Triacsin C

Triacsin C
Names
	IUPAC name N-(((2E,4E,7E)-undeca-2,4,7-trienylidene)amino)nitrous amide
Identifiers
CAS Number	76896-80-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:144441;
ChemSpider	7851228 ;
ECHA InfoCard	100.127.901
PubChem CID	9576787;
UNII	6M6D4602I5 ;
CompTox Dashboard (EPA)	DTXSID70894877 ;
	InChI 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+ Key: NKTGCVUIESDXPU-YLEPRARLSA-N ; InChI=1/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+ Key: NKTGCVUIESDXPU-YLEPRARLBF;
	SMILES O=NN/N=C/C=C/C=C/C/C=C/CCC;
Properties
Chemical formula	C11H17N3O
Molar mass	207.277 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Triacsin C is an inhibitor of long fatty acyl CoA synthetase that has been isolated from Streptomyces aureofaciens.^[1] 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.^[2]

In addition, triacsin C is a vasodilator.^[1]

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 Keizo Yoshida and other Japanese scientists in 1982 in a culture of the microbe Streptomyces aureofaciens.^[1] They identified it as a vasodilator.

References

^ ^a ^b ^c Yoshida K, Okamoto M, Umehara K, Iwami M, Kohsaka M, Aoki H, Imanaka H (1982). "Studies on new vasodilators, WS-1228 A and B. I. Discovery, taxonomy, isolation and characterization". J Antibiot (Tokyo). 35 (2): 151–156. doi:10.7164/antibiotics.35.151. PMID 6804425.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.

[Yoshida-1] Yoshida K, Okamoto M, Umehara K, Iwami M, Kohsaka M, Aoki H, Imanaka H (1982). "Studies on new vasodilators, WS-1228 A and B. I. Discovery, taxonomy, isolation and characterization". J Antibiot (Tokyo). 35 (2): 151–156. doi:10.7164/antibiotics.35.151. PMID 6804425.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[pmid9182714-2] 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.

[1]

[2]

General chemical description

See also

References