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Leukotriene E4

From Wikipedia, the free encyclopedia
Leukotriene E4
Names
Systematic IUPAC name
(5S,6R,7E,9E,11Z,14Z)-6-({(2R)-2-Amino-2-carboxyethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Identifiers
3D model (JSmol)
AbbreviationsLTE4
ChEBI
ChemSpider
KEGG
MeSHLeukotriene+E4
UNII
  • InChI=1S/C23H37NO5S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-21(30-18-19(24)23(28)29)20(25)15-14-17-22(26)27/h6-7,9-13,16,19-21,25H,2-5,8,14-15,17-18,24H2,1H3,(H,26,27)(H,28,29)/b7-6-,10-9-,12-11+,16-13+/t19?,20-,21+/m0/s1
    Key: OTZRAYGBFWZKMX-MPWKMEBCSA-N
  • CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SCC(C(=O)O)N
Properties
C23H37NO5S
Molar mass439.61 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Leukotriene E4 (LTE4) is acysteinylleukotriene involved ininflammation. It is known to be produced by several types ofwhite blood cells, includingeosinophils,mast cells, tissuemacrophages, andbasophils, and recently was also found to be produced byplatelets adhering toneutrophils.[1] It is formed from the sequential conversion ofLTC4 toLTD4 and then to LTE4, which is the final and most stable cysteinyl leukotriene.[2] Compared to the short half lives of LTC4 and LTD4, LTE4 is relatively stable and accumulates in breath condensation, in plasma, and in urine, making it the dominant cysteinyl leukotriene detected in biologic fluids.[3] Therefore, measurements of LTE4, especially in the urine, are commonly monitored in clinical research studies.

Increased production and excretion of LTE4 has been linked to several respiratory diseases, and urinary LTE4 levels are increased during severe asthma attacks and are especially high in people withaspirin-exacerbated respiratory disease.[4]

Studies have suggested that LTE4 works through its own distinct receptor, and although one has not yet been discovered, research is ongoing to isolate and characterize an LTE4-specific receptor.[5][6]

Eicosanoid synthesis (leukotrienes at right)

References

[edit]
  1. ^Laidlaw TM, Kidder MS, Bhattacharyya N, Xing W, Shen S, Milne GL, Castells MC, Chhay H, Boyce JA (2012)."Cysteinyl leukotriene overproduction in aspirin exacerbated respiratory disease is driven by platelet-adherent leukocytes".Blood.119 (16):3790–3798.doi:10.1182/blood-2011-10-384826.PMC 3335383.PMID 22262771.
  2. ^Lee CW, Lewis RA, Corey EJ, Austen KF (1983)."Conversion of leukotriene D4 to leukotriene E4 by a dipeptidase released from the specific granule of human polymorphonuclear leucocytes".Immunology.48 (1):27–35.PMC 1453997.PMID 6293969.
  3. ^Sala A, Voelkel N, Maclouf J, Murphy RC (1990)."Leukotriene E4 elimination and metabolism in normal human subjects".J Biol Chem.265 (35):21771–21778.doi:10.1016/S0021-9258(18)45807-3.hdl:2434/180227.PMID 2174886.
  4. ^Lee TH, Christie PE (1993)."Leukotrienes and aspirin induced asthma".Thorax.48 (12):1189–1190.doi:10.1136/thx.48.12.1189.PMC 464963.PMID 8303620.
  5. ^Maekawa A, Kanaoka Y, Xing W; Kanaoka; Xing; Austen (2008)."Functional recognition of a distinct receptor preferential for leukotriene E4 in mice lacking the cysteinyl leukotriene 1 and 2 receptors".Proc. Natl. Acad. Sci. USA.105 (43):16695–16700.Bibcode:2008PNAS..10516695M.doi:10.1073/pnas.0808993105.PMC 2575482.PMID 18931305.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^Paruchuri, S; Tashimo, H; Feng, C; Maekawa, A; Xing, W; Jiang, Y; Kanaoka, Y; Conley, P; Boyce, JA (2009)."Leukotriene E4-induced pulmonary inflammation is mediated by the P2Y12 receptor".The Journal of Experimental Medicine.206 (11):2543–55.doi:10.1084/jem.20091240.PMC 2768854.PMID 19822647.
Precursor
Prostanoids
Prostaglandins (PG)
Precursor
Active
D/J
E/F
I
Thromboxanes (TX)
Leukotrienes (LT)
Precursor
Initial
SRS-A
Eoxins (EX)
Precursor
Eoxins
Nonclassic
By function
Receptor
(ligands)
BLTTooltip Leukotriene B4 receptor
BLT1Tooltip Leukotriene B4 receptor 1
BLT2Tooltip Leukotriene B4 receptor 2
CysLTTooltip Cysteinyl leukotriene receptor
CysLT1Tooltip Cysteinyl leukotriene receptor 1
CysLT2Tooltip Cysteinyl leukotriene receptor 2
CysLTETooltip Cysteinyl leukotriene receptor E
Enzyme
(inhibitors)
5-LOXTooltip Arachidonate 5-lipoxygenase
12-LOXTooltip Arachidonate 12-lipoxygenase
15-LOXTooltip Arachidonate 15-lipoxygenase
LTA4HTooltip Leukotriene A4 hydrolase
LTB4HTooltip Leukotriene B4 ω-hydroxylase
LTC4STooltip Leukotriene C4 synthase
LTC4HTooltip Leukotriene C4 hydrolase
LTD4Tooltip Leukotriene D4 hydrolase
Others
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