Home>>Signaling Pathways>> Proteases>> Lipoxygenase>>20-hydroxy Leukotriene B4

20-hydroxy Leukotriene B4

(Synonyms: 20-羟基白三烯B4) 目录号 : GC41421

A LTB4 metabolite

20-hydroxy Leukotriene B4 Chemical Structure

Cas No.:79516-82-8

规格 价格 库存 购买数量
25μg
¥2,296.00
现货
50μg
¥4,369.00
现货
100μg
¥8,258.00
现货

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Sample solution is provided at 25 µL, 10mM.

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产品描述

20-hydroxy LTB4 is a metabolite of LTB4 in human neutrophils. In human leukocytes, LTB4 is inactivated by the enzyme LTB4 20-hydroxylase. 20-hydroxy LTB4 is not only much less active (~5%) compared to LTB4 in causing degranulation of PMNL, but actually inhibits LTB4-induced degranulation of human neutrophils (Ki = 13.3 nM). However, 20-hydroxy LTB4 is as active as LTB4 in contracting parenchymal strips from guinea pig lung. 20-hydroxy LTB4 retains considerable ligand binding affinity at the BLT2 receptor, but does not appear to function as an agonist.

Chemical Properties

Cas No. 79516-82-8 SDF
别名 20-羟基白三烯B4
Canonical SMILES OCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(O)=O
分子式 C20H32O5 分子量 352.5
溶解度 DMF: >50 mg/ml (per Rao Maddipati),DMSO: >50 mg/ml (per Rao Maddipati),Ethanol: >50 mg/ml (per Rao Maddipati),PBS pH 7.2: >1 mg/ml (from 13(S)-HODE) 储存条件 Store at -20°C,protect from light
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1 mM 2.8369 mL 14.1844 mL 28.3688 mL
5 mM 0.5674 mL 2.8369 mL 5.6738 mL
10 mM 0.2837 mL 1.4184 mL 2.8369 mL
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Research Update

Formation of leukotriene B4, 20-hydroxy Leukotriene B4 and other arachidonic acid metabolites by macrophages during peritonitis in patients with continuous ambulatory peritoneal dialysis

Prostaglandins Leukot Med 1987 May;27(2-3):151-60.PMID:3039532DOI:10.1016/0262-1746(87)90067-9.

Macrophages, isolated from dialysis fluid of three patients with continuous ambulatory peritoneal dialysis (CAPD) at different times during peritonitis were labelled with 14C-arachidonic acid and stimulated with the calcium ionophore A23187. The main metabolites formed by 5-lipoxygenase activity were leukotriene B4 (LTB4) and 5-hydroxy-6, 9, 11, 14-eicosatetraenoic acid (5-HETE). Smaller amounts of cyclooxygenase metabolites were present and also a major compound with an elution time between 6-keto-prostaglandin F1 alpha (6-keto-PGF1 alpha) and thromboxane B2 (TxB2). This substance was isolated, analyzed by GC-MS and identified as 20-hydroxy-leukotriene B4 (20-OH-LTB4). This indicates that human peritoneal macrophages obtained from CAPD not only produce leukotrienes and prostaglandins, but also the omega-hydroxylase product of LTB4, which has been demonstrated to be present in polymorphonuclear leucocytes. The activity of this enzyme was not correlated with the severity of the peritonitis.

Cytochrome P450 ω-Hydroxylases in Inflammation and Cancer

Adv Pharmacol 2015;74:223-62.PMID:26233909DOI:10.1016/bs.apha.2015.05.002.

Cytochrome P450-dependent ω-hydroxylation is a prototypic metabolic reaction of CYP4 family members that is important for the elimination and bioactivation of not only therapeutic drugs, but also endogenous compounds, principally fatty acids. Eicosanoids, derived from arachidonic acid, are key substrates in the latter category. Human CYP4 enzymes, mainly CYP4A11, CYP4F2, and CYP4F3B, hydroxylate arachidonic acid at the omega position to form 20-HETE, which has important effects in tumor progression and on angiogenesis and blood pressure regulation in the vasculature and kidney. CYP4F3A in myeloid tissue catalyzes the ω-hydroxylation of leukotriene B4 to 20-hydroxy Leukotriene B4, an inactivation process that is critical for the regulation of the inflammatory response. Here, we review the enzymology, tissue distribution, and substrate selectivity of human CYP4 ω-hydroxylases and their roles as catalysts for the formation and termination of the biological effects of key eicosanoid metabolites in inflammation and cancer progression.