Cerulenin
Cerulenin 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.
1: Tamura H, Okada H, Kume K, Koyano T, Goshima T, Nakamura R, Akao T, Shimoi H, Mizunuma M, Ohya Y, Hirata D. Isolation of a spontaneous cerulenin-resistant sake yeast with both high ethyl caproate-producing ability and normal checkpoint integrity. Biosci Biotechnol Biochem. 2015;79(7):1191-9. doi: 10.1080/09168451.2015.1020756. Epub 2015 Mar 19. PubMed PMID: 25787154.
2: Zheng B, Zhu S, Wu X. Clickable analogue of cerulenin as chemical probe to explore protein palmitoylation. ACS Chem Biol. 2015 Jan 16;10(1):115-21. doi: 10.1021/cb500758s. Epub 2014 Oct 23. PubMed PMID: 25322207.
3: Trajtenberg F, Altabe S, Larrieux N, Ficarra F, de Mendoza D, Buschiazzo A, Schujman GE. Structural insights into bacterial resistance to cerulenin. FEBS J. 2014 May;281(10):2324-38. doi: 10.1111/febs.12785. Epub 2014 Apr 9. PubMed PMID: 24641521.
4: Porrini L, Cybulski LE, Altabe SG, Mansilla MC, de Mendoza D. Cerulenin inhibits unsaturated fatty acids synthesis in Bacillus subtilis by modifying the input signal of DesK thermosensor. Microbiologyopen. 2014 Apr;3(2):213-24. doi: 10.1002/mbo3.154. Epub 2014 Feb 14. PubMed PMID: 24574048; PubMed Central PMCID: PMC3996569.
5: Cheng G, Palanisamy AP, Evans ZP, Sutter AG, Jin L, Singh I, May H, Schmidt MG, Chavin KD. Cerulenin blockade of fatty acid synthase reverses hepatic steatosis in ob/ob mice. PLoS One. 2013 Sep 27;8(9):e75980. doi: 10.1371/journal.pone.0075980. eCollection 2013. PubMed PMID: 24086674; PubMed Central PMCID: PMC3785413.
6: Dridi S, Decuypere E, Buyse J. Cerulenin upregulates heat shock protein-70 gene expression in chicken muscle. Poult Sci. 2013 Oct;92(10):2745-53. doi: 10.3382/ps.2013-03242. PubMed PMID: 24046423.
7: Shiragami R, Murata S, Kosugi C, Tezuka T, Yamazaki M, Hirano A, Yoshimura Y, Suzuki M, Shuto K, Koda K. Enhanced antitumor activity of cerulenin combined with oxaliplatin in human colon cancer cells. Int J Oncol. 2013 Aug;43(2):431-8. doi: 10.3892/ijo.2013.1978. Epub 2013 Jun 7. PubMed PMID: 23754252.
8: Tapia V E, Anschau A, Coradini AL, T Franco T, Deckmann AC. Optimization of lipid production by the oleaginous yeast Lipomyces starkeyi by random mutagenesis coupled to cerulenin screening. AMB Express. 2012 Dec 5;2(1):64. doi: 10.1186/2191-0855-2-64. PubMed PMID: 23217098; PubMed Central PMCID: PMC3607992.
9: Banaś W, Furmanek T, Banaś A. Effect of haloxyfop and cerulenin on de novo biosynthesis of lipids in roots of wheat and maize. Acta Biochim Pol. 2012;59(4):567-73. Epub 2012 Nov 27. PubMed PMID: 23189275.
10: Jeong NY, Lee JS, Yoo KS, Oh S, Choe E, Lee HJ, Park BS, Choi YH, Yoo YH. Fatty acid synthase inhibitor cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Apoptosis. 2013 Feb;18(2):226-37. doi: 10.1007/s10495-012-0776-4. PubMed PMID: 23108760.
11: Nguyen LN, Nosanchuk JD. The inhibitory effect of cerulenin to yeasts is fungicidal. Commun Integr Biol. 2011 Nov 1;4(6):631-2. PubMed PMID: 22448300; PubMed Central PMCID: PMC3306321.
12: Jeong NY, Yoo YH. Cerulenin-induced apoptosis is mediated by disrupting the interaction between AIF and hexokinase II. Int J Oncol. 2012 Jun;40(6):1949-56. doi: 10.3892/ijo.2012.1401. Epub 2012 Mar 15. PubMed PMID: 22426850.
13: Liu ZL, Wang G, Shu Y, Zou PA, Zhou Y, Yin QS. Enhanced antitumor activity of epirubicin combined with cerulenin in osteosarcoma. Mol Med Rep. 2012 Feb;5(2):326-30. doi: 10.3892/mmr.2011.661. Epub 2011 Nov 2. PubMed PMID: 22052253.
14: Mao L, Inoue K, Tao Y, Montelione GT, McDermott AE, Inouye M. Suppression of phospholipid biosynthesis by cerulenin in the condensed Single-Protein-Production (cSPP) system. J Biomol NMR. 2011 Feb;49(2):131-7. doi: 10.1007/s10858-011-9469-5. Epub 2011 Jan 30. PubMed PMID: 21279668; PubMed Central PMCID: PMC3164850.
