eet

1-Cyclohexyl-3-dodecyl urea (NCND) 是高选择性的可溶性环氧化物水解酶 (sEH) 抑制剂，能够增强血管紧张素 II (Ang II) 高血压中的环氧二十碳三烯酸 (EETs) 水平，并降低血压。

5R(6S)-EET 是 Arachidonic acid 的代谢产物，可激活内源性前列腺素 (PGE2) 的合成，从而抑制 Na+ 吸收，增加细胞内 Ca2+，促进跨膜电压去极化。5R(6S)-EET 展现出立体选择性，其活性低于 5S(6R)-EET。

(±)11(12)-EET methyl ester (11,12-EET methyl ester) 是一种环氧二十碳三烯酸 (EET)。EET 是一种内源性脂质信号分子，具有心脏保护和血管扩张功能。(±)11(12)-EET methyl ester 可以结合并激活 GPR132，增强小鼠和斑马鱼的造血诱导及移植能力。

(±)5(6)-EET Ethanolamide 是 Anandamide 经细胞色素 P450 酶氧化后生成的代谢产物，同时也是一种具选择性的选择性大麻素受体 2 (CB2) 激动剂。其对人类 CB1 和 CB2 的 Ki 值分别为 11.4 μM 和 8.9 nM。该化合物可用于研究免疫调节和神经炎症。

(±)8(9)-EET Ethanolamide 是 Arachidonic acid 的 CYP450 代谢产物，[可诱导肾小球前血管收缩]。

EET analog 7 是环氧二十碳三烯酸 (EET) 的一种类似物，能够与叶酸受体配体偶联，专门靶向那些高表达叶酸受体的肾细胞。EET analog 7 适用于开发针对肾脏的药物偶联物。

(±)14(15)-EET Ethanolamide ((±)14(15)-Epoxy eicosatrienoyl ethanolamide) 是一种脂肪酸单环氧化物，适用于研究铜绿假单胞菌感染及呼吸系统疾病。

(±)8(9)-EET 是通过花生四烯酸 (Arachidonic Acid) 经过细胞色素 P450 环氧酶途径代谢生成的主要产物之一。它是 COX-1 和 COX-2 的有效底物，并能在 HEK293 细胞中激活 PPARα。此化合物以 PPARα 依赖性和非依赖性机制抑制由 IL-1β 诱导的 NF-κB 活性。此外，其 (8S,9R)-异构体 ((8S,9R)-EET) 能导致血管收缩，从而降低肾血浆流量和肾小球滤过率。

(±)14(15)-EET is a metabolite of arachidonic acid that is formed via epoxidation of arachidonic acid by cytochrome P450.[1],[2] It prevents increases in leukotriene B4, ICAM-1, and chemokine (C-C motif) ligand 1 (CCL2) induced by oxidized LDL in primary rat pulmonary artery endothelial cells (RPAECs) when used at a concentration of 1 μM.[3] (±)14(15)-EET induces dilation of preconstricted isolated canine coronary arterioles (EC50 = 0.2 pM).[4] It reduces myocardial infarct size as a percentage of the area at risk in a canine model of ischemia-reperfusion injury induced by left anterior descending coronary artery (LAD) occlusion when administered at a dose of 0.128 mg/kg prior to occlusion or reperfusion.[5] Reference：[1]. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982).[2]. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J. Biol. Chem. 257(7), 3771-3781 (1982).[3]. Jiang, J.-X., Zhang, S.-J., Xiong, Y.-K., et al. EETs attenuate ox-LDL-induced LTB4 production and activity by inhibiting p38 MAPK phosphorylation and 5-LO/BLT1 receptor expression in rat pulmonary arterial endothelial cells. PLoS One 10(6), e0128278 (2015).[4]. Oltman, C.L., Weintraub, N.L., VanRollins, M., et al. Epoxyeicosatrienoic acids and dihydroxyeicosatrienoic acids are potent vasodilators in the canine coronary microcirculation. Circ. Res. 83(9), 932-939 (1998).[5]. Nithipatikom, K., Moore, J.M., Isbell, M.A., et al. Epoxyeicosatrienoic acids in cardioprotection: Ischemic versus reperfusion injury. Am. J. Physiol. Heart Circ. Physiol. 291(2), H537-H542 (2006).

Arachidonic acid is metabolized in the vascular endothelium to epoxytrienoic acids (EETs or EpETrEs) by cytochrome P450 enzymes. The EETs are released in response to acetylcholine, bradykinin, arachidonic acid, or cyclic stretch. (±)14(15)-EET-SI is the methyl sulfonamide analog of 14(15)-EET. This substitution results in a metabolically more stable compound because it is not sensitive to β-oxidation or membrane esterification. (±)14(15)-EET-SI is equipotent to 14(15)-EET in vascular agonist activity as measured by relaxation of precontracted bovine coronary arteries. In addition, 14(15)-EET and the methyl sulfonamide analog both stimulate tyrosine phosphorylation and induce mitogenesis in renal epithelial cells.

