Diversity in the supramolecular interactions of 5,6-dichloro-2- (trifluoromethyl)-1H-benzimidazole with modified cyclodextrins: Implications for physicochemical properties and antiparasitic activity

Yareli Rojas-Aguirre, Ivan Castillo, David J. Hernández, Benjamín Nogueda-Torres, Adrián Márquez-Navarro, Juan C. Villalobos, Francisco Sánchez-Bartéz, Luvia Sánchez-Torres, Isabel Gracia-Mora, Rafael Castillo, Francisco Hernández-Luis

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The molecular interactions of 5,6-dichloro-2-(trifluoromethyl)-1H- benzimidazole (G2), an antiprotozoa with poor aqueous solubility, with 2-hydroxypropyl-α-cyclodextrin (HPαCD), methyl-β-cyclodextrin (MβCD) and 2-hydroxypropyl-β-cyclodextrin (HPβCD) were examined. The aqueous solubility enhancement by cyclodextrins (CDs) was evidenced in phase-solubility diagrams, and the stoichiometry of G2/CD systems was determined by Job's plots. Two-dimensional NMR spectroscopic data revealed that a different mode of interaction took place between G2 and CDs in solution. With HPαCD, a non-inclusion complex was generated. In the case of MβCD, a typical host-guest system was obtained and with HPβCD a partial inclusion complex through the narrow side of the macrocycle was formed. ESI-mass spectrometric data confirmed the stoichiometry and mode of interaction of these systems in solution. Solid-state characterization (scanning calorimetry and powder X-ray diffraction) supported the inclusion complex formation. The leishmanicidal activity, trypanocidal activity and non-toxic profile of G2/MβCD showed the advantages of using this inclusion complex to promote the biological assays extension of G2.

Original languageEnglish
Pages (from-to)471-479
Number of pages9
JournalCarbohydrate Polymers
Volume87
Issue number1
DOIs
StatePublished - 4 Jan 2012

Keywords

  • Benzimidazole
  • Cyclodextrins
  • Leishmania mexicana
  • Supramolecular association
  • Trypanosoma cruzi

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