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Synthesis, characterization and biological activities of homo-binuclear Cu(II) and Zn(II) complexes derived from 2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde derivatives

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Central European Journal of Chemistry

Abstract

Few novel binuclear Schiff base metal complexes [M2LCl3], where M = Cu(II) and Zn(II); L= 2,6-bis-({2-[(3-hydroxy-4-nitrobenzylidene)amino]ethylimino}methyl)-4-methylphenol (BHEM), 2,6-bis-({2-[(3,4-dimethoxybenzylidene)amino]ethylimino} methyl)-4-methylphenol (BDEM) and 2,6-bis-({2-[(2,3,5-trichlorobenzylidene)amino]ethylimino}methyl)-4-methylphenol (BTEM), have been synthesized and characterized by analytical and spectral data. The data suggest that BHEM/BDEM/BTEM ligands afford square-pyramidal/distorted square-pyramidal geometry on metalation with Zn(II)/Cu(II). The binding behaviour of these complexes with DNA has been investigated using electronic absorption spectroscopy as well as viscosity and voltammetric measurements; the results show that they interact with DNA through intercalating way. From the DNA cleavage study of these complexes, investigated by gel electrophoresis, we found that they efficiently cleave supercoiled pUC19 DNA in the presence of a reducing agent (3-mercaptopropionic acid) and on irradiation with UV light of 360 nm wavelength. The mechanism reveals that singlet oxygen (1O2) plays a significant role in the photo cleavage. The superoxide dismutase (SOD) mimetic activity of the synthesized complexes demonstrates that most of the complexes have promising SOD-mimetic activity. The antimicrobial study indicates that the complexes inhibit the growth of bacteria and fungi more than the free ligands.

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References

  1. M. Shakir, N. Begum, Y. Azim, S. Parveen, Synth. React. Inorg. Met-Org. Chem. 33, 1367 (2003)

    Article  CAS  Google Scholar 

  2. B. Adhikari, A.K. Biswas, K. Nag, P. Zanello, A. Cinquantini, Polyhedron 6, 897 (1987)

    Article  Google Scholar 

  3. K.D. Karlin, Z. Tyeklar, In: G.L. Eichhorn, L. Marzilli (Eds.), Advances in Inorganic Biochemistry (Prentice Hall, Englewood Cliffs, NJ, 1994) Vol. 9