(±)11(12)-EET is a fully racemic version of the R/S enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes.[1][2][3[]A higher proportion of 11(R),12(S)-EET is produced by the CYP450 isoforms CYP2C23 and CYP2C24 while CYP2B2 produces a higher proportion of 11(S),12(R)-EET.[3]11(12)-EET has been shown, along with 8(9)-EET to play a role in the recovery of depleted calcium pools in cultured smooth muscle cells[4] It also inhibits basolateral 18-pS potassium channels in the renal cortical collecting duct when used at a concentration of 100 nM.[5]11(12)-EET (50 μg/kg per day) increases adhesion of isolated peripheral blood leukocytes in a chamber coated with P-selectin and ICAM-1 but does not affect choroidal neovascularization size following laser photocoagulation[6] It also has anti-inflammatory, angiogenic, and cardioprotective properties[7]

5(6)-EET is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes. In solution, 5(6)-EET degrades into 5,6-DiHET and 5(6)-δ-lactone, which can be converted to 5(6)-DiHET and quantified by GC-MS. In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5(6)-EET has been implicated in the mobilization of calcium and hormone secretion. 5(6)-EET is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50 = 0.54 μM), and Cav3.3 and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 μM. In addition, it is a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 μM. (±)5(6)-EET is provided as a mixture of the free acid and lactone.

14S(15R)-EET is an oxylipin and a cytochrome P450 metabolite of arachidonic acid .114S(15R)-EET binds to isolated guinea pig monocytes with a Kivalue of 612.5 nM in a competitive binding assay using [3H]14(15)-EET.2It induces dilation of precontracted isolated canine epicardial arterioles (EC50= 4 pM) and denuded porcine subepicardial arterioles (EC50= 3 pM).3Unlike 14R(15S)-EET, 14S(15R)-EET does not inhibit COX in enzyme assays or isolated platelets.4 1.Daikh, B.E., Lasker, J.M., Raucy, J.L., et al.Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C91J. Pharmacol. Exp. Ther.271(3)1427-1433(1994) 2.Wong, P.Y.-K., Lai, P.-S., and Falck, J.R.Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytesProstaglandins Other Lipid Mediat.62(4)321-333(2000) 3.Zhang, Y., Oltman, C.L., Lu, T., et al.EET homologs potently dilate coronary microvessels and activate BKCa channelsAm. J. Physiol. Heart Circ. Physiol.280(6)H2430-H2440(2001) 4.Fitzpatrick, F.A., Ennis, M.D., Baze, M.E., et al.Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acidsJ. Biol. Chem.261(2)15334-15338(1986)

14S(15R)-EET methyl ester, an oxylipin derived from arachidonic acid through cytochrome P450 metabolism, demonstrates specific biological activities. It exhibits affinity for isolated guinea pig monocytes, evidenced by a competitive binding assay with a Ki value of 612.5 nM using [3H]14(15)-EET. This compound notably enhances the dilation of precontracted isolated canine epicardial arterioles (EC50= 4 pM) and denuded porcine subepicardial arterioles (EC50= 3 pM), indicating potent vasodilatory effects. Unlike its isomer 14R(15S)-EET, 14S(15R)-EET methyl ester does not inhibit COX activity in enzyme assays or affect isolated platelets, highlighting its distinct functional profile.

14R(15S)-EET 是一种氧脂素和花生四烯酸的代谢产物。它通过细胞色素P450 (CYP) 亚型CYP2C8和CYP2C9对花生四烯酸的氧化作用生成。14R(15S)-EET (10 µM) 可诱导预收缩的离体牛冠状动脉放松。

8(S),9(R)-EET是由细胞色素P450从花生四烯酸 (AA) 转化得到的二十烷酸产物。此化合物能以浓度依赖的方式扩张犬心外膜小动脉，其EC50为121 nM。

8(R),9(S)-EET，一种Epoxyeicosatrienoic acid的异构体，通过胞质环氧水解酶 (CEH) 的催化作用生成，其亲和力Km值为41μM。

(±)11(12)-EET-d11 Methyl ester 是 (±)11(12)-EET methyl ester 的氘代物。它是 11,12-环氧二十碳三烯酸 (11,12-EET) 的甲基化衍生物，但无法诱导 G 蛋白偶联受体 GPR132 的 β-arrestin 募集，也不增强造血干细胞和祖细胞 (HSPC) 标志物的表达。11,12-EET-methyl ester 被用作研究 11,12-EET 的结构-功能关系的阴性对照，促进分析氧化脂肪酸-GPR132 信号轴在造血中的作用。

(±)14(15)-Eet-D11 In Ethanol, Concentration: 100 µg/mL (Standard)是(±)14 (15)-Eet-D11 In Ethanol的标准品，适用于定量分析、质量控制及生化实验等相关研究。

14,15-EET-CoA (14,15-Epoxy-(5Z,8Z,11Z)-eicosatrienoyl-coenzyme A) 是一种不饱和的脂肪酰辅酶 A。

11,12-EET-CoA (11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoyl-coenzyme A) 是辅酶 A 的一种衍生物。

8,9-EET-CoA (8,9-Epoxy-(5Z,11Z,14Z)-eicosatrienoyl-coenzyme A) 是一种辅酶 A 的衍生物。

(±)11(12)-EET Ethanolamide是一种Anandamide的可能代谢产物，由细胞色素 P450 (CYP450) 酶催化生成。

14,15-Epoxyeicosatrienoic acid（14,15-EET）是花生四烯酸的代谢物，具有显著的体内抑制血小板聚集的作用。此外，它能促进星形胶质细胞清除Aβ，因而在老年痴呆症的研究中具有潜在应用价值。