Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation

A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3',7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PO, Hep-G2, KB and SK-N-MC cells. However, 3',6-dichloroflavanone (2g) with IC50 value of 2.9 +/- 0.9 mu M was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PO and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PO and MDA-MB-231 cells occurs via apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.