T4540
Triacsin C
From Streptomyces sp., long-chain fatty acyl CoA synthetase inhibitor, powder
Synonyme(s) :
2,4,7-Undecatrienal nitrosohydrazone, WS1228A
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A propos de cet article
Formule empirique (notation de Hill) :
C11H17N3O
Numéro CAS:
Poids moléculaire :
207.27
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Form:
powder
Quality level:
Service technique
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Laissez-nous vous aiderNom du produit
Triacsin C from Streptomyces sp.,
biological source
Streptomyces sp.
Quality Level
form
powder
solubility
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 of action
enzyme | inhibits
shipped in
wet ice
storage temp.
−20°C
SMILES string
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+
InChI key
NKTGCVUIESDXPU-YLEPRARLSA-N
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.
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.
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.
Preparation Note
Triacsin C is soluble in methanol at 4.90 - 5.10 mg/ml and yields a clear, pale yellow to yellow solution.
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
M Shimabukuro et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(16), 9558-9561 (1998-08-05)
Obesity causes its complications through functional and morphologic damage to remotely situated tissues via undetermined mechanisms. In one rodent model of obesity, the Zucker diabetic fatty fa/fa rat, overaccumulation of triglycerides in the pancreatic islets may be responsible for a
R A Igal et al.
The Biochemical journal, 324 ( Pt 2), 529-534 (1997-06-01)
The trafficking of acyl-CoAs within cells is poorly understood. In order to determine whether newly synthesized acyl-CoAs are equally available for the synthesis of all glycerolipids and cholesterol esters, we incubated human fibroblasts with [14C]oleate, [3H]arachidonate or [3H]glycerol in the