NDLI: DNA cleavage and antitumour activity of platinum(II) and copper(II) compounds derived from 4-methyl-2-<i>N</i>-(2-pyridylmethyl)aminophenol: spectroscopic, electrochemical and biological investigation

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DNA cleavage and antitumour activity of platinum(II) and copper(II) compounds derived from 4-methyl-2-N-(2-pyridylmethyl)aminophenol: spectroscopic, electrochemical and biological investigation

Content Provider	Royal Society of Chemistry (RSC)
Author	Roy, Sudeshna Dulk, Hans den Reedijk, Jan Hartl, František Spek, Anthony L. Barends, Sharief Wezel, Gilles P. Lutz, Martin Maheswari, Palanisamy Uma
Copyright Year	2009
Abstract	The reaction of the redox-active ligand, Hpyramol (4-methyl-2-N-(2-pyridylmethyl)aminophenol) with K2PtCl4 yields monofunctional square-planar [Pt(pyrimol)Cl], PtL-Cl, which was structurally characterised by single-crystal X-ray diffraction and NMR spectroscopy. This compound unexpectedly cleaves supercoiled double-stranded DNA stoichiometrically and oxidatively, in a non-specific manner without any external reductant added, under physiological conditions. Spectro-electrochemical investigations of PtL-Cl were carried out in comparison with the analogue CuL-Cl as a reference compound. The results support a phenolate oxidation, generating a phenoxyl radical responsible for the ligand-based DNA cleavage property of the title compounds. Time-dependent in vitro cytotoxicity assays were performed with both PtL-Cl and CuL-Cl in various cancer cell lines. The compound CuL-Cl overcomes cisplatin-resistance in ovarian carcinoma and mouse leukaemia cell lines, with additional activity in some other cells. The platinum analogue, PtL-Cl also inhibits cell-proliferation selectively. Additionally, cellular-uptake studies performed for both compounds in ovarian carcinoma cell lines showed that significant amounts of Pt and Cu were accumulated in the A2780 and A2780R cancer cells. The conformational and structural changes induced by PtL-Cl and CuL-Cl on calf thymus DNA and ϕX174 supercoiled phage DNA at ambient conditions were followed by electrophoretic mobility assay and circular dichroism spectroscopy. The compounds induce extensive DNA degradation and unwinding, along with formation of a monoadduct at the DNA minor groove. Thus, hybrid effects of metal-centre variation, multiple DNA-binding modes and ligand-based redox activity towards cancer cell-growth inhibition have been demonstrated. Finally, reactions of PtL-Cl with DNA model bases (9-Ethylguanine and 5′-GMP) followed by NMR and MS showed slow binding at Guanine-N7 and for the double stranded self complimentary oligonucleotide d(GTCGAC)2 in the minor groove.
Starting Page	10846
Ending Page	10860
Page Count	15
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	0
Issue Number	48
Journal	Dalton Transactions
DOI	10.1039/b911542k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Cu Hpyramol Ligand Aminophenol X-ray crystallography Nuclear magnetic resonance spectroscopy DNA Alkoxy group Cytotoxicity Cancer Carcinoma Mouse Leukemia Thymus Phi X 174 Bacteriophage Electrophoresis Circular dichroism Spectroscopy Redox Nuclear magnetic resonance Oligonucleotide
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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DNA cleavage and antitumour activity of platinum(II) and copper(II) compounds derived from 4-methyl-2-N-(2-pyridylmethyl)aminophenol: spectroscopic, electrochemical and biological investigation

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