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Complexation of sulfonamides with β-cyclodextrin studied by experimental and theoretical methods

✍ Scribed by Ariana Zoppi; Mario A. Quevedo; Alicia Delrivo; Marcela R. Longhi

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
418 KB
Volume
99
Category
Article
ISSN
0022-3549

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✦ Synopsis

The complex formation between three structurally related sulfonamides (sulfadiazine (SDZ), sulfamerazine (SMR), and sulfamethazine (SMT)) and beta-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.

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