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Bioinorganic Chemistry and Applications
Volume 2006 (2006), Article ID 83131, 13 pages
http://dx.doi.org/10.1155/BCA/2006/83131

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

1Department of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan
2Laboratorio di Chimica Bioinorganica, Dipartimento di Chimica, Polo Scientifico e Tecnologico, Università degli Studi di Firenze, Rm 188, Via della Lastruccia 3, Sesto Fiorentino, Florence 50019, Italy

Received 2 July 2006; Revised 12 October 2006; Accepted 13 October 2006

Copyright © 2006 Zahid H. Chohan 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. Z H Chohan, M Praveen, and A Ghaffar, “Structural and biological behaviour of Co(II), Cu(II) and Ni(II) metal complexes of some amino acid derived Schiff-bases,” Metal-Based Drugs, vol. 4, no. 5, pp. 267–272, 1997. View at Publisher · View at Google Scholar
  2. 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
  3. Z H Chohan and S Kausar, “Synthesis, structural and biological studies of nickel(II), copper(II) and zinc(II) chelates with tridentate Schiff bases having NNO and NNS donor systems,” Chemical and Pharmaceutical Bulletin, vol. 41, no. 5, pp. 951–953, 1993. View at Google Scholar
  4. 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
  5. 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. View at Google Scholar
  6. 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
  7. M J Seven and L A Johnson, Metal Binding in Medicine, Lippincott, Philadelphia, Pa, 4th edition, 1960.
  8. R S Srivastava, “Studies on some antifungal transition metal chelates of 2-(2-hydroxybenzylideneamino) benzimidazole,” Indian Journal of Chemistry, vol. 29A, p. 1024, 1990. View at Google Scholar
  9. V K Patel, A M Vasanwala, and C N Jejurkar, “Synthesis of mixed Schiff base complexes of copper(II) and nickel(II) and their spectral, magnetic and antifungal studies,” Indian Journal of Chemistry, vol. 28A, p. 719, 1989. View at Google Scholar
  10. 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. View at Publisher · View at Google Scholar
  11. R Vitturi, C Mansueto, A Gianguzza, F Maggio, A Pellerito, and L Pellerito, “Organometallic complexes with biological molecules. III: in vivo cytotoxicity of diorganotin(IV)chloro and triorganotin(IV)chloro derivatives of penicillin g on chromosomes of aphanius fasciatus (pisces, cyprinodontiformes),” Applied Organometallic Chemistry, vol. 8, no. 6, pp. 509–515, 1994. View at Publisher · View at Google Scholar
  12. L Pellerito, F Maggio, A Consigilo, A Pellerito, G C Stocco, and S Gremaudo, “Organometallic complexes with biological molecules. IV: Di- and tri-organotin (IV) amoxicillin derivatives: solid-state and solution-phase spectroscopic investigations,” Applied Organometallic Chemistry, vol. 9, no. 3, pp. 227–239, 1995. View at Publisher · View at Google Scholar
  13. R Vitturi, B Zava, M S Colomba, A Pellerito, F Maggio, and L Pellerito, “Organometallic complexes with biological molecules. V: in vivo cytotoxicity of diorganotin(IV)-amoxicillin derivatives in mitotic chromosomes of rutilus rubilio (pisces, Cyprinidae),” Applied Organometallic Chemistry, vol. 9, no. 7, pp. 561–566, 1995. View at Publisher · View at Google Scholar
  14. B Rosenberg and L VanCamp, “The successful regression of large solid sarcoma 180 tumors by platinum compounds,” Cancer Research, vol. 30, no. 6, pp. 1799–1802, 1970. View at Google Scholar
  15. M J Cleare and J D Hoeschele, “Studies on the antitumor activity of group VIII transition metal complexes. I. Platinum (II) complexes,” Bioinorganic Chemistry, vol. 2, no. 3, pp. 187–210, 1973. View at Publisher · View at Google Scholar
  16. 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.
