Names
Preferred IUPAC name
(5S ,6Z ,8E ,10E ,12R ,14Z )-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
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/s1
N Key: VNYSSYRCGWBHLG-AMOLWHMGSA-N
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/s1
Key: VNYSSYRCGWBHLG-AMOLWHMGBE
CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O)O
Properties
C 20 H 32 O 4
Molar mass
336.472 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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.[1] 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.[1] It is synthesized by leukotriene-A4 hydrolase from leukotriene A4 .[2]
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.[3] Obesity is the major cause of insulin resistance in type 2 diabetes .[4]
References
^ a b Cotran; Kumar, Collins (1999). Robbins Pathologic Basis of Disease . Philadelphia: W.B Saunders Company. ISBN 0-7216-7335-X .
^ "LTA4H" . uniprot . Retrieved 9 April 2013 .
^ "Molecular Link between Obesity and Type 2 Diabetes Reveals Potential Therapy" . UC San Diego Health . Archived from the original on 2022-02-18.
^ 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 .
Receptor (ligands )
BLT Tooltip Leukotriene B4 receptor
BLT1 Tooltip Leukotriene B4 receptor 1
Antagonists: 20-Carboxy-LTB<sub>4</sub>
Amelubant
CGS-23131 (LY-223982)
CGS-25019C
CP-105696
CP-195543
Etalocib
LY-293111
Moxilubant
ONO-4057
RG-14893
RP-69698
SB-209247
SC-53228
Ticolubant
U-75302
ZK-158252
BLT2 Tooltip Leukotriene B4 receptor 2
Antagonists: CP-195543
LY-255283
ZK-158252
CysLT Tooltip Cysteinyl leukotriene receptor
CysLT1 Tooltip Cysteinyl leukotriene receptor 1
Antagonists: Ablukast
BAYu9773
BAYu9916
BAYx7195
Cinalukast
FPL-55712
ICI-198615
Iralukast
LY-170680
Masilukast
MK-571
Montelukast
ONO-1078
Pobilukast
Pranlukast
Ritolukast
SKF-104353
SR-2640
Sulukast
Tipelukast
Tomelukast
Verlukast
Zafirlukast
ZD-3523
CysLT2 Tooltip Cysteinyl leukotriene receptor 2
Antagonists: BAYu9773
BAYu9916
CysLTE Tooltip Cysteinyl leukotriene receptor E
Enzyme (inhibitors )
5-LOX Tooltip Arachidonate 5-lipoxygenase
FLAP Tooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103
AM-679
BAYx1005
MK-591
MK-886
12-LOX Tooltip Arachidonate 12-lipoxygenase 15-LOX Tooltip Arachidonate 15-lipoxygenase LTA4 H Tooltip Leukotriene A4 hydrolase LTB4 H Tooltip Leukotriene B4 ω-hydroxylase LTC4 S Tooltip Leukotriene C4 synthase LTC4 H Tooltip Leukotriene C4 hydrolase LTD4 Tooltip Leukotriene D4 hydrolase
Others
PPARα Tooltip Peroxisome proliferator-activated receptor alpha PPARδ Tooltip Peroxisome proliferator-activated receptor delta
Antagonists: FH-535
GSK-0660
GSK-3787
PPARγ Tooltip Peroxisome proliferator-activated receptor gamma
Antagonists: FH-535
GW-9662
SR-202
T-0070907
Non-selective
This page was last edited on 13 April 2024, at 21:21