Table of Contents
ISRN Inorganic Chemistry
Volume 2013, Article ID 623962, 6 pages
http://dx.doi.org/10.1155/2013/623962
Research Article

Synthesis, Characterization, and Biological Studies of New Ruthenium Polypyridyl Complexes Containing Noninnocent Ligands

1Department of Chemistry, Faculty of Science, University of Semnan, P.O. Box 35195-363 Semnan, Iran
2Biochemistry Department, Faculty of Medicine, Semnan University of Medical Science, Semnan, Iran

Received 13 November 2012; Accepted 29 November 2012

Academic Editors: B. Sohrabi and B. Yan

Copyright © 2013 Sofia Taheri et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. T. Naota, H. Takaya, and S. L. Murahashi, “Ruthenium-catalyzed reactions for organic synthesis,” Chemical Reviews, vol. 98, no. 7, pp. 2599–2660, 1998. View at Google Scholar · View at Scopus
  2. Z. Zhao, M. Wang, L. Cui, J. He, D. Yu, and Y. Tian, “Semiconducting superhard ruthenium monocarbide,” Journal of Physical Chemistry C, vol. 114, no. 21, pp. 9961–9964, 2010. View at Publisher · View at Google Scholar
  3. M. Al-Noaimi, G. P. A. Yap, and R. J. Crutchley, “Outer sphere perturbation of delocalized mixed-valence complexes,” Inorganic Chemistry, vol. 43, pp. 1773–1784, 2004. View at Publisher · View at Google Scholar
  4. G. L. Xu, R. J. Crutchley, M. C. DeRosa et al., “Strong electronic couplings between ferrocenyl centers mediated by bis-ethynyl/butadiynyl diruthenium bridges,” Journal of the American Chemical Society, vol. 127, no. 38, pp. 13354–13363, 2005. View at Publisher · View at Google Scholar · View at Scopus
  5. D. A. Boyd, R. J. Crutchley, P. E. Fanwick, and T. Ren, “Fc-Fc electronic interaction through equatorial pathways of a diruthenium core,” Inorganic Chemistry, vol. 49, no. 4, pp. 1322–1324, 2010. View at Publisher · View at Google Scholar · View at Scopus
  6. L. Bijeire, B. Elias, J. P. Souchard et al., “Photoelectron transfer processes with ruthenium(II) polypyridyl complexes and Cu/Zn superoxide dismutase,” Biochemistry, vol. 45, no. 19, pp. 6160–6169, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. H. Durr and S. Bossmann, “Ruthenium polypyridine complexes. On the route to biomimetic assemblies as models for the photosynthetic reaction center,” Accounts of Chemical Research, vol. 34, no. 11, pp. 905–917, 2011. View at Publisher · View at Google Scholar
  8. R. Noyori and S. Hashiguchi, “Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes,” Accounts of Chemical Research, vol. 30, pp. 97–102, 1977. View at Publisher · View at Google Scholar
  9. J. J. Concepcion, J. W. Jurss, M. K. Brennaman et al., “Making oxygen with ruthenium complexes,” Accounts of Chemical Research, vol. 42, no. 12, pp. 1954–1965, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. J. R. Winkler and H. B. Gray, “Electron transfer in ruthenium-modified proteins,” Chemical Reviews, vol. 92, no. 3, pp. 369–379, 1992. View at Publisher · View at Google Scholar
  11. R. E. Morris, R. E. Aird, P. Del Socorro Murdoch et al., “Inhibition of cancer cell growth by ruthenium(II) arene complexes,” Journal of Medicinal Chemistry, vol. 44, no. 22, pp. 3616–3621, 2001. View at Publisher · View at Google Scholar · View at Scopus
  12. C. A. Vock, W. H. Ang, C. Scolaro et al., “Development of ruthenium antitumor drugs that overcome multidrug resistance mechanisms,” Journal of Medicinal Chemistry, vol. 50, no. 9, pp. 2166–2175, 2007. View at Publisher · View at Google Scholar · View at Scopus
