Table of Contents
ISRN Inorganic Chemistry
Volume 2013, Article ID 250791, 11 pages
http://dx.doi.org/10.1155/2013/250791
Research Article

Synthesis, Crystal Structure, Antioxidant, Antimicrobial, and Mutagenic Activities and DNA Interaction Studies of Ni(II) Schiff Base 4-Methoxy-3-benzyloxybenzaldehyde Thiosemicarbazide Complexes

1Department of Chemistry, Central College Campus, Bangalore University, Bangalore 560001, India
2Department of Pharmaceutical Technology, Defence Research Laboratory, Tezpur 784001, India
3Department of Fruit and Vegetable Technology, CFTRI, Mysore 570020, India
4Department of Inorganic and Physical Chemistry, Indian Institute of Science, Sir CV Raman Avenue, Bangalore 560012, India

Received 31 July 2013; Accepted 18 August 2013

Academic Editors: P. Deplano and K. Dhara

Copyright © 2013 P. R. Chetana 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. N. Raman, S. Johnson Raja, and A. Sakthivel, “Transition metal complexes with Schiff-base ligands: 4-Aminoantipyrine based derivatives—a review,” Journal of Coordination Chemistry, vol. 62, no. 5, pp. 691–709, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. M. A. Ali, N. E. H. Ibrahim, R. J. Butcher, J. P. Jasinski, J. M. Jasinski, and J. C. Bryan, “Synthesis and characterization of some four-and five-coordinate copper(II) complexes of 6-methyl-2-formylpyridinethiosemicarbazone (HNNS) and the X-ray crystal structures of the [Cu(NNS)(CH3COO)(H2O)] and [Cu(HNNS)(H2O)(SO4)]·H2O complexes,” Polyhedron, vol. 17, no. 11-12, pp. 1803–1809, 1998. View at Google Scholar · View at Scopus
  3. Y.-J. Kim, S.-O. Kim, Y.-I. Kim, and S.-N. Choi, “A mimic molecule of blue copper protein active site [(−)-sparteine-N,N′](maleonitriledithiolato-S,S′)copper(II),” Inorganic Chemistry, vol. 40, no. 17, pp. 4481–4484, 2001. View at Publisher · View at Google Scholar · View at Scopus
  4. M. M. van Dyke and P. B. Dervan, “Echinomycin binding sites on DNA,” Science, vol. 225, no. 4667, pp. 1122–1127, 1984. View at Google Scholar · View at Scopus
  5. 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 Google Scholar · View at Scopus
  6. P. V. Bernhardt, J. Mattsson, and D. R. Richardson, “Complexes of cytotoxic chelators from the dipyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues,” Inorganic Chemistry, vol. 45, no. 2, pp. 752–760, 2006. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Akbar 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 Google Scholar · View at Scopus
  8. C. Costello, T. Karpanen, P. A. Lambert et al., “Thiosemicarbazones active against Clostridium difficile,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 5, pp. 1708–1711, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. J. S. Sebolt, S. V. Scavone, and C. D. Pinter, “Pyrazoloacridines, a new class of anticancer agents with selectivity against solid tumors in vitro,” Cancer Research, vol. 47, no. 16, pp. 4299–4304, 1987. View at Google Scholar · View at Scopus
  10. S. Rekha and K. R. Nagasundara, “Complexes of the Schiff base derived from 4-aminophenyl benzimidazole and 2,2′- dehydropyrollidene-N-aldehyde with Zn (II), Cd (II) and Hg (II) halides,” Indian Journal of Chemistry A, vol. 45, no. 11, pp. 2421–2425, 2006. View at Google Scholar · View at Scopus
  11. D. Kovala-Demertzi, A. Papageorgiou, L. Papathanasis et al., “In vitro and in vivo antitumor activity of platinum(II) complexes with thiosemicarbazones derived from 2-formyl and 2-acetyl pyridine and containing ring incorporated at N(4)-position: synthesis, spectroscopic study and crystal structure of platinum(II) complexes with thiosemicarbazones, potential anticancer agents,” European Journal of Medicinal Chemistry, vol. 44, no. 3, pp. 1296–1302, 2009. View at Publisher · View at Google Scholar · View at Scopus
