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PubMed1992

[On the drug molecular states dispersed in cyclodextrin matrices].

Molecular states of drug molecules in cyclodextrin solid dispersion systems have been studied. The possibility of inclusion compound formation was investigated between drug and cyclodextrin molecules by grinding, sealed heating and freeze drying. Solid state fluorescent spectroscopic measurements were made on the ground mixtures as well as infrared and photo-acoustic spectroscopies. It was found that time resolved solid state fluorescence analysis was effective to investigate the molecular states of fluorescent probe dispersed in cyclodextrins. Sealed heating of drug-cyclodextrin mixture was recognized as a new unique method for preparing cyclodextrin inclusion compound. In the case of freeze drying, the freezing conditions showed great influences on the drug dispersion states and the crystallinity of the products. The results are explained in terms of the inclusion compound formation by grinding, sealed heating and freeze drying.

Cyclodextrins↗

PubMed2005

Cyclodextrins in drug delivery.

Cyclodextrins are a family of cyclic oligosaccharides with a hydrophilic outer surface and a lipophilic central cavity. Cyclodextrin molecules are relatively large with a number of hydrogen donors and acceptors and, thus, in general they do not permeate lipophilic membranes. In the pharmaceutical industry cyclodextrins have mainly been used as complexing agents to increase aqueous solubility of poorly soluble drugs, and to increase their bioavailability and stability. Studies in both humans and animals have shown that cyclodextrins can be used to improve drug delivery from almost any type of drug formulation. However, the addition of cyclodextrins to existing formulations without further optimisation will seldom result in acceptable outcome. Currently there are approximately 30 different pharmaceutical products worldwide containing drug/cyclodextrin complexes on the market.

Administration, Cutaneous↗

PubMed1993

Minimization of shaking-induced formation of insoluble aggregates of insulin by cyclodextrins.

Aggregation is known to complicate insulin delivery and the processing and formulation of biotechnology-derived peptide/protein drugs. Shaking-induced formation of insoluble aggregates in bovine insulin and the potential role of cyclodextrins in preventing such aggregation were investigated. Insulin, dissolved in phosphate buffer, pH 7.2, and preserved with 2 mg/ml of phenol was aggregated, in triplicate, by shaking at 450 rpm for 2.5 days on a gyratory shaker. Visible aggregation was quantitated by measuring optical density in the visible range on a spectrophotometer. Solutions were then filtered through a 0.22 mu filter and the amount of insulin remaining in filtrate was determined by HPLC. Aggregation increased at lower concentrations, with solutions turning milky at 0.5 mg/ml; HPLC assay of filtrate indicated a complete loss of insulin. Under the same conditions, except for shaking, control solutions exhibited no insulin loss, excluding absorption as a cause of the insulin loss. The use of cyclodextrins (0.5 mg/ml) to stabilize insulin was investigated. alpha-, beta-, gamma- and hydroxypropyl-beta-cyclodextrin, each at 1.5% level, were used to prevent aggregation. The efficacy of cyclodextrins in preventing aggregation (% insulin aggregated in parentheses), was: hydroxypropyl-beta- (15) approximately beta- (18) > alpha- (54). No protection was observed with gamma-cyclodextrin.

Adsorption↗

PubMed1990

Group-recognition ability of derivatized beta-cyclodextrin as studied by the ESR spin probing technique.

The effect of modifying the entrance face of beta-cyclodextrin on the inclusion of various functional groups in aminoxyl spin probes was determined by the use of heptakis (2,6-O-dimethyl)-beta-cyclodextrin and heptakis (2,3,6-O-triacetyl)-beta-cyclodextrin. The methylation of six of the secondary hydroxyl groups on the wider end of beta-cyclodextrin has a variable effect on the association constant of inclusion depending on the nature of the included group. The role of the methoxy group on the rim is discussed on the basis of the thermodynamic data derived from association constants. Contrary to the unmodified beta-cyclodextrin the pH of the solution does not influence the inclusion behaviour.

