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T4540

Sigma-Aldrich

Triacsin C from Streptomyces sp.

Sinónimos:

2,4,7-Undecatrienal nitrosohydrazone, WS1228A

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About This Item

Fórmula empírica (notación de Hill):
C11H17N3O
Número de CAS:
76896-80-5
Peso molecular:
207.27
Número MDL:
MFCD00798237
Código UNSPSC:
51111800
ID de la sustancia en PubChem:
24900214
NACRES:
NA.77

origen biológico

Streptomyces sp.

Nivel de calidad

200

formulario

powder

solubilidad

methanol: soluble 4.90-5.10 mg/mL, clear (Pale yellow to yellow)
methanol: soluble 4.90-5.10 mg/mL, clear, pale yellow to yellow

Modo de acción

enzyme | inhibits

Condiciones de envío

wet ice

temp. de almacenamiento

−20°C

cadena SMILES

CCC\C=C\C\C=C\C=C\C=N\NN=O

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+

Clave InChI

NKTGCVUIESDXPU-YLEPRARLSA-N

Descripción general

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.

Aplicación

Triacsin C was found to induce maturation in mouse and Xenopus oocytes in the absence of long-chain acyl-CoA synthetase. Triacsin C can also block palmitoylation of the G-protein alpha S subunit6. Furthermore, triacsin C can stabilize1-oleoyl-2-acetyl-sn-glycerol (OAG) and enhance perilipin 3 recruitment to the endoplasmic reticulum (ER) in mouse cells7.

Acciones bioquímicas o fisiológicas

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.

Nota de preparación

Triacsin C is soluble in methanol at 4.90 - 5.10 mg/ml and yields a clear, pale yellow to yellow solution.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Winsome Cheung et al.
Journal of virology, 84(13), 6782-6798 (2010-03-26)
Rotaviruses are a major cause of acute gastroenteritis in children worldwide. Early stages of rotavirus assembly in infected cells occur in viroplasms. Confocal microscopy demonstrated that viroplasms associate with lipids and proteins (perilipin A, ADRP) characteristic of lipid droplets (LDs).
Viswanathan Saraswathi et al.
Arteriosclerosis, thrombosis, and vascular biology, 29(11), 1937-1943 (2009-08-15)
Obesity is often associated with hypertriglyceridemia and elevated free fatty acids (FFAs), which are independent risk factors for cardiovascular disease and diabetes. Although impairment of cholesterol homeostasis is known to induce toxicity in macrophages, the consequence of altered fatty acid
Y-L Xie et al.
Theriogenology, 78(9), 1917-1928 (2012-10-13)
In vivo and in vitro approaches were used to elucidate mechanisms of palmitate-induced cytotoxicity of follicle granulosa cells in fuel-overloaded broiler hens. In contrast to their energy-restricted counterparts, broiler breeder hens fed ad libitum for 2 wk had dyslipidemia, atresia
H Tomoda et al.
The Journal of biological chemistry, 266(7), 4214-4219 (1991-03-05)
Triacsins A, B, C, and D are new inhibitors of long chain acyl-CoA synthetase (EC 6.2.1.3) and possess different inhibitory potencies against the enzyme (Tomoda, H., Igarashi, K., and Omura, S. (1987) Biochim. Biophys. Acta 921, 595-598). Acyl-CoA synthetase activity
Diane C Adler-Wailes et al.
Endocrinology, 151(5), 2097-2105 (2010-03-17)
Lipodystrophy with high nonesterified fatty acid (FA) efflux is reported in humans receiving highly active antiretroviral therapy (HAART) to treat HIV infection. Ritonavir, a common component of HAART, alters adipocyte FA efflux, but the mechanism for this effect is not
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