Natural and synthetic acetylenic fatty acids have displayed interesting antifungal, antibacterial, and antiprotozoal activities. One such fatty acid is the 2-hexadecynoic acid, a compound that has displayed considerable antiplasmodial (Plasmodium yoelii liver stage, IC50 = 4.9 �g/ml) and antileishmanial activities (Leishmania donovani, IC50 = 4.5 �g/ml) [1]. With the aim of exploring the antineoplastic activities of the normal chain ?2-acetylenic fatty acids we synthesized the hitherto unknown 2-tetradecynoic acid as well as the 2-octadecynoic acid for further scrutiny. To our surprise, we found that the 2-octadecynoic acid displays the best antineoplasitic activity towards the SH-SY5Y, RAW 264.7, and HT29 cell lines, and is a good inhibitor of the human topoisomerase IB enzyme, a possible intracellular target for this fatty acid. Our results demonstrate that chain length is a critical factor in controlling the antineoplastic activities of these acetylenic fatty acids. In this work the synthesis and characterization of these two novel fatty acids will be presented together with results on their antineoplastic and enzyme inhibitory activities.[1] D. Tasdemir, D. Sanabria, I. L. Lauinger, A. Tarun, R. Herman, R. Perozzo, M. Zloh, S. H. Kappe, R. Brun, and N. M. Carballeira, Bioorg. Med. Chem., 18, 7475-7485 (2010).

New synthetic antineoplastic [Delta]2-acetylenic fatty acids

243rd National Meeting (2012)

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