Inclusion complexes of ketosteroids with beta-cyclodextrin.
Inclusion complexes of several steroid derivatives with beta-cyclodextrin (7) were studied in dimethylsulfoxide solution. The investigated molecules were ketosteroids with different functional groups on the skeleton: 3beta-acetoxypregn-5-en-20-one (1), 3beta-acetoxypregna-5,16-dien-20-one (2), 3beta-acetoxyandrost-5-en-17-one (3), 3beta-hydroxyandrost-5-en-17-one (4), 5alpha-androstane-3,17-dione (5) and 17beta-hydroxyandrost-4-en-3-one (6). Complex formation was monitored by two-dimensional ROESY experiments through the detection of intermolecular dipolar interactions. In case of inclusion complex formation, the steroid molecule penetrates the cavity of the cyclodextrin and dipole-dipole interactions (ROEs) can be detected between the glucose H-3 and H-5 protons inside the cyclodextrin cavity and the steroid skeletal protons. Intermolecular interactions were detected in all six cases. However, ROESY experiments provided data indicating only partial immersion (A and B ring of the steroid skeleton) in case of 1, 2 and 6. On the contrary, compounds 3 and 5, showing the most correlation rich spectra, seem to fully immerse in the beta-cyclodextrin cavity.
Forgo
Peter
P
Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged H-6720, Hungary. pforgo@chem.u-szeged.hu
Vincze
Irén
I
Kövér
Katalin E
KE
D003505:Cyclodextrins / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D007664:Ketosteroids / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D012996:Solutions; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D007664:Ketosteroids; D012996:Solutions; D047392:beta-Cyclodextrins; C031215:betadex; D004121:Dimethyl Sulfoxide