Evidence for the 2:1 molecular recognition and inclusion behaviour between β- and γ-cyclodextrins and cinchonine

Wen, Xianhong; Liu, Ziyang; Zhu, Tianqiang; Zhu, Meilin; Jiang, Kezhi; Huang, Qiaoqiao

doi:10.1016/j.bioorg.2004.04.004

Cited by 20 publications

(18 citation statements)

References 25 publications

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“…The coevaporated product showed a single very broad band in witch the diffraction peaks of drug and γ-CD disappeared. This phenomenon confirmed that an inclusion complex between drug and γ-CD was formed and which indicates the formation of a new crystalline phase [21][22][23][24][25][26]. cavity and are very important for the study of the interaction of guest molecules with cyclodextrins.…”

Section: X-ray Diffraction Analysissupporting

confidence: 65%

Improvement of Water Solubility of Josamycin by Inclusion Complex with -Cyclodextrin

Harti

Cherrah

Bouklouze

2012

ISRN Analytical Chemistry

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Josamycin propionate (JMP) is an antibiotic belonging to the family of macrolide. According to the Biopharmaceutical Classification System (BCS), this compound can be classed in class II, low solubility and high permeability. In order to increase its apparent water solubility, inclusion complexation between Josamycin propionate and γ-cyclodextrin (γ-CD) was studied. UV spectrophotometric method was employed to investigate the phase-solubility profile and the stability constant of the complexation in aqueous medium. Solid state of the binary system prepared by coevaporation (in 50%-50% ethanol/water) has been characterized using powder X-ray diffraction (XRD) and Fourier transformation-infrared spectrometry (FTIR). These techniques indicate that JMP forms an association complex with γ-CD. The shift in the nuclear magnetic resonance spectroscopy (1H NMR) confirms the existence of the inclusion complex. Also the results obtained showed an enhancement of the solubility in water of Josamycin propionate.

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Section: X-ray Diffraction Analysissupporting

confidence: 65%

Improvement of Water Solubility of Josamycin by Inclusion Complex with -Cyclodextrin

Harti

Cherrah

Bouklouze

2012

ISRN Analytical Chemistry

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“…The dimeric association constant of piroxicam at 37-C, 1.7Â10 +3 M j j1 , increased to 35Â10 +3 M j j1 at 25-C (21). Solubilizing complexing agents, such as cyclodextrins, can have multiple stoichiometries of association, making interpretations of the phase-solubility diagrams burdensome (25,26). Bergströ m et al (11) accurately characterized the solubilityY Y YpH profiles of 25 sparingly soluble amine drugs, and observed that the HendersonY Y YHasselbalch equation was very unreliable in predicting the pH-dependence of solubility of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Solubility-Excipient Classification Gradient Maps

et al. 2007

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This study assessed the effect of excipients (sodium taurocholate, 2-hydroxypropyl-f-cyclodextrin, potassium chloride, propylene glycol, 1-methyl-2-pyrrolidone, and polyethylene glycol 400) on the apparent intrinsic solubility properties of eight sparingly soluble drugs (four bases, two neutrals, and two acids): astemizole, butacaine, clotrimazole, dipyridamole, griseofulvin, progesterone, glibenclamide, and mefenemic acid. Over 1,200 UV-based solubility measurements (pH 3-10) were made with a high-throughput instrument. New equations, based on the "shift-in-pKa" method, were derived to interpret the complicated solubility-pH dependence observed, and poorly predicted by the Henderson-Hasselbalch equation. An intrinsic solubility-excipient classification gradient map visualization tool was developed to rank order the compounds and the excipients. In excipient-free solutions, all of the ionizable compounds formed either uncharged or mixed-charge aggregates. Mefenamic acid formed anionic dimers and trimers. Glibenclamide displayed a tendency to form monoanionic dimers. Dipyridamole and butacaine tended to form uncharged aggregates. With strong excipients, the tendency to form aggregates diminished, except in the case of glibenclamide. We conclude that a low-cost, compound-sparing, and reasonably accurate high-throughput assay which can be used in early screening to prioritize candidate molecules by their eventual developability via the excipient route is possible with the aid of the "self-organized" intrinsic solubility-excipient classification gradient maps.

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“…Further we could observe in the structures of 1:2 complexes there are several hydrogen bondings between the two neighboring CD molecules (shown as green dotted line in Fig. 7c), which further stabilized the structure of the inclusion complexes (Wen et al, 2004).…”

Section: Molecular Modeling Studiesmentioning

confidence: 73%

Fabrication of cyclodextrins-procainamide supramolecular self-assembly: Shape-shifting of nanosheet into microtubular structure

Siva

Nayaki

Rajendiran

2015

Carbohydrate Polymers

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Evidence for the 2:1 molecular recognition and inclusion behaviour between β- and γ-cyclodextrins and cinchonine

Cited by 20 publications

References 25 publications

Improvement of Water Solubility of Josamycin by Inclusion Complex with -Cyclodextrin

Improvement of Water Solubility of Josamycin by Inclusion Complex with -Cyclodextrin

Solubility-Excipient Classification Gradient Maps

Fabrication of cyclodextrins-procainamide supramolecular self-assembly: Shape-shifting of nanosheet into microtubular structure

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