Synthesis, DNA binding, and oxidative cleavage studies of Fe(II) and Co(III) complexes containing bioactive ligands

Nucleosides, Nucleotides and Nucleic Acids

Volumn 30, Issue 2, 2011, Pages 83-96

  Sreekanth, B ^a   Krishnamurthy, G ^b   Naik, H S Bhojya ^c   Vishnuvardhan, T K ^a   Vinaykumar, B ^c   Sharath, N ^c  

^a ACHARYA INSTITUTE OF TECHNOLOGY   (India)

^b Sahyadri Science College   (India)

^c KUVEMPU UNIVERSITY   (India)

Author keywords

cleavage studies; DNA binding; Fe(II) and Co(III) complexes

Indexed keywords

1 [[2 [(2 HYDROXYNAPHTHALEN 1 YL)METHYLIDINE]AMINO]PHENYL]IMINO]METHYL]NAPHTHALENE 2 OL; COBALT; DNA; FERROUS ION; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; COMPLEX FORMATION; DNA BINDING; DRUG SYNTHESIS; OXIDATIVE STRESS; PH MEASUREMENT; TEMPERATURE STRESS; THYMUS; VISCOSITY;

ANIMALS; BINDING SITES; CATTLE; COBALT; DNA; IRON; LIGANDS; MOLECULAR STRUCTURE; NUCLEIC ACID DENATURATION; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; TEMPERATURE;

EID: 79952129468     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2010.547544     Document Type: Article

References (47)

