Cerulenin - CAS 17397-89-6
Catalog number:
17397-89-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C12H17NO3
Molecular Weight:
223.27
COA:
Inquire
Targets:
Others
Description:
Cerulenin, an epoxydodecadienamide compound, could be extracted from sorts of species and has been found to be an antifungal used to restrain biosynthesis of some lipids through influencing activities of enzymes.
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Purity:
98%
Appearance:
White to off-white powder.
Synonyms:
Cerulenin; Helicocerin; 17397-89-6; EINECS 241-424-8; (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
Storage:
Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years).
MSDS:
Inquire
Quality Standard:
In-house standard
Quantity:
Milligram-Grams
Boiling Point:
456.1ºC at 760 mmHg
Melting Point:
93.5℃
Density:
1.134 g/cm3
InChIKey:
GVEZIHKRYBHEFX-NQQPLRFYSA-N
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
Canonical SMILES:
CC=CCC=CCCC(=O)C1C(O1)C(=O)N
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 S1, Mahesh HB2, Mahadevaiah C2, Prasannakumar MK3. BMC Genomics. 2016 Mar 31;17(1):271. doi: 10.1186/s12864-016-2599-0.
BACKGROUND: Sheath rot disease caused by Sarocladium oryzae is an emerging threat for rice cultivation at global level. However, limited information with respect to genomic resources and pathogenesis is a major setback to develop disease management strategies. Considering this fact, we sequenced the whole genome of highly virulent Sarocladium oryzae field isolate, Saro-13 with 82x sequence depth.
2.Effect of cerulenin on fatty acid composition and gene expression pattern of DHA-producing strain Colwellia psychrerythraea strain 34H.
Wan X1,2, Peng YF3, Zhou XR4,5, Gong YM6, Huang FH7,8, Moncalián G9. Microb Cell Fact. 2016 Feb 6;15:30. doi: 10.1186/s12934-016-0431-9.
BACKGROUND: Colwellia psychrerythraea 34H is a psychrophilic bacterium able to produce docosahexaenoic acid (DHA). Polyketide synthase pathway is assumed to be responsible for DHA production in marine bacteria.
3.Dephosphorylation and mitochondrial translocation of cofilin sensitizes human leukemia cells to cerulenin-induced apoptosis via the ROCK1/Akt/JNK signaling pathway.
Zhang Y1, Fu R1, Liu Y1, Li J1, Zhang H1, Hu X1, Chen Y1, Liu X1, Li Y1, Li P2, Liu E2, Gao N1. Oncotarget. 2016 Mar 8. doi: 10.18632/oncotarget.7994. [Epub ahead of print]
In this study, we determined that cerulenin, a natural product inhibitor of fatty acid synthase, induces mitochondrial injury and apoptosis in human leukemia cells through the mitochondrial translocation of cofilin. Only dephosphorylated cofilin could translocate to mitochondria during cerulenin-induced apoptosis. Disruption of the ROCK1/Akt/JNK signaling pathway plays a critical role in the cerulenin-mediated dephosphorylation and mitochondrial translocation of cofilin and apoptosis. In vivo studies demonstrated that cerulenin-mediated inhibition of tumor growth in a mouse xenograft model of leukemia was associated with mitochondrial translocation of cofilin and apoptosis. These data are consistent with a hierarchical model in which induction of apoptosis by cerulenin primarily results from activation of ROCK1, inactivation of Akt, and activation of JNK. This leads to the dephosphorylation and mitochondrial translocation of cofilin and culminates with cytochrome c release, caspase activation, and apoptosis.
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Chemical Structure

CAS 17397-89-6 Cerulenin

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