Triacsin C
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| Names | |
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| IUPAC name
N-(((2E,4E,7E)-undeca-2,4,7-trienylidene)amino)nitrous amide
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.127.901 |
PubChem CID
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CompTox Dashboard (EPA)
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| 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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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
- ^ 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link)
External links
- The original publication about the discovery of Triacsin
- Triacsin C from Fermentek, a vendor's product page