Triacsin C

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Triacsin C
Triacsin c.png
Names
IUPAC name
N-(((2E,4E,7E)-undeca-2,4,7-trienylidene)amino)nitrous amide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.127.901 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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+ Yes check.svgY
    Key: NKTGCVUIESDXPU-YLEPRARLSA-N Yes check.svgY
  • 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
  • O=NN/N=C/C=C/C=C/C/C=C/CCC
Properties
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).
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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 bacterial secondary metabolites all having an 11-carbon 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. [ citation needed ]

Triacsin C was discovered by a group led by Keizo Yoshida in 1982 from a culture of the actinobacteria now known as Kitasatospora aureofaciens . [1]

See also

References

  1. 1 2 3 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.
  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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