Synthesis of [17,18-3H] trans-13-azaprostanoic acid. A labeled probe for the PGH2/TXA2 receptor

Prostaglandins
N I GhaliD L Venton

Abstract

Because of its highly unstable nature, TXA2, produced by platelet metabolism of arachidonic acid, does not lend itself to use as a receptor probe for its own receptor. As such, the stable TXA2/PGH2 antagonist, trans-13-azaprostanoic acid (trans-13-APA, 12b), was prepared as the [17, 18 3H] derivative [( 3H] trans-13-APA, 12c) to study this receptor and to better evaluate the mechanism of action of these azaprostanoids. Tritiated trans-13-APA, 12c, was prepared in nearly theoretical specific activity (57 Ci/mmole) from (17Z)-trans-13-azaprost-17-enoic acid (11b) by catalytic tritiation. The unsaturated 11b was prepared by condensation of cis-7-amino-3-heptene (8) with 2-(6-carboxyhexyl) cyclopentanone (9), NaBH4 reduction, chromatography, and hydrolysis of the trans isomer so isolated. The olefins 11a and b were also of biochemical interest because of the unsaturation in the lower side chain. The presence of similar unsaturation in PGH3(4) and TXA3 (3) renders these prostaglandins inactive as proaggregatory agents. Evaluation of the antiaggregatory activity of 11a and b indicated it to be about the same potency in inhibiting human platelet aggregation as the parent cis and trans-13-APAs, suggesting that introduction of a double ...Continue Reading

References

Mar 1, 1977·Prostaglandins·R R GormanO V Miller
Feb 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·P NeedlemanH Sprecher
Jun 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·K C NicolaouA M Lefer
Aug 1, 1979·Proceedings of the National Academy of Sciences of the United States of America·G C Le BretonP V Halushka
Mar 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·A M LeferK C Nicolaou

Related Concepts

13-azaprostanoic acid, (trans)-isomer
Eicosatetraenoic Acids
Saturated Fat
Platelet Aggregation
Prostaglandin Endoperoxides, Synthetic
Prostanoic Acids
Hormone Receptors, Cell Surface
Prostaglandin Receptor
Structure-Activity Relationship
Arachidonic Acid, Zinc Salt, (all-Z)-Isomer

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