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]^[2]^[3] 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.^[4]

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

Inhibition of lipid metabolism reduces/removes lipid droplets from HuH7 cells.^[5] In hepatitis C–infected HuH7 cells, this reduction/removal of lipid droplets by triacsin C correlates with a reduction in virion assembly and infectivity.^[6]

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, et al. (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.
^ Tomoda H, Igarashi K, Omura S (1987). "Inhibition of acyl-CoA synthetase by triacsins". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 921 (3): 595–598. doi:10.1016/0005-2760(87)90088-9. PMID 3117118.
^ Tomoda H, Igarashi K, Chong JC, Ōmura S (1991). "Evidence for an Essential Role of Long Chain Acyl-CoA Synthetase in Animal Cell Proliferation". The Journal of Biological Chemistry. 266 (7): 4214–4219. doi:10.1016/S0021-9258(20)64309-5. PMID 1999415.
^ 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) (Pt 2): 529–34. doi:10.1042/bj3240529. PMC 1218462. PMID 9182714.
^ Fujimoto Y, Itabe H, Kinoshita T, Homma KJ, Onoduka J, More M, et al. (2007). "Involvement of ACSL in local synthesis of neutral lipids in cytoplasmic lipid droplets in human hepatocyte HuH7". Journal of Lipid Research. 48 (6): 1280–1292. doi:10.1194/jlr.M700050-JLR200. PMID 17379924.
^ Liefhebber JM, Hague CV, Zhang Q, Wakelam MJ, McLauchlan J (2014). "Modulation of Triglyceride and Cholesterol Ester Synthesis Impairs Assembly of Infectious Hepatitis C Virus". The Journal of Biological Chemistry. 289 (31): 21276–21288. doi:10.1074/jbc.M114.582999. PMC 4118089. PMID 24917668.

[Yoshida-1] Yoshida K, Okamoto M, Umehara K, Iwami M, Kohsaka M, Aoki H, et al. (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.

[2] Tomoda H, Igarashi K, Omura S (1987). "Inhibition of acyl-CoA synthetase by triacsins". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 921 (3): 595–598. doi:10.1016/0005-2760(87)90088-9. PMID 3117118.

[3] Tomoda H, Igarashi K, Chong JC, Ōmura S (1991). "Evidence for an Essential Role of Long Chain Acyl-CoA Synthetase in Animal Cell Proliferation". The Journal of Biological Chemistry. 266 (7): 4214–4219. doi:10.1016/S0021-9258(20)64309-5. PMID 1999415.

[pmid9182714-4] 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) (Pt 2): 529–34. doi:10.1042/bj3240529. PMC 1218462. PMID 9182714.

[5] Fujimoto Y, Itabe H, Kinoshita T, Homma KJ, Onoduka J, More M, et al. (2007). "Involvement of ACSL in local synthesis of neutral lipids in cytoplasmic lipid droplets in human hepatocyte HuH7". Journal of Lipid Research. 48 (6): 1280–1292. doi:10.1194/jlr.M700050-JLR200. PMID 17379924.

[6] Liefhebber JM, Hague CV, Zhang Q, Wakelam MJ, McLauchlan J (2014). "Modulation of Triglyceride and Cholesterol Ester Synthesis Impairs Assembly of Infectious Hepatitis C Virus". The Journal of Biological Chemistry. 289 (31): 21276–21288. doi:10.1074/jbc.M114.582999. PMC 4118089. PMID 24917668.

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[2]

[3]

[4]

[5]

[6]

General chemical description

See also

References