TRIACSIN C

TRIACSIN C Property

Boiling point:

320.7±45.0 °C(Predicted)

Density 

0.94±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

methanol: soluble4.90 - 5.10 mg/mL, clear (Pale yellow to yellow)

form 

Liquid. In DMSO.

pka

-0.10±0.70(Predicted)

color 

clear (Pale yellow to yellow) Solution in DMSO

biological source

Streptomyces sp.

Stability:

Stable for 1 year from date of purchase as supplied. Solutions further diluted with DMSO may be stored at -20° for up to 2 months.

Safety

WGK Germany 

3

HS Code 

29299090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

TRIACSIN C Chemical Properties,Usage,Production

Description

Triacsin C (76896-80-5) is a long-chain fatty acyl CoA synthetase inhibitor (IC50=3.6-8.7 μM).1?Inhibits mouse macrophage-derived foam cell formation2 and displays anti-atherosclerotic activity3. Cell permeable.

Chemical Properties

Solid

Uses

Triacsin, a fatty acyl CoA synthetase inhibitor, reduces myocardial infarct size, attenuates loss of post-reperfusion cardiac function, increases intravascular nitric oxide (NO) concentration, and inhibits leukocyte recruitment. Triacsin C analogs can also be used as potential antivirals against rotavirus infections.

Definition

ChEBI: Triacsin C is a nitroso compound that is N-undecylnitrous hydrazide carrying double bonds at positions 1,2,4, and 7. It is a long-chain fatty acyl CoA synthetase inhibitor and interferes with lipid metabolism by inhibiting the de novo synthesis of glycerolipids and cholesterol esters. It has a role as an EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor, a vasodilator agent, an apoptosis inhibitor, a bacterial metabolite, an EC 3.1.1.64 (retinoid isomerohydrolase) inhibitor and an antimalarial. It is a nitroso compound, an olefinic compound and a hydrazone.

General 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.

Biochem/physiol Actions

Triacsin C is a potent inhibitor of long-chain 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.

storage

Store at -20°C

References

[1] E.J. HARTMAN  M. L  S Omura ∗. Triacsin C: A differential inhibitor of arachidonoyl-CoA synthetase and nospecific long chain acyl-CoA synthetase,[J]. Prostaglandins, 1989, 37 6: Pages 655-671. DOI:10.1016/0090-6980(89)90103-2
[2] I NAMATAME. Complete inhibition of mouse macrophage-derived foam cell formation by triacsin C.[J]. Journal of biochemistry, 1999, 125 2: 319-327. DOI:10.1093/oxfordjournals.jbchem.a022289
[3] DAISUKE MATSUDA. Anti-atherosclerotic Activity of Triacsin C, an Acyl-CoA Synthetase Inhibitor[J]. Journal of Antibiotics, 2008, 61 5: 318-321. DOI:10.1038/ja.2008.45