An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor

Article abstract of DOI:10.1016/S0040-4020(01)88526-4

A stable prostacyclin analogue, (15S)-18c, having an azidophenyl group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC₅₀ value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [³H]-(15S)-18c, is obtainable by reduction of the ketone 16c with [³H]NaBH₄ - CeCl₃ followed by alkaline hydrolysis of the methyl ester.