NS formulation can be used for buccal delivery and topical application.

Topics: Administration, Buccal; Animals; Anti-Inflammatory Agents, Non-Steroidal; beta-Cyclodextrins; Cell Line, Tumor; Cell Proliferation; Cellulose; Cyclodextrins; Drug Carriers; Drug Compounding; Drug Stability; Excipients; Humans; In Vitro Techniques; Nanostructures; Particle Size; Permeability; Rabbits; Resveratrol; Solubility; Stilbenes

Knowledge of the complexation process of oxyresveratrol with beta-cyclodextrin (beta-CD) under different physicochemical conditions is essential if this potent antioxidant compound is to be used successfully in both food and pharmaceutical industries as ingredient of functional foods or nutraceuticals, despite its poor stability and bioavailability. In this paper, the complexation of oxyresveratrol with natural CDs was investigated for first time using RP-HPLC and mobile phases to which alpha-, beta-, and gamma-CD were added. Among natural CDs, the interaction of oxyresveratrol with beta-CD was more efficient than with alpha- and gamma-CD. The decrease in the retention times with increasing concentrations of beta-CD (0-4 mM) showed that the formation constants (KF) of the oxyresveratrol/beta-CD complexes were strongly dependent on both the water-methanol proportion and the temperature of the mobile phase employed. However, oxyresveratrol formed complexes with beta-CD with a 1:1 stoichiometry in all the physicochemical conditions tested. Moreover, to obtain information about the mechanism of the oxyresveratrol affinity for beta-CD, the thermodynamic parameters DeltaG degrees, DeltaH degrees and DeltaS degrees were obtained. Finally, to gain information on the effect of the structure of different compounds belonging to the stilbenoids family on the KF values, the complexation of other molecules, resveratrol, pterostilbene and pinosylvin, was studied and compared with the results obtained for the oxyresveratrol/beta-CD complexes.

Topics: beta-Cyclodextrins; Chromatography, High Pressure Liquid; Chromatography, Reverse-Phase; Methanol; Plant Extracts; Stilbenes; Temperature; Thermodynamics; Water

The excretion characteristics of stilbene glycoside (THSG) and its beta-cyclodextrin inclusion in bile, urine and feces after oral administration to rats were studied. Bile for 24 h, urine and feces for 72 h were collected. The content of THSG was determined by HPLC-UV. The established HPLC-UV method was available for the analysis of THSG in excreta and corresponded to the requirement of biological sample analysis. After given THSG and its beta-cyclodextrin inclusion, the amount of prototype THSG in feces were 3.27% and 0.61%, meanwhile THSG in bile were 0.20% and 0.18%, respectively. Only a little THSG was found in urine. The result showed that beta-cyclodextrin inclusion reduced the fecal excretion of THSG. However, the characteristic of urinary and biliary excretion wasn't changed.

Topics: Administration, Oral; Animals; beta-Cyclodextrins; Bile; Biological Transport; Chromatography, High Pressure Liquid; Feces; Glycosides; Inclusion Bodies; Injections, Intravenous; Male; Rats; Rats, Sprague-Dawley; Stilbenes

A prototype, based on light-active fluorescent rotor grafted to beta-cyclodextrin, shows a good solvent viscosity-sensitive behavior due to the environment-dependent nonradiative decay. With the reversible photoisomerization of the cyanostilbene unit, the viscosity sensitivity of the molecular rotor could be locked and activated, and the two switchable states can be distinguished by fluorescent signals. This cyclodextrin derivative was threaded to form a novel polypseudorotaxane. Such supramolecular assembly displays a lockable ratiometric fluorescent viscosity sensitivity with two emission channels: one aroused by fluorophore's intramolecular excimer without influenced by viscosity is used to gauge the concentration of the compound, while the other corresponding to the monomer's rotor fluorescence acts as a viscosity-sensitive signal and it can be shut off by UV irradiation.

Topics: beta-Cyclodextrins; Biocompatible Materials; Cyclodextrins; Light; Magnetic Resonance Spectroscopy; Models, Chemical; Molecular Conformation; Photochemistry; Rotaxanes; Solvents; Spectrometry, Fluorescence; Stilbenes; Taxoids; Ultraviolet Rays; Viscosity

The complexation of trans-resveratrol with beta-cyclodextrin (beta-CD) was investigated using reversed-phase liquid chromatography and mobile phases to which beta-CD was added. The decrease in the retention times with increasing concentrations of beta-CD (0-2.5 mM) showed that trans-resveratrol forms a 1:1 complex with beta-CD, while the apparent formation constants (K(F)) were strongly dependent of the water-methanol proportion of the mobile phase employed. A slight decrease in K(F) was observed at 50-55% water in the mobile phase but a large increase from 55 to 70% water. The values of K(F) for the trans-resveratrol-beta-CD interaction decreased when the temperature was raised from 20 to 37 degrees C. In order to gain information about the mechanism aspect of the trans-resveratrol affinity for beta-CD, the thermodynamic parameters of the complexation were obtained. Complex formation of trans-resveratrol with beta-CD (DeltaG degrees =-17.01 kJ/mol) is largely driven by enthalpy (DeltaH degrees = -30.62 kJ/mol) and slightly entropy changes (DeltaS degrees = -45.68 J/mol K).

Topics: beta-Cyclodextrins; Chromatography, High Pressure Liquid; Methanol; Resveratrol; Spectrophotometry, Ultraviolet; Stilbenes; Thermodynamics; Water

Topics: alpha-Cyclodextrins; beta-Cyclodextrins; Hot Temperature; Hydrogen Bonding; Light; Macromolecular Substances; Models, Chemical; Molecular Conformation; Movement; Photochemistry; Rotaxanes; Stilbenes; Time Factors

trans-4-Acetylaminostilbene (AAS) is a complete carcinogen in rats and produces quite selectively tumors in Zymbal's glands. On the basis of DNA adduct formation, it has been proposed that this model arylamine initiates neoplastic transformation of cells in many tissues, particularly liver and kidney, which, in the classical sense are considered to be non-target tissues for this chemical. In the present study an initiating treatment with AAS was followed by unilateral nephrectomy and the application of two nephrotoxic substances, gentamycin or beta-cyclodextrin which, among other activities, stimulate cell proliferation specifically in kidney. The initiating dose of AAS, given alone, gave rise to Zymbal's gland and mammary tumors in female Wistar rats within 88 weeks but not to liver or kidney tumors. When the initiation treatment was followed by unilateral nephrectomy, alone or in combination with gentamycin, or by beta-cyclodextrin, four tumors in two out of ten animals, eight tumors in three/ten, and seven tumors in three/ten, respectively, were observed in the kidney. The administered dose of gentamycin was not sufficient to induce tumors on its own. The results support the view that the genotoxic effects of AAS produce promotable lesions in rat kidney. None of the animals that had been treated with AAS, with or without other treatments, developed tumors or the predominant types of preneoplastic lesions in the liver within 88 weeks; this supports the notion that liver, like kidney, is not a target for complete carcinogenesis for this chemical.

Topics: Adenoma, Chromophobe; Animals; beta-Cyclodextrins; Carcinogens; Cocarcinogenesis; Cyclodextrins; Cystadenoma; Female; Gentamicins; Kidney Neoplasms; Nephrectomy; Rats; Rats, Wistar; Stilbenes