title: Photo-DHEA--a functional photoreactive dehydroepiandrosterone (DHEA) analog.
abstract: The steroid hormone dehydroepiandrosterone (DHEA) has beneficial effects on vascular function, survival of neurons, and fatty acid metabolism. However, a specific receptor for DHEA has not been identified to date. Here, we describe the synthesis of a photoreactive DHEA derivative (Photo-DHEA). In Photo-DHEA, typical characteristics of DHEA are conserved: (i) a "planar" tetracyclic ring system with a Δ(5) double bond, (ii) a 3β-hydroxyl group, and (iii) a keto group at C17. In cell-based assays, Photo-DHEA showed the same properties as DHEA. We conclude that Photo-DHEA is suitable for radioiodination to yield a tool for the identification of the elusive DHEA receptor.
authors.affiliation: Institute of Pharmacy and Biochemistry, University of Mainz, Becherweg 30, 55099 Mainz, Germany.
authors.forename: Gustav
authors.initials: G
authors.lastname: Waschatko
authors.forename: Elzbieta
authors.initials: E
authors.lastname: Kojro
authors.forename: Michael
authors.initials: M
authors.lastname: Zahnow
authors.forename: Katja
authors.initials: K
authors.lastname: Gehrig-Burger
mesh_terms: D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006801:Humans; D015335:Molecular Probes / Q000138:chemical synthesis*; D010777:Photochemistry; D011987:Receptors, Steroid
chemical_list: D015335:Molecular Probes; D011987:Receptors, Steroid; C095972:dehydroepiandrosterone receptor; D003687:Dehydroepiandrosterone