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PubMed2006

Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography.

The synthesis and evaluation of new dinitrophenyl (DNP) substituted beta-cyclodextrin (beta-CD) chiral stationary phases (CSPs) for the enantioseparation of various classes of chiral analytes by HPLC are presented. The dinitrophenyl substituted beta-CD derivatives are synthesized and covalently bonded to functionalized 5 microm spherical porous silica gel. These are the first reported derivatized cyclodextrin which contains pi-electron deficient substituents (i.e., pi-acidic moieties). The column performance in terms of their ability to separate enantiomers is evaluated. A variety of different dinitro-substituted aryl groups are investigated and compared. The pH of the mobile phase buffers, the buffer composition, the number and position of the dinitro groups on the phenyl ring substituent, the degree of substitution, and the bonding strategy all greatly affect the performance of the CSPs. A large variety of racemic compounds have been separated successfully on these CSPs. The bonded dinitrophenyl-derivatized cyclodextrins are stable in all three mobile phase modes, namely, the reversed-phase, polar organic, and normal phase modes. No degradation in column performance was observed in any mode of operation even after more than 1000 injections. The analytical applicability of these types of CSPs for enantiomeric separations is discussed in detail.

Alcohols↗
PubMed2006

Chemometric studies of lysozyme upon interaction with sodium dodecyl sulfate and beta-cyclodextrin.

The interaction of hen egg-white lysozyme with sodium n-dodecyl sulfate (SDS) as an anionic surfactant was investigated by UV-vis spectrophotometry at different pHs at 25 degrees C using HCl/glycine and NaOH/glycine for acidic and basic pH ranges, respectively. Analysis of the spectral data using chemometric method gave the evidence for the existence of intermediate components during the cited interaction. Results also indicated a connection between turbidity of the protein solution upon interaction with SDS and distribution of our newly found intermediates. As intermediates are important in aggregation of proteins, beta-cyclodextrin was employed as an anti-aggregation agent and the results obtained for the lysozyme-SDS-beta-cyclodextrin ternary system were compared with those obtained in the absence of beta-cyclodextrin on distribution and mole fraction of intermediates with. It is also shown that as the distribution of intermediates broadens in a range of SDS concentrations, the turbidity and aggregation state of solution are reduced.

Animals↗
PubMed2005

Properties of eight methacrylated beta-cyclodextrin composite formulations.

OBJECTIVES: Methacrylated beta-cyclodextrins (MCDs) are novel candidate dental monomers if all or some of the hydroxyl groups of beta-cyclodextrin are substituted with methacrylate groups. The main objective of this study was to evaluate mechanical properties of a number of composite formulations having MCDs as novel dental comonomers. The properties determined were flexural strength (FS), volumetric shrinkage (VS), and degree of conversion (DC). METHODS: A mass fraction of 50% of MCD monomers was mixed with a mass fraction of 50% each of a series of dimethacrylate or monomethacrylate diluent comonomers to produce consistent formulations of a workable viscosity. For comparison a resin mixture of a mass fraction of 50% Bis-GMA and a mass fraction of 50% triethyleneglycol dimethacrylate (a typical dental resin mixture) was also studied. The mixtures were activated with camphorquinone and ethyl 4-dimethylamino benzoate. One part by mass of each activated resin formulation was mixed with three parts by mass of glass filler. Samples for the FS tests were prepared in (2 x 2 x 25) mm3 molds by light-curing the composites for 2 min on each side. The cured samples were immersed in 37 degrees C water for 24 h, and FS was measured with an Instron machine at a crosshead speed of 0.5 mm/min. VS was measured by a computer-controlled mercury dilatometer. DC was measured by near-infrared spectroscopy. RESULTS: The properties of the MCD-based composites depended on the kind of diluent used. With these MCD monomers, diluents of triethyleneglycol dimethacrylate, 1,10-decamethylenediol dimethacrylate, or benzyl methacrylate yielded the best composite properties. SIGNIFICANCE: Although not yet fully optimized, MCD-based composite formulations containing triethyleneglycol dimethacrylate, 1,10-decamethylenediol dimethacrylate, or benzyl methacrylate yielded flexural strength and volumetric shrinkage values were comparable to those of the Bis-GMA/triethyleneglycol dimethacrylate controls. These findings lend support for further development and evaluations of polymerizable cyclodextrin derivatives for use in dental materials.

