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Molecular interactions of the inclusion complexes of hinokitiol and various cyclodextrins

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Abstract

The aim of this study was to prepare inclusion complexes of hinokitiol (HT)/α-cyclodextrin (α-CD) and HT/β-cyclodextrin (β-CD) by cogrinding and to evaluate the differences in their formation. The physical properties of the preparation were evaluated by Job’s plot, phase solubility studies, differential scanning calorimetry, powder X-ray diffraction, solid fluorescence spectra, and infrared absorption spectra. Intermolecular interaction in the solid state was confirmed to be in the ratios HT/α-CD = 1/2 and HT/β-CD = 1/1. Results indicated that the dissolution property of HT was improved by inclusion in the complexes HT/α-CD and HT/β-CD compared with HT crystals. The 1H-1H ROESY NMR spectrum of HT/α-CD showed that part of the seven-membered ring of HT and the isopropyl group of HT was linked to the wider edges of the two α-CDs. In HT/β-CD, the seven-membered ring of HT interacted with the narrower edge of β-CD and the isopropyl group of HT interacted with the wider edges. This structure of inclusion complexes was attributed to the difference in the cavity diameter of the CD and was thought to influence the dissolution properties.

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Acknowledgements

The authors are grateful to Cyclo Chem Co., Ltd. for the provision of α-CD and β-CD.

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Authors and Affiliations

  1. Laboratory of Drug Safety Management, Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado-shi, Saitama, 350-0295, Japan

    Rina Suzuki, Yutaka Inoue, Isamu Murata & Ikuo Kanamoto

  2. Faculty of Pharmacy, Silpakorn University, Nakhon Pathom, 73000, Thailand

    Sontaya Limmatvapirat

Authors
  1. Rina Suzuki
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  2. Yutaka Inoue
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  3. Sontaya Limmatvapirat
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  4. Isamu Murata
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  5. Ikuo Kanamoto
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Correspondence to Yutaka Inoue.

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Suzuki, R., Inoue, Y., Limmatvapirat, S. et al. Molecular interactions of the inclusion complexes of hinokitiol and various cyclodextrins. AAPS PharmSciTech 18, 2717–2726 (2017). https://doi.org/10.1208/s12249-017-0748-7

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  • DOI: https://doi.org/10.1208/s12249-017-0748-7

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