Complexation of bile acids with 2-hydroxypropyl-beta-cyclodextrin: A C-13-NMR study

被引：20

作者：

Mucci, A

Vandelli, MA

Salvioli, G

Malmusi, L

Forni, F

Schenetti, L

机构：

[1] UNIV MODENA,DIPARTIMENTO SCI FARMACEUT,I-41100 MODENA,ITALY

[2] UNIV MODENA,CATLEDRA GERIATR & GERONTOPOGIA,I-41100 MODENA,ITALY

来源：

SUPRAMOLECULAR CHEMISTRY | 1996年 / 7卷 / 02期

关键词：

D O I：

10.1080/10610279608035186

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The interaction of chenodeoxycholic acid (3 alpha,7 alpha-dihydroxy-5 beta-cholan-24-oic acid) 1; cholic acid (3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholan-24-oic acid) 2, deoxycholic acid (3 alpha,12 alpha-dihydroxy-5 beta-cholan-24-oic acid) 3 and ursodeoxycholic acid (3 alpha,7 beta-dihydroxy-5 beta-cholan-24-oic acid) 4 with 2-hydroxypropyl-beta-cyclodextrin HP beta CD (partially functionalized) is studied by measuring the changes in C-13-NMR chemical shifts induced by complexation in methanol-d(4). The alkyl chain of the bile acids enters the cyclodextrin cavity. The interaction of 1 and 4 with HP beta CD is stronger, in this solvent, with respect that of 2 and 3.

引用

收藏

页码：125 / 127

页数：3

相关论文

共 24 条

[1] SELECTIVE BINDING OF SUGAR TO BETA CYCLODEXTRIN - A PROTOTYPE FOR SUGAR-SUGAR INTERACTIONS IN WATER [J].

AOYAMA, Y ;

NAGAI, Y ;

OTSUKI, J ;

KOBAYASHI, K ;

TOI, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06) :745-747

[2] URSODEOXYCHOLIC ACID IN THE TREATMENT OF CHOLESTEROL CHOLELITHIASIS .1. [J].

BACHRACH, WH ;

HOFMANN, AF .

DIGESTIVE DISEASES AND SCIENCES, 1982, 27 (08) :737-761

[3]

Breitmaier E., 1987, CARBON 13 NMR SPECTR, P115

[4] MECHANISM OF DRUG DISSOLUTION RATE ENHANCEMENT FROM BETA-CYCLODEXTRIN-DRUG SYSTEMS [J].

CORRIGAN, OI ;

STANLEY, CT .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1982, 34 (10) :621-626

[5] HIGH-FIELD NUCLEAR-MAGNETIC-RESONANCE TECHNIQUES FOR THE INVESTIGATION OF A BETA-CYCLODEXTRIN-INDOMETHACIN INCLUSION COMPLEX [J].

DJEDAINI, F ;

LIN, SZ ;

PERLY, B ;

WOUESSIDJEWE, D .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1990, 79 (07) :643-646

[6] C-13 NMR DIFFERENTIATION OF DIASTEREOISOMERIC COMPLEXES OF CIS-DECALIN WITH BETA-CYCLODEXTRIN [J].

DODZIUK, H ;

SITKOWSKI, J ;

STEFANIAK, L ;

JURCZAK, J ;

SYBILSKA, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :207-208

[7] PHARMACEUTICAL USES OF CYCLODEXTRINS AND DERIVATIVES [J].

DUCHENE, D ;

WOUESSIDJEWE, D .

DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, 1990, 16 (17) :2487-2499

[8] A PROTON NUCLEAR-MAGNETIC-RESONANCE STUDY OF THE INCLUSION COMPLEX OF NAPROXEN WITH BETA-CYCLODEXTRIN [J].

GANZAGONZALEZ, A ;

VILAJATO, JL ;

ANGUIANOIGEA, S ;

OTEROESPINAR, FJ ;

BLANCOMENDEZ, J .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1994, 106 (03) :179-185

[9]

Inoue Y., 1993, Annual Reports on NMR Spectroscopy, VVolume 27, P59, DOI DOI 10.1016/S0066-4103(08)60265-3

[10] SOLUTION GEOMETRY OF BETA-CYCLODEXTRIN-1-BROMOADAMANTANE HOST-GUEST COMPLEX AS DETERMINED BY H-1(H-1)-INTERMOLECULAR NOE AND MM2 CALCULATIONS [J].

JAIME, C ;

REDONDO, J ;

SANCHEZFERRANDO, F ;

VIRGILI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4772-4776