Table of Contents
International Journal of Inorganic Chemistry
Volume 2011, Article ID 624756, 8 pages
http://dx.doi.org/10.1155/2011/624756
Research Article

Coordination Chemistry of Polyaromatic Thiosemicarbazones 2: Synthesis and Biological Activity of Zinc, Cobalt, and Copper Complexes of 1-(Naphthalene-2-yl)ethanone Thiosemicarbazone

1Science Division, Lyon College, Batesville, AR 72501, USA
2Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA

Received 25 September 2011; Revised 11 November 2011; Accepted 27 November 2011

Academic Editor: Rabindranath Mukherjee

Copyright © 2011 Marc-Andre LeBlanc 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. E. Hess and G. Bahr, “Über emprotide Schwermetall-Innerkomplexe der α-Diketondithiosemicarbazone (Thiazone). I,” Zeitschrift für Anorganische und Allgemeine Chemie, vol. 268, no. 4–6, pp. 351–363, 1952. View at Google Scholar
  2. G. Bähr, E. Hess, E. Steinkopf, and G. Schleitzer, “Über emprotide Schwermetall-Innerkomplexe der α-Diketondithiosemicarbazone (Thiazone). II,” Zeitschrift für Anorganische und Allgemeine Chemie, vol. 273, no. 6, pp. 325–332, 1953. View at Google Scholar
  3. G. Bahr and E. Schleitzer, “Über emprotide Schwermetall-Innerkomplexe der α-Diketondithiosemicarbazone (Thiazone). III,” Zeitschrift für Anorganische und Allgemeine Chemie, vol. 278, no. 3-4, pp. 136–154, 1955. View at Google Scholar
  4. C. J. Jones and J. A. McCleverty, “Complexes of transition metals with Schiff bases and the factors influencing their redox properties—part I: nickel and copper complexes of some diketone bis-thiosemicarbazones,” Journal of the Chemical Society A, pp. 2829–2836, 1970. View at Publisher · View at Google Scholar · View at Scopus
  5. D. H. Petering, Carcinostatic Copper Complexes, Marcel Dekker, New York, NY, USA, 1980, Edited by H. Sigel.
  6. D. X. West, I. H. Hall, K. G. Rajendran, and A. E. Liberta, “The cytotoxicity of heterocyclic thiosemicarbazones and their metal complexes on human and murine tissue culture cells,” Anti-Cancer Drugs, vol. 4, no. 2, pp. 231–240, 1993. View at Google Scholar · View at Scopus
  7. V. Brabec and O. Nováková, “DNA binding mode of ruthenium complexes and relationship to tumor cell toxicity,” Drug Resistance Updates, vol. 9, no. 3, pp. 111–122, 2006. View at Publisher · View at Google Scholar · View at Scopus
  8. K. Li, L. H. Zhou, J. Zhang et al., “"Self-activating" chemical nuclease: ferrocenyl cyclen Cu(II) complexes act as efficient DNA cleavage reagents in the absence of reductant,” European Journal of Medicinal Chemistry, vol. 44, no. 4, pp. 1768–1772, 2009. View at Publisher · View at Google Scholar · View at Scopus
  9. B. Maity, M. Roy, and A. R. Chakravarty, “Ferrocene-conjugated copper(II) dipyridophenazine complex as a multifunctional model nuclease showing DNA cleavage in red light,” Journal of Organometallic Chemistry, vol. 693, no. 8-9, pp. 1395–1399, 2008. View at Publisher · View at Google Scholar · View at Scopus
  10. I. C. Mendes, J. P. Moreira, A. S. Mangrich, S. P. Balena, B. L. Rodrigues, and H. Beraldo, “Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones,” Polyhedron, vol. 26, no. 13, pp. 3263–3270, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. M. B. Ferrari, F. Bisceglie, G. Pelosi et al., “Synthesis, characterization and X-ray structures of new antiproliferative and proapoptotic natural aldehyde thiosemicarbazones and their nickel(II) and copper(II) complexes,” Journal of Inorganic Biochemistry, vol. 90, no. 3-4, pp. 113–126, 2002. View at Publisher · View at Google Scholar · View at Scopus
