Skip to main content
SpringerLink
Log in

DNA–interactions of ruthenium(II) & cobalt(III) phenanthroline and bipyridine complexes with a planar aromatic ligand 2-(2-fluronyl)1H-imidazo[4,5-f][1,10-Phenanthroline]

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The ligand 2-(2-fluronyl)1H-imidazo[4,5-f][1,10-Phenanthroline] (fyip) was synthesized and four mixed ligand complexes [Ru(phen)2fyip]2+ 1, [Co(phen)2fyip]3+ 2, [Ru(bpy)2fyip]2+ 3 and [Co(bpy)2fyip]3+ 4 are prepared. These complexes are characterized by IR, 1H, 13C NMR and mass. The interaction of these complexes with calf thymus DNA have been studied. DNA binding was monitored by absorption, fluorescence spectroscopy, viscosity and thermal denaturation studies. All complexes bind to DNA through an intercalative mode with comparable strength and their intrinsic binding constants follows the order 1 > 2 > 3 > 4. These four complexes promote the photocleavage of plasmid pBR322 DNA upon irradiation at 302 nm. Antibacterial activity of these complexes have also been studied.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Zeglis, B.M., Pierre, V.C., Barton, JK.: Metallo-intercalators and metallo-insertors. Chem. Commun. 4567–4579 (2007)

  2. Schuster, G.B., Landman, U.: The mechanism of long-distance radical cation transport in duplex DNA ion-gated hopping of polaron-like distortions. Top. Curr. Chem. 236, 139–161 (2004)

    CAS  Google Scholar 

  3. Elias, B., Kirsch-De Mesmaeker, A.: Photo-reduction of polyazaaromatic Ru(II) complexes by biomolecules and possible applications. Coord. Chem. Rev. 250(13–14), 1627–1641 (2006)

    Article  CAS  Google Scholar 

  4. Gao, F., Chao, H., Ji, L.N.: DNA binding, photocleavage, and topoisomerase inhibition of functionalized ruthenium(II)-polypyridine complexes. Chem. Biodivers. 5, 1962–1979 (2008)

    Article  CAS  Google Scholar 

  5. Gratzel, M. (ed.): Energy Resources Through Photochemistry and Catalysis. Academic Press, New York (1983)

    Google Scholar 

  6. Creutz, C., Sutin, N.: Reaction of tris(bipyridine)ruthenium(III) with hydroxide and its application in a solar energy storage system. Proc. Natl Acad. Sci. 72, 2858–2862 (1975)

    Article  CAS  Google Scholar 

  7. Lin, C.T., Sutin, N.: Quenching of the luminescence of the tris(2,2′-bipyridine) complexes of ruthenium(II) and osmium(II). Kinetic considerations and photogalvanic effects. J. Phys. Chem. 80(2), 97–105 (1976)

    Article  CAS  Google Scholar 

  8. Kumar, C.V., Barton, J.K., Turro, N.J.: Photo physics of ruthenium complexes bound to double helical DNA. J. Am. Chem. Soc. 107, 5518–5523 (1985)

    Article  CAS  Google Scholar 

  9. Meyer, T.J.: Photochemistry of metal coordination complexes: metal to ligand charge transfer excited states. Pure Appl. Chem. 58, 1193–1200 (1986)

    Article  CAS  Google Scholar 

  10. Purugganan, M.D., Kumar, C.V., Turro, N.J., Barton, J.K.: Accelerated electron transfer between metal complexes mediated by DNA. Science 241, 1645–1649 (1988)

    Article  CAS  Google Scholar 

  11. Boerner, L.J.K., Zaleski, J.M.: Metal complex–DNA interactions: from transcription inhibition to photoactivated cleavage. Curr. Opin. Chem. Biol. 9, 135–144 (2005)

    Article  CAS  Google Scholar 

  12. Clarke, M.J.: Erratum to ruthenium metallopharmaceuticals. Coord. Chem. Rev. 232, 69–93 (2002)

    Article  CAS  Google Scholar 

  13. Ji, L.-N., Zou, X.-H., Liu, J.-G.: Shape- and enantioselective interaction of Ru(II)/Co(III) polypyridyl complexes with DNA. Coord. Chem. Rev. 216–217, 513–536 (2001)

    Article  Google Scholar 

  14. Erkkila, K.E., Odom, D.T., Barton, J.K.: Recognition and reaction of metallointercalators with DNA. Chem. Rev. 99, 2777–2795 (1999)

    Article  CAS  Google Scholar 

  15. Zhang, Q.-L., Liu, J.-G., Chao, H., Xue, G.-Q., Ji, L.-N.: DNA-binding and photocleavage studies of cobalt(III) polypyridyl complexes: [Co(phen)2IP]3+ and [Co(phen)2PIP]3+. J. Inorg. Biochem. 83, 49–55 (2001)

