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Chemical Compound Review

AG-G-81630     (12S)-12-hydroperoxyicosa- 5,8,10,14...

Synonyms: KBioGR_000041, KBioSS_000041, CBiol_001803, AC1LCV3S, CTK2H5637, ...
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Disease relevance of C05965


High impact information on C05965


Biological context of C05965


Anatomical context of C05965


Associations of C05965 with other chemical compounds


Gene context of C05965

  • Identification of the membrane-bound 12-HETE-forming activity as a 12-lipoxygenase included 12S-stereospecificity of product formation and trapping of 12-hydroperoxyeicosatetraenoic acid as a reaction product [22].
  • In selenium-deficient UT7 cells, which were devoid of GPx-1 but not of PHGPx, the reduction of 12-HPETE was retained, albeit with a lower rate than in control cells containing GPx-1 [23].
  • The activities of platelet 12-HPETE peroxidase and glutathione peroxidase remaining were then assayed by using [1-14C]12-HPETE as substrate [24].
  • A particularly interesting finding was the dose-dependent and apparently complete inhibition of formation of the hydroperoxide of 12L-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HPETE) in human platelets by SIN [25].
  • The effects of molsidomine and its metabolite SIN-1 on coronary vessel tone, platelet aggregation, and eicosanoid formation in vitro--inhibition of 12-HPETE biosynthesis [25].

