Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA).
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.
Olivo
Horacio F
HF
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City, IA 52242, USA. horacio-olivo@uiowa.edu
Perez-Hernandez
Nury
N
Liu
Dongmin
D
Iruthayanathan
Mary
M
O'Leary
Brianne
B
Homan
Laurie L
LL
Dillon
Joseph S
JS
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
D019920:Photoaffinity Labels; D003687:Dehydroepiandrosterone