Eoxin D₄

Eoxin D₄
Names
	IUPAC name S-[(6S,7R,8E,10E,12Z,15Z)-19-Carboxy-6-hydroxy-8,10,12,15-nonadecatetraen-7-yl]-L-cysteinylglycine
	Other names 14,15-Leukotriene D4; 14,15-LTD4
Identifiers
CAS Number	75290-64-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:63985;
ChemSpider	24822074;
PubChem CID	42607304;
CompTox Dashboard (EPA)	DTXSID901032108 ;
	InChI InChI=1S/C25H40N2O6S/c1-2-3-12-15-21(28)22(34-19-20(26)25(33)27-18-24(31)32)16-13-10-8-6-4-5-7-9-11-14-17-23(29)30/h4,6-10,13,16,20-22,28H,2-3,5,11-12,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b6-4-,9-7-,10-8+,16-13+/t20-,21-,22+/m0/s1 Key: BUTLPEVGZIRJOA-SPCGXPCUSA-N;
	SMILES CCCCC[C@@H]([C@@H](/C=C/C=C/C=C\C/C=C\CCCC(=O)O)SC[C@@H](C(=O)NCC(=O)O)N)O;
Properties
Chemical formula	C25H40N2O6S
Molar mass	496.66 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Eoxin D₄ (EXD₄), also known as 14,15-leukotriene D₄, is an eoxin. Cells make eoxins by metabolizing arachidonic acid with a 15-lipoxygenase enzyme to form 15(S)-hydroperoxyeicosapentaenoic acid (i.e. 15(S)-HpETE). This product is then converted serially to EXA₄, EXC₄, EXD₄, and EXE₄ by LTC₄ synthase, an unidentified gamma-glutamyltransferase, and an unidentified dipeptidase, respectively, in a pathway which appears similar if not identical to the pathway which forms leukotreines, i.e. LTA₄, LTC₄, LTD₄, and LTE₄. This pathway is schematically shown as follows:^[1]^[2]

Arachidonic acid + O₂ → 15(S)-HpETE → EXA₄ → EXC₄ → EXD₄ → EXE₄

EXA₄ is viewed as an intracellular-bound, short-lived intermediate which is rapidly metabolized to the downstream eoxins. The eoxins downstream of EXA₄ are secreted from their parent cells and, it is proposed but not yet proven, serve to regulate allergic responses and the development of certain cancers (see eoxins).^[1]^[3]

References

^ ^a ^b Claesson 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. PMID 19130894.
^ 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. PMC 4051344. PMID 21864702.
^ 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. PMC 2206596. PMID 18184802.

This biochemistry article is a stub. You can help Wikipedia by expanding it.

[15-LOX-1_review-1] Claesson 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. PMID 19130894.

[pmid21864702-2] 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. PMC 4051344. PMID 21864702.

[pmid18184802-3] 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. PMC 2206596. PMID 18184802.

[1]

[2]

[3]