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Chemical Compound Review:

AC1Q5COG (6E,8E,11E,14E)-5-oxoicosa- 6,8,11,14...

Synonyms: AR-1G9307, AKOS015911180, FT-0642611, AC1NS43H, I14-39201, ...

Powell, W.S. et al., Stamatiou, P.B. et al., Koike, D. et al., Powell, W.S. et al., Sozzani, S. et al., et al.

O'Flaherty, Rogers, Paumi, Hantgan, Thomas, Clay, High, Chen, Willingham, Smitherman, Kute, Rao, Cramer, Morrow, Brink, Dahlén, Drazen, Evans, Hay, Rovati, Serhan, Shimizu, Yokomizo, Powell, Gravel, Halwani, Hii, Huang, Tan, Ferrante, Powell, Gravel, Khanapure, Rokach,

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High impact information on 5-Oxo-eicosatetraenoate

The most potent native ligand reported is 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE), and the cell membrane receptor activated has now been cloned [1].
Neutrophil-derived 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a potent activator of neutrophils and eosinophils [2].
Lipid mediators are a major class of endogenous chemoattractants, among which 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is the most potent for human eosinophils [3].
5-oxo-6,8,11,14-eicosatetraenoic acid stimulates the release of the eosinophil survival factor granulocyte/macrophage colony-stimulating factor from monocytes [3].
Effects of 5-oxo-6,8,11,14-eicosatetraenoic acid on expression of CD11b, actin polymerization, and adherence in human neutrophils [4].

Biological context of 5-Oxo-eicosatetraenoate

Eotaxin and RANTES enhance 5-oxo-6,8,11,14-eicosatetraenoic acid-induced eosinophil chemotaxis [5].
While screening genes encoding G protein-coupled receptors (GPCRs) in the human genome, we and other groups have identified a GPCR named hGPCR48 as a high affinity receptor for 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE), which is arachidonic acid metabolite and an endogenous chemoattractant for granulocytes [6].

Anatomical context of 5-Oxo-eicosatetraenoate

5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of human eosinophil migration [7].
5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes [8].
The newly described products of 5-hydroxyeicosanoid dehydrogenase, 5-oxo-6,8,11,14-eicosatetraenoic acid (ETE) and 5-oxo-15(OH)ETE, induced directional migration and actin polymerization of human monocytes in vitro [9].
5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent chemoattractant for human basophils [10].
5-Oxo-6,8,11,14-eicosatetraenoic acid induces important eosinophil transmigration through basement membrane components: comparison of normal and asthmatic eosinophils [11].

Associations of 5-Oxo-eicosatetraenoate with other chemical compounds

Human neutrophils contain a highly specific dehydrogenase that converts 5-hydroxy-6,8,11,14-eicosatetraenoic acid to 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) [4].
We recently showed that human neutrophils convert arachidonic acid to its 5-oxo metabolite, 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) [12].
We observed here that eosinophil chemotaxis towards eotaxin or 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) was amplified up to sixfold in the presence of prostaglandin (PG) D(2) [13].

Gene context of 5-Oxo-eicosatetraenoate

Stimulation of human neutrophils by 5-oxo-6,8,11,14-eicosatetraenoic acid by a mechanism independent of the leukotriene B4 receptor [14].
BACKGROUND: The 5-lipoxygenase product 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a potent activator of human eosinophils and, among lipid mediators, is the most active chemoattractant for these cells [5].
The metabolism of arachidonic acid by the 5-lipoxygenase pathway not only leads to the formation of leukotrienes but also to the biologically active eicosanoid 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) [15].
MDA-MB-231, MCF7, and SKOV3 cancer cells, but not HEK-293 cells, expressed mRNA for the leukocyte G protein-coupled 5-oxo-eicosatetraenoate (ETE) OXE receptor [16].

