Cerulenin (synthetic) An antibiotic fatty acid synthase (FAS) inhibitor

Cerulenin (synthetic) (CAS 17397-89-6)

Cerulenin (synthetic) | CAS 17397-89-6 is rated 5.0 out of 5 by 1.
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Synonym: 2,3-Epoxy-4-oxo-7,10-dodecadienamide
Application: An antibiotic fatty acid synthase (FAS) inhibitor
CAS Number: 17397-89-6
Purity: ≥98%
Molecular Weight: 223.27
Molecular Formula: C12H17NO3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Cerulenin is an antibiotic and antifungal agent originally isolated from Cephalosporium caerulens. This product is synthetically derived. The compound acts as a potent and specific Fatty Acid Synthase (FAS) inhibitor and has been shown to block the synthesis of stearoyl-CoA and eicosanoyl-CoA fatty acids in microsomes. Cerulenin binds covalently to the active center cysteine of the condensing enzyme domain and inhibits the FAS. Leptin and Cerulenin have both been reported to affect the rate of metabolism in mice independent of the melanocortin system, with the difference being that cerulenin does not inhibit the neuroendocrine effects of fasting in mice. Mitochondrial investigations indicate that cerulenin induces apoptosis in a caspase-dependent manner in A-375 cells.


References

1. Schneider, F., et al. 1993. Biochim. Biophys. Acta. 1152: 243-252. PMID: 8218325
2. Inokoshi, J., et al. 1994. Mol. Gen. Genet. 244: 90-96. PMID: 8041367
3. Makimura, H., et al. 2001. Diabetes. 50: 733-739. PMID: 11289036
4. Heiligtag, S.J., et al. 2002. Cell Death Differ. 9: 1017-1025. PMID: 12181752
5. Ho, T.S., et al. 2007. Biomed. Pharmacother. 61: 578-587. PMID: 17904792
6. Murata, S., et al. 2010. Cancer Sci. 101: 1861-1865. PMID: 20491775

Physical State :
Solid
Solubility :
Soluble in ethanol (~20 mg/ml), benzene, 1:6 DMF:PBS (~0.2 mg/ml), DMSO (~25 mg/ml), DMF (~30 mg/ml), dichloromethane (5 mg/ml), and acetone.
Storage :
Store at -20° C
Melting Point :
93° C
Boiling Point :
~456.1° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.53
IC50 :
β-keto-acyl-ACP synthase: IC50 = 1.5 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
JR1670000
PubChem CID :
5352018
Merck Index :
14: 2004
MDL Number :
MFCD00077686
EC Number :
241-424-8
Beilstein Registry :
4140423
SMILES :
C/C=C/C/C=C/CCC(=O)C1C(O1)C(=O)N

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Certificate of Analysis

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Cerulenin (synthetic)  Product Citations

See how others have used Cerulenin (synthetic). Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 28775317  Sun, W. et al. 2017. Sci Rep. 7: 7190.

PMID: # 25815810  Ayllón, N. et al. 2015. PLoS Genet. 11: e1005120.

PMID: # 22365411  Kim, Y. et al. 2012. Eur J Med Chem. 50: 311-8.

Citations 1 to 3 of 3 total

Do you recommend storing in solution form?

Asked by: chemicalsmg
Thank you for your question. We do not recommend storing the aqueous solution for more than one day. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-12
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Rated 5 out of 5 by from Bauerschlag Bauerschlag, DO. Et al. (PubMed 25947066) investigated fatty acid synthase (FASN) overexpression as a therapeutic and chemosensitization target in cancer tissue, cell lines, and primary cell cultures. In most cell lines showing overexpression of FASN, the FASN inhibitor Cerulenin markedly decreased FASN expression, cell viability, and induced apoptosis. -SCBT Publication Review
Date published: 2015-07-15
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