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Chemical Compound Review

12-HYDROXY-5,8,10,14-EICOSATETRAENOIC ACID     (5E,8Z,10Z,12S,14Z)-12- hydroxyicosa-5,8,10...

Synonyms: AC1NSO0H, LMFA03060064, 12S-, 12(S)-5,8,10,14-Hydroxyeicosatetraenoic acid, 12-L-Hydroxy-5,8,10,14-eicosatetraenoic acid
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Disease relevance of 12-Hete


High impact information on 12-Hete


Chemical compound and disease context of 12-Hete


Biological context of 12-Hete


Anatomical context of 12-Hete


Associations of 12-Hete with other chemical compounds


Gene context of 12-Hete

  • Second, 12-LOX inhibitors blocked VEGF-induced endothelial cell migration, and this blockage could be partially reversed by the addition of 12(S)-HETE [17].
  • Conversely, the 12-LOX metabolite, 12(S)-HETE (12(S)-hydroxy-(5Z, 8Z, 10E, 14Z)-eicosatetraenoic acid), promoted c-Jun-dependent apoptosis [18].
  • 12(S)-HETE activated the stress-activated protein kinase c-Jun N-terminal kinase and p38 within 15 min, as judged by increased kinase protein phosphorylation [19].
  • The specific MEK inhibitors PD098059 and U0126, which in turn suppress ERK, abolished 12(S)-HETE-stimulated proliferation [20].
  • B16a-cell attachment to fibronectin resulted in increased metabolism of arachidonic acid to 12(S)-HETE, which was inhibited by lipoxygenase but not by cyclo-oxygenase inhibitors [21].

