Luminescent ruthenium(II)-para-cymene complexes of aryl substituted imidazo-1,10-phenanthroline as anticancer agents and the effect of remote substituents on cytotoxic activities

[Display omitted] •Ten new organo-ruthenium complexes were synthesized.•These complexes have the property of DNA binding and cleavage.•All the Ru(II)-complexes are significantly toxic against MDA-MB-231 and HeLa cancer cell lines at low concentration.•Excellent selectivity index. Ruthenium complexes...

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Bibliographic Details
Published in:Inorganica Chimica Acta 2021-01, Vol.515, p.120066, Article 120066
Main Authors: De, Sourav, Selva Kumar, R., Gauthaman, Ashna, Ashok Kumar, S.K., Paira, Priyankar, Moorthy, Anbalagan, Banerjee, Subhasis
Format: Article
Language:English
Subjects:
Anticancer properties
Aromatic compounds
Aromaticity
Binding
Biomolecules
BSA
Chemical analysis
Chemical properties
DNA
Gel electrophoresis
Grooves
In-silico study
Infrared analysis
Intercalation
MTT
NMR
Nuclear magnetic resonance
Ruthenium compounds
Selectivity
Toxicity
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Summary:[Display omitted] •Ten new organo-ruthenium complexes were synthesized.•These complexes have the property of DNA binding and cleavage.•All the Ru(II)-complexes are significantly toxic against MDA-MB-231 and HeLa cancer cell lines at low concentration.•Excellent selectivity index. Ruthenium complexes are currently significant attention in medicinal chemistry as they offer various properties which make them an appropriate choice for drug development. Herein, a series of ruthenium(II)-p-cymene-2-aryl-imidazo-1,10-phenanthroline derivatives have been prepared and characterised by elemental analysis, infrared, LC-mass and NMR techniques. The structural and chemical properties shows that Ru(II) complexes have got rigidity, planarity, aromaticity, hydrogen donating and accepting capability which aids both solubility and interaction with biomolecules. The binding strength of these complexes with DNA and BSA were found to be 104–106 M−1. The competitive displacement of ethidium bromide (EtBr) from DNA in the presence of complex reveals an intercalation or groove binding further this was supported by viscosity and in-silico studies. The cytotoxicity study of these Ru(II) complexes were conducted with two cancer cell lines (MDA-MB-231 and HeLa) and one human embryonic kidney cells (HEK-293). The study revealed that [(η6-p-cymene)RuCl (κ2-N,N-2-(4-fluorophenyl)-1H-imidazo[4,5-f][1,10]Phenanthroline].PF6 (4e), [(η6-p-cymene)RuCl(κ2-N,N-2-(4-bromophenyl)-1H-imidazo[4,5-f][1,10]Phenanthroline].PF6 (4f) and [(η6-p-cymene)RuCl(κ2-N,N-2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]Phenanthro line].PF6 (4g) were found exhibit least inhibitory concentration (IC50) and high selectivity with respect to HeLa and MDA-MB-231. The activity of the Ru(II) complexes were position and substituents dependent.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2020.120066