DNA CLEAVAGE ACTIVITY OF NOVEL SCHIFF BASE COPPER(II) COMPLEXES WITH SULFUR CONTAINING-LIGANDS: (2-(2-METHYLTHIO)PHENYLIMINO)METHYLPHENOL, N-BENZYLIDINE-2-METHYLTHIOANILINE
Abstract
Objective: To study the DNA cleavage activity of all copper(II) complexes using supercoiled pUC19 DNA by agarose gel electrophoresis.
Methods: In this study, six new schiff base mixed ligand copper(II) complexes containing [Cu(L
1
)(8Hq)Cl
2
], [Cu(L
2
)(8Hq)Cl
],
[Cu(L
2
)(phen)Cl
2
], [Cu(L
1
)(Bpy)Cl
2
], and [Cu(L
2
)(Bpy)Cl
] (where, phen=1,10-phenanthroline, Bpy=2, 2'-bipyridyl, 8Hq=8-hydroxy quinoline, ligand
L
1
=(2-(2-methylthio)phenylimino)methylphenol, ligand L
2
=N-benzylidine-2-methylthioaniline) were synthesized. The six novel schiff base ligands
were characterized by molar conductance, ultraviolet, infrared (IR), and cyclic voltammetry (CV) measurements. Low molar conductance values of
copper(II) complexes showed non-electrolyte in nature. The IR spectral data indicate that nitrogen, sulfur, and azomethine nitrogen coordinate to the
central metal ion. The electrochemical properties such as anodic, cathodic peak potential, and electron transfer process of the complexes were studied
using CV measurements. Based on these spectral data, octahedral geometry was proposed to all copper(II) complexes.
Results: The result confirmed that binding constant value of 13.95 × 10
2
3
M
for complex (VI) suggested good intercalative binding with calf thymus
(CT) DNA. When DNA (pUC19) cleavage analyses was performed, copper(II) complexes - I, II, V, VI showed cleavage activity.
−1
Conclusion: The complexes - III and IV did not exhibit DNA binding as well as DNA cleavage potential which may be due to the presence of
O-phenanthroline.
Keywords: (2-(2-methylthio)phenylimino)methylphenol, N-benzylidine-2-methylthioaniline, Copper(II) complexes, Calf thymus DNA, pUC19 DNA,
DNA binding and cleavage activity.
2
], [Cu(L
1
)(phen)Cl
2
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References
Rajendiran V, Karthik R, Palaniandavar M, Stoeckli-Evans H,
Periasamy VS, Akbarsha MA, et al. Mixed-ligand copper(II)-phenolate
complexes: Effect of coligand on enhanced DNA and protein
binding, DNA cleavage, and anticancer activity. Inorg Chem
;46(20):8208-21.
Loganathan R, Ramakrishnan S, Suresh E, Palaniandavar M,
Riyasdeen A, Akbarsha MA. Mixed ligand µ-phenoxo-bridged
dinuclear copper(II) complexes with diimine co-ligands: Efficient
chemical nuclease and protease activities and cytotoxicity. Dalton
Trans 2014;43(16):6177-94.
Jaividhya P, Dhivya R, Akbarsha MA, Palaniandavar M. Efficient DNA
cleavage mediated by mononuclear mixed ligand copper(II) phenolate
complexes: The role of co-ligand planarity on DNA binding and
cleavage and anticancer activity. J Inorg Biochem 2012;114:94-105.
Rajarajeswari C, Ganeshpandian M, Palaniandavar M,
Riyasdeen A, Akbarsha MA. Mixed ligand copper(II) complexes of
,10-phenanthroline with tridentate phenolate/pyridyl/(benz)imidazolyl
Schiff base ligands: Covalent vs non-covalent DNA binding, DNA
cleavage and cytotoxicity. J Inorg Biochem 2014;140:255-68.
Joseyphus RS, Sivasankaran Nair M. Synthesis, characterization and
biological studies of some Co(II), Ni(II) and Cu(II) complexes derived
from indole-3-carboxaldehyde and glycylglycine as Schiff base ligand.
Arab J Chem 2010;3:195-204.
Jayaseelan P, Prasad S, Vedanayaki S, Rajavel R. Synthesis,
characterization, anti-microbial, DNA binding and cleavage studies of
Schiff base metal complexes. Arab J Chem 2011. [Article in press].
