eicosapentaenoic acid

Eicosapentaenoic Acid 是一种 ω-3 脂肪酸,是脂肪酸合酶 (FASN) 的抑制剂。Eicosapentaenoic Acid 促进肿瘤抑制基因 CCAAT/增强子结合蛋白δ (C/EBPδ) 重新表达的 DNA 去甲基化作用。Eicosapentaenoic Acid 通过 H-RAS 内含子 1 CpG 岛去甲基化激活U937 白血病细胞中的 RAS/ERK/C/EBPβ 途径。Eicosapentaenoic Acid 促进血管平滑肌细胞的松弛和血管舒张。

Eicosapentaenoic Acid (EPA) sodium 为口服活性 ω-3 长链多不饱和脂肪酸 (ω-3 LC-PUFAs)。其通过DNA去甲基化，促进肿瘤抑制基因CCAAT/增强子结合蛋白δ (C/EBPδ)的重新表达，并通过H-RAS内含子1 CpG岛的去甲基化，激活U937白血病细胞中RAS/ERK/C/EBPβ途径。此外，该化合物能够促进血管平滑肌细胞松弛和血管舒张。

Eicosapentaenoic acid ethyl ester (Ethyl eicosapentaenoate) 是 一种ω-3 脂肪酸剂和人内源性代谢物。

Heneicosapentaenoic Acid (HPA) is a 21:5 ω-3 fatty acid present in trace amounts in the green alga B. pennata and in fish oils. Its chemical composition is similar to eicosapentaenoic acid (EPA) except elongated with one carbon on the carboxyl end, placing the first double bond in the δ6 position. HPA can be used to study the significance of the position of the double bonds in ω-3 fatty acids. It incorporates into phospholipids and into triacylglycerol in vivo with the same efficiency as EPA and docosahexaenoic acid and exhibits strong inhibition of arachidonic acid synthesis from linoleic acid. HPA is a poor substrate for prostaglandin H synthase (PGHS) (cyclooxygenase) and for 5-lipoxygenase but retains the ability to rapidly inactivate PGHS.

Eicosapentaenoic acid methyl ester is a degradation product derived from monogalactosyl diacylglycerol, which is an apoptosis-inducing anticancer compound.

Heneicosapentaenoic Acid (HPA), a 21:5 ω-3 fatty acid, is found in minute quantities in green algae and fish oils, resembling eicosapentaenoic acid (EPA) but with an added carbon on the carboxyl end, positioning the initial double bond at the Δ6 location. HPA serves as a tool for examining the impact of double bond positions within n-3 fatty acids, as it is incorporated into phospholipids and triacylglycerol in vivo as efficiently as EPA and docosahexaenoic acid (DHA), while significantly inhibiting the synthesis of arachidonic acid from linoleic acid. Moreover, the ethyl ester variant of heneicosapentaenoic acid offers a more lipophilic and stable alternative to the free acid form.

Heneicosapentaenoic Acid (HPA) is a fatty acid found in small amounts in Bryopsis pennata Lamouroux green algae and fish oils, with a structure similar to eicosapentaenoic acid (EPA), but with an additional carbon at the carboxyl end, resulting in the first double bond being in the Δ6 position. HPA is important for researching the impact of double bond positions in n-3 fatty acids, as it integrates into phospholipids and triacylglycerol in vivo as effectively as EPA and docosahexaenoic acid (DHA), while strongly inhibiting the synthesis of arachidonic acid from linoleic acid. Despite being a poor substrate for prostaglandin H (PGH) synthase and 5-lipoxygenase, HPA can rapidly deactivate PGH synthase. HPA methyl ester, in certain formulations, acts as a prodrug to enhance cellular uptake of HPA before being converted into free acid by esterases, and serves as a useful reference standard.

Eicosapentaenoic Acid-d5 是 Eicosapentaenoic Acid 的氘代化合物。Eicosapentaenoic Acid 的 CAS 号为 10417-94-4。Eicosapentaenoic Acid 是一种 ω-3 脂肪酸。

Eicosapentaenoic Acid (Standard) 是 Eicosapentaenoic Acid 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。Eicosapentaenoic Acid 是一种 ω-3 脂肪酸,是脂肪酸合酶 (FASN) 的抑制剂。Eicosapentaenoic Acid 促进肿瘤抑制基因 CCAAT/增强子结合蛋白δ (C/EBPδ) 重新表达的 DNA 去甲基化作用。Eicosapentaenoic Acid 通过 H-RAS 内含子 1 CpG 岛去甲基化激活U937 白血病细胞中的 RAS/ERK/C/EBPβ 途径。Eicosapentaenoic Acid 促进血管平滑肌细胞的松弛和血管舒张。