  17. A J Crowe, “The antitumour activity of tin compounds,” in Metal Based Antitumour Drugs. Vol. 1, pp. 103–149, Freud, London, UK, 1988. View at Google Scholar
  18. A K Saxena, “Organotin compounds: toxicology and biomedicinal applications,” Applied Organometallic Chemistry, vol. 1, no. 1, pp. 39–56, 1987. View at Publisher · View at Google Scholar
  19. A Furst, The Chemistry of Chelation in Cancer, Thomas, Springfield, Ill, 3rd edition, 1963.
  20. D R Williams, “Thermodynamic considerations in co-ordination. Part X. A potentiometric and calorimetric investigation of copper(II) histidine complexes in solution,” Journal of the Chemical Society. Dalton Transactions, no. 7, pp. 790–797, 1972. View at Publisher · View at Google Scholar
  21. A D Jones and D R Williams, “Thermodynamic considerations in co-ordination. Part IX. Heat capacity investigations into complex formation between some lanthanide(III) ions and histidine,” Journal of the Chemical Society A, pp. 3159–3162, 1971. View at Publisher · View at Google Scholar
  22. J M Pratt, Inorganic Chemistry of Vitamin B12, Academic Press, London, UK, 1972.
  23. S K Shapiro and F Schlenk, Transmethylation and Methionine Biosynthesis, University of Chicago Press, Chicago, Ill, 1965.
  24. I Sakyan, E Logoglu, S Arslan, N Sari, and N Akiyan, “Antimicrobial activities of N-(2-hydroxy-1-naphthalidene)-amino acid (glycine, alanine, phenylalanine, histidine, tryptophane) Schiff bases and their manganese(III) complexes,” Biometals, vol. 17, no. 2, pp. 115–120, 2004. View at Publisher · View at Google Scholar
  25. N Sari, S Arslan, E Logoglu, and I Sakiyan, “Antibacterial activities of some Amino acid Schiff bases,” G.U.J.Sci, vol. 16, no. 2, pp. 283–288, 2003. View at Google Scholar
  26. R JP Williams, “Role of transition metal ions in biological processes,” Royal Institute of Chemistry Reviews, vol. 1, no. 1, pp. 13–38, 1968. View at Publisher · View at Google Scholar
  27. H Sigel and D B McCormick, “Discriminating behavior of metal ions and ligands with regard to their biological significance,” Accounts of Chemical Research, vol. 3, no. 6, pp. 201–208, 1970. View at Publisher · View at Google Scholar
  28. E Sinn and C M Harris, “Schiff base metal complexes as ligands,” Coordination Chemistry Reviews, vol. 4, no. 4, pp. 391–422, 1969. View at Publisher · View at Google Scholar
  29. J A Stock, “The chemotherapy of cancer,” in The Biology of Cancer, p. 176, D. Van Nostrand, London, UK, 1966, chapter 9. View at Google Scholar
  30. P Clifford, S Singh, J Stjernswärd, and G Klein, “Long-term survival of patients with Burkitt's lymphoma: an assessment of treatment and other factors which may relate to survival,” Cancer Research, vol. 27, no. 12, pp. 2578–2615, 1967. View at Google Scholar
  31. J A Stock, “Chemotherapy of cancer,” Chemistry in Britain, vol. 6, no. 1, pp. 11–16, 1970. View at Google Scholar
  32. R C Maurya, D D Mishra, and S Pillai, “Studies on some mixed-ligand chelates of cobalt(II) involving acetoacetylarylamides and biologically active heterocyclic oxygen donors,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 27, no. 10, pp. 1453–1466, 1997. View at Google Scholar
