Abstract
Nucleolytic activities of some new oxime-type ligand complexes were investigated by neutral agarose gel electrophoresis. Analysis of the cleavage products in agarose gel indicated that all complexes used converted supercoiled pUC18 plasmid DNA to its nicked or linear form. It was found that nucleolytic activities of the complexes depend on the complex concentration, reaction time and the presence of a cooxidant (magnesium monoperoxyphthalate, MMPP) in the reaction mixture. However, the complexes cleaved pUC18 plasmid DNA at all investigated pH values. Nucleolytic activities of complexes were investigated for different complex concentrations (0.1–100 μmol L−1), pH values (6.0–10.0) and reaction times (0–60 min). Molecular modeling studies performed by the Hyperchem Software together with DNA-binding studies showed that planar sites of the complexes intercalated into double stranded DNA. It can be concluded that all oxime-type ligand complexes used can be evaluated as nuclease mimics.
Similar content being viewed by others
References
Asad, S. F., Singh, S., Ahmad, A., & Hadi, S. M. (1999). Bilirubin-Cu(II) complex degrades DNA. Biochimica et Biophysica Acta (BBA) — General Subjects, 1428, 201–208. DOI: 10.1016/S0304-4165(99)00075-6.
Barnard, C. F. J., Clear, M. J., & Hydes, P. C. (1987). Second generation of anticancer platinum compounds. Chemistry in Britain, 22, 1001–1004.
Belev, T. N., Singh, M., & McCarthy, J. E. G. (1991). A fully modular vector system for the optimisation of gene expression in Escherichia coli. Plasmid, 26, 147–150. DOI: 10.1016/0147-619X(91)90056-3.
Borah, S., Melvin, M. S., Lindquist, N., & Manderville, R. A. (1998). Copper-mediated nuclease activity of a tambjamine alkaloid. Journal of the American Chemical Society, 120, 4557–4562. DOI: 10.1021/ja9729746.
Bowen, W. S., Hill, W. E., & Lodmell, J. S. (2001). Comparison of rRNA cleavage by complementary 1,10-phenanthroline-Cu(II)- and EDTA-Fe(II)-derivatized oligonucleotides. Methods, 25, 344–350. DOI: 10.1006/meth.2001.1246.
Cramer, C. J. (2004). Essentials of computational chemistry: Theories and models, 2nd Ed. Chichester: Wiley.
Cowan, J. A. (2001). Chemical nucleases. Current Opinion in Chemical Biology, 5, 634–642. DOI: 10.1016/S1367-5931(01)00259-9.
Detmer, C. A., Pamatong, F. V., & Bocarsly, J. R. (1996). Nonrandom double strand cleavage of DNA by a monofunctional metal complex: mechanistic studies. Inorganic Chemistry, 35, 6292–6298. DOI: 10.1021/ic960519p.
Dülger, S., Saglam, N., Beldüz, A. O., Güner, S., & Karaböcek, S. (2000). DNA cleavage by homo- and heterotetranuclear Cu(II) and Mn(II) complexes with tetrathioether-tetrathiol moiety. BioMetals, 13, 261–265. DOI: 10.1023/A:1009222705659.
García-Raso, Á., Fiol, J. J., Adrover, B., Moreno, V., Mata, I., Espinosa, E., & Molins, E. (2003). Synthesis, structure and nuclease properties of several ternary copper(II) peptide complexes with 1,10-phenanthroline. Journal of Inorganic Biochemistry, 95, 77–86. DOI: 10.1016/S0162-0134(03)00121-1.
González-álvarez, M., Alzuet, G., Borrás, J., Macías, B., del Olmo, M., Liu-González, M., & Sanz, F. (2002). Nuclease activity of [Cu(sulfathiazolato)2(benzimidazole)2]2MeOH. Synthesis, properties and crystal structure. Journal of Inorganic Biochemistry, 89, 29–35. DOI: 10.1016/S0162-0134(01)00369-5.
Groves, J. T., & Farrell, T. P. (1989). DNA cleavage by a metal chelating tricationic porphyrin. Journal of the American Chemical Society, 111, 4998–5000. DOI: 10.1021/ja00195a074.
Güner, S., & Karaböcek, S. (1998). Superoxide dismutase-mimicking activities of dinuclear Cu(II) complexes with ligands containing a tetrathioether-tetraamino moiety. Journal of Biochemical and Molecular Toxicology, 12, 53–59. DOI: 10.1002/(SICI)1099-0461(1998)12:1〈53::AID-JBT7〉3.0.CO;2-O.
