A Phase Solubility Study on the Chiral Discrimination of Ibuprofen by β-Cyclodextrin Complexes

被引：14

作者：

Crupi, Vincenza ^{[2
]}

Guella, Graziano ^{[3
]}

Majolino, Domenico ^{[2
]}

Mancini, Ines ^{[3
]}

Rossi, Barbara ^{[1
,3
]}

Stancanelli, Rosanna ^{[4
]}

Venuti, Valentina ^{[2
]}

Verrocchio, Paolo ^{[3
]}

Viliani, Gabriele ^{[3
]}

机构：

[1] Fdn Bruno Kessler, I-38123 Povo, Trento, Italy

[2] Univ Messina, Dipartimento Fis, I-98166 Messina, Italy

[3] Univ Trent, Dipartimento Fis, I-38123 Povo, Trento, Italy

[4] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

来源：

FOOD BIOPHYSICS | 2011年 / 6卷 / 02期

关键词：

Ibuprofen; Phase solubility; Cyclodextrins; Inclusion complex; Chiral discrimination; NONSTEROIDAL ANTIINFLAMMATORY DRUGS; CAPILLARY-ELECTROPHORESIS; INCLUSION COMPLEXES; NUMERICAL-SIMULATION; SEPARATION; CHROMATOGRAPHY; SPECTROSCOPY; RECOGNITION; MECHANISMS; RESOLUTION;

D O I：

10.1007/s11483-011-9211-6

中图分类号：

TS2 [食品工业];

学科分类号：

0832 ;

摘要：

The effects of chiral discrimination in inclusion complexes formed by native beta-cyclodextrin and its substituted form (namely methyl-beta-cyclodextrin) with racemate or pure enantiomers of the non-steroidal anti-inflammatory drug ibuprofen have been investigated in water. Stability constants and complexation efficiency have been determined for these host-guest systems with a 1: 1 molar ratio from phase solubility profiles, showing that in aqueous solution, methylated cyclodextrin is a better complex agent than native cyclodextrin, with more enhanced effects for the (R)-enantiomer. These results have been validated using NMR technique. In particular, (1)H NMR spectra in D(2)O show a splitting of the signals for the methyl group and the aromatic protons close to the asymmetric centre of the racemate ibuprofen included in cyclodextrin cavity.

引用

页码：267 / 273

页数：7

共 33 条

[1] DIRECT LIQUID-CHROMATOGRAPHIC SEPARATION OF RACEMATES WITH AN ALPHA-CYCLODEXTRIN BONDED PHASE [J].