Analytical, diagnostic and therapeutic context of C05965


  1. Nitric oxide triggers the toxicity due to glutathione depletion in midbrain cultures through 12-lipoxygenase. Canals, S., Casarejos, M.J., de Bernardo, S., Rodríguez-Martín, E., Mena, M.A. J. Biol. Chem. (2003) [Pubmed]
  2. Role of 12-HPETE in the pathogenesis of cerebral vasospasm. Okamoto, H., Tanabe, M., Iwatsuki, M., Nishiyama, M., Akatsuka, K., Watanabe, T., Hori, T., Nakajima, E. Adv. Exp. Med. Biol. (1997) [Pubmed]
  3. Lipoxygenase metabolism of arachidonic acid in ischemic preconditioning and PKC-induced protection in heart. Chen, W., Glasgow, W., Murphy, E., Steenbergen, C. Am. J. Physiol. (1999) [Pubmed]
  4. Products of heme-catalyzed transformation of the arachidonate derivative 12-HPETE open S-type K+ channels in Aplysia. Belardetti, F., Campbell, W.B., Falck, J.R., Demontis, G., Rosolowsky, M. Neuron (1989) [Pubmed]
  5. A 12R-lipoxygenase in human skin: mechanistic evidence, molecular cloning, and expression. Boeglin, W.E., Kim, R.B., Brash, A.R. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  6. Formation and action of 8-hydroxy-11,12-epoxy-5,9,14-icosatrienoic acid in Aplysia: a possible second messenger in neurons. Piomelli, D., Shapiro, E., Zipkin, R., Schwartz, J.H., Feinmark, S.J. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  7. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid and its metabolites. Piomelli, D., Wang, J.K., Sihra, T.S., Nairn, A.C., Czernik, A.J., Greengard, P. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  8. Deficient induction of leukotriene synthesis in human neutrophils by lipoxygenase-deficient platelets. Kanaji, K., Okuma, M., Uchino, H. Blood (1986) [Pubmed]
  9. Activation of microvascular endothelium by eicosanoid 12(S)-hydroxyeicosatetraenoic acid leads to enhanced tumor cell adhesion via up-regulation of surface expression of alpha v beta 3 integrin: a posttranscriptional, protein kinase C- and cytoskeleton-dependent process. Tang, D.G., Diglio, C.A., Honn, K.V. Cancer Res. (1994) [Pubmed]
  10. A short-chain aldehyde is a major lipoxygenase product in arachidonic acid-stimulated porcine leukocytes. Glasgow, W.C., Harris, T.M., Brash, A.R. J. Biol. Chem. (1986) [Pubmed]
  11. 12-hydroperoxyeicosatetraenoic acid inhibits main platelet functions by activation of soluble guanylate cyclase. Brüne, B., Ullrich, V. Mol. Pharmacol. (1991) [Pubmed]
  12. Evidence that increased 12-lipoxygenase activity induces apoptosis in fibroblasts. Gu, J., Liu, Y., Wen, Y., Natarajan, R., Lanting, L., Nadler, J.L. J. Cell. Physiol. (2001) [Pubmed]
  13. Endothelium is required for 12-hydroperoxyeicosatetraenoic acid-induced vasoconstriction. Nishiyama, M., Okamoto, H., Watanabe, T., Hori, T., Sasaki, T., Kirino, T., Shimizu, T. Eur. J. Pharmacol. (1998) [Pubmed]
  14. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14, 15-leukotriene A4. Bryant, R.W., Schewe, T., Rapoport, S.M., Bailey, J.M. J. Biol. Chem. (1985) [Pubmed]
  15. Transient Receptor Potential Vanilloid Subtype 1 Mediates Microglial Cell Death In Vivo and In Vitro via Ca2+-Mediated Mitochondrial Damage and Cytochrome c Release. Kim, S.R., Kim, S.U., Oh, U., Jin, B.K. J. Immunol. (2006) [Pubmed]
  16. Hepoxilins, potential endogenous mediators of insulin release. Pace-Asciak, C.R., Martin, J.M., Corey, E.J. Prog. Lipid Res. (1986) [Pubmed]
  17. Possible involvement of phospholipase activation in erythroid progenitor cell proliferation. Beckman, B.S., Seferynska, I. Exp. Hematol. (1989) [Pubmed]
  18. Somatostatin inhibition of hippocampal CA1 pyramidal neurons: mediation by arachidonic acid and its metabolites. Schweitzer, P., Madamba, S., Champagnat, J., Siggins, G.R. J. Neurosci. (1993) [Pubmed]
  19. Arachidonic acid epoxides. Demonstration through [18O]oxygen studies of an intramolecular transfer of the terminal hydroxyl group of (12S)-hydroperoxyeicosa-5,8,10,14-tetraenoic acid to form hydroxyepoxides. Pace-Asciak, C.R. J. Biol. Chem. (1984) [Pubmed]
  20. Regeneration of vitamin E in human platelets. Chan, A.C., Tran, K., Raynor, T., Ganz, P.R., Chow, C.K. J. Biol. Chem. (1991) [Pubmed]
  21. 12-lipoxygenase products are potent inhibitors of prostacyclin-induced renin release. Antonipillai, I. Proc. Soc. Exp. Biol. Med. (1990) [Pubmed]
  22. A cryptic, microsomal-type arachidonate 12-lipoxygenase is tonically inactivated by oxidation-reduction conditions in cultured epithelial cells. Shornick, L.P., Holtzman, M.J. J. Biol. Chem. (1993) [Pubmed]
  23. Evidence for the presence of phospholipid hydroperoxide glutathione peroxidase in human platelets: implications for its involvement in the regulatory network of the 12-lipoxygenase pathway of arachidonic acid metabolism. Sutherland, M., Shankaranarayanan, P., Schewe, T., Nigam, S. Biochem. J. (2001) [Pubmed]
  24. Characterization of 12-L-hydroperoxyeicosa-5,8,10,14-tetraenoic acid peroxidase in platelets by monoclonal antibody against glutathione peroxidase. Chang, W.C., Fang, G.S. Prostaglandins Leukot. Essent. Fatty Acids (1990) [Pubmed]
  25. The effects of molsidomine and its metabolite SIN-1 on coronary vessel tone, platelet aggregation, and eicosanoid formation in vitro--inhibition of 12-HPETE biosynthesis. Darius, H., Ahland, B., Rücker, W., Klaus, W., Peskar, B.A., Schrör, K. J. Cardiovasc. Pharmacol. (1984) [Pubmed]
  26. Basal transepidermal water loss is increased in platelet-type 12-lipoxygenase deficient mice. Johnson, E.N., Nanney, L.B., Virmani, J., Lawson, J.A., Funk, C.D. J. Invest. Dermatol. (1999) [Pubmed]
  27. Verapamil decreases the formation of thromboxane from exogenous 14C-arachidonic acid in human platelets in vitro. Dahl, M.L., Uotila, P. Prostaglandins, leukotrienes, and medicine. (1985) [Pubmed]
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