Advancement in specific strand scission of DNA and evaluation of in-vitro biological assessment by pharmacologically significant tetraaza macrocyclic metal complexes constrained by triazole

Abstract A novel ligand, tetra-azamacrocyclic, L(C24H16N12O2S4) and its complexes with the structures, [MLCl2] and [CuL]Cl2 (where M = Ni(II), Fe(II); L = S,S′-[benzene-1,3-diylbis(4H-1,2,4-triazole-5,3-diyl)]bis{[(5-benzene-1,3-diyl-4H-1,2,4-triazol-3yl)sulfanyl] ethanethioate} were described and depicted by the analytical and spectral techniques. These studies revealed an octahedral geometry for Ni(II) and Fe(II) structures, while the Cu(II) complex exhibited a square planar structure. All the integrated metal structures were screened against targeted species of pathogenic fungi and bacterial strains to evaluate in vitro antimicrobial activities. The binding capability of the complexes with CT-DNA was considered by supporting detailed examination followed by viscosity measurements and thermal denaturation studies. The mode of DNA cleavage using gel electrophoreses revealed that the complexes possess photonuclease characteristics against pUC19 DNA under UV–visible irradiation. The newly synthesized novel Cu(II)-L complex has been proven to be a potential DNA cleavage agent and a potent inhibitor against both the bacterial and fungi strains. Introduction

[1]  B. Aslim,et al.  Structural analysis and biological functionalities of iron(III)– and manganese(III)–thiosemicarbazone complexes: in vitro anti-proliferative activity on human cancer cells, DNA binding and cleavage studies , 2019, JBIC Journal of Biological Inorganic Chemistry.

[2]  Sidhali U. Parsekar,et al.  Efficient hydrolytic cleavage of DNA and antiproliferative effect on human cancer cells by two dinuclear Cu(II) complexes containing a carbohydrazone ligand and 1,10-phenanthroline as a coligand , 2019, JBIC Journal of Biological Inorganic Chemistry.

[3]  N. El-Ghamaz,et al.  Synthesis, characterization, DNA binding and antitumor activities of Cu(II) complexes , 2018, Journal of Molecular Liquids.

[4]  S. Prince,et al.  Impact of various lipophilic substituents on ruthenium(II), rhodium(III) and iridium(III) salicylaldimine-based complexes: synthesis, in vitro cytotoxicity studies and DNA interactions , 2018, JBIC Journal of Biological Inorganic Chemistry.

[5]  A. F. Shoair,et al.  Synthesis, structural characterization, molecular docking and DNA binding studies of copper complexes , 2018 .

[6]  M. Sahihi,et al.  DNA and HSA interaction of Vanadium (IV), Copper (II), and Zinc (II) complexes derived from an asymmetric bidentate Schiff-base ligand: multi spectroscopic, viscosity measurements, molecular docking, and ONIOM studies , 2017, JBIC Journal of Biological Inorganic Chemistry.

[7]  A. El‐Bindary,et al.  Synthesis and structural characterization of some divalent metal complexes: DNA binding and antitumor activity , 2017 .

[8]  A. El-Sonbati,et al.  Geometrical structures, thermal properties and spectroscopic studies of Schiff base complexes: Correlation between ionic radius of metal complexes and DNA binding , 2017 .

[9]  A. El-Sonbati,et al.  Thermal properties, antimicrobial activity and DNA binding of Ni(II) complexes of azo dye compounds , 2017 .

[10]  Q. Cheng,et al.  Macrocyclic dinuclear nickel(II) and manganese(II) complexes: synthesis, X-ray crystal structures, DNA cleavage, and antimicrobial activity studies , 2015, Transition Metal Chemistry.

[11]  Prolay Das,et al.  Binding and interaction of di- and tri-substituted organometallic triptycene palladium complexes with DNA , 2014, JBIC Journal of Biological Inorganic Chemistry.

[12]  Dugganna Girija,et al.  Synthesis, DNA-binding, DNA-photonuclease profiling and antimicrobial activity of novel tetra-aza macrocyclic Ni(II), Co(II) and Cu(II) complexes constrained by thiadiazole. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[13]  Q. Cheng,et al.  Synthesis, crystal structures and DNA-binding properties of dinuclear complexes with macrocyclic ligands , 2012, Transition Metal Chemistry.

