Complexation of sulfonamides with beta-cyclodextrin studied by experimental and theoretical methods.
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.
Zoppi
Ariana
A
Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
Quevedo
Mario A
MA
Delrivo
Alicia
A
Longhi
Marcela R
MR
D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012995:Solubility; D013449:Sulfonamides / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D013449:Sulfonamides; D047392:beta-Cyclodextrins; C031215:betadex