| Identification | Back Directory | [Name]
CERULENIN | [CAS]
17397-89-6 | [Synonyms]
Crl
Nsc116069
CERULENIN
Aids000236
Aids-000236
helicocerin
CERULENIN USP/EP/BP
Cerulenin (Synthetic)
2,3-epoxy-4-oxo-10-dodecadienamide
CERULENIN, CEPHALOSPORIUM CAERULENS
2,3-EPOXY-4-OXO-7,10-DODECADIENAMIDE
2R,3S-EPOXY-4-OXO-7,10-DODECADIENAMIDE
CERULENIN FROM CEPHALOSPORIUM CAERULENS
3-(1-oxo-4,7-nonadienyl)oxiranecarboxamide
(2r,3s)-2,3-epoxy-4-oxo-7e,10e-dodecadienamide
(2s)(3r)-2,3-epoxy-4-oxo-7,10-dodecadienoylamide
(2R,3S,E,E)-2,3-EPOXY-4-OXO-7,10-DODECADIENAMIDE
Cerulenin,(2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide
Helicocerin, NSC 116069, 2,3-Epoxy-4-oxo-7,10-dodecadienaMide
(2R,3S)-3-[(4E,7E)-1-Oxo-4,7-nonadien-1-yl]-2-oxiranecarboxamide
Cerulenin, Cephalosporium caerulens - CAS 17397-89-6 - Calbiochem
2-Oxiranecarboxamide,3-[(4E,7E)-1-oxo-4,7-nonadien-1-yl]-, (2R,3S)-
[2R-[2alpha,3alpha(4E,7E)]]-3-(1-oxonona-4,7-dienyl)oxirane-2-carboxamide
3-(1-oxo-4,7-nonadienyl)-,(2r-(2-alpha,3-alpha(4e,7e)))-oxiranecarboxamid
[2R-[2.alpha.,3.alpha.(4E,7E)]]-3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide
Cerulenin/ Helicocerin / (2R,3S)-3-[(4E,7E)-1-Oxo-4,7-nonadien-1-yl]-2-oxiranecarboxamide | [EINECS(EC#)]
241-424-8 | [Molecular Formula]
C12H17NO3 | [MDL Number]
MFCD00077686 | [MOL File]
17397-89-6.mol | [Molecular Weight]
223.27 |
| Chemical Properties | Back Directory | [Melting point ]
93.5℃ | [alpha ]
D16 +63° (c = 2 in methanol) | [Boiling point ]
bp 120° (10-8 mm) | [density ]
1.1223 (rough estimate) | [refractive index ]
1.5300 (estimate) | [storage temp. ]
−20°C
| [solubility ]
acetone: 20 mg/mL, clear, colorless to yellow
| [form ]
White to off-white solid | [pka]
15.19±0.40(Predicted) | [color ]
Off-white | [Merck ]
13,2014 | [BRN ]
4140423 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [Safety Statements ]
24/25 | [WGK Germany ]
3
| [RTECS ]
JR1670000
| [F ]
10-21 | [HS Code ]
29419090 | [Toxicity]
LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964) |
| Hazard Information | Back Directory | [Description]
Cerulenin is a fungal metabolite originally isolated from C. caerulens that has diverse biological activities.1,2,3 It is active against a variety of bacteria, including B. subtilis, E. coli, B. megaterium, and B. anthracis (MICs = 12.5, 12.5, 50, and 50 μg/ml, respectively) and fungi, including strains of C. albicans, T. rubrum, and A. fumigatus (MICs = 0.8-3.7, 3.1-6.2 and 12.5-50 μg/ml, respectively).1 Cerulenin is an inhibitor of fatty acid synthase type I (FAS-I) and FAS-II (IC50s = 3 and 20 μM, respectively, for the E. coli enzymes).2 It inhibits fatty acid synthesis in a panel of human cancer cell lines, including breast, ovarian, and endometrial cancer cells, as well as reduces tumor growth in a OVCAR-3 mouse xenograft model.3 | [Chemical Properties]
White powder | [Uses]
Cerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens and identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity. | [Uses]
Cerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity. | [Definition]
ChEBI: An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function. | [General Description]
An anti-fungal antibiotic that inhibits fatty acid biosynthesis by binding, in equimolar ratio, to β-keto-acyl-ACP synthase. Also inhibits sterol synthesis by blocking the activity of HMG-CoA synthetase activity. Systemic and intracerebroventricular of this compound reduces feeding and induces weight loss. | [Biochem/physiol Actions]
Primary Targetsterol & fatty acid biosynthesis | [Purification Methods]
It forms white needles from *C6H6. It has also been purified by repeated chromatography through Florisil and silica gel. It is soluble in EtOH, MeOH, *C6H6, slightly soluble in H2O and pet ether. The dl-form has m 40-42o (from *C6H6/hexane), and the 2R,3S-tetrahydrocerulenin has m 86-87o, [] 20 +44.4 (c 0.25, MeOH after 24hours). [Ohrui & Emato Tetrahedron Lett 2095 1978, Sneda et al. Tetrahedron Lett 2039 1979, Broeckman & Thomas J Am Chem Soc 99 2805 1977, Jakubowski et al. J Org Chem 47 1221 1982, Beilstein 18/2 V 201.] | [References]
1) Yasuno et al. (2004), Identification and molecular characterization of the beta-ketoacyl-[acyl carrier protein] synthase component of the Arabidopsis mitochondrial fatty acid synthase; J. Biol. Chem., 279 8242
2) Makimura et al. (2001), 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; Diabetes, 50 733
3) Metz et al. (1993), Modulation of insulin secretion from normal rat islets by inhibitors of the post-translational modifications of GTP-binding proteins; Biochem. J., 295 31
4) Ho et al. (2007), Fatty acid synthase inhibitors cerulenin and C75 retard growth and induce caspase-dependent apoptosis in human melanoma A-375 cells; Biomed. Pharmacother., 61 578 |
|
| Company Name: |
T&W GROUP
|
| Tel: |
021-61551611 13296011611 |
| Website: |
www.trustwe.com/ |
|