C75 - CAS 218137-86-1
Catalog number: 218137-86-1
Category: Inhibitor
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Molecular Formula:
C14H22O4
Molecular Weight:
254.32
COA:
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Targets:
Others
Description:
C75 is a novel, potent synthetic inhibitor of fatty acid synthase (FAS), which is used as a tool for studying fatty acid synthesis in metabolic disorders and cancer.
Purity:
>98%
Synonyms:
C 75 trC-75 trans-racemic; trans-C75
MSDS:
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InChIKey:
VCWLZDVWHQVAJU-UHFFFAOYSA-N
InChI:
InChI=1S/C14H22O4/c1-3-4-5-6-7-8-9-11-12(13(15)16)10(2)14(17)18-11/h11-12H,2-9H2,1H3,(H,15,16)
Canonical SMILES:
CCCCCCCCC1C(C(=C)C(=O)O1)C(=O)O
1.Inhibition of Fatty Acid Synthase is Protective in Pulmonary Hypertension.
Singh N1,2, Manhas A1, Kaur G1, Jagavelu K1,2, Hanif K1,2. Br J Pharmacol. 2016 Apr 7. doi: 10.1111/bph.13495. [Epub ahead of print]
BACKGROUND AND PURPOSE: In pulmonary hypertension (PH), similar to cancer, there is altered energy metabolism, apoptosis resistance and cellular proliferation leading to pulmonary vascular remodelling. Proliferating cells exhibit higher rate of de novo fatty acid synthesis to provide lipids for membrane formation, and energy production. As inhibition of de novo fatty acid synthesis proved protective in cancer experimentally, therefore, it was hypothesized that modulation of de novo fatty acid synthesis by inhibition of fatty acid synthase (FAS) may prove beneficial for PH.
2.Fatty acid synthase is a metabolic oncogene targetable in malignant peripheral nerve sheath tumors.
Patel AV1, Johansson G1, Colbert MC1, Dasgupta B1, Ratner N1. Neuro Oncol. 2015 Dec;17(12):1599-608. doi: 10.1093/neuonc/nov076. Epub 2015 Jun 26.
BACKGROUND: Malignant peripheral nerve sheath tumors (MPNSTs) are soft tissue sarcomas with minimal therapeutic opportunities. We observed that lipid droplets (LDs) accumulate in human MPNST cell lines and in primary human tumor samples. The goal of this study was to investigate the relevance of lipid metabolism to MPNST survival and as a possible therapeutic target.
3.Berberine Regulated Lipid Metabolism in the Presence of C75, Compound C, and TOFA in Breast Cancer Cell Line MCF-7.
Tan W1, Zhong Z2, Wang S2, Suo Z1, Yang X1, Hu X1, Wang Y2. Evid Based Complement Alternat Med. 2015;2015:396035. doi: 10.1155/2015/396035. Epub 2015 Aug 13.
Berberine interfering with cancer reprogramming metabolism was confirmed in our previous study. Lipid metabolism and mitochondrial function were also the core parts in reprogramming metabolism. In the presence of some energy-related inhibitors, including C75, compound C, and TOFA, the discrete roles of berberine in lipid metabolism and mitochondrial function were elucidated. An altered lipid metabolism induced by berberine was observed under the inhibition of FASN, AMPK, and ACC in breast cancer cell MCF-7. And the reversion of berberine-induced lipid suppression indicated that ACC inhibition might be involved in that process instead of FASN inhibition. A robust apoptosis induced by berberine even under the inhibition of AMPK and lipid synthesis was also indicated. Finally, mitochondrial function regulation under the inhibition of AMPK and ACC might be in an ACL-independent manner. Undoubtedly, the detailed mechanisms of berberine interfering with lipid metabolism and mitochondrial function combined with energy-related inhibitors need further investigation, including the potential compensatory mechanisms for ATP production and the upregulation of ACL.
4.Assessment of metal-assisted nucleophile activation in the hepatitis delta virus ribozyme from molecular simulation and 3D-RISM.
Radak BK1, Lee TS2, Harris ME3, York DM4. RNA. 2015 Sep;21(9):1566-77. doi: 10.1261/rna.051466.115. Epub 2015 Jul 13.
The hepatitis delta virus ribozyme is an efficient catalyst of RNA 2'-O-transphosphorylation and has emerged as a key experimental system for identifying and characterizing fundamental features of RNA catalysis. Recent structural and biochemical data have led to a proposed mechanistic model whereby an active site Mg(2+) ion facilitates deprotonation of the O2' nucleophile, and a protonated cytosine residue (C75) acts as an acid to donate a proton to the O5' leaving group as noted in a previous study. This model assumes that the active site Mg(2+) ion forms an inner-sphere coordination with the O2' nucleophile and a nonbridging oxygen of the scissile phosphate. These contacts, however, are not fully resolved in the crystal structure, and biochemical data are not able to unambiguously exclude other mechanistic models. In order to explore the feasibility of this model, we exhaustively mapped the free energy surfaces with different active site ion occupancies via quantum mechanical/molecular mechanical (QM/MM) simulations.
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CAS 218137-86-1 C75

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