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Ruthenium(II) complexes containing 4‐methoxybenzhydrazone ligands: synthesis, characterization, DNA binding, DNA cleavage, radical scavenging and in vitro cytotoxic activity
Author(s) -
Mohanraj Maruthachalam,
Ayyannan Ganesan,
Raja Gunasekaran,
Jayabalakrishnan Chinnasamy
Publication year - 2016
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3468
Subject(s) - chemistry , intercalation (chemistry) , hydrazone , ruthenium , denticity , hela , dna , stereochemistry , cleavage (geology) , enol , in vitro , crystal structure , crystallography , organic chemistry , biochemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
Three ruthenium(II) hydrazone complexes of composition [RuCl(CO)(PPh 3 ) 2 L] were synthesized from the reactions of [RuHCl(CO)(PPh 3 ) 3 ] with hydrazones derived from 4‐methoxybenzhydrazide and 4‐formylbenzoic acid (HL 1 ), 4‐methylbenzaldehyde (HL 2 ) and 2‐bromobenzaldehyde (HL 3 ). The synthesized hydrazone ligands and their metal complexes were characterized using elemental analysis and infrared, UV–visible, NMR ( 1 H, 13 C and 31 P) and mass spectral techniques. The hydrazone ligands act as bidentate ones, with O and N as the donor sites, and are predominantly found in the enol form in all the complexes studied. The molecular structures of the ligands HL 1 , HL 2 and HL 3 were determined using single‐crystal X‐ray diffraction. The interactions of the ligands and the complexes with calf thymus DNA were studied using absorption spectroscopy and cyclic voltammetry which revealed that the compounds could interact with calf thymus DNA through intercalation. The DNA cleavage activity of the complexes was evaluated using a gel electrophoresis assay which revealed that the complexes act as good DNA cleavage agents. In addition, all the complexes were subjected to antioxidant assay, which showed that they all possess significant scavenging activity against 2,2‐diphenyl‐2‐picrylhydrazyl, OH and NO radicals. The in vitro cytotoxic effect of the complexes examined on cancerous cell lines (HeLa and MCF‐7) showed that the complexes exhibit substantial anticancer activity. Copyright © 2016 John Wiley & Sons, Ltd.