  13. M. G. Mendoza-Ferri, C. G. Hartinger, M. A. Mendoza et al., “Transferring the concept of multinuclearity to ruthenium complexes for improvement of anticancer activity,” Journal of Medicinal Chemistry, vol. 52, no. 4, pp. 916–925, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. G. A. McLachlan, J. G. Muller, S. E. Rokita, and C. J. Burrows, “Metal-mediated oxidation of guanines in DNA and RNA: a comparison of cobalt(II), nickel(II) and copper(II) complexes,” Inorganica Chimica Acta, vol. 251, no. 1-2, pp. 193–199, 1996. View at Google Scholar · View at Scopus
  15. R. Indumathy, M. Kanthimathi, T. Weyhermuller, and B. U. Nair, “Cobalt complexes of terpyridine ligands: crystal structure and nuclease activity,” Polyhedron, vol. 27, no. 17, pp. 3443–3450, 2008. View at Publisher · View at Google Scholar · View at Scopus
  16. J. C. Genereux and J. K. Barton, “Mechanisms for DNA charge transport,” Chemical Reviews, vol. 110, no. 3, pp. 1642–1662, 2010. View at Publisher · View at Google Scholar
  17. M. Pitie and G. Pratviel, “Activation of DNA carbon—hydrogen bonds by metal complexes,” Chemical Reviews, vol. 110, pp. 1018–1059, 2010. View at Publisher · View at Google Scholar
  18. R. E. Mewis and S. J. Archibald, “Biomedical applications of macrocyclic ligand complexes,” Coordination Chemistry Reviews, vol. 254, pp. 1686–1712, 2010. View at Publisher · View at Google Scholar
  19. L. F. Tan and H. Chao, “DNA-binding and photocleavage studies of mixed polypyridyl ruthenium(II) complexes with calf thymus DNA,” Inorganica Chimica Acta, vol. 360, no. 6, pp. 2016–2022, 2007. View at Publisher · View at Google Scholar
  20. Y. Nakabayashi, H. Inada, Y. Minoura, N. Iwamoto, and O. Yamauchi, “Effects of flexible bridging ligands on DNA-binding of dinuclear ruthenium(II)-2,2′-bipyridine complexes,” Inorganica Chimica Acta, vol. 362, no. 3, pp. 869–877, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. H. J. Yu, H. Chao, L. Jiang, L. Y. Li, S. M. Huang, and L. N. Ji, “Single oxygen-mediated DNA photocleavage of a di-bithiazolyl ruthenium(II) complex [Ru(btz)2(dppz)]2+,” Inorganic Chemistry Communications, vol. 11, pp. 553–556, 2008. View at Publisher · View at Google Scholar
  22. G. Sathyaraj, T. Weyhermuller, and B. U. Nair, “Synthesis, characterization and DNA binding studies of new ruthenium(II)bisterpyridine complexes,” European Journal of Medicinal Chemistry, vol. 45, pp. 284–291, 2010. View at Publisher · View at Google Scholar
  23. A. Sigel and H. Sigel, Metal Ions in Biological Systems, vol. 33, Marcel Dekker, New York, NY, USA, 1996.
  24. K. E. Erkkila, D. T. Odom, and J. K. Barton, “Recognition and reaction of metallointercalators with DNA,” Chemical Reviews, vol. 99, no. 9, pp. 2777–2795, 1999. View at Google Scholar · View at Scopus
  25. I. Kostova, “Ruthenium complexes as anticancer agents,” Current Medicinal Chemistry, vol. 13, pp. 1085–1107, 2006. View at Publisher · View at Google Scholar
  26. C. S. Allardyce and P. J. Dyson, “Ruthenium in medicine: current clinical uses and future prospects,” Platinum Metals Review, vol. 45, no. 2, pp. 62–69, 2001. View at Google Scholar
  27. M. J. Clarke, “Ruthenium metallopharmaceuticals,” Coordination Chemistry Reviews, vol. 236, no. 1-2, pp. 209–233, 2003. View at Publisher · View at Google Scholar
  28. C. G. Hartinger, S. Zorbas-Seifried, M. A. Jakupec, B. Kynast, H. Zorbas, and B. K. Keppler, “From bench to bedside—preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A),” Journal of Inorganic Biochemistry, vol. 100, no. 5-6, pp. 891–904, 2006. View at Publisher · View at Google Scholar · View at Scopus
  29. M. S. Deshpande, A. A. Kumbhar, and A. S. Kumbhar, “Hydrolytic cleavage of DNA by a ruthenium(II) polypyridyl complex,” Inorganic Chemistry, vol. 46, pp. 5450–5452, 2007. View at Publisher · View at Google Scholar