    Article  CAS  Google Scholar 

  16. Zhang, Q.-L., Liu, J.-G., Liu, J.-Z., Li, H., Yang, Y., Xu, H., Chao, H., Ji, L.-N.: Effect of intramolecular hydrogen-bond on the DNA-binding and photocleavage properties of polypyridyl cobalt(III) complexes. Inorg. Chim. Acta 339, 34–40 (2002)

    Article  CAS  Google Scholar 

  17. Zhang, Q.-L., Liu, J.-G., Liu, J., Xue, G.-Q., Li, H., Liu, J.-Z., Zhou, H., Qu, L.-H., Ji, L.-N.: DNA-binding and photocleavage studies of cobalt(III) mixed-polypyridyl complexes containing 2-(2-chloro-5-nitrophenyl)1-H-imidazo[4,5-f][1,10 phenanthroline]. J. Inorg. Bio Chem. 85(4), 291–296 (2001)

    CAS  Google Scholar 

  18. Zhang, Q.-L., Liu, J.-G., Xu, H., Li, H., Liu, J.-Z., Zhou, H., Qu, L.-H., Ji, L.-N.: Synthesis, characterization and DNA-binding studies of cobalt(III) polypyridyl complexes. Polyhedron 20, 3049–3055 (2001)

    Article  CAS  Google Scholar 

  19. Zhang, Q.-L., Liu, J.-H., Ren, X.-Z., Xu, H., Huang, Y., Liu, J.-Z., Ji, L.-N.: A functionalized cobalt(III) mixed-polypyridyl complex as a newly designed DNA molecular light switch. Inorg. Biochem. 95, 194–198 (2003)

    Article  CAS  Google Scholar 

  20. He, X.F., Wang, L., Ji, L.N., et al.: Characterization and DNA binding study of Co(III) polypyridyl mixed-ligand complexes. Polyhedron 17(18), 3161–3166 (1998)

    Article  CAS  Google Scholar 

  21. Shilpa, M., Nagababu, P., Satyanarayana, S.: Studies on DNA-binding and plasmid-cleavage of cobalt (III) mixed ligand complexes. Main Group Chem. 8, 33–45 (2009)

    Article  CAS  Google Scholar 

  22. Nagababu, P., Shilpa, M., Satyanarayana, S., Naveena Lavanya Latha, J., Karthikeyan, K.S., Rajesh, M.: Interaction of cobalt(III) polypyridyl complexes containing asymmetric ligands with DNA. Transit. Met. Chem. 33, 1027–1033 (2008)

    Article  CAS  Google Scholar 

  23. Marmur, J.: A procedure for isolation of deoxyribonucleic acid from microorganism. J. Mol. Biol. 3, 208–214 (1961)

    Article  CAS  Google Scholar 

  24. Reichmann, M.E., Rice, S.A., Thomas, C.A., Doty, P.: A further examination of the molecular weight and size of desoxypentose nucleic acid. J. Am. Chem. Soc. 76, 3047–3053 (1954)

    Article  CAS  Google Scholar 

  25. Wolfe, A., Shimer, G.H., Meehan, T.: Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26, 6392–6396 (1987)

    Article  CAS  Google Scholar 

  26. Chaires, J.B., Dattagupta, N., Crothers, D.M.: self association of daunomycin. Biochemistry 21(17), 3927–3932 (1982)

    Article  CAS  Google Scholar 

  27. Satyanarayana, S., Dabrowiak, J.C., Chaires, J.B.: Tris(phenanathroline) ruthenium(II) enantiomer interactions with DNA: mode and specificity of binding. Biochemistry 32, 2573–2584 (1993)

    Article  CAS  Google Scholar 

  28. Drew, W.L., Barry, A.L., Toole, R.O., Shreeis, J.C.: Reliability of the Kirby-Bauer Disc diffusion method for detecting methicillin-resistant strains of Staphylococcus aureus. Appl. Microbiol. Am. Soc. Microbiol. 24, 240 (1972)

    CAS  Google Scholar 

  29. Yamada, M., Tanaka, Y., Yoshimato, Y., Kuroda, S., Shimao, I.: Synthesis and properties of diamino-substituted dipyrido [3,2-a: 20, 30-c] phenazine. J. Bull. Chem. Soc. Jpn. 65, 1006–1011 (1992)

    Article  CAS  Google Scholar 

  30. Sullivan, B.P., Salmon, D.J., Meyer, T.J.: Mixed phosphine 2,2′-bipyridine complexes of ruthenium. Inorg. Chem. 17, 3334–3341 (1978)

    Article  CAS  Google Scholar 

  31. Vlcek, A.A.: Preparation of Co(dipy)2X2+ complexes (X− = chloride, bromide, iodide, nitrite) by controlled oxidative processes. Inorg. Chem. 6, 1425–1427 (1967)

    Article  CAS  Google Scholar 

  32. Steck, E.A., Day, A.R.: Reactions of phenanthraquinone and retenequinone with aldehydes and ammonium acetate in acetic Acid solution. J. Am. Chem. Soc. 65, 452–456 (1943)