Ganeshpandian M, Loganathan R, Ramakrishnan S, Riyasdeen A,
Akbarsha MA, Palaniyandavar M. Interaction of mixed ligand
copper(II) complexes with CT-DNA and BSA: Effect of primary
ligand hydrophobicity on DNA and protein binding and cleavage and
anticancer activities. J Polyhedron 2013;52:924-38.
Selvakumar B, Rajendiran V, Uma Maheswari P, Stoeckli-Evans H,
Palaniandavar M. Structures, spectra, and DNA-binding properties of
mixed ligand copper(II) complexes of iminodiacetic acid: The novel
role of diimine co-ligands on DNA conformation and hydrolytic
Asian J Pharm Clin Res, Vol 9, Issue 3, 2016, 277-281
Neelaveni et al.
and oxidative double strand DNA cleavage. J Inorg Biochem
;100(3):316-30.
Ganeshpandian M, Ramakrishnan S, Palaniandavar M, Suresh E,
Riyasdeen A, Akbarsha MA. Mixed ligand copper(II) complexes of
,9-dimethyl-1,10-phenanthroline: Tridentate 3N primary ligands
determine DNA binding and cleavage and cytotoxicity. J Inorg Biochem
;140:202-12.
Vasantha S, Nisha DA, Kolunthu SS, Angeline T. Synthesis DNA
binding and activity of mixed ligand copper(II) complexes with sulfur
containing ligand: 1-hydroxy-2 - Acetonaphthonetosylhydrazone. Int J
Sci Res 2013;2:60-3.
Kucková L, Jomová K, Švorcová A, Valko M, Segla P, Moncol J, et al.
Synthesis, crystal structure, spectroscopic properties and potential
biological activities of salicylate? Neocuproine ternary copper(II)
complexes. Molecules 2015;20(2):2115-37.
Raman N, Johnson Raja S. DNA cleavage, structural elucidation
and anti-microbial studies of three novel mixed ligand Schiff base
complexes of copper(II). J Chem Soc 2007;10:983-92.
Vijayalakshmi M, Subramanian P. Synthesis, spectral characterization,
biological studies of Cu(II), Ni(II) and Zn(II) Schiff base complexes
derived from 2,4- dihydroxybenzaldehyde and P-amino phenol. Int J
Pharm Tech 2013;5:5144-55.
Sharma A, Mehta T, Shah MK. Synthesis and spectral studies of
transition metal complexes supported by NO-bidentate Schiff-base
ligand. J Der Chem Sin 2013;4(1):141-6.
Raman N, Ravichandarn S, Thangaraja C. Copper(II), cobalt(II),
nickel(II) and zinc(II) complexes of Schiff base derived from benzil-2,4dinitrophenylhydrazone
with aniline. J
Chem
Soc 2004;116(4):215-9.
Raman N, Thalamuthu S, Dhaveedhu Raja J, Neelakandan MA,
Banerjee S. DNA cleavage and antimicrobial activity studies on
transition metal (II) complex of 4-aminoantipyrine derivative. J Chil
Chem Soc 2008;53(1):1450-4.
Hirohama T, Kuranki Y, Ebina E, Sugizaki T, Aril H, Chikira M,
et al. Copper(II) complexes of 1,10-phenathroline-derived ligands:
Studies on DNA properties and nuclease activity. J Inorg Biochem
;99(55):1205-19.
Krishnaa PM, Reddy KH, Krishna PG, Philipb GH. DNA interactions
of mixed ligand copper(II) complexes with sulphur containing ligands.
Int J Chem 2007;46:904-8.
Adelaide OM, James OO. Antimicrobial, DNA cleavage and antitumoral
properties of some transition metal complexes of 1, 10–phenanthroline
and 2, 2ʹ – bipyridine. Int J Res Pharm Biomed Sci 2013;4(4):1160-70.
Lamour E, Routier S, Bernier JL, Catteau JP, Bailly C, Vezin H.
Oxidation of cu(w) to cu(iii), free radical production, and dna cleavage
by hydroxy-salen-copper complexes. Isomeric effects studied by ESR
and electrochemistry. J Am Chem Soc 1999;121:1862-9.
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