SML2338
4-辛基衣康酸酯
≥98% (HPLC), anti-inflammatory , powder
别名:
β-单辛基衣康酸酯, 3-[(辛基-4-氧基)羰基]丁基-3-酸酯, 4-辛基衣康酸甲酯, 正辛基3-羧基-3-丁烯酸酯
产品名称
4-辛基衣康酸酯, ≥98% (HPLC)
方案
≥98% (HPLC)
表单
powder
储存条件
protect from light
颜色
white to beige
溶解性
DMSO: 2 mg/mL, clear
储存温度
−20°C
SMILES字符串
OC(C(CC(OCCCCCCCC)=O)=C)=O
InChI
1S/C13H22O4/c1-4-6-8-11(7-5-2)17-13(16)10(3)9-12(14)15/h11H,3-9H2,1-2H3,(H,14,15)/p-1
InChI key
GIRJEIMINMHXQS-UHFFFAOYSA-M
应用
4-辛基衣康酸已被用于：
- 研究其对巨噬细胞的抗炎作用
- 用核因子-红系因子2相关因子2 (NRF2)激活羧酸化合物处理骨髓源性巨噬细胞(BMDM)，进行BMDM刺激
- 研究其对系统性硬化症(SSc)真皮成纤维细胞胶原蛋白1表达的影响
生化/生理作用
4-衣脂酸辛酯(4-OI)具有抗炎作用。它能阻断巨噬细胞甘油醛3-磷酸脱氢酶(GAPDH)和糖酵解。它具有巯基反应活性，因此是衣壳酸酯的良好替代品。4-OI的亲电α和β不饱和部分可能有助于通过迈克尔反应使蛋白质半胱氨酸残基中的硫醇烷基化。
内源性代谢物衣脂酸盐最近成为巨噬细胞功能的调节剂。4-辛基衣脂酸盐是可渗透细胞的衣脂酸衍生物，可减少细胞因子的产生，并在体内防止脂多糖诱导的致死性。 小鼠成肌细胞和巨噬细胞中的酯酶将其水解为衣脂酸盐，衣脂酸盐使KEAP1上的半胱氨酸残基烷基化，使得转录因子Nrf2增加抗氧化和抗炎下游基因的表达。
可渗透细胞的衣脂酸衍生物，可减少细胞因子的产生，并在体内防止脂多糖诱导的致死性。
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
H John Sharifi et al.
Journal of virology, 96(23), e0118722-e0118722 (2022-11-16)
The cellular protein SAMHD1 is important for DNA repair, suppressing LINE elements, controlling deoxynucleoside triphosphate (dNTP) concentrations, maintaining HIV-1 latency, and preventing excessive type I interferon responses. SAMHD1 is also a potent inhibitor of HIV-1 and other significant viral pathogens.
4-Octyl itaconate inhibits aerobic glycolysis by targeting GAPDH to exert anti-inflammatory effects.
Shan-Ting Liao et al.
Nature communications, 10(1), 5091-5091 (2019-11-11)
Activated macrophages switch from oxidative phosphorylation to aerobic glycolysis, similar to the Warburg effect, presenting a potential therapeutic target in inflammatory disease. The endogenous metabolite itaconate has been reported to regulate macrophage function, but its precise mechanism is not clear.
Valerio Azzimato et al.
Gastroenterology, 161(6), 1982-1997 (2021-08-24)
Oxidative stress plays a key role in the development of metabolic complications associated with obesity, including insulin resistance and the most common chronic liver disease worldwide, nonalcoholic fatty liver disease. We have recently discovered that the microRNA miR-144 regulates protein
John Henderson et al.
Journal of cellular and molecular medicine, 24(23), 14026-14038 (2020-11-04)
Systemic Sclerosis (SSc) is a rare fibrotic autoimmune disorder for which no curative treatments currently exist. Metabolic remodelling has recently been implicated in other autoimmune diseases; however, its potential role in SSc has received little attention. Here, we aimed to
Ciana Diskin et al.
Journal of immunology (Baltimore, Md. : 1950), 211(6), 1032-1041 (2023-08-14)
Annexin A1 is a key anti-inflammatory effector protein that is involved in the anti-inflammatory effects of glucocorticoids. 4-Octyl itaconate (4-OI), a derivative of the endogenous metabolite itaconate, which is abundantly produced by LPS-activated macrophages, has recently been identified as a
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