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Inclusion complexes of dihydroartemisinin with cyclodextrin and its derivatives: characterization, solubilization and inclusion mode

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Abstract

The characterization, inclusion complexation behavior and binding ability of the inclusion complexes of dihydroartemisinin with β-cyclodextrin and its derivatives, sulfobutyl ether β-cyclodextrin (SBE-β-CD), mono[6-(2-aminoethylamino)-6-deoxy]-β-cyclodextrin (en-β-CD) and mono{6-[2-(2-aminoethylamino)ethylamino]-6-deoxy}-β-cyclodextrin (dien-β-CD), were studied using phenolphthalein as a spectral probe. Spectral titration was performed in aqueous buffer solution (pH ca. 10.5) at 25 °C to determine the binding constants. The inclusion complexation behaviors were investigated in both solution and solid state by means of NMR, TG, XRD. The results showed that the water solubility and thermal stability of dihydroartemisinin were significantly increased in the inclusion complex with cyclodextrins (CDs). According to 1H NMR and 2D NMR spectroscopy (ROESY), the A, B rings of dihydroartemisinin can be included into the cavity of CDs. The enhanced binding ability of CDs towards dihydroartemisinin was discussed from the viewpoint of the size/shape-fit concept and multiple recognition mechanism between host and guest.

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Acknowledgments

This work was supported by National Natural Science Foundation of China (NNSFC) (No. 21062009), and the Natural Science Foundation of Yunnan Province (No. 2011FZ059), which are gratefully acknowledged.

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Authors and Affiliations

  1. Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, 650500, People’s Republic of China

    Dan Xiao, Bo Yang, Xia-Li Liao, Xue-Min Yang & Fen Wang

  2. Faculty of Chemical Engineering, Kunming University of Science and Technology, Kunming, 650500, People’s Republic of China

    Yu-Lin Zhao

  3. Kunming Pharmaceutical Group Corporation, Kunming, 650000, People’s Republic of China

    Yun-Jian Chen & Rong-Guang Zhou

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  1. Dan Xiao
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Correspondence to Bo Yang.

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Xiao, D., Yang, B., Zhao, YL. et al. Inclusion complexes of dihydroartemisinin with cyclodextrin and its derivatives: characterization, solubilization and inclusion mode. J Incl Phenom Macrocycl Chem 79, 349–356 (2014). https://doi.org/10.1007/s10847-013-0358-2

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