Table of Contents
Metal-Based Drugs
Volume 2008 (2008), Article ID 362105, 11 pages
http://dx.doi.org/10.1155/2008/362105
Research Article

Synthesis, Structure, Electrochemistry, and Spectral Characterization of Bis-Isatin Thiocarbohydrazone Metal Complexes and Their Antitumor Activity Against Ehrlich Ascites Carcinoma in Swiss Albino Mice

1P. G. Department of Studies in Chemistry, Karnatak University, Dharwad 580 003, India
2Department of Pharmacology, Manipal College of Pharmaceutical Sciences, Manipal Academy of Higher Education, Manipal 576 104, India

Received 10 May 2007; Revised 7 July 2007; Accepted 6 August 2007

Academic Editor: Jannie C. Swarts

Copyright © 2008 M. P. Sathisha 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. A. Ali and S. E. Livingstone, “Metal complexes of sulphur-nitrogen chelating agents,” Coordination Chemistry Reviews, vol. 13, no. 2-3, pp. 101–132, 1974. View at Publisher · View at Google Scholar
  2. H. Stunzi, “Can chelationbe important in the antiviral activity of isatin β-thiosemicarbazones?,” Australian Journal of Chemistry, vol. 35, no. 6, pp. 1145–1155, 1982.
  3. M. J. M. Campbell, “Transition metal complexes of thiosemicarbazide and thiosemicarbazones,” Coordination Chemistry Reviews, vol. 15, no. 2-3, pp. 279–319, 1975. View at Publisher · View at Google Scholar
  4. S. B. Padhyé and G. B. Kauffman, “Transition metal complexes of semicarbazones and thiosemicarbazones,” Coordination Chemistry Reviews, vol. 63, pp. 127–160, 1985. View at Publisher · View at Google Scholar
  5. A. A. A. Emara, S. M. E. Khalil, and K. A. R. Salib, “Di-, tri- and poly-nuclear transition metal complexes of 3,4-diacetyl-2,5-hexanedione,” Journal of Coordination Chemistry, vol. 36, no. 4, pp. 289–301, 1995. View at Publisher · View at Google Scholar
  6. H. Cheng, D. Chun-Ying, F. Chen-Jie, L. Yong-Jiang, and M. Qing-Jin, “Self-assembled macrocyclic tetranuclear molecular square [Ni(HL)]44+ and molecular rectangle [Cu2Cl2L]2 {H2L = bis[phenyl(2-pyridyl)methanone] thiocarbazone},” Journal of the Chemical Society, Dalton Transactions, no. 7, pp. 1207–1212, 2000. View at Publisher · View at Google Scholar
  7. B. Rosenberg, “Some biological effects of platinum compounds: new agents for the control of tumours,” Platinum Metals Review, vol. 15, no. 2, pp. 42–51, 1971.
  8. D. R. Williams, “Metals, ligands, and cancer,” Chemical Reviews, vol. 72, no. 3, pp. 203–213, 1972. View at Publisher · View at Google Scholar
  9. B. G. Patil, B. R. Havinale, J. M. Shallom, and M. P. Chitnis, “Syntheses and spectroscopic studies of potential antitumor copper(II) complexes with 5-phenylazo-3-methoxy salicylidene thiosemicarbazone and N4 substituted thiosemicarbazones,” Journal of Inorganic Biochemistry, vol. 36, no. 2, pp. 107–113, 1989. View at Publisher · View at Google Scholar
  10. D. L. Klayman, J. P. Scovill, J. F. Bartosevich, and J. Bruce, “2-Acetylpyridine thiosemicarbazones. 5. 1-[1-(2-Pyridyl)ethyl]-3-thiosemicarbazides as potential antimalarial agents,” Journal of Medicinal Chemistry, vol. 26, no. 1, pp. 35–39, 1983. View at Publisher · View at Google Scholar
  11. A. M. Elsome, J. M. T. Hamilton-Miller, W. Brumfitt, and W. C. Noble, “Antimicrobial activities in vitro and in vivo of transition element complexes containing gold(I) and osmium(VI),” Journal of Antimicrobial Chemotherapy, vol. 37, no. 5, pp. 911–918, 1996. View at Publisher · View at Google Scholar
