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T4540

Sigma-Aldrich

Triacsin C from Streptomyces sp.

Synonyme(s) :

2,4,7-Undecatrienal nitrosohydrazone, WS1228A

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About This Item

Formule empirique (notation de Hill) :
C11H17N3O
Numéro CAS:
76896-80-5
Poids moléculaire :
207.27
Numéro MDL:
MFCD00798237
Code UNSPSC :
51111800
ID de substance PubChem :
24900214
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces sp.

Niveau de qualité

200

Forme

powder

Solubilité

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

Mode d’action

enzyme | inhibits

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne 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+

Clé InChI

NKTGCVUIESDXPU-YLEPRARLSA-N

Description générale

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.

Application

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.

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
099M4007V
018M4138V
14180111
096M4013V
015M4029V

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Consulter la Bibliothèque de documents

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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