Open AccessSynthesis and biological properties of a 9,11-azo-prostanoid: highly active biochemical mimic of prostaglandin endoperoxides.
Author(s) -
E. J. Corey,
K. C. Nicolaou,
Yuya Machida,
Curt Malmsten,
Bengt Samuelsson
Publication year - 1975
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.72.9.3355
Subject(s) - chemistry , prostanoid , prostaglandin , prostaglandin analogue , biochemistry , potency , contraction (grammar) , stereochemistry , in vitro , endocrinology , biology
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.