Eicosapentaenoic acid ethyl ester (Standard) 是 Eicosapentaenoic acid ethyl ester 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。Eicosapentaenoic acid ethyl ester (Ethyl eicosapentaenoate) 是 一种ω-3 脂肪酸剂和人内源性代谢物。

Eicosapentaenoic acid methyl ester (Standard) is the standard substance of Eicosapentaenoic acid methyl ester, and it is applicable for quantitative analysis, quality control, and related research in biochemical experiments. Eicosapentaenoic acid methyl ester is a degradation product derived from monogalactosyl diacylglycerol, which is an apoptosis-inducing anticancer compound.

Eicosapentaenoyl Chloride (Eicosapentaenoic acid Chloride; EPA Chloride) 是二十碳五烯酸的衍生物，用于合成脂肪酸缀合物，以提高生物活性化合物如 (–)-表没食子儿茶素没食子酸酯和水杨酸的亲脂性和细胞渗透性。

Icosabutate (NST-4016) 是一种具有口服活性的二十碳五烯酸的衍生物，可抑制 NASH 的肝脏炎症和纤维化，可改善他汀类药物治疗的残留高甘油三酯血症患者的心血管风险状况，降低甘油三脂，可用于研究肝纤维化和动脉粥样硬化。

Resolvin E1(RvE1)是一种衍生于omega-3脂肪酸二十碳五烯酸 (EPA)的内源性脂质介质，具有抗炎性，能够激活炎症消退和促进吞噬细胞的清除，可预防2,4,6-三硝基苯磺酸诱导的结肠炎，改善红细胞增生和严重再生障碍性贫血（SAA）。

1,3-Dieicosapentaenoyl glycerol 是一种二酰甘油，Eicosapentaenoic acid 分别位于它的 sn-1 和 sn-3 位。

Eicosapentaenoyl-L-carnitine chloride 是由 Eicosapentaenoic Acid 和 L-Carnitine 构成的一种长链酰基肉碱。在失焦透镜导致的近视小鼠模型中，喂食富含 n-3/n-6 多不饱和脂肪酸 (PUFAs) 的小鼠，其眼部的 Eicosapentaenoyl-L-carnitine chloride 水平有所上升。

Prostaglandin F3α (PGF3α) 是一种源自二十碳五烯酸 (EPA) 的生物活性脂质介质，具备抗癌和抗炎功效。它是 ABCC4 的底物，Km 值为 12.1 μM。Prostaglandin F3α (PGF3α) 也可用于糖尿病研究。

17(18)-EpETE 是 17(18)-环氧二十碳四烯酸，也是 Eicosapentaenoic acid 的代谢产物。它能够刺激钾离子外向电流，并对人类肺动脉和气道平滑肌产生舒张效果。

Resolvin E2 (RvE2) is a member of the specialized pro-resolving mediator (SPM) family of bioactive lipids.1It is produced from eicosapentaenoic acidviaan 18-HEPE intermediate, which is formed by aspirin-acetylated COX-2-mediated oxidation of EPA, by 5-lipoxygenase (5-LO) in human polymorphonuclear (PMN) neutrophils.2,3RvE2 (20 ng/animal) inhibits increases in inflammatory exudate neutrophil infiltration in a mouse model of peritonitis induced by zymosan A .3Hepatic RvE2 levels are increased in mice fed normal chow, as well as in a mouse model of high-fat diet-induced non-alcoholic fatty liver disease (NAFLD), by dietary supplementation with EPA.4Plasma levels of RvE2 are increased by dietary supplementation with fish oil containing ω-3 polyunsaturated fatty acids (PUFAs) in patients with peripheral artery disease or chronic kidney disease.1,5,6 1.Chiang, N., and Serhan, C.N.Specialized pro-resolving mediator network: An update on production and actionsEssays Biochem.64(3)443-462(2020) 2.Tjonahen, E., Oh, S.F., Siegelman, J., et al.Resolvin E2: Identification and anti-inflammatory actions: Pivotal role of human 5-lipoxygenase in resolvin E series biosynthesisChemistry & Biology131193-1202(2006) 3.Sungwhan, F.O., Pillai, P.S., Recchiuti, A., et al.Pro-resolving actions and stereoselective biosynthesis of 18S E-series resolvins in human leukocytes and murine inflammationJ. Clin. Invest.121(2)569-581(2011) 4.Echeverría, F., Valenzuela, R., Espinosa, A., et al.Reduction of high-fat diet-induced liver proinflammatory state by eicosapentaenoic acid plus hydroxytyrosol supplementation: Involvement of resolvins RvE1/2 and RvD1/2J. Nutr. Biochem.6335-43(2019) 5.Ramirez, J.L., Gasper, W.J., Khetani, S.A., et al.Fish oil increases specialized pro-resolving lipid mediators in PAD (the OMEGA-PAD II trial)J. Surg. Res.238164-174(2019) 6.Barden, A.E., Shinde, S., Burke, V., et al.The effect of n-3 fatty acids and coenzyme Q10 supplementation on neutrophil leukotrienes, mediators of inflammation resolution and myeloperoxidase in chronic kidney diseaseProstaglandins Other Lipid Mediat.1361-8(2018)

Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid and docosahexaenoic acid.[1] In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state.[2] Resolvin D1 is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase.[1] 17(R)-RvD1 is an aspirin-triggered epimer of RvD1 that reduces human polymorphonuclear leukocyte (PMN) transendothelial migration, the earliest event in acute inflammation, with equipotency to RvD1 (EC50 = ~30 nM).[3] 17(R)-RvD1 exhibits a dose-dependent reduction in leukocyte infiltration in a mouse model of peritonitis with maximal inhibition of ~35% at a 100 ng dose.[3] In contrast to RvD1, the aspirin-triggered form resists rapid inactivation by eicosanoid oxidoreductases. Analytical and biological comparisons of synthetic 17(R)-RvD1 with endogenously derived 17(R)-RvD1 have confirmed its identity as matching the natural product.[4]

17R(18S)-EpETE is an oxylipin and a cytochrome P450 metabolite of eicosapentaenoic acid .1,217R(18S)-EpETE is an activator of large-conductance calcium-activated potassium (BKCa) channels, increasing the potassium current amplitude by 15-fold in isolated rat cerebral artery vascular smooth muscle cells (VSMCs) at +60 mV when used at a concentration of 50 nM.2It has negative chronotropic effects in isolated neonatal rat cardiomyocytes (NRCMs; EC50= ~1-2 nM) and prevents calcium-induced increases in the spontaneous beating of NRCMs.3,4 1.Schwarz, D., Kisselev, P., Ericksen, S.S., et al.Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: Highly steroselective formation of 17(R), 18(S)-epoxyeicosatetraenoic acidBiochem. Pharmacol.67(8)1445-1457(2004) 2.Lauterbach, B., Barbosa-Sicard, E., Wang, M.H., et al.Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activatorsHypertension39(2 Pt. 2)609-613(2002) 3.Falck, J.R., Wallukat, G., Puli, N., et al.17(R),18(S)-Epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: Structure-activity relationships and stable analoguesJ. Med. Chem.54(12)4109-4118(2011) 4.Arnold, C., Markovic, M., Blossey, K., et al.Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of omega-3 fatty acidsJ. Biol. Chem.285(43)32720-32733(2010)

Leukotriene B5 (LTB5) is a leukotriene with diverse biological activities. It is a metabolite of eicosapentaenoic acid formed through the 5-lipoxygenase (5-LO) pathway. LTB5 increases contraction of bullfrog lung strips ex vivo in a concentration-dependent manner. In vivo, LTB5 (100 nM) reduces tumor volume in mice injected with Tm1 murine melanoma cells. LTB5 also elicits chemokinesis and lysosomal enzyme release from polymorphonuclear leukocytes (PMNLs) 20- to 30-fold less, and induces platelet aggregation 8-fold less, potently than LTB4 .

Monoacylglycerols (MAGs) of ω-3 polyunsaturated fatty acids have diverse physiological and health effects. In particular, MAGs containing docosahexaenoic acid or eicosapentaenoic acid have anti-proliferative properties against colon and lung cancer cell lines. Eicosapentaenoyl 1-propanol-2-amide is an EPA-containing MAG amide analog that inhibits the growth of human lung carcinoma A549 cells, producing 98.4% growth inhibition when applied at 3 μM. It is an analog of eicosapentaenoyl ethanolamide , a natural N-acylethanolamide that impacts aging and inflammation.

20-HEPE is a metabolite of eicosapentaenoic acid that is formed via ω-oxidation of EPA by cytochrome P450 (CYP) ω-oxidases, including human CYP4F3B. It activates peroxisome proliferator-activated receptor α (PPARα) in COS-7 cells expressing a luciferase reporter when used at a concentration of 10 μM. 20-HEPE also activates murine transient receptor potential vanilloid receptor 1 (mTRPV1) in vitro but lacks antinociceptive activity in rats.