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DNA cleavage and antimicrobial studies of 17-membered schiff base macrocyclic triazoles: synthesis and spectroscopic approach

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Abstract

A novel series of 17-membered complexes [MLCl2] (M = Co2+, Ni2+ and Cu2+) have been synthesized with newly derived biologically active ligands (LI–LIV). These ligands were synthesized by the condensation of 3-subtituted-4-amino-5-hydrazino-1,2,4-triazole with bis(phthalaldehyde)ethylenediamine precursor. The structure of the complexes has been proposed by elemental analyses, IR, EPR, electronic spectral studies, conductivity, magnetic, thermal and electrochemical studies. All the complexes are soluble in DMF and DMSO and are non-electrolytes. All these Schiff bases and their complexes have been screened for their antibacterial (Escherichia coli, Staphylococus aureus, Salmonella typhi, Pseudomonas aeruginosa) and antifungal activities (Aspergillus niger, Aspergillus flavus and Cladosporium) by the Agar and Potato dextrose agar diffusion method. The DNA cleavage study was done by Agarose gel electrophoresis technique.

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Abbreviations

BM:

Bohr Magneton

EPR:

Electron paramagnetic resonance

FAB:

Fast atom bombardment

TG/DTG:

Thermogravimetric/differential thermogravimetric analysis

DMF:

N,N dimethyl formamide

DMSO:

Dimethylsulphoxide

IR:

Infra red

MIC:

Minimum inhibitory concentration

NMR:

Nuclear magnetic resonance

MRI:

Magnetic resonance imaging

TMS:

Tetramethylsilane

References

  1. Hosseini, M.W., Lehn, J.M., Duff, S.R., Gu, K., Mertes, M.P.: Synthesis of mono- and difunctionalized ditopic [24] N6O2 macrocyclic receptor molecules. J. Org. Chem. 52, 1662–1666 (1987)

    Article  CAS  Google Scholar 

  2. Izatt, R.M., Brandshaw, J.S., Nielsen, S.A., Lamb, J.D., Christensen, J.J., Sen, D.: Thermodynamic and kinetic data for cation-macrocycle interaction. Chem. Rev. 85, 271–339 (1985)

    Article  CAS  Google Scholar 

  3. Jones, C.J.: Transition metals as structural components in the construction of molecular containers. Chem. Soc. Rev. 27, 289–300 (1998)

    Article  CAS  Google Scholar 

  4. Philip, D., Stoddart, J.F.: Selbstorganisation in natürlichen und in nichtnatürlichen Systemen. Angew. Chem. 108, 1242–1286 (1996)

    Article  Google Scholar 

  5. Keypour, H., Khanmohammadi, H., Wainwright, K.P., Taylor, M.R.: Syntheis, crystal structure, NMR and ab initio molecular-orbital studies of some magnesium(II)macrocyclic Schiff-base complexes, with two 2-aminoethyl pendant arms. Inorg. Chim. Acta 357, 1283–1291 (2004)

    Article  CAS  Google Scholar 

  6. Ma, W., Tian, Y., Zhang, S., Wu, J., Fun, H.: Synthesis and characterization of 1, 8- bis(ferrocenylmethyl)-5, 5, 7, 12, 12, 14-hexamethyl-1, 4, 8, 11-tetraazacyclote tradecane, a macrocyclic ligand and its complexes. Trans. Met. Chem. 31, 97–102 (2006)

    Article  CAS  Google Scholar 

  7. Muller, J.G., Chen, X., Dadiz, A.C., Rokita, S.E., Burrows, C.J.: Macrocyclic nickel complexes in DNA recognition and oxidation. Pure Appl. Chem. 65, 545–550 (1993)

    Article  CAS  Google Scholar 

  8. Liu, J., Lu, T.B., Deng, H., Ji, L.N., Qu, L.H., Zhou, H.: Synthesis, DNA-binding and cleavage studies of macrocyclic copper(II) complexes. Trans. Met. Chem. 28, 116–121 (2003)

    Article  CAS  Google Scholar 

  9. Kumar, K., Tweedle, M.F.: Macrocyclic polyaminocarboxylate complexes of lanthanides as magnetic resonance imaging contrast agents. Pure Appl. Chem. 65, 515–520 (1993)

