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Leukotriene B4

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Leukotriene B4
Names
Preferred IUPAC name (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
IUPHAR/BPS
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1Key: VNYSSYRCGWBHLG-AMOLWHMGSA-N
  • InChI=1/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1Key: VNYSSYRCGWBHLG-AMOLWHMGBE
SMILES
  • CCCCC/C=C\C(/C=C/C=C/C=C\(CCCC(=O)O)O)O
Properties
Chemical formula C20H32O4
Molar mass 336.472 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Leukotriene B4 (LTB4) is a leukotriene involved in inflammation. It has been shown to promote insulin resistance in obese mice.

Biochemistry

LTB4 is a leukotriene involved in inflammation. It is produced from leukocytes in response to inflammatory mediators and is able to induce the adhesion and activation of leukocytes on the endothelium, allowing them to bind to and cross it into the tissue. In neutrophils, it is also a potent chemoattractant, and is able to induce the formation of reactive oxygen species and the release of lysosomal enzymes by these cells. It is synthesized by leukotriene-A4 hydrolase from leukotriene A4.

Eicosanoid synthesis (leukotrienes at right)

Diabetes

A study at the University of California, San Diego School of Medicine has shown that LTB4 promotes insulin resistance in obese mice. Obesity is the major cause of insulin resistance in type 2 diabetes.

References

  1. ^ Cotran; Kumar, Collins (1999). Robbins Pathologic Basis of Disease. Philadelphia: W.B Saunders Company. ISBN 0-7216-7335-X.
  2. "LTA4H". uniprot. Retrieved 9 April 2013.
  3. "Molecular Link between Obesity and Type 2 Diabetes Reveals Potential Therapy". UC San Diego Health. Archived from the original on 2022-02-18.
  4. Li, P; Oh, DY; Bandyopadhyay, G; Lagakos, WS; Talukdar, S; Osborn, O; Johnson, A; Chung, H; Maris, M; Ofrecio, JM; Taguchi, S; Lu, M; Olefsky, JM (2015). "LTB4 promotes insulin resistance in obese mice by acting on macrophages, hepatocytes and myocytes". Nature Medicine. 21 (3): 239–247. doi:10.1038/nm.3800. PMC 4429798. PMID 25706874.
Eicosanoids
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
Leukotriene signaling modulators
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
See also
Receptor/signaling modulators
Prostanoid signaling modulators
PPARTooltip Peroxisome proliferator-activated receptor modulators
PPARαTooltip Peroxisome proliferator-activated receptor alpha
PPARδTooltip Peroxisome proliferator-activated receptor delta
PPARγTooltip Peroxisome proliferator-activated receptor gamma
Non-selective
See also
Receptor/signaling modulators
Category: