Anticancer activity and biophysical reactivity of copper complexes of 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-alkylhydrazinecarbothioamides

A series of copper complexes were synthesized from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) thiosemicarbazones (RHpTSC where R = H, CH3, C2H5 or C6H5 (Ph)). The complexes show interesting variations in geometry depending on the thiosemicarbazone; a dinuclear complex [Cu(HpTSC)Cl]2, a mononuclear complex [Cu(RHpTSC)2Cl2] (R = CH3 or C2H5) and another mononuclear complex [Cu(PhHpTSC)(PhpTSC)Cl] was generated. The complexes bind in a moderately strong fashion to DNA with binding constants on the order of 104 M− 1. They are also strong binders of human serum albumin with binding constants near 104 M− 1. The complexes show good in vitro cytotoxic profiles against two human colon cancer cell lines (HCT-116 and HT29) and two human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values in the low millimolar concentration range.

Graphical abstractA series of copper complexes that show interesting variations in geometry was synthesized from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) thiosemicarbazones. The complexes show good in vitro cytotoxic profiles against human colon and breast cancer cell lines.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Structural variety among copper(II) thiosemicarbazone complexes. ► The complexes are moderate binders of DNA. ► The complexes also bind strongly to human serum albumin. ► Complexes show anticancer behavior that is not linked to DNA binding.