Studies on 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole/2-hydroxypropyl-β-cyclodextrin association: Characterization, molecular modeling studies, and in vivo anthelminthic activity
2010; Elsevier BV; Volume: 19; Issue: 2 Linguagem: Inglês
10.1016/j.bmc.2010.12.015
ISSN1464-3391
AutoresYareli Rojas-Aguirre, Lilián Yépez-Mulía, Iván Castillo, Fabian López‐Vallejo, Olivia Soria‐Arteche, Alicia Hernández–Campos, Rafael Castillo, Francisco Hernández‐Luis,
Tópico(s)Analytical Methods in Pharmaceuticals
ResumoThe purpose of this work is to study the molecular association that occurs between 2-hydroxypropyl-β-cyclodextrin (HPβCD) and 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole (RCB20), an antiparasitic compound recently found by our research group, with poor aqueous solubility. The complex stability constant and stoichiometric ratio determined by phase-solubility diagram and Job's plot provided evidence that HPβCD enhanced water solubility of RCB20 through inclusion complex formation. Two-dimensional 1H NMR spectroscopy is used to study the molecular arrangement of inclusion complex in solution. These results are further supported using molecular modeling studies. In the solid state, the complexation is confirmed by differential scanning calorimetry, powder X-ray diffraction, and scanning electron microscopy. Finally, RCB20/HPβCD complex has better activity than RCB20 against the adult and muscle larvae phase of Trichinella spiralis.
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