    Google Scholar 

  4. K.D. Karluvi, Z. Tyeklar (Eds.), Bioinorganic Chemistry of Copper (Chapman and Hall, New York, 1993)

    Google Scholar 

  5. A.M. Thomas, G. Neelakanta, S. Mahadevan, M. Nethaji, A.R. Chakravarty, Eur. J. Inorg. Chem. 2720 (2002)

  6. S.C. Zhang, Y. Shao, C. Tu, C.H. Dai, Z.J. Guo, Chin. J. Inorg. Chem. 20, 1159 (2004)

    CAS  Google Scholar 

  7. Q.L. Li, et al., Bioorg. Med. Chem. 14, 4151 (2006)

    Article  CAS  Google Scholar 

  8. S.G. Kang, G.R. Jeong, Inorg. Chem. Commun. 12, 62 (2009)

    Article  CAS  Google Scholar 

  9. K.E. Erkkila, D.T. Odom, J.K. Barton, Chem. Rev. 99, 2777 (1999)

    Article  CAS  Google Scholar 

  10. L.J.K. Boerner, J.M. Zaleski, Curr. Opin. Chem. Biol. 9, 135 (2005)

    Article  CAS  Google Scholar 

  11. R. Bannet, Chemical Aspects of Photodynamic Therapy (Gorden and Breach, London, 2001)

    Google Scholar 

  12. M.R. Detly, S.L. Gibson, S.J. Wagner, J. Med. Chem. 47, 3897 (2004)

    Article  Google Scholar 

  13. F.S. Mackay et al., Proc. Natl. Acad. Sci. USA 104, 207423 (2007)

    Article  Google Scholar 

  14. L.C. Xu, S. Shi, J. Li, S.Y. Liao, K.C. Zheng, L.N. Ji, Dalton Trans. 291 (2008)

  15. A.K. Patra, T. Bhowmick, S. Ramakumar, A.R. Chakravarty, Inorg. Chem. 46, 9030 (2007)

    Article  CAS  Google Scholar 

  16. M.J. Fernandez, B. Wilson, M. Palacios, M.M. Rodrigo, K.B. Grant, A. Lorente, Bioconjugate Chem. 18, 121 (2007)

    Article  CAS  Google Scholar 

  17. D.D. Perrin, W.L.F. Armarego, D.R. Perrin, Purification of Laboratory Chemicals (Pergamon Press, Oxford, 1980)

    Google Scholar 

  18. N. Raman, S.J. Raja, J. Joseph, J.D. Raja, J. Chil. Chem. Soc. 52, 1138 (2007)

    Article  CAS  Google Scholar 

  19. A.D. Naik, V. K. Revankar, Indian J. Chem. 43A, 1447 (2004)

    CAS  Google Scholar 

  20. N. Raman, A. Sakthivel, K. Rajasekaran, J. Coord. Chem. 62, 1661 (2009)

    Article  CAS  Google Scholar 

  21. N.M. Aghatabay, Y. Mahmiani, H. Cevik, B. Dulger, Eur. J. Med. Chem. 44, 365 (2009)

    Article  CAS  Google Scholar 

  22. R.G. Bhirud, T.S. Srivastava, Inorg. Chim. Acta 173, 121 (1990)

    Article  CAS  Google Scholar 

  23. M.C.R. Arguelles et al., J. Inorg. Biochem. 103, 35 (2009)

    Article  Google Scholar 

  24. S. Niu, M. Zhao, R. Ren, S. Zhang, J. Inorg. Biochem. 103, 43 (2009)

    Article  CAS  Google Scholar 

  25. B.J. Hathaway, G. Wilkinson, R.D. Gillard, J.A. McCleverty, Comprehensive Coordination Chemistry (Pergamon Press, Oxford, UK, 1987) vol. 5

    Google Scholar 

  26. U. Mukhopadhyay, I. Bernal, S.S. Massoud, F.A. Mautner, Inorg. Chim. Acta 357, 3673 (2004)

    Article  CAS  Google Scholar 

  27. S. Sathyanarayana, J.C. Daborusak, J.B. Chaires, Biochemistry 32, 2573 (1993)

    Article  Google Scholar 

  28. A. Sitlani, E.C. Long, A.M. Pyle, J.K. Barton, J. Am. Chem. Soc. 114, 2303 (1992)

    Article  CAS  Google Scholar 

  29. T.B. Thederahn, M.D. Kuwabara, T.A. Larsen, D.S. Sigman, J. Am. Chem. Soc. 111, 4941 (1989)

    Article  CAS  Google Scholar 

  30. D.S. Sigman, A. Mazumder, D.M. Perrin, Chem. Rev. 93, 2295 (1993)

    Article  CAS  Google Scholar 

  31. D.T. Sawyer, J.S. Valentine, Acc. Chem. Res. 14, 393 (1981)

    Article  CAS  Google Scholar 

  32. M. Baudry, S. Etienne, A. Bruce, M. Palucki, E. Jacobsen, B. Malfroy, Biochem. Biophy. Res. Commun. 192, 964 (1993)

    Article  CAS  Google Scholar 

  33. Z.H. Chohan, H. Pervez, A. Rauf, K.M. Khan, C.T. Supuran, J. Enzy, Inh. Med. Chem. 19, 417 (2004)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Research Department of Chemistry, VHNSN College, Virudhunagar, 626001, India

    Natarajan Raman, Arumugam Sakthivel & Ramaraj Jeyamurugan

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  1. Natarajan Raman
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  2. Arumugam Sakthivel
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  3. Ramaraj Jeyamurugan
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Correspondence to Natarajan Raman.

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Raman, N., Sakthivel, A. & Jeyamurugan, R. Synthesis, characterization and biological activities of homo-binuclear Cu(II) and Zn(II) complexes derived from 2-hydroxy-5-methyl-1,3-benzenedicarboxaldehyde derivatives. cent.eur.j.chem. 8, 96–107 (2010). https://doi.org/10.2478/s11532-009-0103-2

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