Analysis of Variance↗
PubMed2005

Synthesis of 2-substituted beta-cyclodextrin derivatives with a hydrolytic activity against the organophosphorylester paraoxon.

Beta-cyclodextrin was substituted by an iodosobenzoic acid derivative to create a catalytic hydrolytic activity against neurotoxic organophosphorus agents. The catalytic moiety was introduced on a secondary hydroxy group at the position 2 of a glucose unit. Several beta-cyclodextrin derivatives were obtained. In these derivatives, the methylene linker occupied all potential positions on the aromatic ring. Kinetic assays were carried out with paraoxon as organophosphate model. Three regioisomers hydrolyzed paraoxon, although the paraoxon-leaving group, para-nitrophenol, was not released from the beta-cyclodextrin torus.

Catalysis↗
PubMed2006

Effect of 2,6-di-O-methyl-alpha-cyclodextrin on hemolysis and morphological change in rabbit's red blood cells.

The effects of 2,6-di-O-methyl-alpha-cyclodextrin (DM-alpha-CyD) on hemolysis and morphological changes in rabbit's red blood cells (RBC) were examined, compared with those of alpha-cyclodextrin (CyD) and 2-hydoxypropyl-alpha-cyclodextrin (HP-alpha-CyD). The hemolytic activity of alpha-CyDs increased in the order of HP-alpha-CyD<alpha-CyD<DM-alpha-CyD. The three alpha-CyDs induced morphological changes of RBC from discocyte to stomatocyte. At the same concentration (3mM) of alpha-CyDs, DM-alpha-CyD and alpha-CyD released phospholipids, rather than cholesterol, and DM-alpha-CyD markedly released proteins from RBC membranes, compared to alpha-CyD and HP-alpha-CyD. The treatment of RBC with DM-alpha-CyD lowered the extent of a fluorescent sphingomyelin analogue from lipid rafts of RBC membranes in a concentration-dependent manner. These results suggest that DM-alpha-CyD has higher hemolytic and morphological change activity than alpha-CyD and HP-alpha-CyD through more extraction of phospholipids including sphingomyelin and proteins, not cholesterol, from RBC membranes than alpha-CyD and HP-alpha-CyD.

Animals↗
PubMed2004

Influence of cyclodextrins on in vitro human skin absorption of the sunscreen, butyl-methoxydibenzoylmethane.

The effects of hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and sulfobutylether-beta-CD (SBE7-beta-CD) on in vitro human skin penetration and retention of the sunscreen agent butyl-methoxydibenzoylmethane (BM-DBM) were investigated. The interaction between the UV filter and the cyclodextrins was studied in water by phase-solubility analysis. Solid complexes were prepared by the co-evaporation method and characterized by (1)H NMR spectroscopy, thermal analysis and powder X-ray diffraction. Solutions containing BM-DBM free or complexed with cyclodextrins were applied to excised human skin in Franz diffusion cells and the amount of sunscreen permeated after 6 h into the stratum corneum, viable epidermis, dermis and receptor fluid was assessed by HPLC. As much as 14.10-16.78% of the applied dose of BM-DBM penetrated within the skin tissue. No sunscreen was detected in the dermis and in the receiver phase. The greater proportion (84.6-95.5%) of the absorbed UV filter was localized in the stratum corneum with no significant differences between uncomplexed or complexed BM-DBM. Notable levels (2.29% of the applied dose) of the sunscreen agent accumulated in the epidermis from the preparation containing free BM-DBM. The epidermal concentration of the UV filter was markedly reduced (0.66% of the applied dose) by complexation with SBE7-beta-CD, whereas HP-beta-CD had no effect. The decreased BM-DBM retention in the epidermal region achieved by SBE7-beta-CD limits direct contact of the sunscreen and of its reactive photolytic products with the skin viable tissues.

