Cerulenin

• CAT Number: M084800
• CAS Number: 17397-89-6
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.3
• Purity: ≥95%
• Target: FAS
• Solubility: Soluble in DMSO
• Storage: Store at -20°C
• IUPAC Name: (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
• InChI: InChI=1S/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+/t10-,11-/m1/s1
• InChIKey: GVEZIHKRYBHEFX-NQQPLRFYSA-N
• SMILES: CC=CCC=CCCC(=O)C1C(O1)C(=O)N

Cerulenin(cas 17397-89-6) is an antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. In fatty acid synthesis, it has been reported to bind in equimolar ratio to b-keto-acyl-ACP synthase, blocking the interaction of malonyl-CoA. In sterol synthesis, cerulenin inhibits HMG-CoA synthetase activity. Inhibition of FAS by the irreversible inhibitor cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway.

Reference

1:De novo genome assembly and annotation of rice sheath rot fungus Sarocladium oryzae reveals genes involved in Helvolic acid and Cerulenin biosynthesis pathways. Hittalmani S, Mahesh HB, Mahadevaiah C, Prasannakumar MK.BMC Genomics. 2016 Mar 31;17:271. doi: 10.1186/s12864-016-2599-0. PMID: 27036298 Free PMC Article
2:Dephosphorylation and mitochondrial translocation of cofilin sensitizes human leukemia cells to cerulenin-induced apoptosis via the ROCK1/Akt/JNK signaling pathway. Zhang Y, Fu R, Liu Y, Li J, Zhang H, Hu X, Chen Y, Liu X, Li Y, Li P, Liu E, Gao N.Oncotarget. 2016 Apr 12;7(15):20655-68. doi: 10.18632/oncotarget.7994. PMID: 26967395 Free PMC Article
3:Effect of cerulenin on fatty acid composition and gene expression pattern of DHA-producing strain Colwellia psychrerythraea strain 34H. Wan X, Peng YF, Zhou XR, Gong YM, Huang FH, Moncalián G.Microb Cell Fact. 2016 Feb 6;15:30. doi: 10.1186/s12934-016-0431-9. PMID: 26852325 Free PMC Article
4:Isolation of a spontaneous cerulenin-resistant sake yeast with both high ethyl caproate-producing ability and normal checkpoint integrity. Tamura H, Okada H, Kume K, Koyano T, Goshima T, Nakamura R, Akao T, Shimoi H, Mizunuma M, Ohya Y, Hirata D.Biosci Biotechnol Biochem. 2015;79(7):1191-9. doi: 10.1080/09168451.2015.1020756. Epub 2015 Mar 19. PMID: 25787154
5:Clickable analogue of cerulenin as chemical probe to explore protein palmitoylation. Zheng B, Zhu S, Wu X.ACS Chem Biol. 2015 Jan 16;10(1):115-21. doi: 10.1021/cb500758s. Epub 2014 Oct 23. PMID: 25322207
6:Structural insights into bacterial resistance to cerulenin. Trajtenberg F, Altabe S, Larrieux N, Ficarra F, de Mendoza D, Buschiazzo A, Schujman GE.FEBS J. 2014 May;281(10):2324-38. doi: 10.1111/febs.12785. Epub 2014 Apr 9. PMID: 24641521 Free Article
7:Cerulenin inhibits unsaturated fatty acids synthesis in Bacillus subtilis by modifying the input signal of DesK thermosensor. Porrini L, Cybulski LE, Altabe SG, Mansilla MC, de Mendoza D.Microbiologyopen. 2014 Apr;3(2):213-24. doi: 10.1002/mbo3.154. Epub 2014 Feb 14. PMID: 24574048 Free PMC Article
8:Cerulenin blockade of fatty acid synthase reverses hepatic steatosis in ob/ob mice. Cheng G, Palanisamy AP, Evans ZP, Sutter AG, Jin L, Singh I, May H, Schmidt MG, Chavin KD.PLoS One. 2013 Sep 27;8(9):e75980. doi: 10.1371/journal.pone.0075980. eCollection 2013. PMID: 24086674 Free PMC Article
9:Cerulenin upregulates heat shock protein-70 gene expression in chicken muscle. Dridi S, Decuypere E, Buyse J.Poult Sci. 2013 Oct;92(10):2745-53. doi: 10.3382/ps.2013-03242. PMID: 24046423
10:Enhanced antitumor activity of cerulenin combined with oxaliplatin in human colon cancer cells. Shiragami R, Murata S, Kosugi C, Tezuka T, Yamazaki M, Hirano A, Yoshimura Y, Suzuki M, Shuto K, Koda K.Int J Oncol. 2013 Aug;43(2):431-8. doi: 10.3892/ijo.2013.1978. Epub 2013 Jun 7. PMID: 23754252