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Chemical Compound Review:

CHEMBL88222 (5Z,8Z,11Z,13E)-15- hydroperoxyicosa-5,8,11...

Synonyms: CHEBI:243332, LS-176614, AC1O5MZ5, C20H32O4, 15-Hpete, ...

d'Alarcao, M. et al., Walters, F.P. et al., De Mey, J.G. et al., Marnett, L.J. et al., Claesson, H.E., et al.

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Disease relevance of Arachidonic acid 15-hydroperoxide

The inhibition of PGI2 synthetase within the arterial wall by 15-hydroperoxyarachidonic acid enhances local white platelet thrombosis [1].

High impact information on Arachidonic acid 15-hydroperoxide

Biosynthesis and metabolism of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid by human umbilical vein endothelial cells [2].
Nafazatrom inhibits the hydroperoxide-dependent oxidation of phenylbutazone, stimulates the reduction of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, and is oxidized by microsomal or purified enzyme preparations from ram seminal vesicles [3].
The effects of 15-hydroperoxyarachidonic acid (15-HPAA) on Na+, K+- and Mg+-ATPase activities in the blood-brain barrier (BBB) were examined using rat brain microvessels (MV) [4].
In the mesenteric preparation, precontracted with phenylephrine, both 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid (15-HPETE, ED50 1.6 nmol) and 8,15-dihydroperoxy-5,9,11,13-eicosatetraenoic acid (8,15-diHPETE, ED50 0.3 nmol) induced dose-dependent vasodilatation, whereas 5,15-diHPETE (0.2-100 nmol) had no effect [5].
The oxidation of intracellular myoglobin by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid was studied in suspensions of isolated adult rat heart cells [6].

Anatomical context of Arachidonic acid 15-hydroperoxide

Pharmacological studies of the contraction induced by 15-hydroperoxyarachidonic acid (15-HPAA) were done in the isolated canine basilar artery [7].
Removal of the endothelium abolished the relaxations caused by acetylcholine, ATP, thrombin and 15-hydroperoxy-5,8,11,13 eicosatetraenoic acid, reduced those caused by arachidonic acid, but did not affect the inhibitory effect of prostacyclin [8].
Oxidation of myoglobin in isolated adult rat cardiac myocytes by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid [6].
Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative [9].
Substantiation that the catalyst for the reaction in aortic microsomes was prostacyclin synthetase was obtained by showing that 15-hydroperoxyarachidonic acid strongly inhibited the activity (5) [10].

Associations of Arachidonic acid 15-hydroperoxide with other chemical compounds

Contraction of the canine basilar artery following linoleic, arachidonid 13-hydroperoxylinoleic, or 15-hydroperoxyarachidonic acid [11].

Gene context of Arachidonic acid 15-hydroperoxide

This effect was inhibited by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid, an inhibitor of prostaglandin I2 synthase (Claesson, H.-E., Lindgren, J.A. and Hammarstr!om, S. (1977) FEBS Lett. 81, 415-418) [12].

References

The inhibition of PGI2 synthetase within the arterial wall by 15-hydroperoxyarachidonic acid enhances local white platelet thrombosis. Bourgain, R.H. Haemostasis (1980) [Pubmed]
Biosynthesis and metabolism of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid by human umbilical vein endothelial cells. Hopkins, N.K., Oglesby, T.D., Bundy, G.L., Gorman, R.R. J. Biol. Chem. (1984) [Pubmed]
Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom. Marnett, L.J., Siedlik, P.H., Ochs, R.C., Pagels, W.R., Das, M., Honn, K.V., Warnock, R.H., Tainer, B.E., Eling, T.E. Mol. Pharmacol. (1984) [Pubmed]
Enhancement of ATPase activity by a lipid peroxide of arachidonic acid in rat brain microvessels. Koide, T., Asano, T., Matsushita, H., Takakura, K. J. Neurochem. (1986) [Pubmed]
The vasodilatation induced by hydroperoxy metabolites of arachidonic acid in the rat mesenteric and pulmonary circulation. d'Alarcao, M., Corey, E.J., Cunard, C., Ramwell, P., Uotila, P., Vargas, R., Wroblewska, B. Br. J. Pharmacol. (1987) [Pubmed]
Oxidation of myoglobin in isolated adult rat cardiac myocytes by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid. Walters, F.P., Kennedy, F.G., Jones, D.P. FEBS Lett. (1983) [Pubmed]
Possible mechanisms of 15-hydroperoxyarachidonic acid-induced contraction of the canine basilar artery in vitro. Koide, T., Neichi, T., Takato, M., Matsushita, H., Sugioka, K., Nakano, M., Hata, S. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
Endothelium-dependent inhibitory effects of acetylcholine, adenosine triphosphate, thrombin and arachidonic acid in the canine femoral artery. De Mey, J.G., Claeys, M., Vanhoutte, P.M. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
Suicide inactivation of porcine leukocyte 12-lipoxygenase associated with its incorporation of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid derivative. Kishimoto, K., Nakamura, M., Suzuki, H., Yoshimoto, T., Yamamoto, S., Takao, T., Shimonishi, Y., Tanabe, T. Biochim. Biophys. Acta (1996) [Pubmed]
Radical acetoacetate oxidation by myeloperoxidase, lactoperoxidase, prostaglandin synthetase, and prostacyclin synthetase: implications for atherosclerosis. Harrison, J.E., Saeed, F.A. Biochemical medicine. (1983) [Pubmed]
Contraction of the canine basilar artery following linoleic, arachidonid 13-hydroperoxylinoleic, or 15-hydroperoxyarachidonic acid. Koide, T., Noda, Y., Hata, S., Sugioka, K., Kobayashi, S., Nakano, M. Proc. Soc. Exp. Biol. Med. (1981) [Pubmed]
Prostaglandin I2 synthesis and elevation of cyclic AMP levels in 3T3 fibroblasts. Claesson, H.E. Biochim. Biophys. Acta (1980) [Pubmed]

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