title: Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA).
abstract: We have synthesized an analog of dehydroepiandrosterone (DHEA, 1) containing both a benzophenone (BP) and a biotin (Bt) group (DHEA-BP-Bt, 8). Compound 8 was prepared by functionalization on C-17 of 1. Biocytin was reacted with 4-benzoylbenzoic acid and the product was condensed with 1 containing a diamine-hexane linker. We detected specific protein bands of approximately 55, 80, and 150 kDa by SDS-PAGE analysis of vascular endothelial cell plasma membranes which had been photoirradiated in the presence of 8.
authors.affiliation: Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City, IA 52242, USA. horacio-olivo@uiowa.edu
authors.forename: Horacio F
authors.initials: HF
authors.lastname: Olivo
authors.forename: Nury
authors.initials: N
authors.lastname: Perez-Hernandez
authors.forename: Dongmin
authors.initials: D
authors.lastname: Liu
authors.forename: Mary
authors.initials: M
authors.lastname: Iruthayanathan
authors.forename: Brianne
authors.initials: B
authors.lastname: O'Leary
authors.forename: Laurie L
authors.initials: LL
authors.lastname: Homan
authors.forename: Joseph S
authors.initials: JS
authors.lastname: Dillon
mesh_terms: D000818:Animals; D002417:Cattle; D002462:Cell Membrane / Q000737:chemistry / Q000378:metabolism; D002478:Cells, Cultured; D003687:Dehydroepiandrosterone / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism*; D004730:Endothelium, Vascular / Q000737:chemistry / Q000166:cytology / Q000378:metabolism; D019920:Photoaffinity Labels / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism*; D011485:Protein Binding / Q000502:physiology
chemical_list: D019920:Photoaffinity Labels; D003687:Dehydroepiandrosterone