  33. R C Maurya, R Verma, P K Trivedi, and H Singh, “Synthesis, magnetic and spectral studies of some mixed-ligand chelates of Bis(2-hydroxyacetophenonato)copper(II) with 2-or 3-pyrazoline-5-one derivatives,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 28, no. 2, pp. 311–329, 1998. View at Google Scholar
  34. R C Maurya, D D Mishra, S Mukherjee, and P K Trivedi, “Novel mixed-ligand derivatives of bis(acetylacetonato)-bis(methylacetoacetato) and bis(ethylacetoacetate)-nickel(II) with some potentially mono-, bi- and tri-dentate 2/3-pyrazoline-5-ones,” Transition Metal Chemistry, vol. 16, no. 5, pp. 524–527, 1991. View at Publisher · View at Google Scholar
  35. R C Maurya, D D Mishra, V Choubey, and I B Khan, “Studies on some novel mixed-ligand derivatives of bis(acetylacetonato)-, bis(methylacetoacetato)- and bis(ethylacetoacetato) cobalt(II) with 8-hydroxyquinoline sulfonamides and pyrazolone,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 20, p. 1103, 1990. View at Google Scholar
  36. K C Joshi and V K Pathak, “Metal chelates of fluorinated 1,3-diketones and related compounds,” Coordination Chemistry Reviews, vol. 22, no. 1-2, pp. 37–122, 1977. View at Publisher · View at Google Scholar
  37. R C Maurya, D D Mishra, and P K Trivedi, “Synthesis, magnetic and spectral studies of some mixed-ligand chelates of mercury(II) with acetoacetanilide/o-hydroxyacetophenone and 2/3-pyrazoline-5-one derivatives,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 24, p. 17, 1994. View at Google Scholar
  38. A I Vogel, A Textbook of Quantitative Inorganic Analysis, ELBS and Longman, London, UK, 4th edition, 1978.
  39. Atta-ur-Rahman, M I Choudhary, and W J Thomsen, Bioassay Techniques for Drug Development, Harwood Academic, Amsterdam, The Netherlands, 2001.
  40. J L McLauglin, C J Chang, and D L Smith, ““Bench top” bioassay for the discovery of bioactive natural products: an update,” in Studies in Natural Products Chemistry. Vol. 9, Atta-ur-Rahman, Ed., pp. 383–409, Elsevier Science, Amsterdam, The Netherlands, 1991. View at Google Scholar
  41. D J Finney, Probit Analysis, Cambridge University Press, Cambridge, UK, 3rd edition, 1971.
  42. 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
  43. R L Carlin, Transition Metal Chemistry, Marcel Decker, New York, NY, 2nd edition, 1965.
  44. L J Bellamy, The Infrared Spectra of Complex Molecules, John Wiley & Sons, New York, NY, 1971.
  45. J R Ferrero, Low-Frequency Vibrations of Inorganic and Coordination Compound, John Wiley & Sons, New York, NY, 1971.
  46. K Nakamoto, Infrared Spectra of Inorganic and Coordination Compounds, Wiley Interscience, New York, NY, 2nd edition, 1970.
  47. W W Simmons, The Sadtler Handbook of Proton NMR Spectra, Sadtler Research Laboratories, Philadelphia, Pa, 1978.
  48. D J Pasto, Organic Structure Determination, Prentice Hall, London, UK, 1969.
  49. A BP Lever, J Lewis, and R S Nyholm, “Square-planar bisethylenediamine-metal complexes,” Journal of Chemical Society, p. 2552, 1963. View at Google Scholar
  50. W E Estes, D P Gavel, W E Hatfield, and D J Hodgson, “Magnetic and structural characterization of dibromo- and dichlorobis(thiazole)copper(II),” Inorganic Chemistry, vol. 17, no. 6, pp. 1415–1421, 1978. View at Publisher · View at Google Scholar
