Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2012, Article ID 609796, 7 pages
http://dx.doi.org/10.1155/2012/609796
Research Article

Synthesis, Crystal Structure, and DNA-Binding Studies of a Nickel(II) Complex with the Bis(2-benzimidazolymethyl)amine Ligand

School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, China

Received 20 May 2011; Revised 7 June 2011; Accepted 8 June 2011

Academic Editor: Santiago Gómez-Ruiz

Copyright © 2012 Huilu Wu 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. M. Mrksich and P. B. Dervan, “Antiparallel side-by-side heterodimer for sequence-specific recognition in the minor groove of DNA by a distamycin/1-methylimidazole-2-carboxamide-netropsin pair,” Journal of the American Chemical Society, vol. 115, no. 7, pp. 2572–2576, 1993. View at Google Scholar · View at Scopus
  2. C. Kokubo and T. Katsuki, “Highly enantioselective catalytic oxidation of alkyl aryl sulfides using Mn-salen catalyst,” Tetrahedron, vol. 52, no. 44, pp. 13895–13900, 1996. View at Publisher · View at Google Scholar · View at Scopus
  3. S. Schoumacker, O. Hamelin, J. Pécaut, and M. Fontecave, “Catalytic asymmetric sulfoxidation by chiral manganese complexes: acetylacetonate anions as chirality switches,” Inorganic Chemistry, vol. 42, no. 24, pp. 8110–8116, 2003. View at Publisher · View at Google Scholar · View at Scopus
  4. C. M. Dupureur and J. K. Barton, “Structural Studies of Λ- and Δ-[Ru(phen)2dppz]2+ Bound to d(GTCGAC)2: characterization of Enantioselective Intercalation,” Inorganic Chemistry, vol. 36, no. 1, pp. 33–43, 1997. View at Publisher · View at Google Scholar · View at Scopus
  5. C. Hemmert, M. Pitié, M. Renz, H. Gornitzka, S. Soulet, and B. Meunier, “Preparation, characterization and crystal structures of manganese(II), iron(III) and copper(II) complexes of the bis[di-1,1-(2-pyridyl)ethyl] amine (BDPEA) ligand; evaluation of their DNA cleavage activities,” Journal of Biological Inorganic Chemistry, vol. 6, no. 1, pp. 14–22, 2001. View at Publisher · View at Google Scholar · View at Scopus
  6. V. S. Li, D. Choi, Z. Wang, L. S. Jimenez, M. Tang, and H. Kohn, “Role of the C-10 substituent in mitomycin C-1-DNA bonding,” Journal of the American Chemical Society, vol. 118, no. 10, pp. 2326–2331, 1996. View at Publisher · View at Google Scholar · View at Scopus
  7. G. Zuber, J. C. Quada, and S. M. Hecht, “Sequence selective cleavage of a DNA octanucleotide by chlorinated bithiazoles and bleomycins,” Journal of the American Chemical Society, vol. 120, no. 36, pp. 9368–9369, 1998. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Gellis, H. Kovacic, N. Boufatah, and P. Vanelle, “Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents,” European Journal of Medicinal Chemistry, vol. 43, no. 9, pp. 1858–1864, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. Ö. Ö. Güven, T. Erdoǧan, H. Göker, and S. Yildiz, “Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers,” Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 8, pp. 2233–2236, 2007. View at Publisher · View at Google Scholar
  10. K. Kopańska, A. Najda, J. Zebrowska et al., “Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii,” Bioorganic and Medicinal Chemistry, vol. 12, no. 10, pp. 2617–2624, 2004. View at Publisher · View at Google Scholar · View at Scopus
  11. K. C. Skyrianou, F. Perdih, I. Turel, D. P. Kessissoglou, and G. Psomas, “Nickel-quinolones interaction—part 2: interaction of nickel(II) with the antibacterial drug oxolinic acid,” Journal of Inorganic Biochemistry, vol. 104, no. 2, pp. 161–170, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. K. C. Skyrianou, C. P. Raptopoulou, V. Psycharis, D. P. Kessissoglou, and G. Psomas, “Structure, cyclic voltammetry and DNA-binding properties of the bis(pyridine)bis(sparfloxacinato)nickel(II) complex,” Polyhedron, vol. 28, no. 15, pp. 3265–3271, 2009. View at Publisher · View at Google Scholar · View at Scopus
  13. Y. Jin, M. A. Lewis, N. H. Gokhale, E. C. Long, and J. A. Cowan, “Influence of stereochemistry and redox potentials on the single- and double-strand DNA cleavage efficiency of Cu(II)-and Ni(II)·Lys-Gly-his-derived ATCUN metallopeptides,” Journal of the American Chemical Society, vol. 129, no. 26, pp. 8353–8361, 2007. View at Publisher · View at Google Scholar · View at Scopus
  14. F. Bisceglie, M. Baldini, M. Belicchi-Ferrari et al., “Metal complexes of retinoid derivatives with antiproliferative activity: synthesis, characterization and DNA interaction studies,” European Journal of Medicinal Chemistry, vol. 42, no. 5, pp. 627–634, 2007. View at Publisher · View at Google Scholar · View at Scopus
  15. J. B. Chaires, “Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: mode and specificity of binding,” Biochemistry, vol. 32, no. 10, pp. 2573–2584, 1993. View at Google Scholar · View at Scopus
