T4540
Triacsin C
From Streptomyces sp., long-chain fatty acyl CoA synthetase inhibitor, powder
Synonym(s):
2,4,7-Undecatrienal nitrosohydrazone, WS1228A
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About This Item
Empirical Formula (Hill Notation):
C11H17N3O
CAS Number:
Molecular Weight:
207.27
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Triacsin C from Streptomyces sp.,
SMILES string
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
biological source
Streptomyces sp.
form
powder
solubility
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
mode of action
enzyme | inhibits
shipped in
wet ice
storage temp.
−20°C
Quality Level
Related Categories
Application
Triacsin C was found to induce maturation in mouse and Xenopus oocytes in the absence of long-chain acyl-CoA synthetase. Triacsin C can also block palmitoylation of the G-protein alpha S subunit6. Furthermore, triacsin C can stabilize1-oleoyl-2-acetyl-sn-glycerol (OAG) and enhance perilipin 3 recruitment to the endoplasmic reticulum (ER) in mouse cells7.
Biochem/physiol Actions
Triacsin C is a potent inhibitor of long-chain fatty acyl CoA synthetase. It blocks β-cell apoptosis, induced by fatty acids (lipoapoptosis) in a rat model of obesity. In addition, it blocks the de novo synthesis of triglycerides, diglycerides, and cholesterol esters, thus interfering with lipid metabolism.
General description
Triacsin C belongs to a family of fungal metabolites all having an 11-carbon alkenyl chain with a common N-hydroxytriazene moiety at the terminus.
Preparation Note
Triacsin C is soluble in methanol at 4.90 - 5.10 mg/ml and yields a clear, pale yellow to yellow solution.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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
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
I Namatame et al.
Journal of biochemistry, 125(2), 319-327 (1999-02-17)
Primary mouse peritoneal macrophages effectively take up and metabolize phosphatidylcholine/cholesterol liposomes containing a small amount of phosphatidylserine, which results in the massive accumulation in the cytoplasm of oil red O positive lipid droplets consisting of cholesteryl ester (CE) and triacylglycerol
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