Journal
JOURNAL OF PHARMACEUTICAL SCIENCES
Volume 99, Issue 7, Pages 3166-3176Publisher
ELSEVIER SCIENCE INC
DOI: 10.1002/jps.22062
Keywords
sulfonamides; solubility; cyclodextrins; complexation; phase solubility studies; NMR spectroscopy; molecular modeling
Funding
- Fondo para la Investigacion Cientifica y Tecnologica (FONCyT) [BID 1728/OC-AR PICT 1376]
- Secretaria de Ciencia y Tecnica de la Universidad Nacional de Cordoba (SECyT)
- Consejo Nacional de Investigaciones Cientificas y Tecnologicas de la Nacion (CONICET)
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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
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