Solubilization Effects of β-Cyclodextrin Butenate on Thiabendazole and Antibacterial Activities of Their Complex
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Abstract:
Thiabendazole is a hydrophobic anti-bacterial drug. However, the water solubility of thiabendazole can be significantly enhanced by its complexation with cyclodextrins. In this study, β-cyclodextrin butenate was synthesized by the esterification of butenoic acid and β-cyclodextrin to improve the solubility of β-cyclodextrin in aqueous solutions. The apparent stability coefficients of thiabendazole-β-cyclodextrin and thiabendazole-β-cyclodextrin butenate complexes were determined by phase solubility tests, and the structures of these complexes were analyzed by mid-infrared spectroscopy. β-Cyclodextrin butenate was synthesized by using N,N-carbonyldiimidazole as the carboxylic acid activation reagent, 4-dimethylaminopyridine as the catalyst, and dimethylformamide as the solvent. The solubility of β-cyclodextrin butenate in water (25 ℃) was 2.05 times that of β-cyclodextrin. At a water temperature of 50 ℃, the apparent stability coefficients of the thiabendazole-β-cyclodextrin and thiabendazole-β-cyclodextrin butenate complexes were 59.35 and 52.43 M-1, respectively; no significant difference was observed between them (p>0.05). β-Cyclodextrin butenate could improve the solubility of thiabendazole in water upon complexation, and its solubilization effect is stronger than that of β-cyclodextrin. The solubility of thiabendazole in water is considerably improved, and the thiabendazole-β-cyclodextrin and thiabendazole-β-cyclodextrin butenate complexes exhibit strong anti-bacterial effects.
