Description
Triacsin C (76896-80-5) is a long-chain fatty acyl CoA synthetase inhibitor (IC50=3.6-8.7 μM).1Inhibits mouse macrophage-derived foam cell formation2 and displays anti-atherosclerotic activity3. Cell permeable.
Chemical Properties
Solid
Uses
Triacsin, a fatty acyl CoA synthetase inhibitor, reduces myocardial infarct size, attenuates loss of post-reperfusion cardiac function, increases intravascular nitric oxide (NO) concentration, and inhibits leukocyte recruitment. Triacsin C analogs can also be used as potential antivirals against rotavirus infections.
Definition
ChEBI: Triacsin C is a nitroso compound that is N-undecylnitrous hydrazide carrying double bonds at positions 1,2,4, and 7. It is a long-chain fatty acyl CoA synthetase inhibitor and interferes with lipid metabolism by inhibiting the de novo synthesis of glycerolipids and cholesterol esters. It has a role as an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor, a vasodilator agent, an apoptosis inhibitor, a bacterial metabolite, an EC 3.1.1.64 (retinoid isomerohydrolase) inhibitor and an antimalarial. It is a nitroso compound, an olefinic compound and a hydrazone.
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.
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.
References
[1] E.J. HARTMAN M. L S Omura ∗. Triacsin C: A differential inhibitor of arachidonoyl-CoA synthetase and nospecific long chain acyl-CoA synthetase,[J]. Prostaglandins, 1989, 37 6: Pages 655-671. DOI:
10.1016/0090-6980(89)90103-2[2] I NAMATAME. Complete inhibition of mouse macrophage-derived foam cell formation by triacsin C.[J]. Journal of biochemistry, 1999, 125 2: 319-327. DOI:
10.1093/oxfordjournals.jbchem.a022289[3] DAISUKE MATSUDA. Anti-atherosclerotic Activity of Triacsin C, an Acyl-CoA Synthetase Inhibitor[J]. Journal of Antibiotics, 2008, 61 5: 318-321. DOI:
10.1038/ja.2008.45