  30. C. Bazzicalupi, A. Bencini, A. Bianchi et al., “A zinc(II)-based receptor for ATP binding and hydrolysis,” Chemical Communications, no. 20, pp. 2630–2632, 2005. View at Publisher · View at Google Scholar · View at Scopus
  31. M. J. Clarke, “Ruthenium metallopharmaceuticals,” Coordination Chemistry Reviews, vol. 232, no. 1-2, pp. 69–93, 2002. View at Publisher · View at Google Scholar
  32. L. N. Ji, X. H. Zou, and J. G. Liu, “Shape- and enantioselective interaction of Ru(II)/Co(III) polypyridyl complexes with DNA,” Coordination Chemistry Reviews, vol. 216-217, pp. 513–536, 2001. View at Publisher · View at Google Scholar
  33. X. L. Hong, H. Chao, L. J. Lin et al., “Synthesis, characterization, and DNA-binding properties of the ruthenium(II) complexes [Ru(dipn)(dptp)](ClO4)2 and [Ru(dipn)(pat)](ClO4)2 (dipn=N-(3-aminpropyl)propane-1,3-diamine; dptp=2-(5,6-diphenyl-1,2,4-triazin-3-yl)-1,10-phenanthroline; pat=9-(1,10-phenanthrolin-2-yl)acenaphtho[1,2-e][1,2,4]triazine),” Helvetica Chimica Acta, vol. 87, no. 5, pp. 1180–1193, 2004. View at Publisher · View at Google Scholar
  34. P. U. Maheswari and M. Palaniandavar, “DNA binding and cleavage activity of [Ru(NH3) 4(diimine)]Cl2 complexes,” Inorganica Chimica Acta, vol. 357, no. 4, pp. 901–912, 2004. View at Publisher · View at Google Scholar · View at Scopus
  35. H. Xu, K. C. Zheng, Y. Cheng et al., “Effects of ligand planarity on the interaction of polypyridyl Ru(II) complexes with DNA,” Journal of the Chemical Society, Dalton Transactions, no. 11, pp. 2260–2268, 2003. View at Publisher · View at Google Scholar
  36. P. U. Maheswari, V. Rajendiran, M. Palaniandavar, R. Parthasarathi, and V. Subramanian, “Synthesis, characterization and DNA-binding properties of rac-[Ru(5,6-dmp)2(dppz)]2+—Enantiopreferential DNA binding and co-ligand promoted exciton coupling,” Journal of Inorganic Biochemistry, vol. 100, no. 1, pp. 3–17, 2006. View at Publisher · View at Google Scholar · View at Scopus
  37. R. Liegghio, P. G. Potvin, and A. B. P. Lever, “2,6-dipyrazinylpyridines and their ruthenium(II) complexes: a new polynucleating ligand family,” Inorganic Chemistry, vol. 40, no. 22, pp. 5485–5486, 2001. View at Publisher · View at Google Scholar · View at Scopus
  38. F. B. Dean, J. R. Nelson, T. L. Giesler, and R. S. Lasken, “Rapid amplification of plasmid and phage DNA using Phi29 DNA polymerase and multiply-primed rolling circle amplification,” Genome Research, vol. 11, no. 6, pp. 1095–1099, 2001. View at Publisher · View at Google Scholar · View at Scopus
  39. K. Watanabe, T. Oshima, K. Iijima, Z. Yamaizumi, and S. Nishimura, “Purification and thermal stability of several amino acid-specific tRNAs from an extreme thermophile, Thermus thermophilus HB8,” The Journal of Biochemistry, vol. 87, no. 1, pp. 1–13, 1980. View at Google Scholar
  40. M. Al-Noaimi, G. P. A. Yap, and R. J. Crutchley, “Outer sphere perturbation of delocalized mixed-valence complexes,” Inorganic Chemistry, vol. 43, no. 5, pp. 1770–1778, 2004. View at Publisher · View at Google Scholar · View at Scopus
  41. M. Cusumando and A. Giannetto J, “The interaction of mixed-ligand square-planar complexes with calf thymus DNA,” Journal of Inorganic Biochemistry, vol. 65, pp. 137–144, 1997. View at Publisher · View at Google Scholar
  42. G. A. Neyhart, N. Grover, S. R. Smith et al., “Binding and kinetics studies of oxidation of DNA by oxoruthenium (IV),” Journal of the American Chemical Society, vol. 115, no. 11, pp. 4423–4428, 1993. View at Google Scholar · View at Scopus
  43. National Committee for Clinical and Laboratory Standards, in Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, pp. S.100–S.157, NCCLS, Villanova, Italy, Approved Standard 4th edition, 1997.