References

International Union of Pharmacology XLIV. Nomenclature for the oxoeicosanoid receptor. Brink, C., Dahlén, S.E., Drazen, J., Evans, J.F., Hay, D.W., Rovati, G.E., Serhan, C.N., Shimizu, T., Yokomizo, T. Pharmacol. Rev. (2004) [Pubmed]
Biological inactivation of 5-oxo-6,8,11,14-eicosatetraenoic acid by human platelets. Powell, W.S., Gravel, S., Khanapure, S.P., Rokach, J. Blood (1999) [Pubmed]
5-oxo-6,8,11,14-eicosatetraenoic acid stimulates the release of the eosinophil survival factor granulocyte/macrophage colony-stimulating factor from monocytes. Stamatiou, P.B., Chan, C.C., Monneret, G., Ethier, D., Rokach, J., Powell, W.S. J. Biol. Chem. (2004) [Pubmed]
Effects of 5-oxo-6,8,11,14-eicosatetraenoic acid on expression of CD11b, actin polymerization, and adherence in human neutrophils. Powell, W.S., Gravel, S., Halwani, F., Hii, C.S., Huang, Z.H., Tan, A.M., Ferrante, A. J. Immunol. (1997) [Pubmed]
Eotaxin and RANTES enhance 5-oxo-6,8,11,14-eicosatetraenoic acid-induced eosinophil chemotaxis. Powell, W.S., Ahmed, S., Gravel, S., Rokach, J. J. Allergy Clin. Immunol. (2001) [Pubmed]
5-Oxo-Eicosatetraenoic Acid-Induced Chemotaxis: Identification of a Responsible Receptor hGPCR48 and Negative Regulation by G Protein G12/13. Koike, D., Obinata, H., Yamamoto, A., Takeda, S., Komori, H., Nara, F., Izumi, T., Haga, T. J. Biochem. (2006) [Pubmed]
5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent stimulator of human eosinophil migration. Powell, W.S., Chung, D., Gravel, S. J. Immunol. (1995) [Pubmed]
5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes. O'Flaherty, J.T., Kuroki, M., Nixon, A.B., Wijkander, J., Yee, E., Lee, S.L., Smitherman, P.K., Wykle, R.L., Daniel, L.W. J. Immunol. (1996) [Pubmed]
Stimulating properties of 5-oxo-eicosanoids for human monocytes: synergism with monocyte chemotactic protein-1 and -3. Sozzani, S., Zhou, D., Locati, M., Bernasconi, S., Luini, W., Mantovani, A., O'Flaherty, J.T. J. Immunol. (1996) [Pubmed]
5-Oxo-6,8,11,14-eicosatetraenoic acid is a potent chemoattractant for human basophils. Sturm, G.J., Schuligoi, R., Sturm, E.M., Royer, J.F., Lang-Loidolt, D., Stammberger, H., Amann, R., Peskar, B.A., Heinemann, A. J. Allergy Clin. Immunol. (2005) [Pubmed]
5-Oxo-6,8,11,14-eicosatetraenoic acid induces important eosinophil transmigration through basement membrane components: comparison of normal and asthmatic eosinophils. Guilbert, M., Ferland, C., Bossé, M., Flamand, N., Lavigne, S., Laviolette, M. Am. J. Respir. Cell Mol. Biol. (1999) [Pubmed]
Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils. Powell, W.S., Gravel, S., Gravelle, F. J. Lipid Res. (1995) [Pubmed]
Hierarchy of eosinophil chemoattractants: role of p38 mitogen-activated protein kinase. Schratl, P., Sturm, E.M., Royer, J.F., Sturm, G.J., Lippe, I.T., Peskar, B.A., Heinemann, A. Eur. J. Immunol. (2006) [Pubmed]
Stimulation of human neutrophils by 5-oxo-6,8,11,14-eicosatetraenoic acid by a mechanism independent of the leukotriene B4 receptor. Powell, W.S., Gravel, S., MacLeod, R.J., Mills, E., Hashefi, M. J. Biol. Chem. (1993) [Pubmed]
Synthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid and identification of novel omega-oxidized metabolites in the mouse macrophage. Hevko, J.M., Bowers, R.C., Murphy, R.C. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
5-Oxo-ETE analogs and the proliferation of cancer cells. O'Flaherty, J.T., Rogers, L.C., Paumi, C.M., Hantgan, R.R., Thomas, L.R., Clay, C.E., High, K., Chen, Y.Q., Willingham, M.C., Smitherman, P.K., Kute, T.E., Rao, A., Cramer, S.D., Morrow, C.S. Biochim. Biophys. Acta (2005) [Pubmed]

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