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Three New Copper (II) Complexes with Chiral Schiff Bases: Synthesis, Characterization, DNA Binding and DNA-cleavage Studies.
Author(s):
1. Turgay Tun: Department of Chemistry Engineering and Process, Faculty of Engineering, University of Ahi Evran, Kırsehir
2. Nadir Demirel: Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir, Turkey
3. Mahmut Emir: Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir, Turkey
4. Aslhan Gnel: Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir, Turkey
5. RiIfkiI Kadioglu: Department of Chemistry, Faculty of Science & Art, University of Ahi Evran, Kırsehir, Turkey
6. Nurcan Karacan: Department of Chemistry, Faculty of Science, University of Gazi, Ankara, Turkey
Abstract:
Summary: New mononuclear copper (II) complexes (1, 2 and 3) were synthesized from Schiff bases (H2L) of chiral amino alcohols. The structures of the copper complexes were proposed by a combination of elemental analyses, FTIR, LCMS, magnetic susceptibility and molar conductance measurement methods. Spectroscopic and analytical data of the complexes suggest four-coordinated structures. Geometry optimization carried out with DFT/6-31G (d,p) were proposed to be distorted square planar geometry for the complexes. The similarity between experimental and theoretical IR spectra confirms the proposed structures. The interaction of copper (II) complexes with calf thymus (CT-DNA) was investigated using absorption titration method. The results suggest that the complex 1 and 2 can bind to DNA by intercalation. Binding constants Kb were found to be 2.46×105 for 1, 5.41×105 for 2 and 7.00×104 for 3. Moreover, agarose gel electrophoresis assay demonstrates that all complexes were found to cleavage of plasmid pentry/d-topo plasmid DNA. Complex 2 shows the best cleavage activity (5 µM).
Page(s): 334-344
DOI: DOI not available
Published: Journal: Journal of Chemical Society of Pakistan, Volume: 41, Issue: 2, Year: 2019
Keywords:
Keywords are not available for this article.
References:
[1] K. H. Thompson , C.,Orvig, 2003.,Science 300 -
[2] I.Subramanian,Z. F.Vanek,J. M.Bronstein, 2002.Diagnosis and treatment of Wilson's disease,Curr. Neurol. Neurosci. Rep 2 -
[3] H. D.Lu,L. Z.Wang,B. K.Wilson,S. A.McManus,J.,P. K. Padakanti , A.,Alavi , R. H.,Mach , and R. K.,Prud, 2018.'homme, Copper Loading of Preformed Nanoparticles for PET-Imaging Applications,ACS Applied Materials & Interfaces 10 -
[4] K. D. Mjos and C.,Orvig, 2014.,Metallodrugs in Medicinal Inorganic Chemistry. Chem. Rev 114 -
[5] E. I.Solomon,D. E.Heppner,E. M.Johnston,J. W.Ginsbach,J.Cirera,M.Qayyum,M. T.Kieber-Emmons,C. H.Kjaergaard,R. G.Hadt, 2014., 114 -
[6] C.Santini,M.Pellei,V.Gandin,M.Porchia,F.Tisato,C.Marzano, 2014.Advances In Copper Complexes as Anticancer Agents, Chem, 114 -
[7] F.Tisato,C.Marzano,M.Porchia,M.Pellei,C.Santini,Copper-Based AnticancerStrategies, 2010.,Med. Res. Rev. 30 -
[8] H.Yu,Y.Yang,Q.Li,T.Ma,T.Zhu,J.Xie,W.Zhu,Z.Cao,K.Dong,J.Huang,L.Jia, 2016.Ternary Dinuclear Copper(II) Complexes of a Reduced Schiff Base Ligand with Diimine Coligands: DNA Binding, Cytotoxic Cell Apoptosis, and Apoptotic Mechanism, Chem, 87 -
