Literature DB >> 1059121

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.   

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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Year:  1975        PMID： 1059121      PMCID： PMC432991          DOI： 10.1073/pnas.72.9.3355

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  13 in total

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Authors:  J R VANE
Journal:  Br J Pharmacol Chemother       Date:  1964-10

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Authors:  W P Schneider; R D Hamilton; L E Rhuland
Journal:  J Am Chem Soc       Date:  1972-03-22       Impact factor: 15.419

3.  Prostaglandin nomenclature.

Authors:  N A Nelson
Journal:  J Med Chem       Date:  1974-09       Impact factor: 7.446

4.  A new stereocontrolled synthesis of prostaglandins via prostaglandin A.

Authors:  E J Corey; J Mann
Journal:  J Am Chem Soc       Date:  1973-10-03       Impact factor: 15.419

5.  The occurrence of two new prostaglandin derivatives (15-epi-PGA2 and its acetate, methyl ester) in the gorgonian Plexaura homomalla chemistry of coelenterates. XV.

Authors:  A J Weinheimer; R L Spraggins
Journal:  Tetrahedron Lett       Date:  1969-12       Impact factor: 2.415

6.  Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation.

Authors:  M Hamberg; J Svensson; T Wakabayashi; B Samuelsson
Journal:  Proc Natl Acad Sci U S A       Date:  1974-02       Impact factor: 11.205

7.  Prostaglandin endoperoxides. A new concept concerning the mode of action and release of prostaglandins.

Authors:  M Hamberg; J Svensson; B Samuelsson
Journal:  Proc Natl Acad Sci U S A       Date:  1974-10       Impact factor: 11.205

8.  Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis.

Authors:  M Hamberg; B Samuelsson
Journal:  Proc Natl Acad Sci U S A       Date:  1973-03       Impact factor: 11.205

9.  Physiological role of an endoperoxide in human platelets: hemostatic defect due to platelet cyclo-oxygenase deficiency.

Authors:  C Malmsten; M Hamberg; J Svensson; B Samuelsson
Journal:  Proc Natl Acad Sci U S A       Date:  1975-04       Impact factor: 11.205

10.  Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets.

Authors:  M Hamberg; B Samuelsson
Journal:  Proc Natl Acad Sci U S A       Date:  1974-09       Impact factor: 11.205
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  17 in total

Review 1.  Current concepts for a drug-induced inhibition of formation and action of thromboxane A2.

Authors:  H Patscheke
Journal:  Blut       Date:  1990-05

2.  Prostaglandin receptors on human platelets. Structure-activity relationships of stimulatory prostaglandins.

Authors:  D E MacIntyre; E W Salzman; J L Gordon
Journal:  Biochem J       Date:  1978-09-15       Impact factor: 3.857

3.  Synthesis and biological properties of pinane-thromboxane A2, a selective inhibitor of coronary artery constriction, platelet aggregation, and thromboxane formation.

Authors:  K C Nicolaou; R L Magolda; J B Smith; D Aharony; E F Smith; A M Lefer
Journal:  Proc Natl Acad Sci U S A       Date:  1979-06       Impact factor: 11.205

4.  Perspectives from nearly five decades of total synthesis of natural products and their analogues for biology and medicine.

Authors:  K C Nicolaou; Stephan Rigol
Journal:  Nat Prod Rep       Date:  2020-04-22       Impact factor: 13.423

5.  Effects of synthetic prostaglandin analogues on platelet aggregation and secretion [proceedings].

Authors:  E J Corey; J L Gordon; D E MacIntyre; E W Salzman
Journal:  Br J Pharmacol       Date:  1977-03       Impact factor: 8.739

Review 6.  The prostanoids in hemostasis and thrombosis: a review.

Authors:  J B Smith
Journal:  Am J Pathol       Date:  1980-06       Impact factor: 4.307

7.  Generation of a chemotactic lipid from a arachidonic acid by exposure to a superoxide-generating system.

Authors:  H D Perez; B B Weksler; I M Goldstein
Journal:  Inflammation       Date:  1980-09       Impact factor: 4.092

8.  Binding of thromboxane A2/prostaglandin H2 agonists to human platelets.

Authors:  P V Halushka; P J Kochel; D E Mais
Journal:  Br J Pharmacol       Date:  1987-05       Impact factor: 8.739

9.  Inhibition of prostaglandin endoperoxide synthetase by thiol analogues of prostaglandin.

Authors:  S Ohki; N Ogino; S Yamamoto; O Hayaishi; H Yamamoto
Journal:  Proc Natl Acad Sci U S A       Date:  1977-01       Impact factor: 11.205

10.  A general method, employing arsenazo III in liposomes, for study of calcium ionophores: results with A23187 and prostaglandins.

Authors:  G Weissmann; P Anderson; C Serhan; E Samuelsson; E Goodman
Journal:  Proc Natl Acad Sci U S A       Date:  1980-03       Impact factor: 11.205
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