Mycobiology

The Korean Society of Mycology (한국균학회)
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Antifungal Activities of Copper(II) with Biosensitive Macrocyclic Schiff Base Ligands Derived from 4-Aminoantipyrine Derivatives

  • Gopalakrishnan, S. (Department of Pharmaceutical Chemistry, Manonmaniam Sundaranar University) ;
  • Joseph, J. (Department of Pharmaceutical Chemistry, Manonmaniam Sundaranar University)
  • Published : 2009.06.30
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Abstract

Novel copper(II) complexes have been synthesized from the macrocyclic Schiff bases derived from Knoevenagel condensed ${\beta}$-ketoanilides (obtained by the condensation of acetoacetanilide and substituted benzaldehydes), 4-aminoantipyrine and ophenylene diamine. The structural features have been determined from their analytical and spectral data. All the Cu(II) complexes exhibit square planar geometry. Their high molar conductance values support their 1 : 2 electrolytic nature. The magnetic moment data provide evidence for the monomeric nature of the complexes. The X-band ESR spectra of the |$CuL^1$|$(OAc)_2$ in DMSO solution at 300 and 77 K were recorded and their salient features are reported. The in vitro biological screening effects of the investigated compounds were tested against the bacterial species Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris and Pseudomonas aeruginosa and fungal species Aspergillus niger, Rhizopus stolonifer, Aspergillus flavus, Rhizoctonia bataicola and Candida albicans by well diffusion method. A comparative study of inhibition values of the Schiff bases and their complexes indicate that complexes exhibit higher antimicrobial activity than the Schiff bases. Copper ions proved to be essential for the growth-inhibitor effect. The extent of inhibition appeared to be strongly dependent on the initial cell density and on the growth medium.

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References

  1. Agarwal, R. K., Singh, L. and Sharma, D. K. 2006. Synthesis, spectral, and biological properties of copper(II) complexes of thiosemicarbazones of schiff bases derived from 4-aminoantipyrine and aromatic aldehydes. Bioinorg. Chem. Appl. 2006:59509 1-10.
  2. Anjaneyula, Y. and Rao, R. P. 1986. Preparation, characterization and antimicrobial activity studies on some ternary complexes of Cu(II) with acetylacetone and various salicylic acids. Synth. React. Inorg. Met.-Org. Chem. 16:257-272. https://doi.org/10.1080/00945718608057530
  3. Arguelles, M. C. R., Vazquez, S. M., Touceda, P. T., Matalobos, J. S., Deibe, A. M. G., Ferrari, M. B., Pelosi, G., Pelizzi, C. and Zani, F. 2007. Complexes of 2-thiophene carbonyl and isonicotinoyl hydrazones of 3-(N-methyl)isatin: A study of their antimicrobial activity. J. Inorg. Biochem. 101:138-147. https://doi.org/10.1016/j.jinorgbio.2006.09.004
  4. Brown, D. H., Lewis, A. J., Smith, W. E. and Teape, J. W. 1980. Anti-inflammatory effects of some copper complexes. J. Med. Chem. 23:729-734. https://doi.org/10.1021/jm00181a006
  5. Chandra, S., Gupta, L. K. and Agrawal, S. 2007. Modern spectroscopic and biological approach in the characterization of a novel 14-membered [N4] macrocyclic ligand and its transition metal complexes. Transition Met. Chem. 32:240-245. https://doi.org/10.1007/s11243-006-0155-5
  6. Chandra, S., Jain, D., Amit Kumar, S. and Sharma, P. 2009. Coordination modes of a schiff base pentadentate derivative of 4-aminoantipyrine with cobalt(II), nickel(II) and copper(II) metal ions: Synthesis, spectroscopic and antimicrobial studies. Molecules 14:174-190 https://doi.org/10.3390/molecules14010174
  7. Dharamaraj, N., Viswanathamurthi, P. and Natarajan, K. 2001. Ruthenium (II) complexes containing bidendate Schiff bases and their antifungal activity. Transition Met. Chem. 26:105-109. https://doi.org/10.1023/A:1007132408648
  8. Geary, W. G. 1971. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord. Chem. Rev. 7:81-122. https://doi.org/10.1016/S0010-8545(00)80009-0
  9. Hamming, M. and Foster, N. 1972. Interpretation of Mass Spectra of Organic Compounds; Academic Press: New York, USA
  10. Harikumaran Nair, M. L., Mathew, G. and Sudarasana Kumar, M. R. 2005. Synthesis and characterisation of some new Cu(II) complexes of azo dyes derived from 1,2-dihydro-1,5-dimethyl- 2-phenyl-4-amino-3H-pyrazol-3-one. Ind. J. Chem. 44A:85-89. https://doi.org/10.1021/ie040058c
  11. Hathaway, B. J. and Billing, D. E. 1970. The electronic properties and stereochemistry of mono-nuclear complexes of the copper(II) ion. Coord. Chem. Rev. 5:143-207. https://doi.org/10.1016/S0010-8545(00)80135-6
  12. Kamalakannan, P. and Venkappayya, D. 2002. Synthesis and characterization of cobalt and nickel chelates of 5-dimethylaminomethyl-2-thiouracil and their evaluation as antimicrobial and anticancer agents. J. Inorg. Biochem. 21:22-37.
  13. Kivelson, D. and Neiman, R. 1961. ESR studies on the bonding in copper complexes. J. Chem. Phys. 35:149-155. https://doi.org/10.1063/1.1731880
  14. Lever, A. B. P. 1968. Inorganic Electronic Spectroscopy; Elsevier, Amsterdam, Netherland. Nakamoto K. 1978. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley Interscience, New York, USA
  15. Reiner, R. 1982. In Antibiotics-an introduction. Roche Scientific Services, Switzerland 1:21-25.
  16. Rodriguez-Arguelles, M. C., Lopez-Silva, E. C., Sanmartin, J., Bacchi, A., Pelizzi, C. and Zani, F. 2004. Inorganic Chim. Acta 357:2543-2552. https://doi.org/10.1016/j.ica.2004.02.013
  17. Rosu, T., Pasculescu, S., Lazar, V., Chifiriuc, C. and Cernat, R. 2006. Copper(II) complexes with ligands derived from 4-amino-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one. Molecules11:904-914. https://doi.org/10.3390/11110904
  18. Singh, K., Barwa, M. S. and Tyagi, P. 2007. Synthesis and characterization of cobalt(II), nickel(II), copper(II) and zinc(II) complexes with Schiff base derived from 4-amino-3-mercapto-6-methyl-5-oxo-1,2,4-triazine. Euro. J. Med. Chem. 42:394-402. https://doi.org/10.1016/j.ejmech.2006.10.016
  19. Sorenson, J. R. J. 1976. Copper chelates as possible active forms of the anti-arthritic agents. J. Med. Chem. 19:135-148. https://doi.org/10.1021/jm00223a024
  20. Sorenson, J. R. J. 1984. Copper complexes in biochemistry and pharmacology. Chem. Britain 1110-1113.