15: Murata S, Yanagisawa K, Fukunaga K, Oda T, Kobayashi A, Sasaki R, Ohkohchi N. Fatty acid synthase inhibitor cerulenin suppresses liver metastasis of colon cancer in mice. Cancer Sci. 2010 Aug;101(8):1861-5. doi: 10.1111/j.1349-7006.2010.01596.x. Epub 2010 Apr 21. PubMed PMID: 20491775.
16: Fu DH, Liu ZL, Liu JS, Luo Y, Shu Y, Huang SH, Han ZM. Transepithelial transport of Cerulenin across Caco-2 cell monolayers. Eur J Drug Metab Pharmacokinet. 2009 Apr-Jun;34(2):67-72. PubMed PMID: 19645214.
17: Diwischek F, Morschhäuser J, Holzgrabe U. Cerulenin analogues as inhibitors of efflux pumps in drug-resistant Candida albicans. Arch Pharm (Weinheim). 2009 Mar;342(3):150-64. doi: 10.1002/ardp.200800160. PubMed PMID: 19253321.
18: Van Bogaert IN, Develter D, Soetaert W, Vandamme EJ. Cerulenin inhibits de novo sophorolipid synthesis of Candida bombicola. Biotechnol Lett. 2008 Oct;30(10):1829-32. doi: 10.1007/s10529-008-9764-8. Epub 2008 Jun 21. PubMed PMID: 18568403.
19: Geerts D, Wallick CJ, Koomoa DL, Koster J, Versteeg R, Go RC, Bachmann AS. Expression of prenylated Rab acceptor 1 domain family, member 2 (PRAF2) in neuroblastoma: correlation with clinical features, cellular localization, and cerulenin-mediated apoptosis regulation. Clin Cancer Res. 2007 Nov 1;13(21):6312-9. PubMed PMID: 17975142.
20: Ho TS, Ho YP, Wong WY, Chi-Ming Chiu L, Wong YS, Eng-Choon Ooi V. Fatty acid synthase inhibitors cerulenin and C75 retard growth and induce caspase-dependent apoptosis in human melanoma A-375 cells. Biomed Pharmacother. 2007 Oct;61(9):578-87. Epub 2007 Sep 14. PubMed PMID: 17904792.
2: Zheng B, Zhu S, Wu X. Clickable analogue of cerulenin as chemical probe to explore protein palmitoylation. ACS Chem Biol. 2015 Jan 16;10(1):115-21. doi: 10.1021/cb500758s. Epub 2014 Oct 23. PubMed PMID: 25322207.
3: Trajtenberg F, Altabe S, Larrieux N, Ficarra F, de Mendoza D, Buschiazzo A, Schujman GE. Structural insights into bacterial resistance to cerulenin. FEBS J. 2014 May;281(10):2324-38. doi: 10.1111/febs.12785. Epub 2014 Apr 9. PubMed PMID: 24641521.
4: Porrini L, Cybulski LE, Altabe SG, Mansilla MC, de Mendoza D. Cerulenin inhibits unsaturated fatty acids synthesis in Bacillus subtilis by modifying the input signal of DesK thermosensor. Microbiologyopen. 2014 Apr;3(2):213-24. doi: 10.1002/mbo3.154. Epub 2014 Feb 14. PubMed PMID: 24574048; PubMed Central PMCID: PMC3996569.
5: Cheng G, Palanisamy AP, Evans ZP, Sutter AG, Jin L, Singh I, May H, Schmidt MG, Chavin KD. Cerulenin blockade of fatty acid synthase reverses hepatic steatosis in ob/ob mice. PLoS One. 2013 Sep 27;8(9):e75980. doi: 10.1371/journal.pone.0075980. eCollection 2013. PubMed PMID: 24086674; PubMed Central PMCID: PMC3785413.
6: Dridi S, Decuypere E, Buyse J. Cerulenin upregulates heat shock protein-70 gene expression in chicken muscle. Poult Sci. 2013 Oct;92(10):2745-53. doi: 10.3382/ps.2013-03242. PubMed PMID: 24046423.
7: Shiragami R, Murata S, Kosugi C, Tezuka T, Yamazaki M, Hirano A, Yoshimura Y, Suzuki M, Shuto K, Koda K. Enhanced antitumor activity of cerulenin combined with oxaliplatin in human colon cancer cells. Int J Oncol. 2013 Aug;43(2):431-8. doi: 10.3892/ijo.2013.1978. Epub 2013 Jun 7. PubMed PMID: 23754252.
8: Tapia V E, Anschau A, Coradini AL, T Franco T, Deckmann AC. Optimization of lipid production by the oleaginous yeast Lipomyces starkeyi by random mutagenesis coupled to cerulenin screening. AMB Express. 2012 Dec 5;2(1):64. doi: 10.1186/2191-0855-2-64. PubMed PMID: 23217098; PubMed Central PMCID: PMC3607992.
