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

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

Source and publish data:

Tetrahedron p. 2635 - 2658 (1992)

Update date:2022-07-29

Topics: Mass spectrometry (MS) Click Chemistry Photoaffinity labeling Receptor binding assay Photoaffinity probe

Authors:

Suzuki, Masaaki

Koyano, Hiroshi

Noyori, Ryoji

Hashimoto, Hitoshi

Negishi, Manabu

Ichikawa, Atsushi

Ito, Seiji

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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.

Full text of DOI:10.1016/S0040-4020(01)88526-4

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Product name:Phosphonic acid, [4-(4-azidophenyl)-2-oxobutyl]-, dimethyl ester

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