(−)-trans-C75

(-)-trans-C75 is an enantiomer of C75, a fatty acid synthase (FAS) inhibitor [1][2].

Fatty acid synthase (FAS) catalyzes the reductive synthesis of long-chain fatty acids from acetyl-coenzyme A (acetyl-CoA) and malonyl-CoA. FAS may represent an important link in feeding regulation and may be a potential therapeutic target [1].

C75 is a fatty acid synthase (FAS) inhibitor. (-)-trans-C75 is an enantiomer of C75. In human cancer cells, it also showed significant in vivo antitumor activity, suppressed DNA replication, induced apoptosis [2].

Intraperitoneal (ip) injection of mice with C75 led to a 95% reduction in 14C-acetate incorporation into fatty acids and a 110% increase in the level of hepatic malonyl-CoA. Both systemic and intracerebroventricular treatment of mice with C75 led to inhibition of feeding and dramatic weight loss. In mice, intraperitoneal (ip) injection of mice with C75 led to weight loss in a dose-dependent way, which was due primarily to inhibition of feeding. C75 (15 mg/kg) reduced food intake by more than 90% over the first 24 hours. Forced feeding largely reversed the observed weight loss. C75 also reduced the expression of neuropeptide Y (NPY) in the hypothalamus that control feeding and energy utilization [1].

References:
[1].  Loftus TM, Jaworsky DE, Frehywot GL, et al. Reduced food intake and body weight in mice treated with fatty acid synthase inhibitors. Science. 2000 Jun 30;288(5475):2379-81.
[2].  Chakrabarty, K.,Forzato, C.,Nitti, P., et al. The first kinetic enzymatic resolution of methyl ester of C75. Letters in Organic Chemistry, 2010, 7, 245-248.