Fatty acids have been reported as drug candidates to treat a diversity of physiological and pathological conditions including cancer and infections caused by bacteria and fungi, among other conditions. Previous studies from our group demonstrate that the combination of 2-methoxylation and a C-6 unsaturation enhances the potency of some fatty acids towards these pathological conditions. For example, the (�)-2-methoxy-6-heptadecynoic acid inhibits the Leishmania donovani enzyme TopoIB at EC50=17 �M, but the heptadecenoic and heptadecanoic acids inhibit the enzyme at higher concentrations [1]. It is also know that fatty acids play an important role regulating the loss of homeostasis in cancer cells, inducing cell death. Our results demonstrates that 2-methoxylated ?6 unsaturated fatty acids promote cell death in various cells lines including human neuroblasmoma SH-SY5Y and HeLa cell lines [2]. In this work we present the first total synthesis of the (�)-2-methoxy-6-octadecenoic acid identified in the Caribbean sponge Spheciospongia cuspidifera and its ?6 acetylenic analogs [3]. The antiprotozoal and anticancer potential of this novel fatty acid will also presented.  Carballeira, N.M., Cartagena, M., Li, F., Chen, Z., Prada, C.F., Calvo-Alvarez, E., Regura, R., Bala�a-Fouce, R., Pure Appl. Chem. 2012 , 84, 1867-1875.Orellano, E. A., Cartagena, M. M., Rosado, K., Carballeira, N. M. Chem. Phys. Lipids 2013 , 172-173, 14-19.Carballeira, N. M., Alicea, J. Lipids 2002 , 37, 305-308.

Synthesis of a new 2-methoxylated ?6 unsaturated fatty acid, with potential antiprotozoal and anticancer properties

247th National Meeting (2014)

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