[9] A. M. Abu-Dief , I., 2015.M. A. Mohamed, a Review of Versatile Applications of Transition Metal Complexes Incorporating Schiff Bases,BeniSuef Univ. J. Basic Appl. Sci. 4 -
[10] A.Chakraborty,P.Kumar,K.Ghosh,P.Roy, 2010.Evaluation of a Schiff Base Copper Complex Compound as Potent Anticancer Molecule with Multiple Targets of Action, Eur, 647 -
[11] J. Lu , Q.,Sun , J. L.,Li , L.,Jiang , W.,Gu , X.,Liu , J. L.,Tian , S.P.,Yan,J InorgBiochem, 2014.Protein Binding Activities and in Vitro Anticancer Activity Studies, 137 -
[12] M. Sarigul , P.,Deveci , M.,Kose , U. Arslan, H. Türk,Dagi , M.,Kurtoglu,BiologicalStudies,J.Mol, 2015.New Tridentate Azo Azomethines, and Their Copper(II) Complexes: Synthesis, Solvent Effect on Tautomerism, Electrochemical, 1096 -
[13] V.Lanza,D.Milardi,G. DiNatale,G.Pappalardo, 2018.Repurposing of Copper(II)-chelating Drugs for the Treatment of Neurodegenerative Diseases,Curr. Med 25 -
[14] Grünspan , B. H. M.,Mussulini , S.,Baggio , P. R.,Santos , F.,Dumas , E. P.,Rico , D. L. de Oliveira, S. Moura., 2018.dos,Teratogenic and Anticonvulsant Effects of Zinc and Copper Valproate Complexes in Zebrafish. Epilepsy Research 139 -
[15] C. Wolf, 2007.,Dynamic Stereochemistry of Chiral Compounds. Principles and Applications -
[16] B. H.Ye,Q. L.Zhang,X. H.Zou,Q. X.Zhen,X.Tian,L. N.Ji,J. Biol. Inorg. Chem., 2000.Enantiomeric Ruthenium(II) Complexes Binding to DNA: Binding Modes And Enantioselectivity, 5 -
[17] J. Crassous, 2009.Towards Molecular Materials,Chem. Soc. Rev. 38 -
[18] G. Muller, Luminescent Chiral Lanthanide(III) Complexes as Potential Molecular Probes, Dalt. Trans., 42, 9692 (2009).
[19] B. L.Fei,W.Xu,W.Gao,J.Zhang,Y.Zhao,J.Long,C. E.Anson,A. K.Powell,J.Photochem, 2015.Cytotoxicity Activity of a Chiral Iron (III) Triangle Complex Based on a Natural Rosin Product, 142 -
[20] Z.Dezhahang,M. R.Poopari,J.Cheramy,Y.Xu,-YlSchiff-Base,Ligand And Its Transition Metal Complexes, 2015., 54 -
[21] N. H.Khan,N.Pandya,N. C.Maity,M.Kumar,R. M.Patel,R. I.Kureshy,S. H. R. H.Abdi,S.Mishra,S.Das,H. C.Bajaj,Eur. J.Med, 2011.Influence of Chirality of V(V) Schiff Base Complexes on DNA, BSA Binding and Cleavage Activity, 46 -
[22] R.Alul,M. B.Cleaver,J. S.Taylor,AnticancerDrugst, 1992.Synthesis and Characterization of a Series of Achiral and Chiral Mono-and Bis[(Dien)Pt(Ii)I]I Derivatives as Potential DNA and RNA Structure Probes, 31 -
[23] F.Arjmand,M.Muddassir,I. Yousuf,(S,CytotoxicityStudies,J.Photochem, 2014.- Copper(II) and Diorganotin(IV)-Based Antitumor Agents: Their in Vitro DNA Binding Profile, 136 -
[24] Z.Chu,W.Huang,L.Wang,S.Gou,Schiff-Base Macrocycles, 2008.Their Reactivity with First-Row Transition Metal Ions, 27 -
[25] A.Dhamija,S. A.Ikbal,S. P.Rath, 2016.Induction and Rationalization of Supramolecular Chirality in The Tweezer-Diamine Complexes: Insights from Experimental and DFT Studies, Inorg, 55 -
[26] M.Rodríguez,I. Romero,L.Vaquer,X.Sala,A.Llobet,M.Corbella,M. N.Collomb,X.Fontrodona,Mn(II) Complexes Containing the Polypyridylic Chiral Ligand, 2009.Catalysts for Oxidation Reactions, Dalt,Pinene[5 30 -
