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Chemical Compound Review

HMDB10216     (5S,6E,8Z,11Z,13E,15S)-5,15- dihydroxyicosa...

Synonyms: BML1-D01, LMFA03060010, AC1NR1NK, 5,15-Dihete, 5S,15S-DiHETE, ...
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Disease relevance of AIDS-163835


Psychiatry related information on AIDS-163835


High impact information on AIDS-163835

  • When human neutrophils, prelabeled with [3H]arachidonic acid, were incubated with 5S,15S-dihydroxyeicosatetraenoic acid (5,15-diHETE), a dose-dependent increase in the 15-lipoxygenase product [3H]-15-HETE was observed relative to untreated cells [3].
  • In addition, 5,15-diHETE itself stimulated the inactive 5-lipoxygenase and eight times more [3H]diHETE was bound to cells than became incorporated into cellular lipids [4].
  • Purification of this ECL by high performance liquid chromatography revealed that ECL is structurally different from well known eosinophil chemotactic eicosanoids such as leukotriene B4, 5,15-(6E,8Z,11Z,13E)-dihydroxyeicosatetraenoic acid (5,15-diHETE), and (8S,15S)-(5Z,9E,11Z,13E)-dihydroxyeicosatetra eno ic acid ((8S,15S)-diHETE) [5].
  • Only 5,15-DiHETE as well as 8(S), 15(S)-dihydroxy-5,11-cis-9,13-trans-eicosatetraenoic acid were found to be chemotaxins for human eosinophils, however, with an ED50 near 0.3 microM and 1.5 microM, respectively [6].
  • Similar, if not identical, tetraenes were produced by action of the keratinocyte enzyme on 5(S),15(S)-diHETE, which points to the role of the latter as an intermediate between 5-HETE and the tetraenes [7].

Associations of AIDS-163835 with other chemical compounds


Gene context of AIDS-163835

  • Reversed phase HPLC of incubation supernatants revealed major lipid-like eosinophil chemotactic activity eluting in a peak containing 5(S), 15(S)dihydroxy-6,13-trans-8,11-cis-eicosatetraenoic acid (5,15-DiHETE) as well as a 8,15-dihydroxyeicosatetraenoic acid [6].
  • However, stimulation of neutrophils with PAF resulted in the transformation of the 15-hydroperoxy acid into the 5,15-diHETE, and furthermore, preincubation of neutrophils with GM-CSF resulted in enhanced formation of 5,15-diHETE in response to PAF [9].


  1. Formation of a novel dihydroxy acid from arachidonic acid by lipoxygenase-catalyzed double oxygenation in rat mononuclear cells and human leukocytes. Maas, R.L., Turk, J., Oates, J.A., Brash, A.R. J. Biol. Chem. (1982) [Pubmed]
  2. Conversion of endogenous arachidonic acid to 5,15-diHETE and lipoxins by polymorphonuclear cells from patients with rheumatoid arthritis. Thomas, E., Leroux, J.L., Blotman, F., Chavis, C. Inflamm. Res. (1995) [Pubmed]
  3. 5-Hydroxyeicosanoids selectively stimulate the human neutrophil 15-lipoxygenase to use endogenous substrate. Nichols, R.C., Vanderhoek, J.Y. J. Exp. Med. (1990) [Pubmed]
  4. 15-Hydroxyeicosatetraenoic acid (15-HETE) receptors. Involvement in the 15-HETE-induced stimulation of the cryptic 5-lipoxygenase in PT-18 mast/basophil cells. Vonakis, B.M., Vanderhoek, J.Y. J. Biol. Chem. (1992) [Pubmed]
  5. Identification of 5-oxo-15-hydroxy-6,8,11,13-eicosatetraenoic acid as a novel and potent human eosinophil chemotactic eicosanoid. Schwenk, U., Morita, E., Engel, R., Schröder, J.M. J. Biol. Chem. (1992) [Pubmed]
  6. Identification of a novel and highly potent eosinophil chemotactic lipid in human eosinophils treated with arachidonic acid. Morita, E., Schröder, J.M., Christophers, E. J. Immunol. (1990) [Pubmed]
  7. Transformations of 5-HETE by activated keratinocyte 15-lipoxygenase and the activation mechanism. Green, F.A. Lipids (1990) [Pubmed]
  8. Metabolism of 5(S)-hydroxyeicosanoids by a specific dehydrogenase in human neutrophils. Powell, W.S., Gravelle, F., Gravel, S., Hashefi, M. Journal of lipid mediators. (1993) [Pubmed]
  9. Enhancement of platelet-activating factor-induced leukotriene synthesis in neutrophils by granulocyte-macrophage colony-stimulating factor (GM-CSF): studies on the mechanism of action of GM-CSF. McColl, S.R., Krump, E., McDonald, P.P., Braquet, M., Naccache, P.H., Borgeat, P. Journal of lipid mediators. (1990) [Pubmed]
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