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Synthesis of four new arene ruthenium(II) complexes [(η 6 -C 10 H 14 )RuCl(MFPdpm)] ( 1 ); [(η 6 -C 12 H 18 )Ru-Cl(MFPdpm)] ( 2 ); [(η 6 -C 10 H 14 )RuCl(PFPdpm)] ( 3 ) and [(η 6 -C 12 H 18 )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, 1 H, 13 C 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 . [ABSTRACT FROM AUTHOR]