1. Spillane, C.B.; Dabo, M.N.V.; Fletcher, N.C. The dichotomy in the DNA-binding behavior of ruthenium(II) complexes. J. Biol. Inorg. Chem. 2008, 102, 673-683.
2. Surendra Babu, M.S.; Krishna, P.G.; Hussain Reddy, K.; Philip, G.H. Synthesis, characterization and DNA cleavage activity of nickel(II) adducts with aromatic heterocyclic bases. J. Serb. Chem. Soc. 2010, 75, 61-74.
3. Ramakrishnan, S.; Palaniandavar,M.Mixed-ligand copper(II) complexes of dipicolylamine and 1,10- phenanthrolines: The role of diimines in the i (Pubitemid 40494290)
4. Lu, P.; Zhu, M.L.; Yang, P. Crystal structure and nuclease activity of mano(1,10. phenanthroline) copper complex. J. Inorg. Biochem. 2003, 95, 31-36. (Pubitemid 36434403)
5. Hemmert, C.; Pitie, M.; Renz, M.; Gornitzka, H.;Meunier, S.B. Preparation, characterization and crystal structure of manganese(II), iron(III) and copper(II) complexes of the bis[di-1, 1-(2-pyridal)ethyl] amine (BDPEA) ligands; Evaluation of their DNA cleavage activities. J. Biol. Inorg.Chem. 2001, 6, 14-22.
6. Navarro, M.; Cisneros-Fajardo, E.J.; Sierralta, A.; Fernadez-Mastre, M.; Silva, P.; Arrieche, D.; Marchan, E. Design of copper DNA intercalators with leishmanicidal activity. J. Biol. Inorg. Chem. 2003, 8, 401-408. (Pubitemid 36578191)
7. Zhang, Q.-L.; Liu, J.-G.; Chao, H.; Xue, G.-Q.; Ji, L.-N. DNA-binding and photocleavage studies of cobalt(III) polypyridyl complexes: [Co(phen)2IP]3+ and [Co(phen)2PIP]3+. J. Inorg. Biochem. 2001, 83, 49-55.
8. Zhang, Q.-L.; Liu, J.-G.; Liu, J.-Z.; Li, H.; Yang, Y.; Xu, H.; Chao, H.; Ji, L.-N. Effect of intramolecular hydrogen-bond on the DNA-binding and photocleavage properties of polypyridyl cobalt(III) complexes. Inorg. Chim. Act. 2002, 339, 34-40.
9. Zhang, Q.-L.; Liu, J.-G.; Liu, J.; Xue, G.-Q.; Li, H.; Liu, J.-Z.; Zhou, H.; Qu, L.-H.; Ji, L.-N.J. DNA-binding and photocleavage studies of cobalt(III) mixed-polypyridyl complexes containing 2-(2-chloro-5-nitrophenyl)imidazo [4,5-f][1,10]phenanthroline. J. Inorg. Biochem. 2001, 85, 291-296. (Pubitemid 32717085)
10. Moghaddas, S.; Hendry, P.; Geue, R.J.; Qin, C.; Bygott, A.M.T.; Sargeson, A.M.; Dixon, N.E. Interaction of substituted cobalt(III) cage complexes with DNA. J. Chem. Soc., Dalton Trans. 2000, 2085-2089.
11. Arounaguiri, S.; Maiya, B.G. Dipyridophenazine Complexes of cobalt(III) and nickel(II): DNAbinding and photocleavage studies. Inorg. Chem. 1996, 35, 4267-4720.
12. Murray, V.; Martin, R.F. The sequence specificity of bleomycin-induced DNA damage in intact cells. J Biol Chem. 1985, 260, 19, 10389-10391. (Pubitemid 16252205)
13. Burger, R.M. Cleavage of nucleic acids by bleomycin. Chem. Rev. 1998, 98, 1153-1170.
14. Hertzberg, R.P.; Dervan, P.B. Cleavage of double helical DNA by methidium-propyl-EDTA-iron(II). J Am Chem Soc. 1982, 104, 313-315.
15. Thomas, C.J.; Mc Cormick, M.M.; Vialas, C.; Tao, Z.F.; Leitheiser, C.J.; Rishel, M.J.; Wu, X.; Hecht, S.M. Alteration of the selectivity of DNA cleavage by a deglycobleomycin analogue containing a trithiazole moiety. J. Am. Chem. Soc. 2002, 124, 3875-3884. (Pubitemid 34310902)
16. Wilox, D.E. Binuclear metallohydrolases. Chem. Rev. 1996, 96, 2435-2458.
17. Neves, A.; Terenzi, H.; Horner, R.; Horn, A. Jr.; Szpoganicz, B.; Sugai, J. Hydrolytic DNA cleavage promoted by a dinuclear iron(III) complex. Inorg. Chem. Commun. 2001, 4, 388-391. (Pubitemid 32641036)
18. Routier, S.; Vezin, H.; Lamour, E.; Bernier, J-L.; Ca Heau, J-P.; Bailly, C. DNA cleavage by hydroxysalicylidene- ethylendiamine-iron complexes. Nucleic Acid Res. 1999, 27, 4160-4166.
19. Horn, A. Jr.; Vencato, I.; Bortoluzzi, A.J.; Horner, R.; Silva, R. A. N.; Spoganicz, B.; Drago, V.; Terenzi, H.; De Oliveria, M.C.B.; Werner, R.; Haase, W.; Neves, A. Synthesis, crystal structure and properties of dinuclear iron (III) complexes containing terminally coordinated phenolate/H2O/OH- groups as models for purple acid phosphatases: Efficient hydrolytic DNA cleavage. Inorg. Chim. Acta 2005, 358, 339-345.
20. Arun, K.S.; Arati, S.; Dhimant, D.; Madhunapantula, SubbaRao V.; Sung, J.H.; Gavin, P.R.; Shantu, A. Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates. J. Med. Chem. 2008, 51, 7820-7826.
21. Mlochowski, J.; Kloc, K.; Lisiak, R.; Potaczek, P.; Wójtowicz, H. Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology (JE- 1901MR). ARKIVOC, 2006, 6, 14-46.
22. Fletcher, M.D. Synthetic methods. Part (IV). Heteroatom methods. Annu. Rep. Prog. Chem., Sect. B, 2002, Bangor, Gwynedd, UK, 98, 61-89.
