6533b7cffe1ef96bd1258f0d

RESEARCH PRODUCT

Photo-DHEA--a functional photoreactive dehydroepiandrosterone (DHEA) analog.

Gustav WaschatkoMichael ZahnowKatja Gehrig-burgerElzbieta Kojro

subject

endocrine systemmedicine.medical_specialtyReceptors SteroidDouble bondPhotochemistrymedicine.medical_treatmentClinical BiochemistryDehydroepiandrosteroneBiochemistrychemistry.chemical_compoundEndocrinologyInternal medicinepolycyclic compoundsmedicineHumansskin and connective tissue diseasesReceptorMolecular BiologyG protein-coupled receptorPharmacologychemistry.chemical_classificationFatty acid metabolismPhotoaffinity labelingOrganic ChemistryDHEA receptorDehydroepiandrosteroneSteroid hormoneEndocrinologychemistryMolecular Probeshuman activitieshormones hormone substitutes and hormone antagonists

description

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.

yearjournalcountryeditionlanguage
2011-04-01Steroids
10.1016/j.steroids.2011.01.009https://pubmed.ncbi.nlm.nih.gov/21291900