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. 1975 Sep;72(9):3355-8.
doi: 10.1073/pnas.72.9.3355.

Synthesis and biological properties of a 9,11-azo-prostanoid: highly active biochemical mimic of prostaglandin endoperoxides

E J Corey, K C Nicolaou, Y Machida, C L Malmsten, B Samuelsson

Synthesis and biological properties of a 9,11-azo-prostanoid: highly active biochemical mimic of prostaglandin endoperoxides

E J Corey et al. Proc Natl Acad Sci U S A. 1975 Sep.

Abstract

The 9,11-azo-prostanoid III [(5Z, 9alpha, 11alpha, 13E, 15S)-9, 11-azo-15-hydroxyprosta-5,13-dienoic acid] has been obtained by synthesis and tested for biological activity in systems which are responsive to the prostaglandin endoperoxides PGH2 (I) and PGG2 (II). The azo analog III is a powerful mimic of these endoperoxides with reference to platelet aggregation and release of serotonin when added to human platelet-rich plasma. The analog III is substantially more active (about 7 fold) than PGG2 in stimulating muscle contraction in the isolated rabbit aorta strip. The very great stability of III relative to PGH2 and PGG2 and its potency as a mimic of these important substances suggest that this azo analog will be of considerable value in future studies of the prostaglandin endoperoxides.

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References

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