Güner, S., Karaböcek, S., & Kaklikkaya, I. (1999). Models for superoxide dismutases: characterization of mononuclear Cu(II), Fe(III), and Mn(II) complexes with 4′,5′-bis(salicylideneimino)benzo-15-crown-5. Bioorganic & Medicinal Chemistry, 7, 329–333. DOI: 10.1016/S0968-0896(98)00240-5.
Hirohama, T., Kuranuki, Y., Ebina, E., Sugizaki, T., Arii, H., Chikira, M., Selvi, P. T., & Palaniandavar, M. (2005). Copper(II) complexes of 1,10-phenanthroline-derived ligands: Studies on DNA binding properties and nuclease activity. Journal of Inorganic Biochemistry, 99, 1205–1219. DOI: 10.1016/j.jinorgbio.2005.02.020.
Kane, S. A., & Hecht, M. S. (1994). Polynucleotide recognition and degradation by bleomycin. Progress in Nucleic Acid Research and Molecular Biology, 49, 313–352. DOI: 10.1016/S0079-6603(08)60054-9.
Karaböcek, N., Armutcu, A., & Karaböcek, S. (2006a). Synthesis and structural studies of 2E,3E)-3-[(6-{[(1E,2E)-2-(hydroxyimino)-1-methylpropylidene]amino} pyridin-2-yl) imino]butan-2-one oxime, ligand and its mono-, di- and trinuclear copper(II) complexes. Transition Metal Chemistry, 31, 938–942. DOI: 10.1007/s11243-006-0089-y.
Karaböcek, S., Karaböcek, N., & Armutcu, A. (2006b). Synthesis and structural studies of 2-(hydroxyimino)-1-methylpropylideneamino-phenyliminobutan-2-one oxime, ligand and its complexes with Cu(II) and Ni(II). Transition Metal Chemistry, 31, 459–464. DOI: 10.1007/s11243-006-0012-6.
Kumar, R. S., Arunachalam, S., Periasamy, V. S., Preethy, C. P., Riyasdeen, A., & Akbarsha, M. A. (2008). DNA binding and biological studies of some novel water-soluble polymercopper(II)-phenantroline complexes. European Journal of Medicinal Chemistry, 43, 2082–2091. DOI: 10.1016/j.ejmech.2007.09.017.
Lerman, L. S. (1961). Structural considerations in the interaction of DNA and acridines. Journal of Molecular Biology, 3, 18–30.
Liu, C., Wang, M., Zhang, T., & Sun, H. (2004). DNA hydrolysis promoted by di- and multi-nuclear metal complexes. Coordination Chemistry Reviews, 248, 147–168. DOI: 10.1016/j.cct.2003.11.002.
Liu, C., Zhou, J., Li, Q., Wang, L., Liao, Z., & Xu, H. (1999). DNA damage by copper(II) complexes: coordination-structural dependence of reactivities. Journal of Inorganic Biochemistry, 75, 233–240. DOI: 10.1016/S0162-0134(99)00037-9.
McLachlan, G. A., Muller, J. G., Rokita, S. E., & Burrows, C. J. (1996). Metal-mediated oxidation of guanines in DNA and RNA: a comparison of cobalt(II), nickel(II) and copper(II) complexes. Inorganica Chimica Acta, 251, 193–199. DOI: 10.1016/S0020-1693(96)05272-3.
Papavassiliou, A. G. (1995). Chemical nucleases as probes for studying DNA-protein interactions. Biochemical Journal, 305, 345–357.
Pindur, U., Haber, M., & Sattler, K. (1993). Antitumor active drugs as intercalators of deoxyribonucleıc acid: molecular models of intercalatıon complexes. Journal of Chemical Education, 70, 263–272.
Pryor, W. A. (1988). Why is the hydroxyl radical the only radical that commonly adds to DNA? Hypothesis: It has a rare combination of high electrophilicity, high thermochemical reactivity, and a mode of production that can occur near DNA. Free Radical Biology & Medicine, 4, 219–223. DOI: 10.1016/0891-5849(88)90043-3.
Rappe, A. K., & Casevit, C. J. (1996). Molecular mechanics across chemistry. California, University Science Books.
