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  • Title: Phase solubility and structure of the inclusion complexes of prednisolone and 6 alpha-methyl prednisolone with various cyclodextrins.
    Author: Larsen KL, Aachmann FL, Wimmer R, Stella VJ, Kjølner UM.
    Journal: J Pharm Sci; 2005 Mar; 94(3):507-15. PubMed ID: 15627254.
    Abstract:
    The purpose of this work was to study the inclusion binding interaction of two structurally related steroids, prednisolone and 6alpha-methyl prednisolone with a wide variety of cyclodextrins (CDs), both native (alpha-, beta- and gamma-CD) as well as modified (hydroxypropyl-, sulfobutyl ether-, glucosyl-, and maltosyl-beta-CD and sulfobutyl ether-gamma-CD), and to relate the binding constants to structural differences in the steroids. Phase-solubility diagrams of the steroids with various CDs were obtained. The stability constants (K1:1) revealed that beta-CD formed the strongest complex with prednisolone, followed by gamma-CD. With 6alpha-methyl prednisolone, the stability constants of both beta- and alpha-CD were considerably lower compared with prednisolone. In contrast, gamma-CD formed a stronger complex with 6alpha-methyl prednisolone compared with prednisolone. Derivatives of beta-CD gave slightly altered stability constants compared with native beta-CD. The structures of the complexes between the two guest molecules and native beta-CD were studied by nuclear magnetic resonance spectroscopy. This clearly showed that the introduction of the methyl group led to a different binding geometry of 6alpha-methyl prednisolone compared with prednisolone. Additionally, the nuclear magnetic resonance results indicate the presence of an additional, weaker binding site, which is less populated in prednisolone.
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