Adult↗
PubMed2005

Incorporation of the sunscreen agent, octyl methoxycinnamate in a cellulosic fabric grafted with beta-cyclodextrin.

The aim of the study was to investigate the incorporation of the sunscreen agent, octyl methoxycinnamate into cyclodextrin cavities covalently bound to cloth fibres. Tencel, a cellulosic fabric, was grafted with beta-cyclodextrin molecules through reaction with monochlorotriazinyl-beta-cyclodextrin (beta-CDMCT). The finished and untreated textiles were soaked in water-methanol mixtures containing 2% (v/v) of sunscreen agent and subsequently subjected to several washing cycles. The unmodified and modified fabrics were characterized by UV spectrophotometry and thermogravimetric analysis. The level of octyl methoxycinnamate entrapped in the Tencel tissue was determined by high-performance liquid chromatography and was found to be much higher (0.0203%, w/w) for the textile functionalised with beta-CDMCT compared to the unmodified fabric (0.0025%, w/w). In addition, spectrophotometric assessment of UV transmission through the fabric samples using the Transpore test showed that the in vitro sun protection factor of the textile support was markedly enhanced (3.2-fold increase) by impregnation with octyl methoxycinnamate of the beta-CDMCT grafted textile. Hence, even after repeated washings, the beta-CD finished fabric exhibits higher sunscreen agent retention and photoprotective properties than the unmodified textile material.

Cellulose, Oxidized↗
PubMed2006

Physicochemical characteristics and bioavailability of a novel intestinal metabolite of ginseng saponin (IH901) complexed with beta-cyclodextrin.

In an effort to improve the bioavailability (BA) of the insoluble compound 20-O-(beta-d-glucopyranosyl)-20(S)-protopanaxadiol (IH901), we prepared beta-cyclodextrin (betaCD) and hydroxypropyl-beta-cyclodextrin (HPbetaCD) inclusion complexes containing IH901. IH901 is a major metabolite formed by intestinal bacteria from protopanaxadiol ginseng saponins. We developed and validated an HPLC-based method to measure IH901 levels from samples prepared in vitro. The phase solubility profiles with both cyclodextrins (CDs) were classified as AL-type, indicating the formation of a 1:1 stoichiometric inclusion complex. Stability constants (Ks) calculated from the phase solubility diagrams showed that the betaCD complex was more stable than the HPbetaCD complex. Consequently, complexes of IH901 and betaCD were prepared by a freeze-drying method and were analyzed by fourier transformation-infrared spectroscopy (FT-IR), X-ray diffraction, differential scanning calorimetry (DSC), and scanning electron microscopy (SEM). From these physicochemical characterizations, we confirmed the presence of a new solid phase in the freeze-dried samples. The IH901 released from the complex in a pH 1.2 solution, the pH range of gastric fluids, was considerably lower than the amount released in the other solutions. The IH901 released from the complex in pH 6.8 solution, the range of intestinal fluids, was 9.0-fold greater than pure IH901 powder. However, the amount of IH901 released from the complex in pH 4.0-8.0 was less than 20%. After oral administration of the IH901-betaCD inclusion complex (30 mg/kg IH901) into rats, plasma concentrations were determined by LC/MS/MS. The peak concentration (Cmax) for the inclusion complex was 2.8-fold higher than that for pure IH901 powder. The BA, calculated from the ratio of the AUCoral to the AUCi.v., for the pure IH901 powder, the IH901-betaCD physical mixture, and the inclusion complex was 3.52, 4.34, and 6.57%, respectively. These results indicate that the BA for the inclusion complex was 1.9-fold higher than that for the pure IH901 powder.

