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Chemical Compound Review

ETYA     icosa-5,8,11,14-tetraynoic acid

Synonyms: CHEMBL458328, AG-K-12657, BSPBio_001449, KBioGR_000169, KBioSS_000169, ...
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Disease relevance of 5,8,11,14-eicosatetraynoic acid


High impact information on 5,8,11,14-eicosatetraynoic acid


Chemical compound and disease context of 5,8,11,14-eicosatetraynoic acid


Biological context of 5,8,11,14-eicosatetraynoic acid


Anatomical context of 5,8,11,14-eicosatetraynoic acid


Associations of 5,8,11,14-eicosatetraynoic acid with other chemical compounds


Gene context of 5,8,11,14-eicosatetraynoic acid

  • Using 5,8,11,14-eicosatetraynoic acid and inhibitors of AA metabolism, AP-1 and NF-kappaB activation required the lipoxygenase/cytochrome P450 monooxygenase pathways [28].
  • However, when assayed in a human liver cell line (HepG2) we noticed that ETYA was a more efficient activator of hPPAR alpha than rPPAR alpha [29].
  • Indomethacin and ETYA completely suppressed prostanoids, 11-HETE and 15-HETE formation in resting and IL-1 beta-activated cells [30].
  • The calcium influx in response to U46619 (TxA2 analogue) of CD36-deficient platelets was not different from normal platelets in the presence of indomethacin and ETYA [31].
  • Incubation of the cell-free preparations with [14C]AA in the presence of ETYA, NDGA (inhibitors of cyclooxygenase and lipoxygenase pathways) as well as with 15-HETE (an inhibitor of lipoxygenase pathway) resulted in decreased formation of [14C] 12-HETE and the [14C]LTB4-like metabolite [32].

Analytical, diagnostic and therapeutic context of 5,8,11,14-eicosatetraynoic acid


