Synthesis, characterization, DNA binding and cytotoxicity of fluoro-dipyrrin based arene ruthenium(II) complexes

Abstract

Synthesis of four new arene ruthenium(II) complexes [(η6-C10H14)RuCl(MFPdpm)] (1); [(η6-C12H18)Ru-Cl(MFPdpm)] (2); [(η6-C10H14)RuCl(PFPdpm)] (3) and [(η6-C12H18)RuCl(PFPdpm)] (4) containing dipyrrin ligands 5-(4-fluoro)phenyldipyrromethene (MFPdpm) and 5-(penta-fluoro)phenyldipyrromethene (PFPdpm) have been described. The ligands and complexes have been thoroughly characterized by elemental analyses, spectroscopic studies (ESI-MS, IR,1H,13C NMR, UV–Vis) and structure of the representative complex 4 determined by X-ray single crystal analyses. DNA binding activities of 1–4 have been investigated by UV–Vis and fluorescence spectroscopy and their binding through the minor groove of DNA has been established by molecular docking studies. The complexes 1–4 exhibit significant cytotoxicity toward human lung cancer cell line (A549). Cytotoxicity, morphological changes, and apoptosis studies have been evaluated through MTT assay, Hoechst 33342/PI staining, and cell cycle analysis by fluorescence activated cell sorting (FACS). In vitro antitumor activity and cytotoxicity of the complexes lie in the order 4 > 3 > 2 > 1. © 2016 Elsevier B.V.