    Article  CAS  Google Scholar 

  10. Watson, A.D., Rockladge, S.M.: Structure, synthesis and characterization of contrast agents for magnetic resonance molecular imaging. In: Higgins, CB (ed.) Magnetic Resonance Imaging of the Body. Raven Press, New York (1992)

  11. Chan, K.W., Barra, S., Botta, M., Wong, W.: Novel gadolinium(III) polyaminocarboxylate macrocyclic complexes as potential magnetic resonance imaging contrast agents. J. Inorg. Biochem. 98, 677–682 (2004)

    Article  CAS  Google Scholar 

  12. Kong, D., Xie, Y.: Synthesis, structural characterization of tetraazamacrocyclic ligand, five-coordinated zinc(II) complex. Inorg. Chim. Acta 338, 142–148 (2002)

    Article  CAS  Google Scholar 

  13. Seto, J., Tamura, S., Asai, N., Kishii, N., Kijima, Y., Matsuzawa, N.: Macrocyclic functional dyes: applications to optical disk media, photochemical hole burning and nonlinear optics. Pure Appl. Chem. 68, 1429–1434 (1996)

    Article  CAS  Google Scholar 

  14. Chaudhary, A., Bansal, N., Gajraj, A., Singh, R.V.: Antifertility, antibacterial, antifungal and percent disease incidence aspects of macrocyclic complexes of manganese(II). J. Inorg. Biochem. 96, 393–400 (2003)

    Article  CAS  Google Scholar 

  15. Singh, R.V., Chaudhary, A.: Biologically relevant tetraaza macrocyclic complexes of manganese: synthetic, spectral, antimicrobial, antifertility and anti-inflammatory approach. J. Inorg. Biochem. 98, 1712–1721 (2004)

    Article  CAS  Google Scholar 

  16. Polya, J.P.: 1, 2, 4-triazole in comperhensive heterocyclic chemistry. In: Katritzky, A.R., Ress, C.W. (eds.) Comperhensive Heterocyclic Chemistry, vol. 5, p. 733. Pergamon Press, London (1984)

  17. Kornis, G.I.: 1, 3, 4-triazole in comperhensive heterocyclic chemistry. In: Katritzky, A.R., Ress, C.W., Scriven, E.F.V. (eds.) Comperhensive Heterocyclic Chemistry, vol. 4, p. 379. Pergamon Press, London (1996)

  18. Avaji, P.G., Patil, S.A.: Synthesis, spectral characterization and microbiological studies of Co(II), Ni(II) and Cu(II) complexes with some novel 20-membered macrocyclic hydrazino-1, 2, 4-triazole Schiff bases. J. Enzyme Inhib. Med. Chem. 24, 140–150 (2009)

    Article  CAS  Google Scholar 

  19. Bagihalli, G.B., Patil, S.A.: Synthesis, spectral characterization, in vitro biological and DNA cleavage studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with 1, 2, 4-triazole Schiff bases. J. Coord. Chem. 62, 1690–1700 (2009)

    Article  CAS  Google Scholar 

  20. Xu, S., Xie, Y., Jiang, H.: Lanthanide(III) complexes with a hydrazone derived from a novel amido acid and isonicotinic acid hydrazide: synthesis and characterization and antibacterial activity. Synth. React. Inorg. Met. Org. Chem. 25, 511 (1995)

    Google Scholar 

  21. Audrieth, L.F., Scott, E.S., Kipper, P.S.: Hydrazine derivatives of the carbonic and thiocarbonic acids. I. The preparation and properties of thiocarbohydrazide. J. Org. Chem. 19, 733–741 (1954)

    Article  CAS  Google Scholar 

  22. Patil, S.A., Kamble, U.V., Badami, P.S.: Template synthesis, characterization, in vitro antimicrobial, and DNA cleavage studies of Co(II), Ni(II), Cu(II), and Zn(II) complexes with 15-membered N2O2 diazadioxa macrocycles. Main Group Chem. 8, 189–206 (2009)

    Article  CAS  Google Scholar 

  23. Vogel, A.I.: A text book of quantitative inorganic analyses, 3rd edn. ELBS Longman’s Green and Co. Ltd., London (1962)