Chemical Phenomena↗

PubMed2001

[Reduction of the volatility of volatile organic compounds with cyclodextrins: application to their capture].

The interactions existing between beta-cyclodextrin, hydroxypropyl-beta-cyclodextrin and six volatile organic compounds (VOC) were studied and used for capture of such pollutants. The reduction of volatility for these VOC appeared to be equivalent for the two kinds of cyclodextrins at equal concentrations, while a higher solubility conferred higher efficiency to hydroxypropyl-beta-cyclodextrin. The use of such cyclodextrins in traps allowed a two-fold increase in VOC capture compared with genuine water. Application of this process to an industrial site showed its efficacity qualitatively while several optimization procedure are needed to achieve quantitative efficacy.

Cyclodextrins↗

PubMed2004

Influence of cyclodextrin complexation on the photodegradation and antioxidant activity of alpha-tocopherol.

The influence of complexation with beta-cyclodextrin (beta-CD), hydroxypropyl-beta-cyclodextrin (HP-beta-CD) or hydroxypropyl-gamma-cyclodextrin (HP-gamma-CD) on the antioxidant activity and light-induced decomposition of vitamin E (alpha-tocopherol) was investigated. The interaction of the vitamin with the cyclodextrins was ascertained by nuclear magnetic resonance spectroscopy. The photodegradation of alpha-tocopherol was examined in emulsion vehicles and was not significantly influenced by complexation with beta-CD (the extent of decomposition was 39.9% for the beta-CD complex compared to 47.2% for the free vitamin) whereas HP-beta-CD and HP-gamma-CD enhanced the light-induced decomposition of alpha-tocopherol (the loss of the vitamin reached 64.6% for the HP-beta-CD complex and 65.8% for the HP-gamma-CD complex). On the other hand, accelerated stability studies indicated that the degradation of non-irradiated alpha-tocopherol was reduced by complexation with HP-beta-CD or HP-gamma-CD. The radical scavenging activity of alpha-tocopherol was evaluated in vitro using the xanthine/xanthine oxidase enzymatic system. No significant differences were observed between the free form of the vitamin and its complexes with beta-CD, HP-beta-CD or HP-gamma-CD. Therefore, complexation of alpha-tocopherol with these cyclodextrins does not interfere with the vitamin antioxidant activity.

Antioxidants↗

PubMed2004

[Determination of constant for the inclusion complex of Yinqiao volatile oil with beta-cyclodextrin].

OBJECTIVE: To determine the constant for the inclusion complex of Yinqiao volatile oil with beta-cyclodextrin. METHOD: The stability constant for the inclusion complex of Yinqiao the volatile oil with beta-cyclodextrin was detemined under multiwavelength by ultraviolet spectroscopy, and spectroscopy feature for inclusion complex was studied. The phase solubility-curve showed the inclusion proportion. The inclusion complex of Yinqiao the volatile oil with beta-cyclodextrin was prepared by saturated aqueous solution. The DTA spectroscopy of inclusion complex was different from not only oil with beta-cyclodextrin but also the mixture of them. RESULT: The inclusion complex of Yinqiao the volatile oil with beta-cyclodextrin was formed. The experimental data of inclusion complex fitted well to the molar ratio of 1:1. There was good liner feature under multiwavelength of ultraviolet spectroscopy. CONCLUSION: Adopting multiwavelength method may determine the appearant stability constant of multicomponential traditional drug. The determination of the stability constant of the inclusion complex can be used in traditional drug.

Calorimetry, Differential Scanning↗

PubMedDate not supplied

[Physical and chemical characterization of allantoin-beta-cyclodextrin inclusion complex].

