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AdipoGen Life Sciences
Cerulenin
180
CHF
CHF 180.00
In stock
AG-CN2-0513-M0055 mgCHF 180.00
| Product Details | |
|---|---|
| Synonyms | 2R,3S-Epoxy-4-oxo-7,10-dodecadienamide; Helicocerin |
| Product Type | Chemical |
| Properties | |
| Formula |
C12H17NO3 |
| MW | 223.3 |
| CAS | 17397-89-6 |
| RTECS | JR1670000 |
| Source/Host Chemicals | Isolated from Cephalosporium caerulens. |
| Purity Chemicals | ≥98% |
| Appearance | White to off-white solid. |
| Solubility | Soluble in DMSO (25mg/ml), ethanol (20mg/ml) or DMF (25mg/ml). |
| Other Product Data |
Stock Solution: Prior to performing biological experiments the stock solution should be further diluted into water or other aqueous buffers to ensure that the residual amount of DMSO/ethanol is insignificant, since DMSO and ethanol may have physiological effects at high concentrations. |
| InChi Key | GVEZIHKRYBHEFX-NQQPLRFYSA-N |
| Smiles | O=C(CC/C=C/C/C=C/C)[C@@H]1[C@H](C(N)=O)O1 |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice |
Keep cool and dry. Protect from light. Protect from moisture and oxygen. |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Antibiotic and antifungal compound. Inhibitor of bacterial fatty acid synthesis (inhibits FabH, FabB and FabF condensation enzymes).
- Irreversible fatty acid synthase (FASN) inhibitor. Inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, reported to bind in equimolar ratio to β-keto-acyl-ACP synthase, thus inhibiting protein acylation. In sterol synthesis, inhibits HMG-CoA synthetase activity.
- Palmitoylation (a post-translational lipidation) inhibitor.
- Anticancer agent. Apoptosis inducer in tumor cell lines, with upregulated expression and activity of fatty acid synthase (FAS). Shown to induce apoptosis via disruption of the interaction between AIF and Hexokinase II (HKII).
- Necroptosis inhibitor by blocking very long-chain fatty acids (VLCFA) synthesis and accumulation, which is important in the process of necroptosis (RIP1-dependent cell death).
- Also leads to profound weight loss and feeding inhibition in both high-fat diet wild type obese and leptin-deficient ob/ob mice.
Product References
- Studies on cerulenin, 3. Isolation and physico-chemical properties of cerulenin: Y. Sato, et al.; J. Antibiot. (Tokyo) 200, 344 (1967)
- Inhibition of fatty acid synthetases by the antibiotic cerulenin: D. Vance, et al.; Biochem. Biophys. Res. Commun. 48, 649 (1972)
- The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis: S. Omura; Bacteriol. Rev. 40, 681 (1976) (Review)
- Cerulenin is a potent inhibitor of antigen processing by antigen-presenting cells: L.D. Falo, et al.; J. Immunol. 139, 3918 (1987)
- Modulation of insulin secretion from normal rat islets by inhibitors of the post-translational modifications of GTP-binding proteins: S.A. Metz, et al.; Biochem. J. 295, 31 (1993)
- Inhibitory effects of cerulenin on protein palmitoylation and insulin internalization in rat adipocytes: A.L. Jochen, et al.; Biochim. Biophys. Acta 1259, 65 (1995)
- Reduced food intake and body weight in mice treated with fatty acid synthase inhibitors: T.M. Loftus, et al.; Science 288, 2379 (2000)
- Cerulenin, an inhibitor of protein acylation, selectively attenuates nutrient stimulation of insulin release: a study in rat pancreatic islets: H. Yajima, et al.; Diabetes 49, 712 (2000)
- Cerulenin mimics effects of leptin on metabolic rate, food intake, and body weight independent of the melanocortin system, but unlike leptin, cerulenin fails to block neuroendocrine effects of fasting: H. Makimura, et al.; Diabetes 50, 733 (2001)
- Key role of mitochondria in cerulenin-mediated apoptosis: S.J. Heiligtag, et al.; Cell Death Differ. 9, 1017 (2002)
- Fatty acid synthase inhibitors cerulenin and C75 retard growth and induce caspase-dependent apoptosis in human melanoma A-375 cells: T.S. Ho, et al.; Biomed. Pharmacother. 61, 578 (2007)
- Fatty acid synthase inhibitor cerulenin suppresses liver metastasis of colon cancer in mice: S. Murata, et al.; Cancer Sci. 101, 1861 (2010)
- Cerulenin-induced apoptosis is mediated by disrupting the interaction between AIF and hexokinase II: N.Y. Jeong & Y.H. Yoo; Int. J. Oncol. 40, 1949 (2012)
- Very long chain fatty acids are functionally involved in necroptosis: L.R. Parisi, et al.; Cell Chem. Biol. 24, 1445 (2017)