  12. M. C. Rodrìguez-Argüelles, M. B. Ferrari, F. Bisceglie et al., “Synthesis, characterization and biological activity of Ni, Cu and Zn complexes of isatin hydrazones,” Journal of Inorganic Biochemistry, vol. 98, no. 2, pp. 313–321, 2004. View at Publisher · View at Google Scholar · View at Scopus
  13. F. Liang, P. Wang, X. Zhou et al., “Nickle(II) and cobalt(II) complexes of hydroxyl-substituted triazamacrocyclic ligand as potential antitumor agents,” Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 8, pp. 1901–1904, 2004. View at Publisher · View at Google Scholar · View at Scopus
  14. J. Suh, “Synthetic artificial peptidases and nucleases using macromolecular catalytic systems,” Accounts of Chemical Research, vol. 36, no. 7, pp. 562–570, 2003. View at Publisher · View at Google Scholar · View at Scopus
  15. R. T. Kovacic, J. T. Welch, and S. J. Franklin, “Sequence-selective DNA cleavage by a chimeric metallopeptide,” Journal of the American Chemical Society, vol. 125, no. 22, pp. 6656–6662, 2003. View at Publisher · View at Google Scholar · View at Scopus
  16. D. S. Sigman, “Nuclease activity of 1,10-phenanthroline-copper ion,” Accounts of Chemical Research, vol. 19, no. 6, pp. 180–186, 1986. View at Google Scholar · View at Scopus
  17. D. S. Sigman, T. W. Bruice, A. Mazumder, and C. L. Sutton, “Targeted chemical nucleases,” Accounts of Chemical Research, vol. 26, no. 3, pp. 98–104, 1993. View at Google Scholar · View at Scopus
  18. 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
  19. R. M. Burger, “Cleavage of nucleic acids by bleomycin,” Chemical Reviews, vol. 98, no. 3, pp. 1153–1169, 1998. View at Google Scholar · View at Scopus
  20. B. M. Zeglis, V. C. Pierre, and J. K. Barton, “Metallo-intercalators and metallo-insertors,” Chemical Communications, no. 44, pp. 4565–4579, 2007. View at Publisher · View at Google Scholar · View at Scopus
  21. M. A. S. Aslam, S.-U. Mahmood, M. Shahid, A. Saeed, and J. Iqbal, “Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors,” European Journal of Medicinal Chemistry, vol. 46, no. 11, pp. 5473–5479, 2011. View at Publisher · View at Google Scholar · View at Scopus
  22. R. Rao, A. K. Patra, and P. R. Chetana, “Synthesis, structure, DNA binding and oxidative cleavage activity of ternary (l-leucine/isoleucine) copper(II) complexes of heterocyclic bases,” Polyhedron, vol. 27, no. 5, pp. 1343–1352, 2008. View at Publisher · View at Google Scholar · View at Scopus
  23. N. Walker and D. Stuart, “An empirical method for correcting diffractometer data for absorption effects,” Acta Crystallographica A, vol. 39, no. 1, pp. 158–166, 1983. View at Google Scholar · View at Scopus
  24. G. M. Sheldrick, SHELX-97, “Program For Crystal Structure Solution and Refinement”, University of Göttingen, Göttingen, Germany, 1997.
  25. B. Matthäus, “Antioxidant activity of extracts obtained from residues of different oilseeds,” Journal of Agricultural and Food Chemistry, vol. 50, no. 12, pp. 3444–3452, 2002. View at Publisher · View at Google Scholar · View at Scopus
  26. W. Brand-Williams, M. E. Cuvelier, and C. Berset, “Use of a free radical method to evaluate antioxidant activity,” Lebensmittel-Wissenschaft & Technologie, vol. 28, no. 1, pp. 25–30, 1995. View at Google Scholar · View at Scopus
  27. P. K. Mukherjee, R. Balasubramanian, K. Saha, B. P. Saha, and M. Pal, “Antibacterial efficiency of Nelumbo nucifera (nymphaeaceae) rhizomes extract,” Indian Drugs, vol. 32, no. 6, pp. 274–276, 1995. View at Google Scholar · View at Scopus
  28. D. M. Maron and B. N. Ames, “Revised methods for the Salmonella mutagenicity test,” Mutation Research, vol. 113, no. 3-4, pp. 173–215, 1983. View at Google Scholar · View at Scopus
  29. J. Marmur, “A procedure for the isolation of deoxyribonucleic acid from micro-organisms,” Journal of Molecular Biology, vol. 3, pp. 208–218, 1961. View at Google Scholar
