Investigation of DNA cleavage activities of new oxime-type ligand complexes and molecular modeling of complex-DNA interactions

[1] 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. http://dx.doi.org/10.1016/S0304-4165(99)00075-610.1016/S0304-4165(99)00075-6Suche in Google Scholar

[2] Barnard, C. F. J., Clear, M. J., & Hydes, P. C. (1987). Second generation of anticancer platinum compounds. Chemistry in Britain, 22, 1001–1004. Suche in Google Scholar

[3] 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. http://dx.doi.org/10.1016/0147-619X(91)90056-310.1016/0147-619X(91)90056-3Suche in Google Scholar

[4] 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. http://dx.doi.org/10.1021/ja972974610.1021/ja9729746Suche in Google Scholar

[5] 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. http://dx.doi.org/10.1006/meth.2001.124610.1006/meth.2001.1246Suche in Google Scholar

[6] Cramer, C. J. (2004). Essentials of computational chemistry: Theories and models, 2nd Ed. Chichester: Wiley. Suche in Google Scholar

[7] Cowan, J. A. (2001). Chemical nucleases. Current Opinion in Chemical Biology, 5, 634–642. DOI: 10.1016/S1367-5931(01)00259-9. http://dx.doi.org/10.1016/S1367-5931(01)00259-910.1016/S1367-5931(01)00259-9Suche in Google Scholar

[8] 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. http://dx.doi.org/10.1021/ic960519p10.1021/ic960519pSuche in Google Scholar

[9] 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. http://dx.doi.org/10.1023/A:100922270565910.1023/A:1009222705659Suche in Google Scholar

[10] 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. http://dx.doi.org/10.1016/S0162-0134(03)00121-110.1016/S0162-0134(03)00121-1Suche in Google Scholar

[11] 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. 10.1016/S0162-0134(01)00369-5Suche in Google Scholar

[12] 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. http://dx.doi.org/10.1021/ja00195a07410.1021/ja00195a074Suche in Google Scholar

[13] 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. http://dx.doi.org/10.1002/(SICI)1099-0461(1998)12:1<53::AID-JBT7>3.0.CO;2-OSuche in Google Scholar

[14] 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. http://dx.doi.org/10.1016/S0968-0896(98)00240-510.1016/S0968-0896(98)00240-5Suche in Google Scholar

[15] 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. http://dx.doi.org/10.1016/j.jinorgbio.2005.02.02010.1016/j.jinorgbio.2005.02.020Suche in Google Scholar

[16] 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. http://dx.doi.org/10.1016/S0079-6603(08)60054-910.1016/S0079-6603(08)60054-9Suche in Google Scholar

[17] 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. http://dx.doi.org/10.1007/s11243-006-0089-y10.1007/s11243-006-0089-ySuche in Google Scholar

[18] 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. http://dx.doi.org/10.1007/s11243-006-0012-610.1007/s11243-006-0012-6Suche in Google Scholar

[19] 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. http://dx.doi.org/10.1016/j.ejmech.2007.09.01710.1016/j.ejmech.2007.09.017Suche in Google Scholar

[20] Lerman, L. S. (1961). Structural considerations in the interaction of DNA and acridines. Journal of Molecular Biology, 3, 18–30. 10.1016/S0022-2836(61)80004-1Suche in Google Scholar

[21] 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. http://dx.doi.org/10.1016/j.cct.2003.11.00210.1016/j.cct.2003.11.002Suche in Google Scholar

[22] 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. http://dx.doi.org/10.1016/S0162-0134(99)00037-910.1016/S0162-0134(99)00037-9Suche in Google Scholar

[23] 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. http://dx.doi.org/10.1016/S0020-1693(96)05272-310.1016/S0020-1693(96)05272-3Suche in Google Scholar

[24] Papavassiliou, A. G. (1995). Chemical nucleases as probes for studying DNA-protein interactions. Biochemical Journal, 305, 345–357. 10.1042/bj3050345Suche in Google Scholar

[25] 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. http://dx.doi.org/10.1021/ed070p26310.1021/ed070p263Suche in Google Scholar

[26] 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. http://dx.doi.org/10.1016/0891-5849(88)90043-310.1016/0891-5849(88)90043-3Suche in Google Scholar

[27] Rappe, A. K., & Casevit, C. J. (1996). Molecular mechanics across chemistry. California, University Science Books. Suche in Google Scholar

[28] 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. http://dx.doi.org/10.1023/A:100702701121610.1023/A:1007027011216Suche in Google Scholar

[29] 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. http://dx.doi.org/10.1002/(SICI)1099-0682(199903)1999:3<557::AID-EJIC557>3.0.CO;2-Y10.1002/(SICI)1099-0682(199903)1999:3<557::AID-EJIC557>3.0.CO;2-YSuche in Google Scholar

[30] 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. http://dx.doi.org/10.1007/s00706-004-0178-610.1007/s00706-004-0178-6Suche in Google Scholar

[31] 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. http://dx.doi.org/10.1023/A:102022872329910.1023/A:1020228723299Suche in Google Scholar

[32] 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. http://dx.doi.org/10.1023/A:101107321250210.1023/A:1011073212502Suche in Google Scholar

[33] Sigman, D. S. (1986). Nuclease activity of 1,10-phenanthrolinecopper ion. Accounts of Chemical Research, 19, 180–186. DOI: 10.1021/ar00126a004. http://dx.doi.org/10.1021/ar00126a00410.1021/ar00126a004Suche in Google Scholar

[34] 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. http://dx.doi.org/10.1146/annurev.bi.59.070190.00123110.1146/annurev.bi.59.070190.001231Suche in Google Scholar

[35] 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. 10.1016/S0021-9258(19)86305-6Suche in Google Scholar

[36] 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. http://dx.doi.org/10.1016/j.jinorgbio.2006.06.00110.1016/j.jinorgbio.2006.06.001Suche in Google Scholar

[37] 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. http://dx.doi.org/10.1016/j.jinorgbio.2008.08.01110.1016/j.jinorgbio.2008.08.011Suche in Google Scholar

[38] Travers, A. A. (1993). DNA-protein interactions. London: Chapman and Hall. 10.1007/978-94-011-1480-6Suche in Google Scholar

[39] 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. http://dx.doi.org/10.1016/j.jphotochem.2008.10.02210.1016/j.jphotochem.2008.10.022Suche in Google Scholar

[40] 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. http://dx.doi.org/10.1016/S0162-0134(00)00132-X10.1016/S0162-0134(00)00132-XSuche in Google Scholar