Photo-DHEA-A functional photoreactive dehydroepiandrosterone (DHEA) analog

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 Delta(5) double bond, (ii) a 3 beta-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. (C) 2011 Elsevier Inc. All rights reserved.