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C75 is stable fatty acid synthase (FASN) inhibitor that when administered in racemic form leads to profound weight loss and feeding inhibition in both high-fat diet wild type obese and leptin-deficient ob/ob mice.1 C75 is also cytotoxic to many human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FASN pathway.2 (?)-trans-C75 is an enantiomer of C75.3 Its biologicial activity has not been reported. | [Definition]
ChEBI:(2S,3R)-C75 is a 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid that has 2S,3R-configuration. It is an enantiomer of a (2R,3S)-C75. | [References]
1. Loftus, T.M., Jaworsky, D.E., Frehywot, G.L., et al. Reduced food intake and body weight in mice treated with fatty acid synthase inhibitors Science 288,2379-2381(2000).
2. Pizer, E.S., Thupari, J., Han, W.F., et al. Malonyl-coenzyme-A is a potential mediator of cytotoxicity induced by fatty-acid synthase inhibition in human breast cancer cells and xenografts Cancer Res. 60,213-218(2000).
3. Chakrabarty, K., Forzato, C., Nitti, P., et al. The first kinetic enzymatic resolution of methyl ester of C75 Lett. Org. Chem. 7,245-248(2010). |
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