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Issue 5, 2002
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Complexation of steroid hormones: prednisolone, ethinyloestradiol and estriol with β-cyclodextrin. An aqueous 1H NMR study

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Abstract

The inclusion complexes of β-cyclodextrin (β-CD) with prednisolone 1, ethinyloestradiol 2 and estriol 3 in aqueous solution were investigated using 1H NMR and molecular modelling. The NMR spectra of the steroids studied in the presence of β-CD are fully assigned and interpreted by means of 2D GCOSY and NOESY spectra. The parallel interpretation of β-CD chemical shift changes and dipolar contacts allows the mode of binding to be established. On the basis of ROESY data, the “low resolution” β-cyclodextrin complexes of 1, 2 and 3 have been determined by multistep restrained molecular dynamics calculations. Calculated structures of β-cyclodextrin complexes with 1, 2 and 3 fully agree with experimental data. Combined approaches allow the distinction of weak nonspecific binding for 1 as compared to stronger, “through cavity”, inclusion established for 2 and 3.

Graphical abstract: Complexation of steroid hormones: prednisolone, ethinyloestradiol and estriol with β-cyclodextrin. An aqueous 1H NMR study

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Publication details

The article was received on 14 Nov 2001, accepted on 08 Mar 2002 and first published on 05 Apr 2002


Article type: Paper
DOI: 10.1039/B110435G
Citation: J. Chem. Soc., Perkin Trans. 2, 2002, 999-1004
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    Complexation of steroid hormones: prednisolone, ethinyloestradiol and estriol with β-cyclodextrin. An aqueous 1H NMR study

    E. Bednarek, W. Bocian, J. Poznański, J. Sitkowski, N. Sadlej-Sosnowska and L. Kozerski, J. Chem. Soc., Perkin Trans. 2, 2002, 999
    DOI: 10.1039/B110435G

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