  16. J. Marmur, “A procedure for the isolation of deoxyribonucleic acid from microorganisms,” Methods in Enzymology, vol. 6, pp. 726–738, 1963. View at Publisher · View at Google Scholar · View at Scopus
  17. A. Wolfe, G. H. Shimer, and T. Meehan, “Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA,” Biochemistry, vol. 26, no. 20, pp. 6392–6396, 1987. View at Google Scholar · View at Scopus
  18. M. Chauhan, K. Banerjee, and F. Arjmand, “DNA binding studies of novel copper(II) complexes containing L-tryptophan as chiral auxiliary: in vitro antitumor activity of Cu-Sn2 complex in human neuroblastoma cells,” Inorganic Chemistry, vol. 46, no. 8, pp. 3072–3082, 2007. View at Publisher · View at Google Scholar · View at Scopus
  19. J. R. Lakowicz and G. Weber, “Quenching of fluorescence by oxygen. A probe for structural fluctuations in macromolecules,” Biochemistry, vol. 12, no. 21, pp. 4161–4170, 1973. View at Google Scholar · View at Scopus
  20. S. Satyanarayana, J. C. Dabrowiak, and J. B. Chaires, “Neither Δ- nor Λ-tris(phenanthroline)ruthenium(II) binds to DNA by classical intercalation,” Biochemistry, vol. 31, no. 39, pp. 9319–9324, 1992. View at Publisher · View at Google Scholar
  21. H. P. Berends and D. W. Stephan, “Copper(I) and copper(II) complexes of biologically relevant tridentate ligands,” Inorganica Chimica Acta, vol. 93, no. 4, pp. 173–178, 1984. View at Google Scholar · View at Scopus
  22. Bruker, Smart Saint and Sadabs, Bruker Axs, Inc., Madison, Wisc, USA, 2000.
  23. G. M. Sheldrick, SHELXTL, Siemmens Analytical X-Ray Instruments, Inc., Madison, Wisc, USA, 1996.
  24. W. J. Geary, “The use of conductivity measurements in organic solvents for the characterisation of coordination compounds,” Coordination Chemistry Reviews, vol. 7, no. 1, pp. 81–122, 1971. View at Google Scholar · View at Scopus
  25. C. Y. Su, B. S. Kang, C. X. Du, Q. C. Yang, and T. C. W. Mak, “Formation of mono-, bi-, tri-, and tetranuclear Ag(I) complexes of C3-symmetric tripodal benzimidaxole ligands,” Inorganic Chemistry, vol. 39, no. 21, pp. 4843–4849, 2000. View at Publisher · View at Google Scholar · View at Scopus
  26. R. J. Sundberg and R. B. Martin, “Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems,” Chemical Reviews, vol. 74, no. 4, pp. 471–517, 1974. View at Google Scholar · View at Scopus
  27. V. McKee, M. Zvagulis, and C. A. Reed, “Further insight into magnetostructural correlations in binuclear copper(II) species related to methemocyanin: X-ray crystal structure of a 1,2-μ-nitrito complex,” Inorganic Chemistry, vol. 24, no. 19, pp. 2914–2919, 1985. View at Google Scholar
  28. T. J. Lane, I. Nakagawa, J. L. Walter, and A. J. Kandathil, “Infrared investigation of certain imidazole derivatives and their metal chelates,” Inorganic Chemistry, vol. 1, pp. 267–276, 1962. View at Google Scholar
  29. H. Wu, R. Yun, K. Li, K. Wang, X. Huang, and T. Sun, “Synthesis, crystal structure and spectra properties of the nickel (II) complex with 1,3-bis(1-benzylbenzimidazol2-yl)-2-oxopropane,” Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, vol. 39, no. 9, pp. 614–617, 2009. View at Publisher · View at Google Scholar
  30. H. Li, X. Y. Le, D. W. Pang, H. Deng, Z. H. Xu, and Z. H. Lin, “DNA-binding and cleavage studies of novel copper(II) complex with L-phenylalaninate and 1,4,8,9-tetra-aza-triphenylene ligands,” Journal of Inorganic Biochemistry, vol. 99, no. 11, pp. 2240–2247, 2005. View at Publisher · View at Google Scholar · View at Scopus
  31. V. G. Vaidyanathan and B. U. Nair, “Synthesis, characterization, and DNA binding studies of a chromium(III) complex containing a tridentate ligand,” European Journal of Inorganic Chemistry, no. 19, pp. 3633–3638, 2003. View at Google Scholar · View at Scopus
  32. V. G. Vaidyanathan and B. U. Nair, “Nucleobase oxidation of DNA by (terpyridyl)chromium(III) derivatives,” European Journal of Inorganic Chemistry, no. 9, pp. 1840–1846, 2004. View at Publisher · View at Google Scholar · View at Scopus
  33. J. Liu, T. Zhang, T. Lu et al., “DNA-binding and cleavage studies of macrocyclic copper(II) complexes,” Journal of Inorganic Biochemistry, vol. 91, no. 1, pp. 269–276, 2002. View at Publisher · View at Google Scholar · View at Scopus
  34. A. M. Pyle, J. P. Rehmann, R. Meshoyrer, C. V. Kumar, N. J. Turro, and J. K. Barton, “Mixed-ligand complexes of ruthenium(II): factors governing binding to DNA,” Journal of the American Chemical Society, vol. 111, no. 8, pp. 3051–3058, 1989. View at Google Scholar · View at Scopus
  35. B. C. Baguley and M. Le Bret, “Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect,” Biochemistry, vol. 23, no. 5, pp. 937–943, 1984. View at Google Scholar · View at Scopus