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Inclusion complexes of melatonin with modified cyclodextrins

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Abstract

The solubility of melatonin (MT) was improved with the addition of modified cyclodextrins (CDs). The solubilities of MT in the presence of β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD), mono-6-O-maltosyl-β-cyclodextrin (mono-G2-β-CD), methyl-β-cyclodextrin (Me-β-CD), and sulfobutylether-β-cyclodextrin (SBE-β-CD) were higher than that of MT itself. In particular, the solubility of MT in the presence of SBE-β-CD was 11 times higher than that of MT itself. The stability constant (K) obtained based on the fluorescence intensity was 490 L/mol for the MT/SBE-β-CD inclusion complex. The structure of the MT/SBE-β-CD complex in aqueous solution was examined by 1H–1H rotating frame nuclear overhauser effect spectroscopy NMR. A 5-methoxy moiety of MT was included from the secondary hydroxyl face of SBE-β-CD. The MT/SBE-β-CD inclusion complex was prepared by the freeze-drying method. The results of X-ray diffraction and differential scanning calorimetry confirmed the formation of the complex in solid.

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Acknowledgments

The authors thank Assistant Professor C. Tode of Kobe Pharmaceutical University for the measurements of 1H–1H COSY and 1H–1H ROESY NMR spectra.

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  1. Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe, 658-8558, Japan

    Hideko Maeda, Yu Ogawa & Hirokazu Nakayama

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  1. Hideko Maeda
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  2. Yu Ogawa
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  3. Hirokazu Nakayama
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Correspondence to Hirokazu Nakayama.

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Maeda, H., Ogawa, Y. & Nakayama, H. Inclusion complexes of melatonin with modified cyclodextrins. J Incl Phenom Macrocycl Chem 78, 217–224 (2014). https://doi.org/10.1007/s10847-013-0290-5

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  • DOI: https://doi.org/10.1007/s10847-013-0290-5

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