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J Med Chem. 2014 Sep 11;57(17):7459-64. doi: 10.1021/jm501083y. Epub 2014 Aug 29.

Synthetic ω-3 epoxyfatty acids as antiproliferative and pro-apoptotic agents in human breast cancer cells.

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Discipline of Pharmacology, School of Medical Sciences, Sydney Medical School, University of Sydney , Sydney, New South Wales 2006, Australia.


ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

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