Solubility and bioavailability of poorly water-soluble drugs have been improved by the preparation as cyclodextrin inclusion complexes. The aim of this study is to obtain and characterize the inclusion compound allantoin-beta-cyclodextrin. Allantoin is a vegetable drug, poorly water-soluble (1:300), isolated from roots of Symphytum off. The solid inclusion complex was prepared by mixing with a adequate quantity of water and drying at 50 degrees C to the constant weight. It was used a different proportions between allantoin and beta-cyclodextrin (1:4, 3:7). The inclusion complex was characterized with RMN and IR spectrum and compared with results obtained from beta-cyclodextrin and allantoin alone. The experimental results were demonstrated the inclusion of allantoin in the lipophilic cavity of beta-cyclodextrin without physico-chemical changes.

Allantoin↗

PubMed2005

Inclusion complexation of diazepam with different cyclodextrins in formulations for parenteral use.

A parenteral formulation for the water-insoluble benzodiazepine diazepam was developed. Different cyclodextrins (CDs) suitable for parenteral injection: hydroxypropyl-beta-cyclodextrin (HP-beta-CD), hydroxy-propyl-gamma-cyclodextrin (HP-gamma-CD), sulfobutylether-7-beta-cyclodextrin (SBE-7-beta-CD) and maltosyl-beta-cyclodextrin (malt-beta-CD) were used as alternatives to cosolvents to increase solubility. The increase in solubility displayed a concentration dependency for the four CDs used. Diazepam's solubility is enhanced linearly as a function of each CD concentration. The highest improvements in solubility (dissolved concentration circa 3.5 mg/ml in 40% CD) were found by adding HP-beta-CD or SBE-7-beta-CD. The additional use of polyvinylpyrrolidone (PVP) did not further increase the solubility of diazepam with HP-beta-CD. A parenteral aqueous diazepam solution was prepared containing 10 mg diazepam/5 ml 30% HP-beta-CD or SBE-7-beta-CD solution. The preparations are in agreement with the requirements for parenteralia. Sterilisation by filtration is required since autoclaving degrades the active compound. The stability of the preparations, with and without pH adjustment to pH 5, was investigated during 18 months and during this period no noticeable degradation was observed.

Algorithms↗

PubMed2006

[Plasma levobupivacaine concentrations following epidural administration of levobupivacaine conjugated with or without maltosyl-beta-cyclodextrin].

BACKGROUND: To investigate the pharmacokinetics of complexation of levobupivacaine with maltosyl-beta-cyclodextrin, the plasma concentrations of levobupivacaine were measured following epidural administration of levobupivacaine conjugated with maltosyl-beta-cyclodextrin or levobupivacaine alone in a rabbit model. METHODS: Rabbits were randomly divided into two groups, levobupivacaine (1%) group (n = 6) and levobupivacaine (1%) conjugated with maltosyl-beta-cyclodextrin (100 mM) group (n = 6). One ml of each solution was randomly injected through an epidural catheter placed at L5-6. The plasma levobupivacaine concentrations were measured before and 5, 10, 15, 30, 60, 120, 240, 360, and 480 min after injection. RESULTS: The plasma levobupivacaine concentrations were significantly higher in the levobupivacaine conjugated with maltosyl-beta-cyclodextrin group than in levobupivacaine group at 5 min (1,465 +/- 311, 1,033 +/- 347 ng x ml(-1)), 10 min (1,068 +/- 237, 731 +/- 191), and 15 min (958 +/- 311, 605 +/- 118). There were no differences in area under the curve (1,551 +/- 387, 1,176 +/- 154 ng x hr x ml(-1)) and elimination half life (100 +/- 54, 78 +/- 37 min) between the two groups. CONCLUSIONS: The results of this study indicated that the absorption of levobupivacaine conjugated with maltosyl-beta-cyclodextrin from the epidural space and the elimination from the blood were similar to plain levobupivacaine.

Anesthesia, Epidural↗

PubMed1990

Flocculation of serum lipoproteins with cyclodextrins: application to assay of hyperlipidemic serum.

