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Inclusion complexes of fluconazole with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin in aqueous solution: preparation, characterization and a structural insight

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Abstract

Inclusion complexes of fluconazole (HFlu) with β-cyclodextrin (β-CD) and hydroxypropyl- β-cyclodextrin (HP-β-CD) had been prepared by the coprecipitation method. The 1:1 stoichiometry of complexation for both inclusion complexes was achieved in the binary system by phase solubility and fluorimetric study. The inclusion complexes were also characterized by DSC-TGA analyses and ESI–MS spectra. The molecular assemblies were proposed that a triazolyl ring of HFlu was inserted into the narrower end of the CD cavity and the 2, 4-difluorophenyl ring into the wider end to generate 1-D chain structure on the basis of physical characters. The comparative work indicated that the higher stability was obviously observed for HFlu-HP-β-CD than for HFlu-β-CD, and provided a crucial clue to find out the dependency: cavity size, van der Waals and hydrophobic interactions as well as hydrogen bonding.

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Acknowledgments

This work was supported by the Foundation of Guangdong Provincial Department of Science and Technology (2012A080800002 and S2013010012018).

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Authors and Affiliations

  1. School of Bioscience and Bioengineering, South China University of Technology, Guangzhou, 510006, China

    Jing Li, Shuo Zhang, Yan Zhou, Su Guan & Lei Zhang

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  1. Jing Li
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  2. Shuo Zhang
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  3. Yan Zhou
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  4. Su Guan
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  5. Lei Zhang
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Correspondence to Lei Zhang.

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Li, J., Zhang, S., Zhou, Y. et al. Inclusion complexes of fluconazole with β-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin in aqueous solution: preparation, characterization and a structural insight. J Incl Phenom Macrocycl Chem 84, 209–217 (2016). https://doi.org/10.1007/s10847-016-0598-z

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