Inclusion complexes of ketosteroids with β-cyclodextrin

P. Forgó, Irén Vincze, K. Kövér

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Inclusion complexes of several steroid derivatives with β-cyclodextrin (7) were studied in dimethylsulfoxide solution. The investigated molecules were ketosteroids with different functional groups on the skeleton: 3β-acetoxypregn-5-en-20-one (1), 3β-acetoxypregna-5,16-dien-20-one (2), 3β-acetoxyandrost-5-en-17-one (3), 3β-hydroxyandrost-5-en-17-one (4), 5α-androstane-3,17-dione (5) and 17β-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 β-cyclodextrin cavity.

Original languageEnglish
Pages (from-to)321-327
Number of pages7
JournalSteroids
Volume68
Issue number4
DOIs
Publication statusPublished - Apr 1 2003

Fingerprint

Ketosteroids
Cyclodextrins
Steroids
Skeleton
Protons
Molecules
Immersion
Dimethyl Sulfoxide
Functional groups
Experiments
Derivatives
Glucose

Keywords

  • Cyclodextrin
  • Inclusion complexes
  • NMR spectroscopy
  • ROESY
  • Steroids

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Molecular Biology

Cite this

Inclusion complexes of ketosteroids with β-cyclodextrin. / Forgó, P.; Vincze, Irén; Kövér, K.

In: Steroids, Vol. 68, No. 4, 01.04.2003, p. 321-327.

Research output: Contribution to journalArticle

Forgó, P. ; Vincze, Irén ; Kövér, K. / Inclusion complexes of ketosteroids with β-cyclodextrin. In: Steroids. 2003 ; Vol. 68, No. 4. pp. 321-327.
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