Complexation of Sulfonamides With β-Cyclodextrin Studied by Experimental and Theoretical Methods

被引：32

作者：

Zoppi, Ariana ^{[1
]}

Quevedo, Mario A. ^{[1
]}

Delrivo, Alicia ^{[1
]}

Longhi, Marcela R. ^{[1
]}

机构：

[1] Univ Nacl Cordoba, Dept Farm, Fac Ciencias Quim, RA-5000 Cordoba, Argentina

来源：

JOURNAL OF PHARMACEUTICAL SCIENCES | 2010年 / 99卷 / 07期

关键词：

sulfonamides; solubility; cyclodextrins; complexation; phase solubility studies; NMR spectroscopy; molecular modeling; IN-VITRO PERMEATION; INCLUSION COMPLEX; PHYSICOCHEMICAL CHARACTERIZATION; SULFAMETHAZINE; SULFAMERAZINE; SULFADIAZINE; SOLUBILITY; WATER;

D O I：

10.1002/jps.22062

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The complex formation between three structurally related sulfonamides (sulfadiazine (SDZ), sulfamerazine (SMR), and sulfamethazine (SMT)) and P-cyclodextrin (beta-CD) was studied, by exploring its structure affinity relationship. In all the cases, 1:1 stoichiometries were determined with different relative affinities found by phase solubility (SDZ:beta-CD > SMR:beta-CD > SMT:beta-CD) and nuclear magnetic resonance (NMR) (SMT:beta-CD > SMR:beta-CD > SDZ:beta-CD) studies. The spatial configurations determined by NMR were in agreement with those obtained by molecular modeling, showing that SDZ included its aniline ring into beta-CD, while SMR and SMT included the substituted pyrimidine ring. Energetic analyses demonstrated that hydrophobicity is the main driving force to complex formation. (C) 2010 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 99:3166-3176, 2010

引用

页码：3166 / 3176

页数：11

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