[27] T. E. Kokina , L. A.,Glinskaya , A. V.,Tkachev , V. F.,Plyusnin , Y. V.,Tsoy , I. Y.,Bagryanskaya , E. S.,Vasilyev , D. A.,Piryazev , L. A.,Sheludyakova , S. V.,Larionov,-Α- PineneFragments,CrystalStructures,PhotophysicalProperties, 2016.Chiral Zinc(II) and Cadmium(II) Complexes with a Dihydrophenanthroline Ligand Bearing (-, 117 -
[28] H. L. Kwong , H. L.,Yeung , C. T.,Yeung , W. S.,Lee , C. S.,Lee , W. L.,Wong, 2007., 251 -
[29] B. L.Fei,Z. X.Huang,W. S.Xu,D. D.Li,Y.Lu,W. L.Gao,Y.Zhao,Y.Zhang and Q. B. Liu,J.Photochem, 2016.Chiral Copper(II) Complex Based on Natural Product Rosin Derivative as Promising Antitumour Agent, 160 -
[30] M. K. Paul , G. Kalita, A. R.,Laskar , T. D.,Choudhury and N. V. S.,Rao,J.Mol, 2013.Synthesis and Mesomorphism of New Chiral Imines and Copper(II) Complexes, 1039 -
[31] R.Arunachalam,M. K.Choudhary,R. I.Kureshy,P. S.Subramanian, 2016.Binuclear Cu(II) Chiral Complexes: Synthesis, Characterization and Application in Enantioselective Nitroaldol (Henry) Reaction, 30 -
[32] Feldman anf J. M. Fraile, 2016.Non-Covalent Immobilization of Chiral Copper Complexes on Al-Mcm41: Effect of The Nature of The Ligand, Catal, 83 -
[33] C. Hee , C.,Wei , J.,Wei , I. Hong, K.,Vei , M.,Jamil and H.,Ling,J.Inorg, 2016.Enantiomeric Pair of Copper (II) Polypyridyl-Alanine Complexes : Effect of Chirality on Their Interaction with Biomolecules, 160 -
[34] S.Muche,I.Levacheva,O.Samsonova,A.Biernasiuk,A.Malm,R.Lonsdale,U.Bakowsky,M.Hołyńska,Complex , J.,Mol, 2017.Synthesis, Structure and Stability of a Chiral Imine-Based SchiffBased Ligand Derived from L-Glutamic Acid, 1127 -
[35] W. C.Zhang,X.Tang,X.Lu,One-Dimensional Chiral,J.Inorg, 2016.Copper (II) Complexes with Novel NanoStructures and Superior Antitumor Activity, 156 -
[36] N. H.Khan,N.Pandya,K. J.Prathap,R. I.Kureshy,S. H. R.Abdi,S.Mishra,H. C.Bajaj,AntibacterialActivities,Spectrochim. Acta. A.Mol, 2011.Antioxidant, 81 -
[37] X.Zhou,Y.Li,D.Zhang,Y.Nie,Z.Li,W.Gu, 2016.Copper Complexes Based on Chiral Schiff-Base Ligands : DNA/BSA Binding Ability, DNA Cleavage Activity, Cytotoxicity and Mechanism of Apoptosis, Eur,J. Med 114 -
[38] F.Arjmand,F.Sayeed,M.Muddassir,CleavageActivity,J.Photochem, 2011.Synthesis of New Chiral Heterocyclic Schiff Base Modulated Cu(II)/Zn(II) Complexes: Their Comparative Binding Studies with Ct-DNA, Mononucleotides, 103 -
[39] C. Da Silveira , J. S.,Luz , C. C.,Oliveira , I. Graziani, M. R.,Ciriolo,A. M. Da C. Ferreira,J.Inorg, 2008.Double-Strand DNA Cleavage Induced by Oxindole-Schiff Base Copper(II) Complexes with Potential Antitumor Activity, 102 -
[40] M. Çolak , T.,Aral , H.,Hoşgören and N.,Demirel, 2007.Synthesis of Novel Chiral Schiff-Base Ligands and Their Application in Asymmetric Nitro Aldol (Henry) Reaction, Tetrahedron Asymmetry, 18 -
