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Current Drug Discovery Technologies


ISSN (Print): 1570-1638
ISSN (Online): 1875-6220

Thermodynamic Study of Cyclodextrins Complexation with Benzimidazolic Antihelmintics in Different Reaction Media

Author(s): Maria-Josefa Bernad-Bernad, Jesus Gracia-Mora, David Diaz and Silvia Elena Castillo-Blum

Volume 5, Issue 2, 2008

Page: [146 - 153] Pages: 8

DOI: 10.2174/157016308784746274

Price: $65


The main purpose of this work was to accomplish a comparative study about cyclodextrins complexation equilibria with three benzimidazolic antihelmintics: albendazole (Alb), mebendazole (Meb) and thiabendazole (Thiab).The complexation process with four different cyclodextrins (α-, β-, γ-, and HP-β-CDs) was investigated under various temperatures and different reaction media (aqueous solution buffered at pH 7.5, dimethylsulfoxide (DMSO) and DMSO/water at 25/75, 50/50, 75/50 (w/w) mixtures). It was studied by electronic absorption and 1H NMR (NOESY) spectroscopy. Binding constants were determined by electronic absorption spectroscopic method, the ΔH and ΔS complexation values were evaluated and discussed according to the diverse factors that affect the chemical interactions in these systems. Solubility has also been determined by the Higuchi and Connors method. In general, albendazole and mebendazole exhibit similar complexation behavior, while thiabendazole acts differently. Classic and non-classic solvophobic effects are mainly the driving and stabilizing forces for complex formation, with the exception in some Thiab-CDs interactions. In all cases, DMSO, an aprotic solvent, should be considered as an active component of the reaction systems.

Keywords: Benzimidazolic antihelmintics, cyclodextrins, aqueous solutions, dimethylsulfoxide, thermodynamic parameters, binding constants, solubility, inclusion complexes

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