Eicosadienoic acid
(Synonyms: 二十碳二烯酸) 目录号 : GC30726
Eicosadienoic acid能够抑制小鼠5'-单磷酸肌苷脱氢酶(IMPDH)的活性,并且与IMPDH的结合具有竞争性(Ki=3.1μM)。
Cas No.:2091-39-6
Sample solution is provided at 25 µL, 10mM.
Eicosadienoic acid can inhibit the activity of mouse 5'-monophosphoadenosine diphosphate reductase (IMPDH), and its binding to IMPDH is competitive (Ki = 3.1μM) [1]. Eicosadienoic acid is a rare natural n-6 type polyunsaturated fatty acid mainly present in animal tissues. It is metabolized into stearidonic acid (SCA) in macrophages [2]. Eicosadienoic acid is used to study the effects of fatty acid composition on the fluidity and function of cell membranes [3].
In vitro, Eicosadienoic acid (0, 10, 25, 50 and 100μM; 24 hours) increased the proportion of n-6 type polyunsaturated fatty acids (such as LA, GLA, DGLA, AA and adrenal acid) in mouse RAW264.7 macrophages in a dose-dependent manner, and significantly reduced the percentage of monounsaturated fatty acids (MUFA) [4]. Eicosadienoic acid (10μM; 24 hours) inhibited the decrease in cell viability induced by lipopolysaccharide (LPS) in RAW264.7 cells, and downregulated the expression of iNOS and COX-2 in cells and the level of ROS [5].
References:
[1] Mizushina Y, Dairaku I, Yanaka N, et al. Inhibitory action of polyunsaturated fatty acids on IMP dehydrogenase. Biochimie. 2007;89(5):581-590.
[2] Yagaloff KA, et al. Essential fatty acids are antagonists of the leukotriene B4 receptor. Prostaglandins Leukot Essent Fatty Acids. 1995 May;52(5):293-7.
[3] Yang X, Sheng W, Sun G Y, et al. Effects of fatty acid unsaturation numbers on membrane fluidity and α-secretase-dependent amyloid precursor protein processing[J]. Neurochemistry international, 2011, 58(3): 321-329.
[4] Huang YS, Huang WC, Li CW, Chuang LT. Eicosadienoic acid differentially modulates production of pro-inflammatory modulators in murine macrophages. Mol Cell Biochem. 2011;358(1-2):85-94.
[5] Pereira D M, Correia-da-Silva G, Valentão P, et al. Anti-inflammatory effect of unsaturated fatty acids and ergosta-7, 22-dien-3-ol from Marthasterias glacialis: Prevention of CHOP-mediated ER-stress and NF-κB activation[J]. PloS one, 2014, 9(2): e88341.
Eicosadienoic acid能够抑制小鼠5'-单磷酸肌苷脱氢酶(IMPDH)的活性,并且与IMPDH的结合具有竞争性(Ki=3.1μM)[1]。Eicosadienoic acid是一种主要存在于动物组织中的罕见的天然存在的n-6型多不饱和脂肪酸,在巨噬细胞中代谢为stearidonic acid(SCA) [2]。Eicosadienoic acid被用于研究脂肪酸组成对细胞膜流动性和功能的影响[3]。
在体外,Eicosadienoic acid(0, 10, 25, 50和100μM; 24h)以剂量依赖性方式增加了小鼠RAW264.7巨噬细胞中n-6型多不饱和脂肪酸(如LA、GLA、DGLA、AA和肾上腺酸)的比例,并显著降低了单不饱和脂肪酸(MUFA)的百分比 [4]。Eicosadienoic acid(10μM; 24h)抑制了脂多糖(LPS)诱导的RAW264.7细胞活力的降低,并下调了细胞iNOS、COX-2的表达和ROS的水平 [5]。
Cell experiment [1]: | |
Cell lines | RAW 264.7 cells |
Preparation Method | The murine RAW 264.7 macrophage-like cells were cultured in DMEM supplemented with 10% (v/v) heated–inactivated FBS, and maintained in a 5% CO2 fully humidified environment at 37°C. Macrophages (5×105/ml) were seeded in a 100mm tissue culture plate, and allowed to adhere for 4h at 37°C. After cells had adhered, the culture medium was replaced by serum containing DMEM medium supplemented. To determine whether the uptake of Eicosadienoic acid was dose-dependent, the same number of macrophages (5 × 105/ml) was cultured in the same DMEM medium supplemented with different final concentrations of Eicosadienoic acid (0, 10, 25, 50, or 100μM) for 24h. To monitor cell viability, an assay based on the exclusion of 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), and trypan blue dye was used. |
Reaction Conditions | 0, 10, 25, 50, 100, 200, and 400μM; 24h |
Applications | When the concentration is less than 200μM, Eicosadienoic acid has no negative impact on cell viability. |
References: |
Cas No. | 2091-39-6 | SDF | |
别名 | 二十碳二烯酸 | ||
Canonical SMILES | CCCCC/C=C/C/C=C/CCCCCCCCCC(O)=O | ||
分子式 | C20H36O2 | 分子量 | 308.5 |
溶解度 | 0.15 M Tris-HCl pH 8.5: >1 mg/ml (from Oleic Acid),DMF: >100 mg/ml (from Oleic Acid),DMSO: >100 mg/ml (from Oleic Acid),Ethanol: >100 mg/ml (from Oleic Acid),PBS pH 7.2: <100 µ g/ml (from Oleic Acid) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
1 mM | 3.2415 mL | 16.2075 mL | 32.4149 mL |
5 mM | 648.3 μL | 3.2415 mL | 6.483 mL |
10 mM | 324.1 μL | 1.6207 mL | 3.2415 mL |
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% DMSO % % Tween 80 % saline | ||||||||||
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2.
一定要按照顺序依次将溶剂加入,进行下一步操作之前必须保证上一步操作得到的是澄清的溶液,可采用涡旋、超声或水浴加热等物理方法助溶。
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