Leukotriene B4

Leukotriene B4
Names
Preferred IUPAC name
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid
Identifiers
CAS Number
  • 71160-24-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15647 ☒N
ChEMBL
  • ChEMBL65061 ☒N
ChemSpider
  • 4444132 ☒N
IUPHAR/BPS
  • 2487
KEGG
  • C02165 ☒N
PubChem CID
  • 5280492
UNII
  • 1HGW4DR56D checkY
CompTox Dashboard (EPA)
  • DTXSID4037162 Edit this at Wikidata
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/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
Chemical formula
C20H32O4
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).
☒N verify (what is checkY☒N ?)
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.[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

  1. ^ a b 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.
  • v
  • t
  • e
PrecursorProstanoids
Prostaglandins (PG)
Precursor
  • H2
Active
D/J
  • D2
E/F
  • E2 (Dinoprostone)
  • E1 (Alprostadil)
  • F (Dinoprost):
I
  • I2 (Prostacyclin/Epoprostenol):
Thromboxanes (TX)
  • A2
  • B2
Leukotrienes (LT)
Precursor
Initial
  • A4
  • B4
SRS-A
  • C4
  • D4
  • E4
Eoxins (EX)
Precursor
  • Arachidonic acid 15-hydroperoxide
Eoxins
  • A4
  • C4
  • D4
  • E4
Nonclassic
By function
  • labor stimulation:
    • PGE2 (Dinoprostone)
    • PGF (Dinoprost)
  • v
  • t
  • e
Receptor
(ligands)
BLTTooltip Leukotriene B4 receptor
BLT1Tooltip Leukotriene B4 receptor 1
  • Agonists: 12-HETE
  • 20-Hydroxy-LTB4
  • Leukotriene B4
  • LY-255283
  • Antagonists: 20-Carboxy-LTB4
  • 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
BLT2Tooltip Leukotriene B4 receptor 2
  • Antagonists: CP-195543
  • LY-255283
  • ZK-158252
CysLTTooltip Cysteinyl leukotriene receptor
CysLT1Tooltip Cysteinyl leukotriene receptor 1
  • Agonists: Leukotriene C4
  • Leukotriene D4
  • Leukotriene E4
  • 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
CysLT2Tooltip Cysteinyl leukotriene receptor 2
  • Agonists: Leukotriene C4
  • Leukotriene D4
  • Leukotriene E4
  • Antagonists: BAYu9773
  • BAYu9916
CysLTETooltip Cysteinyl leukotriene receptor E
  • Agonists: Leukotriene E4
Enzyme
(inhibitors)
5-LOXTooltip Arachidonate 5-lipoxygenase
  • FLAPTooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103
  • AM-679
  • BAYx1005
  • MK-591
  • MK-886
12-LOXTooltip Arachidonate 12-lipoxygenase
15-LOXTooltip Arachidonate 15-lipoxygenase
LTA4HTooltip Leukotriene A4 hydrolase
LTB4HTooltip Leukotriene B4 ω-hydroxylase
  • 17-Octadecynoic acid
LTC4STooltip Leukotriene C4 synthase
LTC4HTooltip Leukotriene C4 hydrolase
LTD4Tooltip Leukotriene D4 hydrolase
Others
See also
Receptor/signaling modulators
Prostanoid signaling modulators
  • v
  • t
  • e
PPARTooltip Peroxisome proliferator-activated receptor modulators
PPARαTooltip Peroxisome proliferator-activated receptor alpha
PPARδTooltip Peroxisome proliferator-activated receptor delta
  • Antagonists: FH-535
  • GSK-0660
  • GSK-3787
PPARγTooltip Peroxisome proliferator-activated receptor gamma
  • SPPARMsTooltip Selective PPARγ modulator: BADGE
  • EPI-001
  • INT-131
  • MK-0533
  • S26948
  • Antagonists: FH-535
  • GW-9662
  • SR-202
  • T-0070907
  • Unknown: SR-1664
Non-selective
See also
Receptor/signaling modulators