9: Banaś W, Furmanek T, Banaś A. Effect of haloxyfop and cerulenin on de novo biosynthesis of lipids in roots of wheat and maize. Acta Biochim Pol. 2012;59(4):567-73. Epub 2012 Nov 27. PubMed PMID: 23189275.
10: Jeong NY, Lee JS, Yoo KS, Oh S, Choe E, Lee HJ, Park BS, Choi YH, Yoo YH. Fatty acid synthase inhibitor cerulenin inhibits topoisomerase I catalytic activity and augments SN-38-induced apoptosis. Apoptosis. 2013 Feb;18(2):226-37. doi: 10.1007/s10495-012-0776-4. PubMed PMID: 23108760.
11: Nguyen LN, Nosanchuk JD. The inhibitory effect of cerulenin to yeasts is fungicidal. Commun Integr Biol. 2011 Nov 1;4(6):631-2. PubMed PMID: 22448300; PubMed Central PMCID: PMC3306321.
12: Jeong NY, Yoo YH. Cerulenin-induced apoptosis is mediated by disrupting the interaction between AIF and hexokinase II. Int J Oncol. 2012 Jun;40(6):1949-56. doi: 10.3892/ijo.2012.1401. Epub 2012 Mar 15. PubMed PMID: 22426850.
13: Liu ZL, Wang G, Shu Y, Zou PA, Zhou Y, Yin QS. Enhanced antitumor activity of epirubicin combined with cerulenin in osteosarcoma. Mol Med Rep. 2012 Feb;5(2):326-30. doi: 10.3892/mmr.2011.661. Epub 2011 Nov 2. PubMed PMID: 22052253.
14: Mao L, Inoue K, Tao Y, Montelione GT, McDermott AE, Inouye M. Suppression of phospholipid biosynthesis by cerulenin in the condensed Single-Protein-Production (cSPP) system. J Biomol NMR. 2011 Feb;49(2):131-7. doi: 10.1007/s10858-011-9469-5. Epub 2011 Jan 30. PubMed PMID: 21279668; PubMed Central PMCID: PMC3164850.
15: Murata S, Yanagisawa K, Fukunaga K, Oda T, Kobayashi A, Sasaki R, Ohkohchi N. Fatty acid synthase inhibitor cerulenin suppresses liver metastasis of colon cancer in mice. Cancer Sci. 2010 Aug;101(8):1861-5. doi: 10.1111/j.1349-7006.2010.01596.x. Epub 2010 Apr 21. PubMed PMID: 20491775.
16: Fu DH, Liu ZL, Liu JS, Luo Y, Shu Y, Huang SH, Han ZM. Transepithelial transport of Cerulenin across Caco-2 cell monolayers. Eur J Drug Metab Pharmacokinet. 2009 Apr-Jun;34(2):67-72. PubMed PMID: 19645214.
17: Diwischek F, Morschhäuser J, Holzgrabe U. Cerulenin analogues as inhibitors of efflux pumps in drug-resistant Candida albicans. Arch Pharm (Weinheim). 2009 Mar;342(3):150-64. doi: 10.1002/ardp.200800160. PubMed PMID: 19253321.
18: Van Bogaert IN, Develter D, Soetaert W, Vandamme EJ. Cerulenin inhibits de novo sophorolipid synthesis of Candida bombicola. Biotechnol Lett. 2008 Oct;30(10):1829-32. doi: 10.1007/s10529-008-9764-8. Epub 2008 Jun 21. PubMed PMID: 18568403.
19: Geerts D, Wallick CJ, Koomoa DL, Koster J, Versteeg R, Go RC, Bachmann AS. Expression of prenylated Rab acceptor 1 domain family, member 2 (PRAF2) in neuroblastoma: correlation with clinical features, cellular localization, and cerulenin-mediated apoptosis regulation. Clin Cancer Res. 2007 Nov 1;13(21):6312-9. PubMed PMID: 17975142.
20: Ho TS, Ho YP, Wong WY, Chi-Ming Chiu L, Wong YS, Eng-Choon Ooi V. Fatty acid synthase inhibitors cerulenin and C75 retard growth and induce caspase-dependent apoptosis in human melanoma A-375 cells. Biomed Pharmacother. 2007 Oct;61(9):578-87. Epub 2007 Sep 14. PubMed PMID: 17904792.
| Chemical | |
|---|---|
| CAS Num | 17397-89-6 |
| Chemical Formula | C12H17NO3 |
| Molecular Weight | 223.27 |
| IUPAC Chemical Name | (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide |
| Exact Mass | 223.12084 |
| Elemental Analysis | C, 64.55; H, 7.67; N, 6.27; O, 21.50 |
| Synonym | Cerulenin; Helicocerin; 17397-89-6; CHEMBL45627; CHEBI |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | CC=CCC=CCCC(=O)C1C(O1)C(=O)N |
| Biological | |
| Targets and Effects | N/A |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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