We describe the complexation of isolated and native lipoproteins by natural macrocyclic polymers of glucose ("cyclodextrins"). Treatment of serum with cyclodextrin produces an immediate flocculation of the lipoproteins. The formation of cyclodextrin-lipoprotein complexes was evident on agarose electrophoresis gels. The concentration-dependent ability of alpha-cyclodextrin to precipitate chylomicrons and very-low-, low-, and high-density lipoproteins was used for clarifying lipemic serum. Results for normal and lipemic patients' specimens for some routinely measured analytes showed a good correlation between cyclodextrin treatment and ultracentrifugation. Unlike the use of organic solvents or ultracentrifugation, the proposed system provides a simple, mild, non-hazardous, and effective means for removing interfering lipid particles from biological specimens.

Chemical Precipitation↗

PubMed1989

Retention behavior of cardiac steroids using cyclodextrin in the mobile phase in high-performance liquid chromatography.

The retention behaviour of twenty cardiac steroids and four fluorescent derivatives was examined by the addition of cyclodextrin to the mobile phase in reversed-phase high-performance liquid chromatography. The addition of a suitable cyclodextrin improved the separation of isomeric cardiac steroids. The steroid A/B ring junction is the most important factor in the choice of the optimum cyclodextrin to be added; the C/D ring junction is less important. The hydroxyl group at the 3- or 12-position of the steroid enhanced the changes in retention times of these compounds. The effect of an unsaturated lactone ring at the 17 beta-position on the retention in the presence of cyclodextrin was also determined with cardenolide (five-membered ring) and bufadienolide (six-membered ring) but little difference was observed. Isomeric cardiac steroids, whose separation has not been done by the conventional method, were clearly separated by this method. The fluorescence intensity of 3-(1-anthroyl)-cardiac steroid was enhanced by the addition of cyclodextrin to the mobile phase.

Animals↗

PubMed1980

Intestinal absorption of 14C-labelled beta-cyclodextrin in rats.

beta-Cyclodextrin and glucose labelled universally by 14C was administered orally to rats and blood radioactivity level was followed. In the case of glucose about 20% of the administered radioactivity, related to 10 ml blood was to be found and this appeared in the blood within 10 min following the oral administration. In the case of beta-cyclodextrin maximum 5% of the administered activity could be found in blood, and even this only 4 to 10 h following administration. Presumably, beta-cyclodextrin cannot be absorbed either from the stomach or from the small intestine, only the labelled open-chain dextrins and glucose formed from cyclodextrins on amylase action. Therefore it is very likely that the orally administered beta-cyclodextrin cannot provoke toxic symptoms.

Animals↗

PubMed1997

The effect of cyclodextrin modifiers on electrophoretic separation of aromatic hydrocarbons.

Cyclodextrin-modified capillary electrophoresis has been developed for separation and analysis of benzene and its derivatives. The procedure used a mixture of negatively charged sulfobutyl ether-beta-cyclodextrin (SB beta CD) and neutral hydroxypropyl-beta-cyclodextrin (HP beta CD) to effect differential distribution (partitioning) of the aromatic hydrocarbons between the buffer and CD phases. In 80 mM phosphate buffer, containing 15 mM SB beta CD and 5 mM HP beta CD, benzene, toluene, ethyl benzene and three xylene isomers (BTEXs) were well resolved with a number of theoretical plates well above 100,000, for 50 cm of effective length. Some halogenated benzenes were also observed to separate well from the BTEX components to indicate their suitability as an internal standard for BTEX analyses. Equilibrium complexation models were used for investigating the effect of the cyclodextrin(s) at different concentrations and temperature on the electrophoretic mobility.

2-Hydroxypropyl-beta-cyclodextrin↗

PubMed1985

Quantitative structure-stability relationships among inclusion complexes of cyclodextrins. I: Barbituric acid derivatives.