  51. C J Ballhausen , An Introduction to Ligand Field Theory, McGraw Hill, New York, NY, 1962.
  52. A BP Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, The Netherlands, 1984.
  53. K Y Lau, A Mayr, and K-K Cheung, “Synthesis of transition metal isocyanide complexes containing hydrogen bonding sites in peripheral locations,” Inorganica Chimica Acta, vol. 285, no. 2, pp. 223–232, 1999. View at Publisher · View at Google Scholar
  54. PP Dholakiya and MN Patel, “Metal complexes: Preparation, magnetic, spectral, and biocidal studies of some mixed-ligand complexes with Schiff bases containing NO and NN donor atoms,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 34, no. 3, pp. 553–563, 2004. View at Publisher · View at Google Scholar
  55. Z H Chohan, “Synthesis and biological properties of Cu(II) complexes with 1,1-disubstituted ferrocenes,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 34, no. 5, pp. 833–846, 2004. View at Publisher · View at Google Scholar
  56. Z H Chohan, C T Supuran, and A Scozzafava, “Metalloantibiotics: synthesis and antibacterial activity of cobalt(II), copper(II), nickel(II) and zinc(II) complexes of kefzol,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 19, no. 1, pp. 79–84, 2004. View at Publisher · View at Google Scholar
  57. Z H Chohan, A Scozzafava, and C T Supuran, “Synthesis of biologically active Co(II), Cu(II), Ni(II), and Zn(II) complexes of symmetrically 1,1-disubstituted ferrocene-derived compounds,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, vol. 33, no. 2, pp. 241–257, 2003. View at Publisher · View at Google Scholar
  58. Z H Chohan, “Antibacterial copper(II) complexes of 1,1-symmetric ferrocene-derived Schiff-base ligands: studies of the effect of anions on their antibacterial properties,” Applied Organometallic Chemistry, vol. 16, no. 1, pp. 17–20, 2002. View at Publisher · View at Google Scholar
  59. Z H Chohan, M A Farooq, A Scozzafava, and C T Supuran, “Antibacterial schiff bases of oxalyl-hydrazine/diamide incorporating pyrrolyl and salicylyl moieties and of their zinc(II) complexes,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 17, no. 1, pp. 1–7, 2002. View at Publisher · View at Google Scholar
  60. S U Rehman, Z H Chohan, F Gulnaz, and C T Supuran, “In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 20, no. 4, pp. 333–340, 2005. View at Publisher · View at Google Scholar
  61. Z H Chohan and C T Supuran, “Organometallic compounds with biologically active molecules: in vitro antibacterial and antifungal activity of some 1,1-(dicarbohydrazono) ferrocenes and their cobalt(II), copper(II), nickel(II) and zinc(II) complexes,” Applied Organometallic Chemistry, vol. 19, no. 12, pp. 1207–1214, 2005. View at Publisher · View at Google Scholar
  62. Z H Chohan and C T Supuran, “In-vitro antibacterial and cytotoxic activity of cobalt (II), copper (II), nickel (II) and zinc (II) complexes of the antibiotic drug cephalothin (keflin),” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 20, no. 5, pp. 463–468, 2005. View at Publisher · View at Google Scholar
  63. Z H Chohan, C T Supuran, and A Scozzafava, “Metal binding and antibacterial activity of ciprofloxacin complexes,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 20, no. 3, pp. 303–307, 2005. View at Publisher · View at Google Scholar
  64. Z H Chohan, “Antibacterial and antifungal ferrocene incorporated dithiothione and dithioketone compounds,” Applied Organometallic Chemistry, vol. 20, no. 2, pp. 112–116, 2006. View at Publisher · View at Google Scholar
  65. Z H Chohan, M Arif, Z Shafiq, M Yaqub, and C T Supuran, “In vitro antibacterial, antifungal & cytotoxic activity of some isonicotinoylhydrazide Schiff's bases and their cobalt (II), copper (II), nickel (II) and zinc (II) complexes,” Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 21, no. 1, pp. 95–103, 2006. View at Publisher · View at Google Scholar
  66. B N Meyer, N R Ferrigni, J E Putnam, L B Jacobsen, D E Nichols, and J L McLaughlin, “Brine shrimp: a convenient general bioassay for active plant constituents,” Planta Medica, vol. 45, no. 1, pp. 31–34, 1982. View at Google Scholar