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Merck
CN

T4540

Sigma-Aldrich

三氮菌素 C 来源于链霉菌

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别名:
2,4,7-十一碳三烯酸亚硝基腙, WS1228A
经验公式(希尔记法):
C11H17N3O
CAS号:
分子量:
207.27
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.77

生物来源

Streptomyces sp.

质量水平

形式

powder

溶解性

methanol: soluble 4.90-5.10 mg/mL, clear (Pale yellow to yellow)
methanol: soluble 4.90-5.10 mg/mL, clear, pale yellow to yellow

作用机制

enzyme | inhibits

运输

wet ice

储存温度

−20°C

SMILES字符串

CCC\C=C\C\C=C\C=C\C=N\NN=O

InChI

1S/C11H17N3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h4-5,7-11H,2-3,6H2,1H3,(H,13,15)/b5-4+,8-7+,10-9+,12-11+

InChI key

NKTGCVUIESDXPU-YLEPRARLSA-N

一般描述

Triacsin C属于真菌代谢物,所有这类真菌代谢物都具有11-碳链烯基链,在末端具有共同的N-羟基三苯基部分。

应用

已有研究发现,当不存在长链酰基辅酶A合成酶时,Triacsin C可诱导小鼠和非洲爪蟾卵母细胞成熟。 Triacsin C还可以阻断G蛋白αS亚基6的棕榈酰化。此外,triacsin C可以稳定1-油酰基-2-乙酰基-sn-甘油(OAG)并增强小鼠细胞中内质网(ER)的perilipin 3募集7

生化/生理作用

Triacsin C是长链脂肪酰辅酶A合成酶的有效抑制剂。它能阻断肥胖大鼠模型中由脂肪酸诱导的β细胞凋亡(脂肪细胞凋亡)。此外,它还能阻断甘油三酯、甘油二酯和胆固醇酯的从头合成,从而干扰脂质代谢。

制备说明

Triacsin C可溶于甲醇,浓度为4.90-5.10 mg/ml,得到澄清的浅黄色至黄色溶液。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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M Shimabukuro et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(16), 9558-9561 (1998-08-05)
Obesity causes its complications through functional and morphologic damage to remotely situated tissues via undetermined mechanisms. In one rodent model of obesity, the Zucker diabetic fatty fa/fa rat, overaccumulation of triglycerides in the pancreatic islets may be responsible for a
Sanjay Basak et al.
Prostaglandins, leukotrienes, and essential fatty acids, 88(2), 155-162 (2012-11-17)
Fatty acids regulate angiogenesis although no such information is available in first trimester placental trophoblast cells despite the fact that angiogenesis is a critical step involving these cells in early placentation. We investigated effects of different fatty acids on angiogenesis
Yulia Y Tyurina et al.
FEBS letters, 586(3), 235-241 (2012-01-03)
Peroxidation of cardiolipin in mitochondria is essential for the execution of apoptosis. We suggested that integration of oleic acid into cardiolipin generates non-oxidizable cardiolipin species hence protects cells against apoptosis. We synthesized mitochondria-targeted triphenylphosphonium oleic acid ester. Using lipidomics analysis
H Tomoda et al.
The Journal of biological chemistry, 266(7), 4214-4219 (1991-03-05)
Triacsins A, B, C, and D are new inhibitors of long chain acyl-CoA synthetase (EC 6.2.1.3) and possess different inhibitory potencies against the enzyme (Tomoda, H., Igarashi, K., and Omura, S. (1987) Biochim. Biophys. Acta 921, 595-598). Acyl-CoA synthetase activity
R A Igal et al.
The Biochemical journal, 324 ( Pt 2), 529-534 (1997-06-01)
The trafficking of acyl-CoAs within cells is poorly understood. In order to determine whether newly synthesized acyl-CoAs are equally available for the synthesis of all glycerolipids and cholesterol esters, we incubated human fibroblasts with [14C]oleate, [3H]arachidonate or [3H]glycerol in the

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