Synthesis and biological properties of a 9,11-azo-prostanoid: highly active biochemical mimic of prostaglandin endoperoxides.
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.
D001011:Aorta / Q000187:drug effects; D001391:Azo Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D009119:Muscle Contraction / Q000187:drug effects; D010545:Peroxides; D010973:Platelet Adhesiveness / Q000187:drug effects; D011453:Prostaglandins / Q000138:chemical synthesis / Q000494:pharmacology; D011463:Prostaglandins H; D012701:Serotonin / Q000378:metabolism; D013268:Stimulation, Chemical
D001391:Azo Compounds; D010545:Peroxides; D011453:Prostaglandins; D011463:Prostaglandins H; D012701:Serotonin; C013824:azo analog II