    Google Scholar 

  24. Singh, N.K., Singh, S.B.: Synthesis, characterization and biological properties of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cr(III) and Fe(III) complexes with a new thiosemicarbazide derivative. Ind. J. Chem. 40, 1047–1052 (2001)

    Google Scholar 

  25. Shakir, M., Kumar, O., Varkey, S.P.: 3-mercapto-1, 2-propanediol and its 1-methoxy and 1-ethoxy derivatives, HSCH2CH(OH)CH2OR′ (R′ = H, CH3, C2H5), as uninegative bidentate bridging ligands: synthesis and characterization of dimeric complexes with cobalt, copper and silver. Polyhedron 11, 2831–2836 (1992)

    Article  CAS  Google Scholar 

  26. Rana, V.B., Singh, P., Singh, D.P., Teotia, M.P.: Trivalent chromium, manganese, iron and cobalt chelates of a tetradentate N6 macrocyclic ligand. Trans. Met. Chem. 7, 174–177 (1982)

    Article  CAS  Google Scholar 

  27. Sami, A.Z., Jejurkar, C.R.: Synthesis and characterization of macrocyclic quadridentate schiff base ligands and their Cu(II), Ni(II) and Zn(II) complexes. Indian J. Chem. 34A, 241–242 (1995)

    Google Scholar 

  28. Saha, N., Saha, A.: Five-coordinate complexes of Nickel(II) and Copper(II) with a pyrazole-derived macrocycle. J. Indian Chem. Soc. 69, 517–520 (1992)

    CAS  Google Scholar 

  29. Yang, H., Sun, W.H., Li, Z., Wang, L.: Solvent-free syntheses of salicylaldimines assisted by microwave irradiation. Synth. Commun. 32, 2395–2402 (2002)

    Article  CAS  Google Scholar 

  30. Shakir, M., Chishti, H.T.N., Chingasubam, P.: Metal ion-directed synthesis of 16-membered tetraazamacrocyclic complexes and their physico-chemical studies. Spectrochim. Acta A 64, 512–517 (2006)

    Article  Google Scholar 

  31. Avaji, P.G., Patil, S.A.: Synthesis, spectral, thermal, solid state d.c. electrical conductivity, fluorescence and biological studies of lanthanum(III) and thorium(IV) complexes of 24-membered macrocyclic triazoles. J. Coord. Chem. 16, 2570–2583 (2008)

    Article  Google Scholar 

  32. Jeewoth, T., Bhowan, M.G., Wah, H.L.K.: Synthesis, characterization and antibacterial properties of Schiff bases and Schiff base metal complexes derived from 2, 3-diaminopyridine. Trans. Met. Chem. 24, 445–448 (1999)

    Article  CAS  Google Scholar 

  33. Chandra, S., Kumar, R., Singh, R.: Nickel (II) complexes with different chromospheres containing macrocyclic ligands: Spectroscopic and electrochemical studies. Spectrochim. Acta A 65, 215–220 (2006)

    Article  Google Scholar 

  34. Lever, A.B.P.: Inorganic Electronic Spectroscopy, 2nd edn. Elsevier, Amsterdam (1984)

    Google Scholar 

  35. Ballahausen, C.J.: Introduction to ligand field theory. McGraw-Hill, New York (1962)

    Google Scholar 

  36. Chandra, S., Gupta, S.: Copper(II) complexes with twelve to fourteen membered ring macrocyclic ligands. J. Indian Chem. Soc. 82, 1087–1090 (2005)

    CAS  Google Scholar 

  37. Bard A.J., Izatt, L.R. Electrochemical Methods Fundamentals and Applications, 2nd ed. Wiley, New York (2001)

  38. Sadana, A.K., Miraza, Y., Aneja, K.R., Prakash, O.: Hypervalent iodine mediated synthesis of 1-aryl/hetryl-1, 2, 4-triazolo[4, 3-a] pyridines and 1-aryl/hetryl 5-methyl-1, 2, 4-triazolo[4, 3-a]quinolines as antibacterial agents. Eur. J. Med. Chem. 38, 533–536 (2003)