  12. A. Scozzafava, L. Menabuoni, F. Mincione, G. Mincione, and C. T. Supuran, “Carbonic anhydrase inhibitors: synthesis of sulfonamides incorporating dtpa tails and of their zinc complexes with powerful topical antiglaucoma properties,” Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 4, pp. 575–582, 2001. View at Publisher · View at Google Scholar
  13. C. Walsh, “Enabling the chemistry of life,” Nature, vol. 409, no. 6817, pp. 226–231, 2001. View at Publisher · View at Google Scholar · View at PubMed
  14. S. Kirschner, Y.-K. Wei, D. Francis, and J. Bergman, “Anticancer and potential antiviral activity of complex inorganic compounds,” Journal of Medicinal Chemistry, vol. 9, no. 3, pp. 369–372, 1966. View at Publisher · View at Google Scholar
  15. W. Beerheide, M. M. Sim, Y.-J. Tan, H.-U. Bernard, and A. E. Ting, “Inactivation of the human papillomavirus-16 e6 oncoprotein by organic disulfides,” Bioorganic and Medicinal Chemistry, vol. 8, no. 11, pp. 2549–2560, 2000. View at Publisher · View at Google Scholar
  16. Z. H. Chohan, A. Scozzafava, and C. T. Supuran, “Unsymmetrical 1,1-disubstituted ferrocenes: synthesis of Co(ii), Cu(ii), Ni(ii) and Zn(ii) chelates of ferrocenyl -1-thiadiazolo-1-tetrazole, -1-thiadiazolo-1-triazole and -1-tetrazolo-1-triazole with antimicrobial properties,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 17, no. 4, pp. 261–266, 2002. View at Publisher · View at Google Scholar · View at PubMed
  17. M. Ul-Hassan, Z. H. Chohan, A. Scozzafava, and C. T. Supuran, “Carbonic anhydrase inhibitors: schiff's bases of aromatic and heterocyclic sulfonamides and their metal complexes,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 19, no. 3, pp. 263–267, 2004. View at Publisher · View at Google Scholar · View at PubMed
  18. M. Ul-Hassan, Z. H. Chohan, and C. T. Supuran, “Antibacterial Zn(II) compounds of Schiff bases derived from some benzothiazoles,” Main Group Metal Chemistry, vol. 25, no. 5, pp. 291–296, 2002.
  19. Z. H. Chohan, A. Scozzafava, and C. T. Supuran, “Zinc complexes of benzothiazole-derived Schiff bases with antibacterial activity,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 18, no. 3, pp. 259–263, 2003. View at Publisher · View at Google Scholar
  20. F. Maggio, A. Pellerito, L. Pellerito, S. Grimaudo, C. Mansueto, and R. Vitturi, “Organometallic complexes with biological molecules II. Synthesis, solid-state characterization and in vivo cytotoxicity of diorganotin(IV)chloro and triorganotin(IV)chloro derivatives of penicillin G,” Applied Organometallic Chemistry, vol. 8, no. 1, pp. 71–85, 1994.
  21. V. A. Narayanan, M. Nasr, and K. D. Paull, in Tin Based Antitumour Drugs, vol. H 37 of NATO ASI Series, Springer, Berlin, Germany, 1990.
  22. Z. H. Chohan, M. Arif, M. A. Akhtar, and C. T. Supuran, “Metal-based antibacterial and antifungal agents: synthesis, characterization, and in vitro biological evaluation of Co(II), Cu(II), Ni(II), and Zn(II) complexes with amino acid-derived compounds,” Bioinorganic Chemistry and Applications, vol. 2006, Article ID 83131, 13 pages, 2006. View at Publisher · View at Google Scholar · View at PubMed
  23. L. F. Audrieth, E. S. Scott, and P. S. Kippur, “Hydrazine derivatives of the carbonic and thiocarbonic acids. I. The preparation and properties of thiocarbohydrazide,” Journal of Organic Chemistry, vol. 19, no. 5, pp. 733–741, 1954. View at Publisher · View at Google Scholar
