𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Inclusion complex formation of captopril with α- and β-cyclodextrins in aqueous solution: NMR spectroscopic and molecular dynamic studies

✍ Scribed by Yoichi Ikeda; Sohko Motoune; Toshikazu Matsuoka; Hidetoshi Arima; Fumitoshi Hirayama; Kaneto Uekama

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
197 KB
Volume
91
Category
Article
ISSN
0022-3549

No coin nor oath required. For personal study only.

✦ Synopsis

The inclusion complex formation of alpha-cyclodextrin (alpha-CyD), beta-cyclodextrin (beta-CyD), and 2-hydroxylpropyl-beta-cyclodextrin (HP-beta-CyD) with an angiotensin converting enzyme inhibitor, captopril, in aqueous solution was studied by (1)H- and (13)C-nuclear magnetic resonance spectroscopies, including ROESY and GROESY techniques, by kinetic methods and by molecular dynamic calculations. The oxidative degradation of captopril was markedly suppressed in alpha-CyD solutions, whereas beta-CyD and HP-beta-CyD had negligible stabilizing effects. These NMR and kinetic results suggested that alpha-CyD includes preferably the propyl thioalcohol moiety of captopril, depositing the proline moiety outside the cavity. On the other hand, beta-CyD includes a whole molecule of captopril in the cavity, locating the carboxylic acid within the cavity and the terminal thiol moiety outside the cavity. These inclusion structures were supported by molecular dynamic studies.

📜 SIMILAR VOLUMES

1H NMR spectroscopic study of complexati
1H NMR spectroscopic study of complexation of citalopram with β-cyclodextrin in aqueous solution
✍ Syed Mashhood Ali; Arti Maheshwari; Bharat Inder Fozdar 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 164 KB

## Abstract ^1^H NMR spectroscopic study of citalopram (CT) in the absence as well as in the presence of β‐cyclodextrin (β‐CD) in aqueous solution revealed the formation of four 1:1 β‐CD–CT inclusion complexes. The stoichiometry of the complexes was determined by the continuous variation (Job) meth

Inclusion complex formation of 1,8-dihyd
Inclusion complex formation of 1,8-dihydroxyanthraquinone with cyclodextrins in aqueous solution and in solid state
✍ Giulietta Smulevich; Alessandro Feis; Giovanni Mazzi; Franco F. Vincieri 📂 Article 📅 1988 🏛 John Wiley and Sons 🌐 English ⚖ 451 KB

Complex formation between cyclodextrins and 1 ,d-dihydroxyanthraquinone in buffer solution has been investigated using absorption, its second derivative (D'), and fluorescence spectroscopy. The results showed that whereas the self-association process was found for 1,8-dihydroxyanthraquinone alone, t

NMR spectroscopic characterization of in
NMR spectroscopic characterization of inclusion complexes comprising cyclodextrins and gallated catechins in aqueous solution: cavity size dependency
✍ Takashi Ishizu; Hiroyuki Tsutsumi; Hideji Yamamoto; Kazunobu Harano 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 253 KB

## Abstract The structure of inclusion complexes of γ‐cyclodextrin (γ‐CD), (–)‐gallocatechin gallate (GCg), and (–)‐epigallocatechin gallate (EGCg) in D~2~O was investigated using several NMR techniques. GCg formed a 1:1 inclusion complex with γ‐CD in which the A and C rings of GCg were inserted de

Multimodal inclusion complexes between b
Multimodal inclusion complexes between barbiturates and 2-hydroxypropyl-β-cyclodextrin in aqueous solution: Isothermal titration microcalorimetry, 13C NMR spectrometry, and molecular dynamics simulation
✍ Hatsumi Aki; Tokihiro Niiya; Yukiko Iwase; Magobei Yamamoto 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 273 KB

Multiple types (structures) of inclusion complexes between barbiturates and 2-hydroxypropyl-b-cyclodextrin (HPCD) were evaluated by isothermal titration microcalorimetry and 13 C NMR spectroscopy. The geometries of the inclusion complexes were suggested by molecular dynamics simulation. Barbituric a

Molecular Mechanics Study of the Inclusi
Molecular Mechanics Study of the Inclusion Complexes of 2-Methyl Naphthoate with α- and β-Cyclodextrins
✍ Jose Manuel Madrid; Javier Pozuelo; Francisco Mendicuti; Wayne L. Mattice 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 308 KB

Molecular mechanics calculations were employed to study the inclusion of 2-methyl naphthoate in alpha- and beta-cyclodextrin in vacuo and in the presence of water as a solvent. The driving forces for complexation are dominated by nonbonded van der Waals host:guest interactions in both environments.