    Article  CAS  Google Scholar 

  39. Greenwood, D., Snack, R., Peurtherer, J.: Medical Microbiology: A Guide to Microbial Infections: Pathogensis, Immunity, Laboratory Diagnosis and Control, 15th edn. Churchill Livingstone, Edinburgh, UK (1997)

    Google Scholar 

  40. Salmon, S.A., Watts, J.L., Case, L.J., Haffmann, H.C., Wegener, J.: Comparison of MICs of ceftiofur and other antimicrobial agents against bacterial pathogens of swine from the United States, Canada and Denmark. J. Clin. Microbiol. 33, 2435–2444 (1995)

    CAS  Google Scholar 

  41. Bauer, A.W., Kirby, W.M., Sherris, J.C., Turck, M.: Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol. 45, 493–496 (1966)

    CAS  Google Scholar 

  42. Chohan, Z.H., Supuran, C.T., Scozzafava, A.: Metalloantibiotics: synthesis and antibacterial activity of Cobalt(II), Copper(II), Nickel(II) and Zinc(II) complexes of kefzol. J. Enzyme Inhib. Med. Chem. 19, 79–84 (2004)

    Article  CAS  Google Scholar 

  43. Chohan, Z.H., Praveen, M.: Synthesis, characterization, coordination and antibacterial properties of novel asymmetric 1, 1#-disubstituted ferrocene-derived Schiff-base ligands and their Co(II), Cu(II) Ni(II) and Zn(II) complexes. Appl. Organomet. Chem. 15, 617–625 (2001)

    Article  CAS  Google Scholar 

  44. Chohan, Z.H., Pervez, H., Rauf, A., Khan, K.M., Supuran, C.T.: Isatin-derived antibacterial and antifungal compounds and their transition metal complexes. J. Enzyme Inhib. Med. Chem. 19, 417–423 (2004)

    Article  CAS  Google Scholar 

  45. Chohan, Z.H., Supuran, C.T., Scozzafava, A.: Metal binding and antibacterial activity of ciprofloxacin complexes. J. Enzyme Inhib. Med. Chem. 20, 303–307 (2005)

    Article  CAS  Google Scholar 

  46. Chohan, Z.H., Scozzafava, A., Supuran, C.T.: 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. J. Enzyme Inhib. Med. Chem. 17, 261–266 (2002)

    Article  CAS  Google Scholar 

  47. Chohan, Z.H., Hassan, M.U., Khan, K.M., Supuran, C.T.: In vitro antibacterial, antifungal and cytotoxic properties of sulfonamide-derived Schiff’s bases and their metal complexes. J. Enzyme Inhib. Med Chem. 20, 183–188 (2005)

    Article  CAS  Google Scholar 

  48. Sambrook, J., Fritsch, E.F., Maniatis, T.: Molecular Cloning, A Laboratory Manual, 2nd edn. Cold Spring Harbor Laboratory, Cold Spring Harbor, New York (1989)

    Google Scholar 

  49. Sigman, D.S., Graham, D.R., Aurora, V., Stern, A.M.: Oxygen-dependent cleavage of DNA by the 1, 10-phenanthroline cuprous complex. Inhibition of Escherichia coli DNA polymerase. J. Biol. Chem. 254, 122–169 (1979)

    Google Scholar 

  50. Umezawa, H.: Structure and action of bleomycin. Prog. Biochem. Pharmacol. 11, 18–27 (1976)

    CAS  Google Scholar 

  51. Burger, R.M.: Cleavage of nucleic acids by bleomycin. Chem. Rev. 98, 1153–1169 (1998)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to the Chairman, Department of Chemistry, Karnatak University, Dharwad for the facilities. One of the authors (UVK) grateful to the University Grant Commission, New Delhi for grant of Research Fellowship in Science for Meritorious Students.

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Correspondence to Sangamesh A. Patil.

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Kamble, U.V., Patil, S.A. & Badami, P.S. DNA cleavage and antimicrobial studies of 17-membered schiff base macrocyclic triazoles: synthesis and spectroscopic approach. J Incl Phenom Macrocycl Chem 68, 347–358 (2010). https://doi.org/10.1007/s10847-010-9794-4

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