METAL (II) COMPLEXES OF BIOINORGANIC AND MEDICINAL RELEVANCE: ANTIBACTERIAL, ANTIOXIDANT AND DNA CLEAVAGE STUDIES OF TETRADENTATE COMPLEXES INVOLVING O, N-DONOR ENVIRONMENT OF 3, 3'-DIHYDROXYBENZIDINE-BASED SCHIFF BASES

A new potentially tetradentate Schiff base ligand H2L and their binuclear metal complexes have been prepared on the condensation of 3, 3′dihydroxybenzidine, o- phthalaldehyde and 2-aminophenol in the molar ratio of 1:2:2. The Schiff base, H2L, ligand acts as dibasic with two N2O2tetradentate sites and can coordinate with two metal ions to form binuclear complexes after the deprotonation of the hydrogen atoms of the phenolic groups in all the complexes. All the metal complexes have been fully characterized with the help of elemental analyses, molecular weights, molar conductance values, magnetic moments and Spectral studies. The analytical data helped to elucidate the structure of the metal complexes. All the complexes are non-electrolyte in DMF due to their low molar conductance value. The IR spectral data suggest the involvement of azomethine nitrogen in co-ordination to the central metal ion. Electronic, ESR and magnetic data proposed the square planar geometry for Cu(II), Ni(II) and square pyramidal for VO(II) complexes under investigations. Cyclic voltammetry and controlled electrolysis studies indicate that the metal ion in the binuclear complexes undergo quasireversible one electron reduction and oxidation. The nucleolytic cleavage activities of the complexes were assayed on pUC18 plasmid DNA using gel electrophoresis in the presence and absence of H2O2 and the complexes show promising nuclease activity. The complexes show significant growth inhibitory activity against the bacteria like Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Klebsilla pneumonia than the free ligands. In addition, the antioxidant activities of the complexes were also investigated through scavenging effect on DPPH radicals. The obtained IC50 value of the DPPH activity for the copper complex (IC50 = 5.46 mg/ml) was higher than other compounds.

[1]  Y. Elerman,et al.  Synthesis, spectral characterization, structural investigation and antimicrobial studies of mononuclear Cu(II), Ni(II), Co(II), Zn(II) and Cd(II) complexes of a new potentially hexadentate N2O4 Schiff base ligand derived from salicylaldehyde , 2013 .

[2]  K. Seshaiah,et al.  Synthesis, spectral characterization and antioxidant activity studies of a bidentate Schiff base, 5-methyl thiophene-2-carboxaldehyde-carbohydrazone and its Cd(II), Cu(II), Ni(II) and Zn(II) complexes. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[3]  Keerthi Kumar SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF HETEROCYCLIC AZO DYES DERIVED FROM 2-AMINOBENZOTHIOZOLE , 2013 .

[4]  G. Kalyani,et al.  THIAZOLIDINONE BASED 2,5-DISUBSTITUTED-1,3,4-THIADIAZOLE: SYNTHESIS AND ANTIMICROBIAL EVALUATION , 2013 .

[5]  S. Tabassum,et al.  Synthesis of heterobimetallic complexes: in vitro DNA binding, cleavage and antimicrobial studies. , 2012, Journal of photochemistry and photobiology. B, Biology.

[6]  W. Linert,et al.  Synthesis, spectroscopic and biological activities studies of acyclic and macrocyclic mono and binuclear metal complexes containing a hard-soft Schiff base. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[7]  M. M. El-Naggar,et al.  Synthesis, spectral characterization, DNA binding ability and antibacterial screening of copper(II) complexes of symmetrical NOON tetradentate Schiff bases bearing different bridges , 2012 .

[8]  F. El-saied,et al.  Synthesis and characterization of some bi, tri and tetravalent transition metal complexes of N'-(furan-2-yl-methylene)-2-(p-tolylamino)acetohydrazide HL1 and N'-(thiophen-2-yl-methylene)-2-(p-tolylamino)acetohydrazide HL2. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[9]  N. Raman,et al.  Studies on DNA binding behaviour of biologically active transition metal complexes of new tetradentate N2O2 donor Schiff bases: inhibitory activity against bacteria. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  A. Ramadan Macrocyclic nickel(II) complexes: Synthesis, characterization, superoxide scavenging activity and DNA-binding , 2012 .

[11]  S. Vedanayaki,et al.  Synthesis, spectral characterization, electrochemical and anti-microbial activities of new binuclear Schiff base metal complexes derived from 3,3’ diaminobenzedine , 2011 .

[12]  M. Ibrahim,et al.  Synthesis, characterization, and tyrosinase biomimetic catalytic activity of copper(II) complexes with schiff base ligands derived from α-diketones with 2-methyl-3-amino-(3H)-quinazolin-4-one , 2011 .

[13]  S. Sallam,et al.  DNA interaction with octahedral and square planar Ni(II) complexes of aspartic-acid Schiff-bases , 2011 .

[14]  B. Liu,et al.  A V-shaped ligand 1,3-bis(1-methylbenzimidazol-2-yl)-2-oxapropane and its Cu(II) complex: synthesis, crystal structure, antioxidation and DNA-binding properties. , 2011, Journal of photochemistry and photobiology. B, Biology.

