Triacsin C

Triacsin C
Names
IUPAC name
N-(((2E,4E,7E)-undeca-2,4,7-trienylidene)amino)nitrous amide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.127.901
Properties
C11H17N3O
Molar mass 207.137 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Triacsin C is a potent inhibitor of long 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.[1]

In addition, triacsin C is a potent vasodilator.

Inhibition of lipid metabolism reduces/removes lipid droplets from HuH7 cells. In hepatitis C infected HuH7 cells, this reduction/removal of lipid droplets significantly reduces virion formation and release.

General chemical 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. Due to the N-hydroxytriazene group, triacsin C has acidic properties and may be considered a polyunsaturated fatty acid analog.

Triacsin C was discovered by Yoshida K, and other Japanese scientists, in 1982, in a culture of the microbe Streptomyces aureofaciens. They identified it as a vasodilator.

See also

References

  1. ↑ Igal RA, Wang P, Coleman RA (June 1997). "Triacsin C blocks de novo synthesis of glycerolipids and cholesterol esters but not recycling of fatty acid into phospholipid: evidence for functionally separate pools of acyl-CoA". Biochem. J. 324. ( Pt 2): 529–34. PMC 1218462. PMID 9182714.
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