  1. Bradykinin-stimulated electrolyte secretion in rabbit and guinea pig intestine. Involvement of arachidonic acid metabolites. Musch, M.W., Kachur, J.F., Miller, R.J., Field, M., Stoff, J.S. J. Clin. Invest. (1983) [Pubmed]
  2. Reduced growth rate of transplantable mammary adenocarcinoma in C3H mice fed eicosa-5,8,11,14-tetraynoic acid. Rao, G.A., Abraham, S. J. Natl. Cancer Inst. (1977) [Pubmed]
  3. Regulation of hepatic delta-6 desaturase expression and its role in the polyunsaturated fatty acid inhibition of fatty acid synthase gene expression in mice. Nakamura, M.T., Cho, H.P., Clarke, S.D. J. Nutr. (2000) [Pubmed]
  4. Suppression of rat liver fatty acid synthesis by eicosa-5,8,11,14-tetraynoic acid without a reduction in lipogenic enzymes. Clarke, B.A., Clarke, S.D. J. Nutr. (1982) [Pubmed]
  5. Inhibitors of the lipoxygenase pathway specifically block orthopoxvirus replication. Palumbo, G.J., Buller, R.M. Virology (1991) [Pubmed]
  6. Conditional ectopic expression of C/EBP beta in NIH-3T3 cells induces PPAR gamma and stimulates adipogenesis. Wu, Z., Xie, Y., Bucher, N.L., Farmer, S.R. Genes Dev. (1995) [Pubmed]
  7. Downregulation of human platelet reactivity by neutrophils. Participation of lipoxygenase derivatives and adhesive proteins. Valles, J., Santos, M.T., Marcus, A.J., Safier, L.B., Broekman, M.J., Islam, N., Ullman, H.L., Aznar, J. J. Clin. Invest. (1993) [Pubmed]
  8. Alteration of leukotriene release by macrophages ingesting Toxoplasma gondii. Locksley, R.M., Fankhauser, J., Henderson, W.R. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  9. Stimulation of leukotriene biosynthesis in human blood leukocytes by platelet-derived 12-hydroperoxy-icosatetraenoic acid. Maclouf, J., de Laclos, B.F., Borgeat, P. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  10. Inhibition of U937 eicosanoid and DNA synthesis by 5,8,11,14-eicosatetraynoic acid, an inhibitor of arachidonic acid metabolism and its partial reversal by leukotriene C4. Ondrey, F., Harris, J.E., Anderson, K.M. Cancer Res. (1989) [Pubmed]
  11. Arachidonic acid metabolism and modulation of in vitro anaphylaxis by 5,8,11,14-eicosatetraynoic acid and 9a,12a-octadecadiynoic acid. Hitchcock, M., Kokolis, N.A. Br. J. Pharmacol. (1981) [Pubmed]
  12. Mechanism of phosgene-induced lung toxicity: role of arachidonate mediators. Guo, Y.L., Kennedy, T.P., Michael, J.R., Sciuto, A.M., Ghio, A.J., Adkinson, N.F., Gurtner, G.H. J. Appl. Physiol. (1990) [Pubmed]
  13. Mechanisms of response to antigen in isolated guinea pig trachea after active sensitization. Mansour, S., Daniel, E.E. Can. J. Physiol. Pharmacol. (1986) [Pubmed]
  14. Induction of apoptosis in blood cells from a patient with acute myelogenous leukemia by SC41661A, a selective inhibitor of 5-lipoxygenase. Anderson, K.M., Levin, J., Jajeh, A., Seed, T., Harris, J.E. Prostaglandins Leukot. Essent. Fatty Acids (1993) [Pubmed]
  15. Cytochrome P-450-dependent vasodilator responses to arachidonic acid in the isolated, perfused kidney of the rat. Oyekan, A.O., McGiff, J.C., Quilley, J. Circ. Res. (1991) [Pubmed]
  16. Arachidonic acid influences proinflammatory gene induction by stabilizing the inhibitor-kappaBalpha/nuclear factor-kappaB (NF-kappaB) complex, thus suppressing the nuclear translocation of NF-kappaB. Stuhlmeier, K.M., Kao, J.J., Bach, F.H. J. Biol. Chem. (1997) [Pubmed]
  17. Differentiation of U937 cells induced by 5,8,11,14-eicosatetraynoic acid, a competitive inhibitor of arachidonic acid metabolism. Ondrey, F., Anderson, K., Hoeltgen, D., Harris, J. Exp. Cell Res. (1988) [Pubmed]
  18. Leukocyte 12-lipoxygenase: expression, purification, and investigation of the role of methionine residues in turnover-dependent inactivation and 5,8,11,14-eicosatetraynoic acid inhibition. Richards, K.M., Marnett, L.J. Biochemistry (1997) [Pubmed]
  19. Lipid metabolism during mediator release from mast cells: studies of the role of arachidonic acid metabolism in the control of phospholipid metabolism. Marquardt, D.L., Nicolotti, R.A., Kennerly, D.A., Sullivan, T.J. J. Immunol. (1981) [Pubmed]
  20. Inhibition of cytotoxic T lymphocyte-mediated lysis by ETYA: effect independent of arachidonic acid metabolism. Taylor, A.S., Howe, R.C., Morrison, A.R., Sprecher, H., Russell, J.H. J. Immunol. (1985) [Pubmed]
  21. Horse eosinophil degranulation induced by the ionophore A23187. Ultrastructure and role of phospholipase A2. Henderson, W.R., Chi, E.Y., Jörg, A., Klebanoff, S.J. Am. J. Pathol. (1983) [Pubmed]
  22. Effects of nitroprusside on the bradykinin responsiveness of human fibroblasts. Tsai, S.C., Adamik, R., Hom, B.E., Manganiello, V.C., Moss, J. Mol. Pharmacol. (1986) [Pubmed]
  23. Reticulocyte lipoxygenase exhibits both n-6 and n-9 activities. Kühn, H., Wiesner, R., Schewe, T., Rapoport, S.M. FEBS Lett. (1983) [Pubmed]
  24. Events associated with mouse skin tumor promotion with respect to arachidonic acid metabolism: a comparison between SENCAR and NMRI mice. Fischer, S.M., Fürstenberger, G., Marks, F., Slaga, T.J. Cancer Res. (1987) [Pubmed]
  25. Evidence for inhibition of leukotriene A4 synthesis by 5,8,11,14-eicosatetraynoic acid in guinea pig polymorphonuclear leukocytes. Bokoch, G.M., Reed, P.W. J. Biol. Chem. (1981) [Pubmed]
  26. Arachidonic acid metabolism of the murine eosinophil. II. Involvement of the lipoxygenase pathway in the response to the lymphokine eosinophil stimulation promoter. Rand, T.H., Turk, J., Maas, R.L., Colley, D.G. J. Immunol. (1982) [Pubmed]
  27. Differential regulation of biosynthesis of cell surface and secreted TNF-alpha in LPS-stimulated murine macrophages. Chaudhri, G. J. Leukoc. Biol. (1997) [Pubmed]
  28. Arachidonic acid activates a functional AP-1 and an inactive NF-kappaB complex in human HepG2 hepatoma cells. Bécuwe, P., Bianchi, A., Didelot, C., Barberi-Heyob, M., Dauça, M. Free Radic. Biol. Med. (2003) [Pubmed]
  29. Human and rat peroxisome proliferator activated receptors (PPARs) demonstrate similar tissue distribution but different responsiveness to PPAR activators. Mukherjee, R., Jow, L., Noonan, D., McDonnell, D.P. J. Steroid Biochem. Mol. Biol. (1994) [Pubmed]
  30. Interleukin-1 increases 15-hydroxyeicosatetraenoic acid formation in cultured human endothelial cells. López, S., Vila, L., Breviario, F., de Castellarnau, C. Biochim. Biophys. Acta (1993) [Pubmed]
  31. Platelet membrane protein CD36. Ikeda, H. Hokkaido Igaku Zasshi (1999) [Pubmed]
  32. Lipoxygenation of arachidonic acid by subcellular preparations from murine keratinocytes. Ziboh, V.A., Casebolt, T.L., Marcelo, C.L., Voorhees, J.J. J. Invest. Dermatol. (1984) [Pubmed]
  33. A new regulation of non-capacitative calcium entry in insect pacemaker neurosecretory neurons. Involvement of arachidonic acid, no-guanylyl cyclase/cGMP, and cAMP. Wicher, D., Messutat, S., Lavialle, C., Lapied, B. J. Biol. Chem. (2004) [Pubmed]
  34. Effect of eicosatetraynoic acid on liver and plasma lipids. Wood, R. Lipids (1982) [Pubmed]
  35. Role of endogenous prostaglandins in regulating the tone of opossum lower esophageal sphincter in vivo. Daniel, E.E., Sarna, S., Waterfall, W., Crankshaw, J. Prostaglandins (1979) [Pubmed]
  36. Lipoxygenase inhibitors block O2 responses of hamster cheek pouch arterioles. Jackson, W.F. Am. J. Physiol. (1988) [Pubmed]
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