Quantitative structure-stability relationships (QSSRs) are formulated for the inclusion complexation of 17 barbituric acid derivatives with alpha- and beta-cyclodextrin. The variation in the complex stability constants K alpha and K beta is found to be partly accounted for by the molar refractivity or the hydrophobicity of the substituent R1 at position 5 of the barbiturate ring. In addition, K alpha also depends upon whether or not R1 is branching or cyclic, and K beta also depends upon whether the guest molecule is a barbiturate or a thiobarbiturate. The results suggest that in alpha-cyclodextrin-barbiturate complexes the cyclodextrin cavity includes only R1, while in beta-cyclodextrin complexes both R1 and (part of) the barbiturate ring are included. This complexation model is compared with those proposed by other authors.

Barbiturates↗

PubMed1995

Safety of parenteral hydroxypropyl beta-cyclodextrin.

Post-treatment data were collected on a patient who received intravenous hydroxypropyl beta-cyclodextrin in a dose of 1.5 g/kg in 1985. Although no untoward effects were observed in this patient, rarely occurring agitation and pulmonary edema have been noted after injections into rabbits and dogs, respectively. These complications are analyzed here on the basis of symptoms and on the effects of hydroxypropyl beta-cyclodextrin on the biochemistry of a representative lipid, cholesterol, which were studied in rats. It is hypothesized that these untoward effects of parenteral hydroxypropyl beta-cyclodextrin are due to complex formation, with lipid mediators of pathological responses, of which prostaglandins are one example. These mediators normally have brief and localized functions; if hydroxypropyl beta-cyclodextrin happens to be injected when these mediator systems are activated, their influence and the responses of the organism may be increased.

2-Hydroxypropyl-beta-cyclodextrin↗

PubMed2000

Comparative study on camphor enantiomers behavior under the conditions of gas-liquid chromatography and reversed-phase high-performance liquid chromatography systems modified with alpha- and beta-cyclodextrins.

The dependence of retention and selectivity parameters of camphor enantiomers on the concentration of alpha- and beta-cyclodextrins were studied under conditions of GLC (matrix solvent: Glycerol, 95 degrees C) and RP-HPLC (matrix solvent: Aqueous methanolic, 20 degrees C). It has been found that beta-cyclodextrin forms complex of 1:1 stoichiometry and does not recognize enantiomers of camphor. In contrast alpha-CD forming complexes of 1:2 stoichiometry appeared to be very efficient chiral selector of (+) and (-)-camphor. Relatively considerable differences have been observed between stability constants determined by GLC and RP-HPLC, what may be explained by the various natures of the matrix solvents and the various temperatures of the measurements. On the contrary, the enantioseparation factor alpha observed at higher concentrations of alpha-cyclodextrin stabilizes on the very similar value alpha+/-(GLC) approximately = alpha-/+(HPLC) approximately = 1.6. Simple theoretical considerations focusing on the differences in the mechanisms of the studied processes have been performed. According to them the enantiomer forming the more stable complex with the cyclodextrin should be eluted from the RP-HPLC column first and GLC column last. This fact has been confirmed experimentally.

Antipruritics↗

PubMed1988

Use of hydroxypropyl- and hydroxyethyl-derivatized beta-cyclodextrins for the thin-layer chromatographic separation of enantiomers and diastereomers.

Partially substituted hydroxypropyl-beta-cyclodextrin and hydroxyethyl-beta-cyclodextrin proved to be effective chiral mobile phase additives (CMAs) for the thin-layer chromatographic (TLC) resolution of racemic benzyl-2-oxazolidinone, 5-(4-methyl-phenyl)-5-phenylhydantoin, mephenytoin and several dansyl and beta-naphthylamide amino acids. Several diastereomeric compounds including steroid epimers and alkaloids were separated as well. The derivatized beta-cyclodextrins tended to be much more soluble in water and hydro-organic solvents than native beta-cyclodextrin. Their chromatographic selectivity also was somewhat different. The use of CMAs in TLC is a potentially useful and powerful method that has not been considered adequately. The relative lack of chiral stationary phases available in planar format makes the use of CMAs particularly attractive.

2-Hydroxypropyl-beta-cyclodextrin↗