Eoxin E4
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IUPAC name
(5Z,8Z,10E,12E,14R,15S)-14-{[(2R)-2-Amino-2-carboxyethyl]sulfanyl}-15-hydroxy-5,8,10,12-icosatetraenoic acid
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Other names
EXE4; 14,15-LTE4; 14,15-Leukotriene E4
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
PubChemCID
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CompTox Dashboard(EPA)
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Properties | |
C23H37NO5S | |
Molar mass | 439.61g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Eoxin E4(EXE4),also known as14,15-leukotriene E4,is aneoxin.Cells make eoxins by metabolizingarachidonic acidwith a15-lipoxygenaseenzyme to form15(S)-hydroperoxyeicosapentaenoic acid(i.e. 15(S)-HpETE). This product is then converted serially toEXA4,EXC4,EXD4,and EXE4byLTC4synthase,an unidentifiedgamma-glutamyltransferase,and an unidentifieddipeptidase,respectively, in a pathway which appears similar if not identical to the pathway which forms leukotreines, i.e.LTA4,LTC4,LTD4,andLTE4.This pathway is schematically shown as follows:[1][2]
EXA4is viewed as an intracellular-bound, short-lived intermediate which is rapidly metabolized to the downstream eoxins. The eoxins downstream of EXA4are secreted from their parent cells and, it is proposed but not yet proven, serve to regulate allergic responses and the development of certain cancers (seeeoxins).[1][3]
References
[edit]- ^abClaesson HE (September 2009). "On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma".Prostaglandins Other Lipid Mediat.89(3–4): 120–5.doi:10.1016/j.prostaglandins.2008.12.003.PMID19130894.
- ^Greene ER, Huang S, Serhan CN, Panigrahy D (2011)."Regulation of inflammation in cancer by eicosanoids".Prostaglandins & Other Lipid Mediators.96(1–4): 27–36.doi:10.1016/j.prostaglandins.2011.08.004.PMC4051344.PMID21864702.
- ^Feltenmark S, Gautam N, Brunnström A, Griffiths W, Backman L, Edenius C, Lindbom L, Björkholm M, Claesson HE (2008)."Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells".Proceedings of the National Academy of Sciences of the United States of America.105(2): 680–5.Bibcode:2008PNAS..105..680F.doi:10.1073/pnas.0710127105.PMC2206596.PMID18184802.