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.
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.
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).