[15]  I. Demirtaş,et al.  Antioxidant, electrochemical, thermal, antimicrobial and alkane oxidation properties of tridentate Schiff base ligands and their metal complexes. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[16]  F. Arjmand,et al.  Synthesis of new chiral heterocyclic Schiff base modulated Cu(II)/Zn(II) complexes: their comparative binding studies with CT-DNA, mononucleotides and cleavage activity. , 2011, Journal of photochemistry and photobiology. B, Biology.

[17]  R. Patel Structural, magnetic and spectroscopic characterization of two unusual end-on bis(μ-acetato/μ-nitrato) bridged copper(II) complexes with N′-[phenyl(pyridin-2-yl)methylidene]furan-2-carbohydrazide and (2E,4Z)-N,2-dimethylhepta-2,4,6-trienamide-1-phenyl-1-pyridin-2-ylmethanimine (1:1) as capping ligan , 2010 .

[18]  S. Kashanian,et al.  Comparative DNA binding and DNA cleavage studies of a water soluble dinitrogen Schiff base ligand and its cobalt (II) complex , 2010 .

[19]  P. M. Reddy,et al.  Binuclear cobalt(II), nickel(II), copper(II) and palladium(II) complexes of a new Schiff-base as ligand: synthesis, structural characterization, and antibacterial activity. , 2010, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[20]  A. Emara Structural, spectral and biological studies of binuclear tetradentate metal complexes of N3O Schiff base ligand synthesized from 4,6-diacetylresorcinol and diethylenetriamine. , 2010, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[21]  S. Mapolie,et al.  Cu(II) and Ni(II) complexes based on monofunctional and dendrimeric pyrrole-imine ligands: Applications in catalytic liquid phase hydroxylation of phenol , 2010 .

[22]  M. Mostafa,et al.  Synthesis and spectroscopic studies of 2,5-hexanedione bis(isonicotinylhydrazone) and its first raw transition metal complexes. , 2010, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[23]  Sankaralingam Arunachalam,et al.  DNA binding and antimicrobial studies of polymer-copper(II) complexes containing 1,10-phenanthroline and L-phenylalanine ligands. , 2009, European journal of medicinal chemistry.

[24]  N. Mohan,et al.  Synthesis and characterization of a new series of unsymmetrical macrocyclic binuclear vanadyl(IV) complexes: Electrochemical, antimicrobial, DNA binding and cleavage studies , 2009 .

[25]  V. McKee,et al.  Synthesis, structural characterization, thermal and electrochemical studies of the N,N'-bis[(3,4-dichlorophenyl)methylidene]cyclohexane-1,4-diamine and its Cu(II), Co(II) and Ni(II) metal complexes. , 2009, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[26]  L. Jagadish,et al.  Synthesis, electrochemical, catalytic and antimicrobial activities of novel unsymmetrical macrocyclic dicompartmental binuclear nickel(II) complexes , 2008 .

[27]  P. Viswanathamurthi,et al.  Ruthenium(II) Carbonyl Complexes Containing Tetradentate Schiff Bases and Their Catalytic Activities , 2006 .

[28]  Bo-wan Wu,et al.  Synthesis and Characterization of Metal Complexes of Cu(II), Ni(II), Zn(II), Co(II), Mn(II) and Cd(II) with Tetradentate Schiff Bases , 2006 .

[29]  Y. Inada,et al.  Equilibrium and kinetics of the dinuclear complex formation between N,N'-ethylenebis(salicylideneiminato)copper(II) and metal(II,I) ions in acetonitrile , 2005 .

[30]  M. Thirumavalavan,et al.  Synthesis of mono and binuclear copper(II) complexes using new macrobicyclic tricompartmental unsymmetrical ligands: magnetic, electrochemical and catalytic studies , 2003 .

[31]  J. Manonmani,et al.  Synthesis, characterization and electrochemical studies of unsymmetrical macrocyclic mono and binuclear nickel(II) complexes , 2003 .

[32]  M. Palaniandavar,et al.  Spectral, viscometric and electrochemical studies on mixed ligand cobalt(III) complexes of certain diimine ligands bound to calf thymus DNA , 2002 .

[33]  R. Butcher,et al.  The preparation and characterization of mono- and bis-chelated cadmium(II) complexes of the di-2-pyridylketone Schiff base of S-methyldithiocarbazate (Hdpksme) and the X-ray crystal structure of the [Cd(dpksme)2] · 0.5 MeOH complex , 2002 .

[34]  K. Natarajan,et al.  Ruthenium(II) carbonyl complexes with tridentate Schiff bases and their antibacterial activity , 2002 .

[35]  P. Akilan,et al.  Synthesis, spectral, electrochemical and magnetic properties of new symmetrical and unsymmetrical dinuclear copper(II) complexes derived from binucleating ligands with phenol and benzimidazole donors , 1999 .

[36]  M. Ali,et al.  Magnetic and spectroscopic studies on metal complexes of ons donor ligands—I complexes of Schiff bases formed by condensation of 2-hydroxy-1-naphthaldehyde with N-methyl-S-alkyldithiocarbazates , 1978 .

[37]  K. S. Kale,et al.  Magnetic and spectral properties of oxovanadium(IV) complexes of schiff bases derived from halo-substituted salicylaldehyde and aniline , 1977 .