Administration, Oral↗
PubMed2005

Zwitterion formation in gas-phase cyclodextrin complexes.

Protonated complexes of amino acids and underivatized beta-cyclodextrin, produced by electrospray ionization and trapped in the Fourier transform mass spectrometer, undergo formation of ternary complexes when reacted with alkyl amine. Based on the reactivities of the protonated amino acid complexes with alkylamines, the reactivities of the corresponding amino acid esters, and partially derivatized beta-cyclodextrin hosts, we conclude that the ternary complexes are salt-bridge zwitterionic species composed of amino acid zwitterions and protonated alkylamine all interacting with the hydroxyl groups on the narrow rim of the cyclodextrin. Molecular modeling calculations and experimental results suggest that the interactions of the amino acids with the rims contribute greatly to the formation of the zwitterionic species.

Amino Acids↗
PubMed2006

Chiral separation of salbutamol and bupivacaine by capillary electrophoresis using dual neutral cyclodextrins as selectors and its application to pharmaceutical preparations and rat blood samples assay.

An attempt for the simultaneous separation of salbutamol (Sal) and bupivacaine (Bup) enantiomers was performed by capillary elecytrophoresis with a dual mixture of neutral cyclodextrins as chiral selector. The influence on the separation of several parameters such as buffer composition, pH, the concentration ratio of 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD) to dimethyl-beta-cyclodextrin (DM-beta-CD) was investigated. A better separation was obtained for Sal and Bup with the CD mixtures compared to the use of HP-beta-CD or DM-beta-CD alone. The best simultaneous separation of Sal and Bup enantiomers was achieved with a 20 mM HP-beta-CD and 20 mM DM-beta-CD at pH 2.5 in a triethanolamine (TEA)/phosphate buffer. This method-utilized chlorphenamine (Chl) as an internal standard was found to be linear in the range 0.5-100 microg/mL and 0.5-150 microg/mL for Sal and Bup enantiomers, respectively. The limits of detection for both enantiomers of Sal and Bup were 0.18 and 0.24 microg/mL, respectively. The proposed method was applied to monitor Sal and Bup enantiomers concentration change in rat blood samples obtained from a male rat after celiac doses administration 0-30 min of Sal and Bup racemate. The method could also be used to determine Sal enantiomers in a pharmaceutical aerosol.

Albuterol↗
PubMed2006

Solubilisation of chlorinated solvents by cyclodextrin derivatives: a study by static headspace gas chromatography and molecular modelling.

The capacity of alpha-cyclodextrin (alpha-CD) and four beta-cyclodextrins (beta-CDs) in reducing the volatility of volatile organic compounds (VOCs) and particularly carbon tetrachloride (CT), chloroform (TCM) and dichloromethane (DCM) is investigated by using static headspace gas chromatography (HSGC). The experiments allowed the determination of Henry's law constant (H(c)) in absence and in presence of cyclodextrins (CDs). The use of CDs may lead to a reduction of 95% of the Henry's law constant for some VOCs. The association constants of the inclusion complexes formed between CDs and the three guests are determined using a new method involving an algorithmic treatment bringing the shortening of experimental time required for the determination of the stability constant. The complementarities of the host and the guest are investigated by molecular modelling. The complexation energies obtained are in good agreement with the experimental formation constants. Furthermore, this study shows the effectiveness of CDs in trapping pollutants and reducing their volatility in the viewpoint of pollution prevention.

Chromatography, Gas↗
PubMed2005

Enantioselective capillary electrophoretic separation of tryptophane- and tyrosine-methylesters in a dual system with a tetra-oxadiaza-crown-ether derivative and a cyclodextrin.

