IUPAC Name: (2R,3S)-3-[(4E,7E)-Nona-4,7-dienoyl]oxirane-2-carboxamide
||Cerulenin: an antifungal antibiotic, fatty acids and sterols biosynthesis inhibitor.|
|Canonical SMILES: ||
|Cerulenin is soluble in DMSO, Methanol, Ethanol, Dichloromethane, Acetone, Benzene and most common solvents. Concentrations up to 20 mg/ml can be achieved. Slightly soluble in H2O. Concentrations up to 0.2 mg/ml are achievable.|
Not soluble in Petrol Ether.
Attention: Cerulenin is unstable in aqueous solutions, and very unstable in basic solutions
||Off white powder|
||At least 98% by TLC |
|Melting point||86°C-94 °C|
||Clear colorless solution at 5 mg/ml of Dichloromethane|
||+4°C. Protect from light.|
||Cerulenin was originally proposed as
antifungal antibiotic. |
Cerulenin is used as a biochemical tool.
has been shown to cause dramatic weight loss in animals.
Cerulenin blocks synthesis of fatty acids and sterols by
binding to the enzyme fatty-acid-synthase. In some tumor
lines, this triggers apoptosis., an effect believed to be
mediated by the accumulation of malonyl-coenzyme A in cells
with an upregulated FAS pathway.
||TOXIC. POTENTIAL CARCINOGEN|
||Fatty acid antibiotic.|
||For Research use only. Not for Human or Drug use|
GMP/API grade available on request
No genetically modified organisms are used.
Wang WQ, Zhao XY, Gong XB, Zhang XH. |
apoptosis related genes expression in multiple myeloma cell
Zhonghua Xue Ye Xue Za Zhi. 2007 Apr;28(4):239-42.
Bajsa J, Singh K, Nanayakkara D, Duke SO, Rimando AM,
Evidente A, Tekwani BL. |
survey of synthetic and natural phytotoxic compounds and
phytoalexins as potential antimalarial compounds.
Biol Pharm Bull. 2007 Sep;30(9):1740-4.
||Jin YJ, Li SZ, Zhao ZS, An JJ, Kim RY, Kim YM, Baik JH, Lim SK.|
Carnitine palmitoyltransferase-1 (CPT-1) activity stimulation by cerulenin via sympathetic nervous system activation overrides cerulenin's peripheral effect.
Endocrinology. 2004 Jul;145(7):3197-204
||Straub SG, Sharp GW.|
Inhibition of insulin secretion by cerulenin might be due to impaired glucose metabolism.
Diabetes Metab Res Rev. 2006 May 16
||Liu X, Shi Y, Giranda VL, Luo Y.|
Inhibition of the phosphatidylinositol 3-kinase/Akt pathway sensitizes MDA-MB468 human breast cancer cells to cerulenin-induced apoptosis.
Mol Cancer Ther. 2006 Mar;5(3):494-501
||Dridi S, Ververken C, Hillgartner FB, Lutgarde A, Van der Gucht E, Cnops L, Decuypere E, Buyse J.|
FAS inhibitor cerulenin reduces food intake and melanocortin receptor gene expression without modulating the other (an)orexigenic neuropeptides in chickens.
Am J Physiol Regul Integr Comp Physiol. 2006 Jul;291(1):R138-47