Prostaglandin Photoaffinity Probes: Synthesis And Biological Activity of Azide-Substituted 16-Phenoxy- and 17-Phenyl-PGF2αProstaglandins

Kenji Kawada, E. Kurt Dolence, Hiroyuki Morita, L. E. Gerschenson, Tadashi Kometani, David S. Watt, David J. Orlicky, Tony A. Fitz, Anil Balapure

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18 Scopus citations


The development of a prostaglandin PGF2aphotoaffinity probe led to the synthesis and biological evaluation of azide-substituted 17-phenyl-18,19,20-trinorprostaglandin F2aand 16-phenoxy-17,18,19,20-tetranorprostaglandin E2aderivatives. Two approaches for the preparation of iodinated versions of these prostaglandins were evaluated: (1) iodination of a phenyl azide bearing an activating hydroxyl group and (2) iodination of an aniline precursor to the phenyl azide group and subsequent conversion of the aniline to the phenyl azide. In the first approach, 17-(4-azido-2-hydroxyphenyl)-18,19,20-trinorprostaglandin F2a, 16-(5-azido-3-hydroxyphenoxy)-17,18,19,20-tetranorprostaglandin F2a, and 16-(4-azido-2-hydroxyphenoxy)-17,18,19,20-tetranorprostaglandin F2awere prepared by using the Corey synthesis, but were biologically inactive presumably as a result of the hydrophilic phenolic hydroxyl group. In the second approach, the iodination of a 17-(4-aminophenyl)-18,19,20-trinorprostaglandin F2aderivative delivered 17-(4-azido-3-iodophenyl)-18,19,20-trinorprostaglandin F2α, which exhibited competitive binding with natural [3H]PGF2α to ovine luteal cells and to plasma membranes of bovine corpora lutea. [125I]-17-(4-Azido-3-iodophenyl)-18,19,20-trinorprostaglandin F2awas utilized in a preliminary photoaffinity cross-linking experiment.

Original languageEnglish
Pages (from-to)256-264
Number of pages9
JournalJournal of Medicinal Chemistry
Issue number1
StatePublished - Jan 1 1989

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


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