    Article  CAS  Google Scholar 

  33. Barton, J.K., Danishefsky, A.T., Goldberg, J.M.: Tris(phenanthroline)ruthenium(II): stereoselectivity in binding to DNA. J. Am. Chem. Soc. 106, 2172–2176 (1984)

    Article  CAS  Google Scholar 

  34. Tysoe, S.A., Morgan, R.J., Baker, A.D., Strelkas, T.C.: Spectroscopic investigation of differential binding modes of .DELTA.- and .LAMBDA.-Ru(bpy)2(ppz)2+ with calf thymus DNA. J. Phys. Chem. 97, 1707–1711 (1993)

    Article  CAS  Google Scholar 

  35. Kelly, T.M., Tossi, A.B., McConnell, D.J., OhUigin, C.: A study of the interactions of some polypyridylruthenium (II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation. Nucleic Acids Res. 13, 6017–6034 (1985)

    Article  CAS  Google Scholar 

  36. Wu, J.-Z., Li, L., Zen, T.-X., Ji, L.N.: Synthesis, characterization and luminescent DNA-binding study of a series of ruthenium complexes containing 2-arylimidazo[f]1,10-phenanthroline. Polyhedron 16, 103–107 (1997)

    Article  CAS  Google Scholar 

  37. Pyle, A.M., Rehmann, J.P., Meshoyrer, R., Kumar, C.V., Turro, N.J., Barton, J.K.: Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA. J. Am. Chem. Soc. 111, 3051–3058 (1989)

    Article  CAS  Google Scholar 

  38. Joseph, R., Lakowicz, G.W.: Quenching of fluorescence by oxygen. Probe for structural fluctuations in macromolecules. Biochemistry 12, 4161–4170 (1973)

    Article  Google Scholar 

  39. Lakowicz, J.R.: Principles of Fluorescence Spectroscopy. Plenum Press, New York (1983)

    Google Scholar 

  40. Kumar, C.V., Turro, N.J., Barton, J.K.: Photophysics of ruthenium complexes bound to double helical DNA. J. Am. Chem. Soc. 107, 9319–9324 (1985)

    Article  Google Scholar 

  41. Sigma, D.S., Mazumder, A., Perrin, D.M.: Chemical nucleases. Chem. Rev. 93, 2295–2316 (1993)

    Article  Google Scholar 

  42. Satyanarayana, S., Dabrowiak, J.C., Chaires, J.B.: Neither d- nor l-tris (phenanathroline) ruthenium (II) binds to DNA by classical intercalation. Biochemistry 31, 9319–9324 (1992)

    Article  CAS  Google Scholar 

  43. Waring, M.J.: Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol. 13, 269–282 (1965)

    Article  CAS  Google Scholar 

  44. Neyhart, G.A., Grover, N., Smith, S.R., Kalsbeck, W.A., Fairly, T.A., Cory, M., Thorp, H.H.: Binding and kinetics studies of oxidation of DNA by oxoruthenium(IV). J. Am. Chem. Soc. 115, 4423–4428 (1993)

    Article  CAS  Google Scholar 

  45. Tselepi-Kalouli, E., Katsaros, N.: The interaction of [Ru(NH3)5Cl]2+ and [Ru(NH3)6]3+ ions with DNA. J. Inorg. Biochem. 37, 271–282 (1989)

    Article  CAS  Google Scholar 

  46. Jin, L., Yang, P.: Synthesis and studied of Co(III) mixed-ligand complex containing dipyrido[3, 2-a-c] phenazine and phen. Polyhedron 16, 3395–3398 (1997)

    Article  CAS  Google Scholar 

  47. Tweedy, B.G.: Phytopathology, 55, 910 (1964)

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Osmania University, Hyderabad, 500007, Andhra Pradesh, India

    Mynam Shilpa, A. Gayatri Devi, Yata Praveen Kumar, Penumaka Nagababu & S. Satyanarayana

  2. Department of Biotechnology, Krishna University, Machilipatnam, India

    J. Naveena Lavanya Latha

  3. Department of Microbiology, Osmania University, Hyderabad, India

    A. Nagarjuna

Authors
  1. Mynam Shilpa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. Naveena Lavanya Latha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Gayatri Devi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. Nagarjuna
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yata Praveen Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Penumaka Nagababu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. Satyanarayana
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. Satyanarayana.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shilpa, M., Latha, J.N.L., Gayatri Devi, A. et al. DNA–interactions of ruthenium(II) & cobalt(III) phenanthroline and bipyridine complexes with a planar aromatic ligand 2-(2-fluronyl)1H-imidazo[4,5-f][1,10-Phenanthroline]. J Incl Phenom Macrocycl Chem 70, 187–195 (2011). https://doi.org/10.1007/s10847-010-9891-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-010-9891-4

Keywords

Search

Navigation