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
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)
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)
Jones, C.J.: Transition metals as structural components in the construction of molecular containers. Chem. Soc. Rev. 27, 289–300 (1998)
Philip, D., Stoddart, J.F.: Selbstorganisation in natürlichen und in nichtnatürlichen Systemen. Angew. Chem. 108, 1242–1286 (1996)
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)
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)
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)
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)
Kumar, K., Tweedle, M.F.: Macrocyclic polyaminocarboxylate complexes of lanthanides as magnetic resonance imaging contrast agents. Pure Appl. Chem. 65, 515–520 (1993)
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)
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)
Kong, D., Xie, Y.: Synthesis, structural characterization of tetraazamacrocyclic ligand, five-coordinated zinc(II) complex. Inorg. Chim. Acta 338, 142–148 (2002)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Vogel, A.I.: A text book of quantitative inorganic analyses, 3rd edn. ELBS Longman’s Green and Co. Ltd., London (1962)
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)
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)
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)
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)
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)
Yang, H., Sun, W.H., Li, Z., Wang, L.: Solvent-free syntheses of salicylaldimines assisted by microwave irradiation. Synth. Commun. 32, 2395–2402 (2002)
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)
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)
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)
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)
Lever, A.B.P.: Inorganic Electronic Spectroscopy, 2nd edn. Elsevier, Amsterdam (1984)
Ballahausen, C.J.: Introduction to ligand field theory. McGraw-Hill, New York (1962)
Chandra, S., Gupta, S.: Copper(II) complexes with twelve to fourteen membered ring macrocyclic ligands. J. Indian Chem. Soc. 82, 1087–1090 (2005)
Bard A.J., Izatt, L.R. Electrochemical Methods Fundamentals and Applications, 2nd ed. Wiley, New York (2001)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
Sambrook, J., Fritsch, E.F., Maniatis, T.: Molecular Cloning, A Laboratory Manual, 2nd edn. Cold Spring Harbor Laboratory, Cold Spring Harbor, New York (1989)
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)
Umezawa, H.: Structure and action of bleomycin. Prog. Biochem. Pharmacol. 11, 18–27 (1976)
Burger, R.M.: Cleavage of nucleic acids by bleomycin. Chem. Rev. 98, 1153–1169 (1998)
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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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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DOI: https://doi.org/10.1007/s10847-010-9794-4