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Complexation behavior of antiestrogen drug tamoxifen citrate with natural and modified β-cyclodextrins

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Abstract

Inclusion complexes of the poorly-soluble antiestrogen drug tamoxifen citrate (TMX) were prepared with β-cyclodextrin (β-CD) and 2,3-di-O-hexanoyl-β-cyclodextrin (β-CDC6) being natural and amphiphilic cyclodextrins, respectively using the co-lyophilization technique. Complexation occurred in aqueous medium for natural cyclodextrin β-CD and a medium of water:ethanol mixture for the amphiphilic cyclodextrin β-CDC6. The complexes were characterized using analytical techniques including Differential Scanning Calorimetry (DSC), Fourier Transform Infrared spectroscopy (FTIR) and proton Nuclear Magnetic Resonance Spectrometry (1H NMR). Anticancer efficacies of the complexes were determined against MCF-7 human breast carcinoma cell line with MTT assay. It was found that tamoxifen citrate can be incorporated in the cavity for β-CD and both in the cavity and the aliphatic chains for β-CDC6. The latter having two hydrophobic sites for inclusion of water-insoluble drug exhibited significantly higher anticancer efficacy accordingly.

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Acknowledgements

Authors wish to thank TUBITAK-CNRS (SBAG-CNRS-3) project and Hacettepe University Research Fund (0202301005) for financial support.

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Authors and Affiliations

  1. Faculty of Pharmacy, Department of Pharmaceutical Technology, Hacettepe University, 06100, Ankara, Turkey

    Erem Bilensoy & Atilla Hıncal

  2. Faculty of Medicine Oncology Institute, Department of Basic Oncology, Hacettepe University, 06100, Ankara, Turkey

    Lale Doğan

  3. Department of Chemistry, Polymer Chemistry Division, Hacettepe University, Beytepe, 06532, Ankara, Turkey

    Murat Şen

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  1. Erem Bilensoy
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  2. Lale Doğan
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  3. Murat Şen
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  4. Atilla Hıncal
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Correspondence to Erem Bilensoy.

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Bilensoy, E., Doğan, L., Şen, M. et al. Complexation behavior of antiestrogen drug tamoxifen citrate with natural and modified β-cyclodextrins. J Incl Phenom Macrocycl Chem 57, 651–655 (2007). https://doi.org/10.1007/s10847-006-9268-x

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  • DOI: https://doi.org/10.1007/s10847-006-9268-x

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