17397-89-6 Usage
Description
Cerulenin is a fungal metabolite originally isolated from Cephalosporium caerulens that has diverse biological activities. It is an epoxy fatty acid amide with antifungal properties and has found broad application in lipid biochemistry as an inhibitor of fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase, blocking the interaction of malonyl CoA, and also inhibits bacterial fatty acid synthesis by acting on the FabH, FabB, and FabF condensation enzymes. Additionally, it stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity.
Uses
Used in Antifungal Applications:
Cerulenin is used as an antifungal antibiotic for inhibiting sterol and fatty acid biosynthesis. It is effective against a variety of fungi, including strains of Candida albicans, Trichophyton rubrum, and Aspergillus fumigatus.
Used in Bacterial Inhibition:
Cerulenin is used as a bacterial inhibitor, active against a variety of bacteria such as Bacillus subtilis, Escherichia coli, Bacillus megaterium, and Bacillus anthracis. It inhibits bacterial fatty acid synthesis by acting on the FabH, FabB, and FabF condensation enzymes.
Used in Cancer Research:
Cerulenin is used as a biochemical tool for studying the metabolism and function of fatty acids in human cancer cell lines, including breast, ovarian, and endometrial cancer cells. It has been shown to reduce tumor growth in an OVCAR-3 mouse xenograft model.
Used in Lipid Biochemistry Research:
Cerulenin is used as an inhibitor of fatty acid synthase type I (FAS-I) and FAS-II in lipid biochemistry research. It provides valuable insights into the mechanisms of fatty acid and sterol biosynthesis.
Used in Drug Development:
Cerulenin can be a useful biochemical tool for the development of new drugs targeting fatty acid and sterol biosynthesis pathways, with potential applications in the treatment of various diseases, including cancer and fungal infections.
Chemical Properties:
Cerulenin is a white powder with diverse biological activities and is classified as an epoxydodecadienamide.
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
Check Digit Verification of cas no
The CAS Registry Mumber 17397-89-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,3,9 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 17397-89:
(7*1)+(6*7)+(5*3)+(4*9)+(3*7)+(2*8)+(1*9)=146
146 % 10 = 6
So 17397-89-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+
17397-89-6Relevant articles and documents
A concise synthesis of (+)-cerulenin from a chiral oxiranyllithium
Mani, Neelakandha S.,Townsend, Craig A.
, p. 636 - 640 (1997)
(+)-Cerulenin, a potent fungal inactivator of fatty acid synthases, has been prepared in optically pure form by a sequence involving reaction of a chiral oxiranyllithium with (4E,7E)-nonadienal. Synthesis of the former takes advantage of a particularly favorable Sharpless epoxidation and metalation to a configurationally stable organolithium, while the latter is available in quantity by a direct and improved route.
Synthesis of 4-alkyl-4-alkoxybutenolides having unsaturated side chains via chromium carbene complex photochemistry: (+)-cerulenin
Kedar, Tracey E.,Miller, Michael W.,Hegedus, Louis S.
, p. 6121 - 6126 (2007/10/03)
The photochemical reaction between optically active ene carbamates and chromium alkoxycarbene complexes containing unsaturated aliphatic side chains was further developed. Although remote olefinic groups, including conjugated dienes, were tolerated, a homoallylic side chain underwent intramolecular reaction to give a strained cyclobutanone. (+)-Cerulenin was synthesized utilizing the photochemical reaction of an alkynylcarbene complex with an optically active ene carbamate and the bis(π-crotyl)nickel halide alkylation of a vinyl bromide as key steps.
A novel stereoselective synthesis of (+)-cerulenin and (+)-tetrahydrocerulenin
Yoda,Katagiri,Takabe
, p. 6771 - 6774 (2007/10/02)
An antibiotic natural (+)-cerulenin and (+)-tetrahydrocerulenin have been synthesized, based on successive alkylation and reduction of chiral cyclic imide with C2-symmetry derived from D-tartaric acid.