Analytical, diagnostic and therapeutic context of 12-Hete


  1. 12(S)-HETE enhancement of prostate tumor cell invasion: selective role of PKC alpha. Liu, B., Maher, R.J., Hannun, Y.A., Porter, A.T., Honn, K.V. J. Natl. Cancer Inst. (1994) [Pubmed]
  2. A 12(S)-hydroxyeicosatetraenoic acid receptor interacts with steroid receptor coactivator-1. Kurahashi, Y., Herbertsson, H., Söderström, M., Rosenfeld, M.G., Hammarström, S. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  3. 12(S)-hydroxyeicosatetraenoic acid and 13(S)-hydroxyoctadecadienoic acid regulation of protein kinase C-alpha in melanoma cells: role of receptor-mediated hydrolysis of inositol phospholipids. Liu, B., Khan, W.A., Hannun, Y.A., Timar, J., Taylor, J.D., Lundy, S., Butovich, I., Honn, K.V. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  4. Endogenous 12(S)-HETE production by tumor cells and its role in metastasis. Chen, Y.Q., Duniec, Z.M., Liu, B., Hagmann, W., Gao, X., Shimoji, K., Marnett, L.J., Johnson, C.R., Honn, K.V. Cancer Res. (1994) [Pubmed]
  5. Complement-independent Ab-induced peroxide lysis of platelets requires 12-lipoxygenase and a platelet NADPH oxidase pathway. Nardi, M., Feinmark, S.J., Hu, L., Li, Z., Karpatkin, S. J. Clin. Invest. (2004) [Pubmed]
  6. Stimulation of human eosinophil and neutrophil polymorphonuclear leukocyte chemotaxis and random migration by 12-L-hydroxy-5,8,10,14-eicosatetraenoic acid. Goetzl,, E.J., Woods, J.M., Gorman, R.R. J. Clin. Invest. (1977) [Pubmed]
  7. 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]
  8. Enhancement of delayed hypersensitivity inflammatory reactions in guinea pig skin by 12(R)-hydroxy-5,8,14-eicosatrienoic acid. Conners, M.S., Schwartzman, M.L., Quan, X., Heilman, E., Chauhan, K., Falck, J.R., Godfrey, H.P. J. Invest. Dermatol. (1995) [Pubmed]
  9. Rapid induction of apoptosis in prostate cancer cells by selenium: reversal by metabolites of arachidonate 5-lipoxygenase. Ghosh, J. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  10. The priming effect of 12(S)-hydroxyeicosatetraenoic acid on lymphocyte phospholipase D involves specific binding sites. Zakaroff-Girard, A., Dubois, M., Gilbert, M., Meskini, N., Némoz, G., Lagarde, M., Prigent, A.F. Life Sci. (1999) [Pubmed]
  11. Enhanced tumor cell adhesion to the subendothelial matrix resulting from 12(S)-HETE-induced endothelial cell retraction. Honn, K.V., Grossi, I.M., Diglio, C.A., Wojtukiewicz, M., Taylor, J.D. FASEB J. (1989) [Pubmed]
  12. Tumor cell-derived 12(S)-hydroxyeicosatetraenoic acid induces microvascular endothelial cell retraction. Honn, K.V., Tang, D.G., Grossi, I., Duniec, Z.M., Timar, J., Renaud, C., Leithauser, M., Blair, I., Johnson, C.R., Diglio, C.A. Cancer Res. (1994) [Pubmed]
  13. Protein kinase C-dependent effects of 12(S)-HETE on endothelial cell vitronectin receptor and fibronectin receptor. Tang, D.G., Chen, Y.Q., Diglio, C.A., Honn, K.V. J. Cell Biol. (1993) [Pubmed]
  14. Elevation of 12/15 lipoxygenase products in AD and mild cognitive impairment. Yao, Y., Clark, C.M., Trojanowski, J.Q., Lee, V.M., Praticò, D. Ann. Neurol. (2005) [Pubmed]
  15. Eicosanoid activation of extracellular signal-regulated kinase1/2 in human epidermoid carcinoma cells. Szekeres, C.K., Tang, K., Trikha, M., Honn, K.V. J. Biol. Chem. (2000) [Pubmed]
  16. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., Nelson, K.K., Diglio, C.A., Taylor, J.D., Honn, K.V. Cancer Res. (1989) [Pubmed]
  17. Eicosanoid regulation of angiogenesis: role of endothelial arachidonate 12-lipoxygenase. Nie, D., Tang, K., Diglio, C., Honn, K.V. Blood (2000) [Pubmed]
  18. Blockade of 12-lipoxygenase expression protects cortical neurons from apoptosis induced by beta-amyloid peptide. Lebeau, A., Terro, F., Rostene, W., Pelaprat, D. Cell Death Differ. (2004) [Pubmed]
  19. Activation of 12-lipoxygenase in proinflammatory cytokine-mediated beta cell toxicity. Chen, M., Yang, Z.D., Smith, K.M., Carter, J.D., Nadler, J.L. Diabetologia (2005) [Pubmed]
  20. 12-lipoxygenase metabolite 12(S)-HETE stimulates human pancreatic cancer cell proliferation via protein tyrosine phosphorylation and ERK activation. Ding, X.Z., Tong, W.G., Adrian, T.E. Int. J. Cancer (2001) [Pubmed]
  21. The lipoxygenase metabolite 12(S)-HETE promotes alpha IIb beta 3 integrin-mediated tumor-cell spreading on fibronectin. Timar, J., Chen, Y.Q., Liu, B., Bazaz, R., Taylor, J.D., Honn, K.V. Int. J. Cancer (1992) [Pubmed]
  22. Transcriptional activation of endothelial cell integrin alpha v by protein kinase C activator 12(S)-HETE. Tang, D.G., Diglio, C.A., Bazaz, R., Honn, K.V. J. Cell. Sci. (1995) [Pubmed]
  23. The lipoxygenase metabolite, 12(S)-HETE, induces a protein kinase C-dependent cytoskeletal rearrangement and retraction of microvascular endothelial cells. Tang, D.G., Timar, J., Grossi, I.M., Renaud, C., Kimler, V.A., Diglio, C.A., Taylor, J.D., Honn, K.V. Exp. Cell Res. (1993) [Pubmed]
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