Different dual selector systems containing a cyclodextrin derivative (methyl-beta-cyclodextrin and dimethyl-beta-cyclodextrin) and a new diaza-crown-ether derivative (N-[2-(1,4,10,13-tetraoxa-7,16-diazacyclooctadecan-7-yl)propanoyl]glycine) were studied in the enantioselective separation of tryptophan-methylester and tyrosine-methylester enantiomers. This paper deals with the systematic study of the effects of changing the composition of the background electrolyte on the resolution of the d- and l- forms using an experimental design approach. It was found that the dual systems allowed a better chiral separation of the amino acid derivatives. The experimental design approach also allowed improving the separation compared to the starting conditions (center point of the design), which were adopted from a previous study.

Algorithms↗
PubMed2005

Determination of the molecular complexation constant between alprostadil and alpha-cyclodextrin by conductometry: implications for a freeze-dried formulation.

The binding constant between alprostadil (PGE1) and alpha-cyclodextrin (alpha-CD) was determined at four temperatures using conductance measurements. Alpha-cyclodextrin is an excipient material in Caverject dual chamber syringe (DCS) that was added to enhance stability. The binding constant was used to calculate the amount of PGE1 free upon reconstitution and injection, since only the free drug is clinically active. The conductivity measurement is based on a decrease in specific conductance as alprostadil is titrated with alpha-CD. The change in conductivity was plotted versus free ligand concentration (alpha-CD) to generate a binding curve. As the value of the binding constant proved to be dependent on substrate concentration, it is really a pseudo binding constant. A value of 742+/-60 M(-1) was obtained for a 0.5 mM solution of alprostadil at 27 degrees C and a value of 550+/-52 M(-1) at 37 degrees C. These results compare favorably to values previously obtained by NMR and capillary electrophoresis. Calculation of the fraction PGE1 free upon reconstitution and injection show it to approach the desired outcome of one. Hence, the amount of drug delivered by Caverject DCS is nominally equivalent to that delivered by Caverject S. Po., a predecessor product that contains no alpha-cyclodextrin.

Algorithms↗
PubMed2006

Polymorphism, pseudopolymorphism, and amorphism of peracetylated alpha-, beta-, and gamma-cyclodextrins.

Polymorphism, pseudopolymorphism, and amorphism of hexakis(2,3,6-tri-O-acetyl)-alpha-cyclodextrin (TAalphaCyD), heptakis(2,3,6-tri-O-acetyl)-beta-cyclodextrin (TAbetaCyD), and octakis(2,3,6-tri-O-acetyl)-gamma-cyclodextrin (TAgammaCyD) were investigated using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), powder X-ray diffractometry (XRPD), Fourier transform infrared spectroscopy (FTIR) and optical microscopy. An anhydrous and a bi-hydrate crystalline forms of TAalphaCyD, two monotropic anhydrous polymorphs and three pseudopolymorphs (i.e. methanolate, hydrate, and isopropanolate-hydrate) of TAbetaCyD, as well as two monotropic anhydrous polymorphs and isostructural pseudopolymorphs (e.g. hydrate and isopropanolate-hydrate) of TAgammaCyD were isolated and characterized. The amorphous forms of each TACyD were also obtained. Thermal data for desolvation of TAalphaCyD.2H2O and TAbetaCyD.CH3OH were reconciled with their crystal packing features. Melting temperatures and enthalpies of the crystalline forms of each TACyD can be referred to for possible solid-state interactions with drugs.

Calorimetry, Differential Scanning↗
PubMed2006

A validated chiral CE method for Frovatriptan, using cyclodextrin as chiral selector.

A cyclodextrin modified capillary zone electrophoretic method has been developed for the evaluation of chiral purity of Frovatriptan using sulfobutyl ether beta cyclodextrin (SB-beta-CD) as the chiral selector. The method is highly specific, accurate and reproducible. The method was optimized with a systematic method development approach by optimizing the pH of electrolyte, attempting the separation in different classes of chiral selectors and modifying parameters such as cyclodextrin concentration and the organic modifier type and concentration. The optimized method was validated for specificity, precision, linearity, accuracy and stability in solution using Imidazole as the internal standard. The limit of detection (LOD) and limit of quantification (LOQ) were 1.0 microg/mL and 5.0 microg/mL respectively for each isomer. The method was applied for estimating the chiral purity of various batches of Frovatriptan.