  44. V. I. Ivanov, L. E. Minchenkova, A. K. Schyolkina, and A. I. Poletayev, “Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism.,” Biopolymers—Peptide Science Section, vol. 12, no. 1, pp. 89–110, 1973. View at Google Scholar · View at Scopus
  45. Y. Liu, C. G. Liu, S. L. Sun, G. C. Yang, and Y. Q. Qiu, “Redox-switching second-order nonlinear optical responses of NNN ruthenium complexes,” Computational and Theoretical Chemistry, vol. 979, pp. 112–118, 2012. View at Google Scholar
  46. Q. X. Zhou, F. Yang, W. H. Lei et al., “Ruthenium(II) terpyridyl complexes exhibiting DNA photocleavage: the role of the substituent on monodentate ligand,” The Journal of Physical Chemistry B, vol. 113, pp. 11521–11526, 2009. View at Publisher · View at Google Scholar
  47. E. Grueso, G. López-Pérez, M. Castellano, and R. Prado-Gotor, “Thermodynamic and structural study of phenanthroline derivative ruthenium complex/DNA interactions: probing partial intercalation and binding properties,” Journal of Inorganic Biochemistry, vol. 106, no. 1, pp. 1–9, 2012. View at Publisher · View at Google Scholar
  48. S. Maji, S. Patra, S. Chakraborty et al., “Valence-state distribution in the ruthenium o-quinonoid systems [Ru(trpy)-(Cl)(L1)]+ and [Ru(trpy)(Cl)(L2)]+ (L1 = o-iminobenzoquinone, L2 = o-diiminobenzoquinone; trpy = 2,2′:6′,2-terpyridine),” European Journal of Inorganic Chemistry, no. 2, pp. 314–323, 2007. View at Publisher · View at Google Scholar · View at Scopus
  49. N. Gupta, N. Grover, G. A. Neyhart, P. Singh, and H. H. Thorp, “Synthesis and properties of new DNA cleavage agents based on oxoruthenium(IV),” Inorganic Chemistry, vol. 32, no. 3, pp. 310–316, 1993. View at Google Scholar · View at Scopus
  50. J. L. Boyer, J. Rochford, M. K. Tsai, J. T. Muckerman, and E. Fujita, “Ruthenium complexes with non-innocent ligands: electron distribution and implications for catalysis,” Coordination Chemistry Reviews, vol. 254, no. 3-4, pp. 309–330, 2010. View at Publisher · View at Google Scholar · View at Scopus
  51. J. Liu, R. Cao, Q. Wu et al., “Synthesis and antibacterial evaluation of novel 4-alkyl substituted phenyl β-aldehyde ketone derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 4, pp. 1737–1744, 2009. View at Publisher · View at Google Scholar
  52. V. Mahalingam, N. Chitrapriya, F. R. Fronczek, and K. Natarajan, “New Ru(II)-dmso complexes with heterocyclic hydrazone ligands towards cancer chemotherapy,” Polyhedron, vol. 27, no. 7, pp. 1917–1924, 2008. View at Publisher · View at Google Scholar · View at Scopus
  53. V. Mahalingam, N. Chitrapriya, M. Zeller, and K. Natarajan, “Ru(II)-DMSO complexes containing aromatic and heterocyclic acid hydrazides: structure, electrochemistry and biological activity,” Polyhedron, vol. 28, no. 8, pp. 1532–1540, 2009. View at Publisher · View at Google Scholar · View at Scopus
  54. V. Mahalingam, N. Chitrapriya, F. R. Fronczek, and K. Natarajan, “New Ru(II)-DMSO complexes of ON/SN chelates: synthesis, behavior of Schiff bases towards hydrolytic cleavage of CN bond, electrochemistry and biological activities,” Polyhedron, vol. 29, no. 18, pp. 3363–3371, 2010. View at Publisher · View at Google Scholar · View at Scopus
  55. P. Gameiro, C. Rodrigues, T. Baptista, I. Sousa, and B. de Castro, “Solution studies on binary and ternary complexes of copper(II) with some fluoroquinolones and 1,10-phenanthroline: antimicrobial activity of ternary metalloantibiotics,” International Journal of Pharmaceutics, vol. 334, no. 1-2, pp. 129–136, 2007. View at Publisher · View at Google Scholar · View at Scopus