Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts

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This study addresses the poor solubility of two potent steroid hormones, 17β-estradiol (BES) and progesterone (PRO), via their complexation with two water-soluble native cyclodextrins (CDs) namely β-CD and γ-CD. The hydrated inclusion complexes β-CD·BES, β-CD·PRO, γ-CD·BES and γ-CD·PRO were prepared via kneading and co-precipitation, and 1H NMR spectroscopic analysis of solutions of their pure complex crystals yielded the host–guest stoichiometries 2:1, 2:1, 1:1 and 3:2, respectively. Both powder X-ray diffraction (PXRD) and single-crystal X-ray diffraction (SCXRD) were employed for focused studies of the isostructurality of the CD complexes with known complexes and structural elucidation of the new complexes, respectively. SCXRD was employed to deduce structural features of the complexes at the molecular level, while the occurrence of severe guest disorder prompted the non-routine application of a method for yielding complex composition from the residual electron density peaks in the respective crystal structures.

Alexios I. Vicatos, Zakiena Hoossen and Mino R. Caira (2022) Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements. Beilstein J. Org. Chem. 2022, 18, 1749–1762. https://doi.org/10.3762/bjoc.18.184

This article is part of the thematic issue “Cyclodextrins as building blocks for new materials”.
Guest Editor: S. Fourmentin

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