Accession NumberHMDB05093
Common_Name20-trifluoromethyl-leukotriene B4
Description20-trifluoromethyl-leukotriene B4 (20CF3-LTB4) is synthesized from 20,20,20-trifluoroarachidonic acid. 20CF3-LTB4 is a stable derivative of leukotriene B4 (LTB4) that is not subjected to omega-oxidation to less active metabolites. 20CF3-LTB4 is as potent as LTB4 as a chemotactic, adhesion-promoting and aggregatory agent for human neutrophils, but with only 11 +/- 3% of the ability to induce an oxidative response. The insertion of the trifluoromethyl group into the LTB4 molecule causes a shift of the biological activity profile, suggesting that 20CF3-LTB4 binds mainly to high affinity LTB4 receptors. 20CF3-LTB4 has been synthesized as an LTB4 analog and evaluated with human neutrophils for effects on chemotaxis and degranulation. 20CF3-LTB4 can modulate arachidonic acid metabolism in several inflammatory cells. Leukotriene B4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/ 15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted into human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before w-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. (PMID: 1850167, 2543037, 2835934, 17623009, 8816421)
Chemical_IUPAC_Name(5S,6Z,8E,10E,12R,14Z)-20,20,20-trifluoro-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Chemical FormulaC20H29F3O4
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