Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA)

Horacio F. Olivo, Nury Perez-Hernandez, Dongmin Liu, Mary Iruthayanathan, Brianne O'Leary, Laurie L. Homan, Joseph S. Dillon

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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.

Original languageEnglish
Pages (from-to)1153-1155
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number3
DOIs
StatePublished - 1 Feb 2010
Externally publishedYes

Keywords

  • Benzophenone
  • Biotin
  • Chemical probe
  • DHEA
  • Photoaffinity

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