  12. D. X. West, J. S. Ives, J. Krejci et al., “Copper(II) complexes of 2-benzoylpyridine 4N-substituted thiosemicarbazones,” Polyhedron, vol. 14, no. 15-16, pp. 2189–2200, 1995. View at Google Scholar · View at Scopus
  13. S. Jayasree and K. K. Aravindakshan, “Structural and antitumour studies of metal complexes with thiosemicarbazones of β-diketoesters,” Polyhedron, vol. 12, no. 10, pp. 1187–1192, 1993. View at Google Scholar · View at Scopus
  14. U. Krach-Hansen, V. T. G. Chuang, and M. Otagiri, “Practical aspects of the ligand-binding and enzymatic properties of human serum albumin,” Biological and Pharmaceutical Bulletin, vol. 25, no. 6, pp. 695–704, 2002. View at Publisher · View at Google Scholar · View at Scopus
  15. F. A. Beckford, J. Thessing, M. Shaloski Jr. et al., “Synthesis and characterization of mixed-ligand diimine-piperonal thiosemicarbazone complexes of ruthenium(II): biophysical investigations and biological evaluation as anticancer and antibacterial agents,” Journal of Molecular Structure, vol. 992, no. 1–3, pp. 39–47, 2011. View at Google Scholar
  16. M. M. Mostafa, A. El-Hammid, M. Shallaby, and A. A. El-Asmy, “Copper(II), cobalt(II), nickel(II) and mercury(II) complexes of 1,4-diphenylthiosemicarbazide,” Transition Metal Chemistry, vol. 6, no. 5, pp. 303–305, 1981. View at Publisher · View at Google Scholar · View at Scopus
  17. A. Ambroise and B. G. Maiya, “Ruthenium(II) complexes of redox-related, modified dipyridophenazine ligands: synthesis, characterization, and DNA interaction,” Inorganic Chemistry, vol. 39, no. 19, pp. 4256–4263, 2000. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Jiang, Y. T. Li, Z. Y. Wu, Z. Q. Liu, and C. W. Yan, “Synthesis, crystal structure, cytotoxic activities and DNA-binding properties of new binuclear copper(II) complexes bridged by N,N′-bis(N-hydroxyethylaminoethyl)oxamide,” Journal of Inorganic Biochemistry, vol. 103, no. 5, pp. 833–844, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. Q. Liu, J. Zhang, M. Q. Wang et al., “Synthesis, DNA binding and cleavage activity of macrocyclic polyamines bearing mono- or bis-acridine moieties,” European Journal of Medicinal Chemistry, vol. 45, no. 11, pp. 5302–5308, 2010. View at Publisher · View at Google Scholar · View at Scopus
  20. K. S. Ghosh, B. K. Sahoo, D. Jana, and S. Dasgupta, “Studies on the interaction of copper complexes of ()-epicatechin gallate and ()-epigallocatechin gallate with calf thymus DNA,” Journal of Inorganic Biochemistry, vol. 102, no. 9, pp. 1711–1718, 2008. View at Publisher · View at Google Scholar · View at Scopus
  21. J. R. Lacowicz, Principles of Fluorescence Spectroscopy, Springer, New York, NY, USA, 3rd edition, 2006.
  22. J. P. Peberdy, J. Malina, S. Khalid, M. J. Haman, and A. Rodger, “Influence of surface shape on DNA binding of bimetallo helicates,” The Journal of Inorganic Biochemistry, vol. 101, no. 11-12, pp. 1937–1945, 2007. View at Google Scholar
  23. M. R. Eftink and C. A. Ghiron, “Fluorescence quenching of indole and model micelle systems,” Journal of Physical Chemistry, vol. 80, no. 5, pp. 486–493, 1976. View at Google Scholar · View at Scopus
  24. M. R. Eftink and C. A. Ghiron, “Fluorescence quenching studies with proteins,” Analytical Biochemistry, vol. 114, no. 2, pp. 199–227, 1981. View at Google Scholar · View at Scopus