  30. M. E. Reichmann, S. A. Rice, C. A. Thomas, and P. Doty, “A further examination of the molecular weight and size of desoxypentose nucleic acid,” Journal of the American Chemical Society, vol. 76, no. 11, pp. 3047–3053, 1954. View at Google Scholar · View at Scopus
  31. A. Wolfe, G. H. Shimer Jr., 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
  32. J. B. LePecq and C. Paoletti, “A fluorescent complex between ethidium bromide And nucleic acids. Physical-chemical characterization,” Journal of Molecular Biolology, vol. 27, pp. 87–106, 1967. View at Google Scholar
  33. S. Neidle, “DNA minor-groove recognition by small molecules,” Natural Product Reports, vol. 18, pp. 291–309, 2001. View at Google Scholar
  34. J. Bernadou, G. Pratviel, F. Bennis, M. Girardet, and B. Meunier, “Potassium monopersulfate and a water-soluble manganese porphyrin complex, [Mn(TMPyP)](OAc)5, as an efficient reagent for the oxidative cleavage of DNA,” Biochemistry, vol. 28, no. 18, pp. 7268–7275, 1989. View at Google Scholar · View at Scopus
  35. 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
  36. S. Chandra and U. Kumar, “Spectral studies of coordination compounds of cobalt(II) with thiosemicarbazone of heterocyclic ketone,” Spectrochimica Acta A, vol. 62, no. 4-5, pp. 940–944, 2005. View at Publisher · View at Google Scholar · View at Scopus
  37. N. S. Youssef and K. H. Hegab, “Synthesis and characterization of some transition metal complexes of thiosemicarbazones derived from 2-acetylpyrrole and 2-acetylfuran,” Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, vol. 35, no. 5, pp. 391–399, 2005. View at Publisher · View at Google Scholar · View at Scopus
  38. C. Sanchez-Moreno, J. A. Larrauri, and F. Saura-Calixto, “A procedure to measure the antiradical efficiency of polyphenols,” Journal of the Science of Food and Agriculture, vol. 76, no. 2, pp. 270–276, 1998. View at Google Scholar
  39. A. R. Burkanudeen, R. S. Azarudeen, M. A. R. Ahamed, and W. B. Gurnule, “Kinetics of thermal decomposition and antimicrobial screening of terpolymer resins,” Polymer Bulletin, vol. 67, no. 8, pp. 1553–1568, 2011. View at Publisher · View at Google Scholar · View at Scopus
  40. M. S. Refat and N. M. El-Metwaly, “Spectral, thermal and biological studies of Mn(II) and Cu(II) complexes with two thiosemicarbazide derivatives,” Spectrochimica Acta A, vol. 92, pp. 336–346, 2012. View at Publisher · View at Google Scholar · View at Scopus
  41. C. V. Kumar, J. K. Barton, and N. J. Turro, “Photophysics of ruthenium complexes bound to double helical DNA,” Journal of the American Chemical Society, vol. 107, no. 19, pp. 5518–5523, 1985. View at Google Scholar · View at Scopus
  42. S. Mahadevan and M. Palaniandavar, “Spectroscopic and voltammetric studies of copper (II) complexes of bis(pyrid-2-yl)-di/trithia ligands bound to calf thymus DNA,” Inorganica Chimica Acta, vol. 254, no. 2, pp. 291–302, 1997. View at Google Scholar · View at Scopus
  43. M. Asadi, E. Safaei, B. Ranjbar, and L. Hasani, “Thermodynamic and spectroscopic study on the binding of cationic ZD(II) and Co(II) tetrapyridinoporphyrazines to calf thymus DNA: the role of the central metal in binding parameters,” New Journal of Chemistry, vol. 28, no. 10, pp. 1227–1234, 2004. View at Publisher · View at Google Scholar · View at Scopus
  44. J. M. Kelly, A. B. Tossi, D. J. Mcconnell, and C. Ohuigin, “A study of the interactions of some polypyridylruthenium(II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation,” Nucleic Acids Research, vol. 13, no. 17, pp. 6017–6034, 1985. View at Publisher · View at Google Scholar · View at Scopus
  45. O. Zelenko, J. Gallagher, and D. S. Sigman, “Scission of DNA with Bis(1,10-phenanthroline)copper without Intramolecular Hydrogen Migration,” Angewandte Chemie (International Edition), vol. 36, no. 24, pp. 2776–2778, 1997. View at Google Scholar · View at Scopus
  46. D. S. Sigman, “Chemical nucleases,” Biochemistry, vol. 29, no. 39, pp. 9097–9105, 1990. View at Google Scholar · View at Scopus