Carbazoles↗
PubMed2006

Evaluation of supercritical fluid technology as preparative technique of benzocaine-cyclodextrin complexes--comparison with conventional methods.

The objective of this study was to investigate the effect of the preparation method on the physico-chemical properties of complexes prepared between beta-cyclodextrin (beta-Cyd) and benzocaine (BZC). In particular, the effectiveness of a new technique based on supercritical carbon dioxide (SC CO(2)) for preparing solid drug-cyclodextrin complexes was investigated and compared to other more conventional methods such as kneading (KN), co-evaporation (COE), co-grinding (GR) and sealed-heating (S.H.). Effects of temperature, pressure and exposure time on the properties of complexes prepared by SC CO(2) technology were also studied. The different systems were characterized by differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), powder X-ray diffractometry (PXRD) and dissolution test according to the dispersed amount method. The co-grinding (GR) method resulted in amorphous products while other methods led to crystalline or partially amorphous products depending on both the method and its experimental conditions. SC CO(2) method revealed to be an effective technique for preparing solid systems between beta-cyclodextrin and benzocaine, avoiding the use of organic solvents (and problems of their complete removal) and allowing an easy scale-up of the process. As for the influence of the experimental conditions in promoting the solid-state drug-carrier interaction when using the SC CO(2) method, temperature seemed to play the major role, whereas pressure and exposure times had more limited effects. Dissolution tests confirmed a limited but favourable effect in increasing the exposure time, while indicated a possible interaction effect between temperature and pressure in influencing the dissolution performance of the final product. The best product obtained by the SC CO(2) method showed dissolution properties similar to those of the co-ground product and only slightly lower than the system obtained by sealed-heating, which was the most effective technique.

Anesthetics, Local↗
PubMed2005

Encapsulation of norharmane in cyclodextrin: formation of 1:1 and 1:2 inclusion complexes.

Steady state absorption and fluorometric techniques have been used to investigate the photophysics of norharmane (NHM), a bioactive fluorophore, in aqueous as well as aqueous cyclodextrin (CD) environments. The absorption and steady state fluorescence spectral studies reveal the formation of two types of inclusion complexes between the fluorophore and beta-cyclodextrin (beta-CD) depending on the relative population of the two. The stoichiometries and association constants of these complexes have been determined monitoring the fluorescence data. alpha-and gamma-cyclodextrin (alpha-CD, gamma-CD) do not have appreciable effect on the spectral pattern of the fluorophore. The differential fluorimetric behavior of NHM in different CD environments has been rationalized from the variation of the relative dimensions of the probe and the CD cavities.

Carbolines↗
PubMed2006

Controlled 2D crystallization of membrane proteins using methyl-beta-cyclodextrin.

High-resolution structural data of membrane proteins can be obtained by studying 2D crystals by electron crystallography. Finding the right conditions to produce these crystals is one of the major bottlenecks encountered in 2D crystallography. Many reviews address 2D crystallization techniques in attempts to provide guidelines for crystallographers. Several techniques including new approaches to remove detergent like the biobeads technique and the development of dedicated devices have been described (dialysis and dilution machines). In addition, 2D crystallization at interfaces has been studied, the most prominent method being the 2D crystallization at the lipid monolayer. A new approach based on detergent complexation by cyclodextrins is presented in this paper. To prove the ability of cyclodextrins to remove detergent from ternary mixtures (lipid, detergent and protein) in order to get 2D crystals, this method has been tested with OmpF, a typical beta-barrel protein, and with SoPIP2;1, a typical alpha-helical protein. Experiments over different time ranges were performed to analyze the kinetic effects of detergent removal with cyclodextrins on the formation of 2D crystals. The quality of the produced crystals was assessed with negative stain electron microscopy, cryo-electron microscopy and diffraction. Both proteins yielded crystals comparable in quality to previous crystallization reports.

Aquaporins↗