Reddy, K. H., Reddy, P. S., & Babu, P. R. (2000). Nuclease activity of 2-substituted heteroaromatic thiosemicarbazone and semicarbazone copper(II) complexes. Transition Metal Chemistry, 25, 154–160. DOI: 10.1023/A:1007027011216.
Ross, S. A., Pittie, M., & Meunier, B. (1999). Synthesis of two acridine conjugates of the bis(phenanthroline) ligand “clip-phen” and evaluation of the nuclease activity of the corresponding copper complexes. European Journal of Inorganic Chemistry, 1999, 557–563. DOI: 10.1002/(SICI)1099-0682(199903)1999:3〈557::AID-EJIC557〉3.0.CO;2-Y.
Saglam, N., Colak, A., Serbest, K., Karaböcek, S., & Güner, S. (2004). DNA hydrolysis by homo- and heteronuclear Cu(II)-Ni(II) complexes of two diester-type ligands. Monatshefte für Chemie, 135, 1023–1031. DOI: 10.1007/s00706-004-0178-6.
Saglam, N., Colak, A., Serbest, K., Dülger, S., Güner, S., Karaböcek, S., & Beldüz, A. O. (2002). Oxidative cleavage of DNA by homo- and heteronuclear Cu(II)-Mn (II) complexes of an oxime-type ligand, BioMetals, 15, 357–365. DOI: 10.1023/A:1020228723299.
Serbest, K, Karaböcek, S., Değirmencioğlu, İ., Güner, S., & Kormali, F. (2001). Mono-, di- and trinuclear copper(II) dioxime complexes; 3-{2-[2-(2-hydroxyimino-1-methylpropylideneamino) ethylamino]ethylimino}butan-2-one oxime. Transition Metal Chemistry, 26, 375–379. DOI: 10.1023/A:1011073212502.
Sigman, D. S. (1986). Nuclease activity of 1,10-phenanthrolinecopper ion. Accounts of Chemical Research, 19, 180–186. DOI: 10.1021/ar00126a004.
Sigman, D. S., & Chen, C. B. (1990). Chemical nucleases: new reagents in molecular biology. Annual Review of Biochemistry, 59, 207–236. DOI: 10.1146/annurev.bi.59.070190.0012-31.
Sigman, D. S., Graham, D. R., D’Aurura, V., & Stern, A. M. (1979). Oxygen-dependent cleavage of DNA by the l,l0-phenanthroline cuprous complex. The Journal of Biological Chemistry, 254, 12269–12272.
Song, Y.-M, Wu, Q., Yang, P.-J, Luan, N.-N, Wang, L.-F, & Liu, Y.-M (2006). DNA binding and cleavage activity of Ni(II) complex with all-trans retinoic acid. Journal of Inorganic Biochemistry, 100, 1685–1691. DOI: 10.1016/j.jinorgbio.2006.06.001.
Terenzi, A., Barone, G., Silvestri, A., Giuliani, A. M., Ruggirello, A., & Liveri, V. T. (2009). The interaction of native calf thymus DNA with FeIII-dipyrido[3,2-a:2′,3′-c]phenazine. Journal of Inorganic Biochemistry, 103, 1–9. DOI: 10.16/j.jinorgbio.2008.08.011.
Travers, A. A. (1993). DNA-protein interactions. London: Chapman and Hall.
Wang, J., Yang, Z.-Y., Yi, X.-Y., & Wang, B.-D. (2009). DNA-binding properties studies and spectra of a novel fluorescent Zn(II) complex with a new chromone derivative. Journal of Photochemistry and Photobiology A: Chemistry, 201, 183–190. DOI: 10.1016/j.jphotochem.2008.10.022.
Zhang, Q.-L., Liu, J.-G., Chao, H., Xue, G.-Q., & Ji, L.-N. (2001). DNA-binding and photocleavage studies of cobalt (III) polypyridyl complexes: [Co(phen)2IP]3+ and [Co(phen)2 PIP]3+. Journal of Inorganic Biochemistry, 83, 49–55. DOI: 10.1016/S0162-0134(00)00132-X.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Colak, A., Cekirge, E., Karaböcek, S. et al. Investigation of DNA cleavage activities of new oxime-type ligand complexes and molecular modeling of complex-DNA interactions. Chem. Pap. 63, 554–561 (2009). https://doi.org/10.2478/s11696-009-0058-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-009-0058-y