| Source: |
Cephalosporium caerulens |
| Synonyms |
Cerulenin
Helicocerin
2,3-Epoxy-4-oxo-10-dodecadienamide
IUPAC Name: (2R,3S)-3-[(4E,7E)-Nona-4,7-dienoyl]oxirane-2-carboxamide
Systematic name:
(2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxiranecarboxamide
EINECS: 241-424-8 |
| Description: |
Cerulenin: an antifungal antibiotic, fatty acids and sterols biosynthesis inhibitor. |
| CAS number: |
17397-89-6 |
| Merck index: |
12, 2047 |
| Molecular weight: |
223.27 |
| Structure: |
 |
| Molecular Formula: |
C12H17NO3 |
| Canonical SMILES: |
CC=CCC=CCCC(=O)C1C(O1)C(=O)N |
Solubility
information: |
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 |
| Specifications |
|
| Appearance: |
Off white powder |
| Purity: |
At least 98% by TLC |
λmax: |
|
| Melting point | 86°C-94 °C |
| Solubility |
Clear colorless solution at 5 mg/ml of Dichloromethane |
| Storage |
+4°C. Protect from light. |
| Applications |
Cerulenin was originally proposed as
antifungal antibiotic.
Cerulenin is used as a biochemical tool.
Cerulenin
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. |
| Warnings |
TOXIC. POTENTIAL CARCINOGEN |
| Classification |
Fatty acid antibiotic.
Apoptosis inducer
Antifungal antibiotic
Mycobacteria inhibitor |
| Related products |
|
| |
For Research use only. Not for Human or Drug use
GMP/API grade available on request
No genetically modified organisms are used. |
| Publications |
Wang WQ, Zhao XY, Gong XB, Zhang XH.
Cerulenin changes
apoptosis related genes expression in multiple myeloma cell
line U266
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.
A
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 |
