Synthesis and Antitumor Invasive Activity of Novel Ionone Alkaloid Derivatives

Hai-Jun      Fang; Qian      Liu; Chun-Chun      Gan; Mei-Na      Jin; Nan      Qin; Hong-Quan      Duan

doi:10.2174/15701808113106660094

Abstract

Two series of new ionone alkaloid derivatives were synthesized and evaluated for antitumor invasive activities in human MDA-MB-231 breast cancer cells. The structures of derivatives were elucidated by ¹H, ¹³C NMR and mass spectrometric methods. Ionone alkaloid derivatives 1a, 1c, 1d, 4i, 4j and 4k revealed significant inhibitory effects on the invasion of MDA-MB-231 cells in invasion assay, and compound 4j bearing a 4-fluoro benzene group of ionone alkaloid exhibited potent anti-invasive activity with an IC₅₀ value of 0.054 µM.

Keywords: Antitumor metastasis, Breast cancer cells, Derivative synthesis, Invasion assay, Ionone alkaloid, (E)-4-(3-[(4- fluorobenzyl)(methyl)amino]but-1-en-1-yl)-3, 5, 5-trimethylcyclohex-2-en-1-one.