  24. B. N. Mayer, N. R. Ferrigni, J. E. Putnam, L. B. Jacobsen, D. E. Nichols, and J. L. McLaughlin, “Brine shrimp: a convenient general bioassay for active plants constituents,” Planta Medica, vol. 45, pp. 31–34, 1982. View at Publisher · View at Google Scholar · View at PubMed
  25. M. N. Ghosh, Fundamentals of Experimental Pharmacology, Scientific Book Agency, Calcutta, India, 2nd edition, 1984.
  26. P. U. Devi, F. E. Solomon, and A. C. Sharada, “In vivo tumor inhibitory and radiosensitizing effects of an Indian medicinal plant, Plumbago rosea on experimental mouse tumors,” Indian Journal of Experimental Biology, vol. 32, no. 8, pp. 523–528, 1994.
  27. P. U. Devi, B. S. S. Rao, and F. E. Solomon, “Effect of plumbagin on the radiation induced cytogenetic and cell cycle changes in mouse Ehrlich ascites carcinoma in vivo,” Indian Journal of Experimental Biology, vol. 36, no. 9, pp. 891–895, 1998.
  28. A. E. Eckhardt, B. N. Malone, and I. J. Goldstein, “Inhibition of Ehrlich ascites tumor cell growth by Griffonia simplicifolia I lectin in vivo,” Cancer Research, vol. 42, no. 8, pp. 2977–2979, 1982.
  29. F. E. D'Amour, F. R. Blood, and D. A. Belden Jr., Manual for Laboratory Work in Mammalian Physiology, The University of Chicago Press, Chicago, Tex, USA, 3rd edition, 1965.
  30. H. W. Seeley and P. J. van Demark, Microbs in Action: A laboratory Manual of Microbiology, D. B. Taraporevala Sons & Co. Pvt., Bombay, India, 2nd edition, 1975.
  31. 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 Publisher · View at Google Scholar
  32. K. Nakomoto, Infrared Spectra of Inorganic and Coordination Compounds, Wiley-Interscience, New York, NY, USA, 2nd edition, 1970.
  33. P. Bindu, M. R. Kurup, and T. R. Satyakeerty, “Epr, cyclic voltammetric and biological activities of copper(II) complexes of salicylaldehyde N(4)-substituted thiosemicarbazone and heterocyclic bases,” Polyhedron, vol. 18, no. 3-4, pp. 321–331, 1998. View at Publisher · View at Google Scholar
  34. N. W. Alcock, V. M. Tracy, and T. C. Waddington, “Acetates and acetato-complexes—part 2: spectroscopic studies,” Journal of Chemical Society, Dalton Transactions, no. 21, pp. 2243–2246, 1979. View at Publisher · View at Google Scholar
  35. W. E. Estes, J. R. Wasson, J. W. Hall, and W. E. Hatfield, “Characterization of some mixed-halide copper(II) dimers of the general formula [Cu2XnX6n]2 (X = Cl and X = Br): evidence for the preference of chloride bridges in the mixed-halide species,” Inorganic Chemistry, vol. 17, no. 12, pp. 3657–3664, 1978. View at Publisher · View at Google Scholar
  36. K. Balakrishnan and K. K. Aravindakshan, “Metal complexes of 3,4-dimethoxybenzaldehyde thiosemicarbazone,” Journal of the Indian Chemical Society, vol. 68, no. 4, pp. 187–190, 1991.
  37. A. B. P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, The Netherlands, 1984.
  38. Z. Shirin and R. N. Mukherj, “Synthesis, spectra and electrochemistry of ruthenium(III) complexes with cage-like Schiff-base ligands,” Polyhedron, vol. 11, no. 20, pp. 2625–2630, 1992. View at Publisher · View at Google Scholar
  39. R. I. Geran, N. H. Greenberg, M. M. MacDonald, A. M. Schumacher, and B. J. Abbott, “Protocols for screening chemical agents and natural products against animal tumors and other biological systems,” Cancer Chemotherapy Reports, vol. 3, p. 1, 1972.
  40. C. Orberlling and M. Guerin, “The role of virus in the production of cancer,” Advances in Cancer Research, vol. 2, pp. 353–423, 1954.
  41. J. M. Vincent, “Distortion of fungal hyphae in the presence of certain inhibitors,” Nature, vol. 159, p. 850, 1947.