[41] M. J. Frisch , G. W.,Trucks , H. B.,Schlegel , G. E.,Scuseria , M. A.,Robb , J. R.,Cheeseman , J. A.,Montgomery , Jr., T.,Vreven , K. N.,Kudin , J. C.,Burant , J. M.,Millam , S. S.,Iyengar , J.,Tomasi , V.,Barone , B.,Mennucci , M.,Cossi , G. Scalmani, N.,Rega , G. A.,Petersson , H.,Nakatsuji , M.,Hada , M.,Ehara , K.,Toyota , R.,Fukuda , J.,Hasegawa , M.,Ishida , T.,Nakajima , Y.,Honda , O.,Kitao , H.,Nakai , M.,Klene , X.,Li , J. E.,Knox , H. P.,Hratchian , J. B.,Cross , V.,Bakken , C.,Adamo , J.,Jaramillo , R.,Gomperts , R. E.,Stratmann , O.,Yazyev , A. J.,Austin , R.,Cammi , C.,Pomelli , J. W.,Ochterski , P. Y.,Ayala , K.,Morokuma , G. A.,Voth , P.,Salvador , J. J.,Dannenberg , V. G.,Zakrzewski , S.,Dapprich , A. D.,Daniels , M. C.,Strain , O.,Farkas , D. K.,Malick , A. D.,Rabuck , K.,Raghavachari , J. B.,Foresman , J. V.,Ortiz , Q.,Cui , A. G.,Baboul , S.,Clifford , J.,Cioslowski , B. B.,Stefanov , G. Liu, A.,Liashenko , P.,Piskorz , I. Komaromi,R. L.Martin,D. J.Fox,T.Keith,M. A.Al-Laham,C. Y.Peng,A.Nanayakkara,M.Challacombe,P. M. W.Gill,B.Johnson,M. W.Wong,C.Gonzalez,J. A.Pople,RevisionB.,WallingfordCt., 2004., 03 -
[42] M. E. Reichmann , S. A.,Rice , C. A.,Thomas , P.,Doty, 1954.A Further Examination of The Molecular Weight and Size of Desoxypentose Nucleic Acid,J. Am. Chem. Soc. 76 -
[43] L. H.Abdel-Rahman,R. M.El-Khatib,L. A. E.Nassr,A. M.Abu-Dief,J.Mol, 2013.Synthesis, Physicochemical Studies, Embryos Toxicity and DNA Interaction of Some New Iron(II) Schiff Base Amino Acid Complexes, 1040 -
[44] S.Sujarani,A.Ramu,J.Mol, 2015.Docking of Ethanamine Schiff Base Imines & Metal (II) Complexes, Cytotoxicity & DNA Interaction Studies, 1079 -
[45] A.Wolfe,G. H.Shimer,Biochemistry, 1987.Polycyclic Aromatic Hydrocarbons Physically Intercalate Into Duplex Regions of Denatured DNA, 26 -
[46] A. Wolfe, G. H. Shimer, T. Meehan, Polycyclic Aromatic Hydrocarbons Physically Intercalate Into Duplex Regions of Denatured DNA., Biochemistry., 26, 6392 (1987).
[47] Geary, 1971.The Use of Conductivity Measurements in Organic Solvents for The Characterisation of Coordination Compounds, Coord, 7 -
[48] M. Niu , Z.,Li , H.,Li , X.,Li , J.,Dou , S.,Wang, 2015.Cytotoxic Activity and Magnetic Properties of Amino-Alcohol Schiff Base Derived Cu(II)/Ni(II) Metal Complexes: Influence of The Nuclearity and Metal Ions, Rsc Adv, 5 -
[49] M. Niu , Z.,Li , X.,Li , X.,Huang, 2016.Two Chiral Alkanolamine Schiff Base Cu(II) Complexes as Potential Anticancer Agents: Synthesis, Structure, 6 -
[50] Y. A. N.Hui,Struc, 2016.Cytotoxic Activity of a Chiral Amino-Alcohol Schiff Base Derived Cu (II) Complex, Chin, 465 -
[51] M. Rezaeivala , R.,Golbedaghi , M.,Khalili,Coor, 2016.Coordination Chemistry of Some New Cu (II), Ni (II) and Co (II) Macroacyclic (N2O4) Schiff Base Complexes: X-Ray Crystal Structure of Cu (II) Complex, Russ, 42 -
[52] D.Ghosh,K.Bera,M.Kumar,S. H. R.Abdi,N. H.Khan,H. C.Bajaj, 2014.Asymmetric Allylation of Sulfonyl Imines Catalyzed by in Situ Generated Cu (II) Complexes of Chiral Amino Alcohol Based Schiff Bases, Rsc Adv, 4 -
[53] J. Lu , W.,Pan , R.,He , S.,Jin , X.,Liao , B.,Wu , P.,Zhao , H.,Guo, 2012.DNA-Binding and Photocleavage Studies of Metallofluorescein-Porphyrin Complexes of Zinc(II) and Copper(II), Transition Met, 37 -
[54] U.Chaveerach,A.Meenongwa,Y.Trongpanich,C.Soikum,O-Methylurea, 2010.Cleavage Behaviors of Copper(II) Complexes with Amidino-O-Methylurea and NMethylphenyl-Amidino-, 29 -
[55] K.Nakamoto,M.Tsuboi, 2008.Structures and Spectra, Methods Biochem Anal, 51 -
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