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MedKoo Cat#: 317459 | Name: Cerulenin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Cerulenin
CAS#17397-89-6

Theoretical Analysis

MedKoo Cat#: 317459

Name: Cerulenin

CAS#: 17397-89-6

Chemical Formula: C12H17NO3

Exact Mass: 223.1208

Molecular Weight: 223.27

Elemental Analysis: C, 64.55; H, 7.67; N, 6.27; O, 21.50

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 650.00 2 Weeks
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Related CAS #
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Synonym
Cerulenin; Helicocerin; CHEMBL45627; CHEBI:171741; Cerulenin, Cephalosporium caerulens; AC1NQZF4; EINECS 241-424-8; NSC 116069; NSC116069; NSC-116069
IUPAC/Chemical Name
(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
InChi Key
GVEZIHKRYBHEFX-ZIMISOLQSA-N
InChi Code
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+
SMILES Code
CC=CCC=CCCC(=O)C1C(O1)C(=O)N
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).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C20M06C04
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Cerulenin, the best known natural inhibitor of fatty acid synthase (FASN), is an epoxide produced by the fungus Cephalosporium caeruleus.
In vitro activity:
Cerulenin, a fatty acid synthase (FAS) inhibitor, induces apoptosis of variety of tumor cells. To elucidate mode of action by cerulenin, the proteomics approach was employed using Schizosaccharomyces pombe. The differential protein expression profile of S. pombe revealed that cerulenin modulated the expressions of proteins involved in stresses and metabolism, including both ade10 and adk1 proteins. The nutrient supplementation assay demonstrated that cerulenin affected enzymatic steps transferring a phosphoribosyl group. This result suggests that cerulenin accumulates AMP and p-ribosyl-s-amino-imidazole carboxamide (AICAR) and reduces other necessary nucleotides, which induces feedback inhibition of enzymes and the transcriptional regulation of related genes in de novo and salvage adenine metabolic pathway. Furthermore, the deregulation of adenine nucleotide synthesis may interfere ribonucleotide reductase and cause defects in cell cycle progression and chromosome segregation. In conclusion, cerulenin induces apoptosis through deregulation of adenine nucleotide biosynthesis resulting in nuclear division defects in S. pombe. Reference: Biochem Biophys Res Commun. 2006 Oct 27;349(3):1025-31. https://linkinghub.elsevier.com/retrieve/pii/S0006-291X(06)01947-4
In vivo activity:
Cerulenin treatment of ob/ob mice has obvious effects on body weight. With 2 days of treatment, body weight in treated mice is decreased compared to a 5.7% weight gain in the controls. With prolonged (7 days) treatment, no body weight loss is observed, but body weight gain is slowed. In all groups, 60 mg/kg of Cerulenin is more effective than 30 mg/kg in inhibiting weight gain. If given daily or every other day, ATP content are increased 58.1% and 61.5% respectively by 7-day treatment of 60 mg/kg Cerulenin. Significant ATP elevation is also observed with only 2 days of treatment with 60 mg/kg Cerulenin. In contrast, 30 mg/kg Cerulenin, given either 2 or 7 days, does not show any significant effect on cellular ATP content. Reference: PLoS One. 2013 Sep 27;8(9):e75980. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24086674/
Solvent mg/mL mM comments
Solubility
DMSO 100.0 447.89
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 223.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Chung KS, Sun NK, Lee SH, Lee HJ, Choi SJ, Kim SK, Song JH, Jang YJ, Song KB, Yoo HS, Simon J, Won M. Cerulenin-mediated apoptosis is involved in adenine metabolic pathway. Biochem Biophys Res Commun. 2006 Oct 27;349(3):1025-31. doi: 10.1016/j.bbrc.2006.08.130. Epub 2006 Aug 30. PMID: 16962997. 2. Guo CB, Cui NH, Yu GY, Liu DX, Meng SC, Song Q. Effects of cerulenin on the endogenous fatty acid synthetic activity in squamous cell carcinoma of the oral cavity. J Oral Maxillofac Surg. 2003 Aug;61(8):909-12. doi: 10.1016/s0278-2391(03)00237-4. PMID: 12905443.
In vivo protocol:
1. 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. PMID: 24086674; PMCID: PMC3785413. 2. Bermeo S, Al Saedi A, Vidal C, Khalil M, Pang M, Troen BR, Myers D, Duque G. Treatment with an inhibitor of fatty acid synthase attenuates bone loss in ovariectomized mice. Bone. 2019 May;122:114-122. doi: 10.1016/j.bone.2019.02.017. Epub 2019 Feb 16. PMID: 30779961.
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.

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