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DNA-binding properties of ruthenium(II) complexes with the bidentate ligand 5-chloro-2-(phenylazo)pyridine

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Abstract

A bidentate ligand, 5-chloro-2-(phenylazo)pyridine (Clazpy), and its two polypyridyl ruthenium(II) complexes, [Ru(Clazpy)2bpy]Cl2·7H2O (1) and [Ru(Clazpy)2phen]Cl2·8H2O (2), were synthesized and characterized. The DNA-binding properties of these complexes with DNA, the breast cancer susceptibility gene 1 (BRCA1), and the pBIND plasmid DNA were probed by photocleavage, electronic absorption titration, ethidium bromide quenching, and thermal denaturation. Both complexes were found to bind to the BRCA1 fragment through the intercalative mode into the base pairs of DNA, and the DNA-binding constants (Kb) for 1 and 2 were 7.0 × 104 M−1 and 5.1 × 105 M−1, respectively. In addition, both complexes enhanced the single-stranded cleavage of the plasmid DNA. Under comparable experimental conditions, 2 cleaved DNA more effectively than 1, in a dose–response manner. The data indicated that the binding affinity of these two complexes to DNA was dependent on the aromatic planarity and hydrophobicity of the intercalative polypyridyl ligand.

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Acknowledgments

This work was financially supported in part by the research grants from the Graduate School, Prince of Songkla University, the Center for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education and the Thailand Research Fund under the Royal Golden Jubilee Ph.D. Program (to P.T.). The authors would like to thank Prof. S.A.R. Knox and Prof. N. Connelly for results of the elemental analysis and FAB mass spectroscopic data, and L. Sahavisit for assistance in the synthesis of some ruthenium complexes. We are grateful to Dr. Brian Hodgson for assistance with the English and the Pharmaceutical Laboratory Service Center, Faculty of Pharmaceutical Sciences, Prince of Songkla University for research facilities.

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Authors and Affiliations

  1. Laboratory of Pharmaceutical Biotechnology, Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat-Yai, Songkhla, 90112, Thailand

    Adisorn Ratanaphan, Tidarat Nhukeaw & Pornvichai Temboot

  2. Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla, 90112, Thailand

    Kanidtha Hansongnern

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  1. Adisorn Ratanaphan
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  2. Tidarat Nhukeaw
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  3. Pornvichai Temboot
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  4. Kanidtha Hansongnern
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Correspondence to Adisorn Ratanaphan.

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Ratanaphan, A., Nhukeaw, T., Temboot, P. et al. DNA-binding properties of ruthenium(II) complexes with the bidentate ligand 5-chloro-2-(phenylazo)pyridine. Transition Met Chem 37, 207–214 (2012). https://doi.org/10.1007/s11243-012-9576-5

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  • DOI: https://doi.org/10.1007/s11243-012-9576-5

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