[14]  H. Naik,et al.  Synthesis and Biological Evaluation of New Tetra‐aza Macrocyclic Scaffold Constrained Oxadiazole, Thiadiazole and Triazole Rings , 2012, Archiv der Pharmazie.

[15]  B. Kumar,et al.  Metal Complexes of New Tetraazamacrocyclic Constrained Oxadiazole Ring as Subunits: Synthesis, DNA Binding and Photonuclease Activity , 2012 .

[16]  H. Naik,et al.  Synthesis, DNA Binding, and Oxidative Cleavage Studies of Fe(II) and Co(III) Complexes Containing Bioactive Ligands , 2011, Nucleosides, nucleotides & nucleic acids.

[17]  H. den Dulk,et al.  Ruthenium polypyridyl complexes and their modes of interaction with DNA: Is there a correlation between these interactions and the antitumor activity of the compounds? , 2008, JBIC Journal of Biological Inorganic Chemistry.

[18]  S. Parveen,et al.  Metal-ion directed synthesis of binuclear octaazamacrocyclic complexes of manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) and their physico-chemical studies , 2007 .

[19]  H. Naik,et al.  Co(III) and Ni(II) Complexes Containing Bioactive Ligands: Synthesis, DNA Binding, and Photocleavage Studies , 2007, Bioinorganic chemistry and applications.

[20]  F. Hueso-Ureña,et al.  Synthesis, structure and biological activity of a new and efficient Cd(II)–uracil derivative complex system for cleavage of DNA , 2005, JBIC Journal of Biological Inorganic Chemistry.

[21]  Ashutosh Kumar Singh,et al.  Macrocyclic metal complexes: synthesis and characterization of 14- and 16- membered tetraaza macrocyclic complexes of transition metals , 2004 .

[22]  Weijun Niu,et al.  Comparative in vivo stability of copper-64-labeled cross-bridged and conventional tetraazamacrocyclic complexes. , 2004, Journal of medicinal chemistry.

[23]  T. Hubin.  Synthesis and coordination chemistry of topologically constrained azamacrocycles , 2003 .

[24]  C. Reynolds,et al.  Towards new transition metal-based hypoxic selective agents for therapy and imaging. , 2001, Journal of inorganic biochemistry.

[25]  J. Cowan,et al.  Catalytic hydrolysis of DNA by metal ions and complexes , 2001, JBIC Journal of Biological Inorganic Chemistry.

[26]  J. F. Wheeler,et al.  Photoredox behavior and chiral discrimination of DNA bound M(diimine)3n+ complexes (M=Ru2+, Cr3+) , 2001 .

[27]  A. Bansal,et al.  TEMPLATE SYNTHESIS, STRUCTURAL AND BIOLOGICAL STUDIES OF NEW TETRAAZAMACROCYCLIC COMPLEXES OF LEAD(II) , 2000 .

[28]  S. Serin,et al.  Nickel ion as a template in the synthesis of macrocyclic imine-oxime complexes from carbonyl compounds and o-phenylenediamine , 2000 .

[29]  M. Aguirre,et al.  Complexes of macrocycles with pendant arms as models for biological molecules , 2000 .

[30]  J. Forman,et al.  Molecular recognition in aqueous media. New binding studies provide further insights into the cation-π interaction and related phenomena , 1993 .

[31]  D. P. Mack,et al.  Sequence-specific oxidative cleavage of DNA by a designed metalloprotein, Ni(II).GGH(Hin139-190). , 1992, Biochemistry.

[32]  E. Taillandier,et al.  Interaction of transition metal ions with Z form poly d(A-C).poly d(G-T) and poly d(A-T) studied by I.R. spectroscopy. , 1986, Nucleic acids research.

[33]  E. Taillandier,et al.  Interaction of Z form poly(dG-dC).poly(dG-dC) with divalent metal ions: localization of the binding sites by I.R. spectroscopy. , 1984, Nucleic acids research.

[34]  T. Hampton,et al.  Nickel carbonate induces DNA-protein crosslinks and DNA strand breaks in rat kidney. , 1981, Cancer letters.

[35]  B. Hathaway,et al.  The electronic properties and stereochemistry of mono-nuclear complexes of the copper(II) ion , 1970 .