23. Dhar, S.; Senapati, D.; Das, P.K.; Chattopadhyay, P.; Nethaji, M.; Chakravarty, A.R. Ternary copper complexes for photocleavage ofDNAby red light: direct evidence for sulfur-to-copper charge transfer and d-d band involvement. J. Am. Chem. Soc. 2003, 125, 12118-12124. (Pubitemid 37238846)
24. Narajji, C.; Karvekar, M.D.; Das, A.K. Biological importance of organoselenium compounds. Indian J. Pharm. Sci. 2007, 69, 344-351. (Pubitemid 47379260)
25. Tangali Ravikumar, R.; Halehatty Bhojya Naik, S.; Ramesh, S.; Raghavendra, M.; Krishnamurthy, G. One-pot synthesis of 2-seleno-4- methylquinoline. Molbank. 2007, M543.
26. Sreekanth, B.; Krishnamurthy, G.; Bhojya Naik, H. S.; Vishnuvardhan, T.K. Fe(II) complexes containing bioactive ligands: Synthesis, DNA binding and cleavage studies. Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry 2010, 40, 955-962.
27. Reichmann, M.E.; Rice, S.A.; Thomas, C.A.; Doty, P. A further examination of the molecular weight and size of deoxypentose nucleic acid. J. Am. Chem. Soc. 1954, 76, 3047-3053.
28. Wolfe, A.; Shimer, G.H.; Meehan, T. Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 1987, 26, 6392-6396. (Pubitemid 17155512)
29. Augamuthu, R.; Rajendiran, V.; Uma Maheshwari, P.; Balamurugan, R.; Kilner, C.A.; Halcrow, M.A.; Palaniandavar, M. Copper(II) complexes of tridentate pyridylmethylethylnediamines: Role of ligand steric hindrance on DNA binding and cleavage. J. Inorg. Biochem. 2005, 99, 1717-1732. (Pubitemid 41039932)
30. Zhang. H.; Liu, C-S.; Bu, X-H.; Yang, M. Synthesis, crystal structure, cytotoxic activity and DNAbinding properties of the copper (II) and zinc (II) complexes with 1-[3-(2-pyridyl)pyrazol-1- ylmethyl]naphthalene. J. Inorg. Biochem., 2005, 99, 1119-1125.
31. Sudhamani, C.N.; Bhojya Naik, H.S.; Ravikumar Naik, T.R.; Prabhakar, M.C. Synthesis, DNA binding, and cleavage studies of Ni(II) complexes with fused aromatic N-containing ligands. Spectrochemica Acta Part A 2009, 72, 643-647.
32. Mishra, L.; Ajay K.Y.; Ratna S.P.; Choi, C.S.; Koji, A. Studies on some new Ru(iii) complexes using arylazo pentane-2,4-dione and 2,6-bis (2-benzimidazolyl) pyridine as ligands: Synthesis, spectroscopic, luminescent, electrochemical and biological activities. Metal Based Drugs 2001, 8, 65-71.
33. Barton, J.K.; Danishefsky, A.T.; Goldberg, J.M. Tris(phenanthroline) ruthenium(II): stereoselectivity in binding to DNA. J. Am. Chem. Soc. 1984, 106, 2172-2176.
34. Tysoe, S.A.;Morgan, R.J.; Baker, A.D.; Strekas, T.C. Spectroscopic investigation of differential binding modes of.DELTA.- and .LAMBDA.-Ru(bpy) 2(ppz)2+ with calf thymus DNA. J. Phys. Chem. 1993, 97, 1707-1711.
35. Liu, J.; Lu, T.B.., Li, H.; Zhang, Q.-L..; Ji, L.-N..; Zhang, T.-X.; Qu, L.-H..; Zhou, H. DNA-binding and cleavage studies of a dinuclear copper(II) complex with a 26-membered hexaazamacrocycle. Transition Metal Chem. 2002, 27, 686-690.
36. Laxma Reddy, K.; Harish Kumar Reddy, Y.; Satyanarayana, S. DNA-binding and photocleavage properties of Ru(II) polypyridyl complexes with DNA and their toxicity studies on eukaryotic microorganis. Nucleosides, Nucleotides Nucleic Acids 2009, 28, 953-968.
37. Chao, H.; Yuan, Y.-X..; Zhou, F..; Ji, L.-N..; Zhang, J. DNA interactions of a dinuclear ruthenium(II) complex bridged by 1,3-bis(1,10-phenanthroline[5, 6-d]imidazol-2-yl)benzene. Transition Metal Chem. 2006, 31, 465-469.
38. Archika, C.B.; Smita, G.; Anupa, A.K.; Avinash, S.K.; Vedavati, G. DNA-binding studies of mixed ligand cobalt(III) complexes. Transition Metal Chem. 2005, 30, 312-316.
39. Surendrababu, M.; Krishna, P.G.; Hussain Reddy, K.; Phillip, G.H, Synthesis, characterization, electrochemical studies, DNA binding and cleavage of mixed copper(II) oxime complexes. Main Group Chem. 2009, 8, 101-114.
40. Anbu, S.; Kandaswamy, M.; Varghese, B. Structural, electrochemical, phosphate-hydrolysis, DNA binding and cleavage studies of new macrocyclic binuclear nickel (II) complexes. Dalton Trans. 2010, 39, 3823-3832.
41. Peng, B.; Chen, X..; Du, K.-J.; Yu, B.-L..; Chao, H..; Ji, L.-N. Synthesis, characterization and DNA-binding studies of ruthenium (II) mixed complexes containing dipyrido[1,2,5]oxiazolo[3,4- b]quinoxaline. Spectrochimica Acta Part A 2009, 74, 896-901.
42. Arounaguiri, A.; Eshwaramoorthy, D.; Ashokkumar, A.; Dattagupta, A.; Maiya, B.G. Cobalt(III), nickel(II) and ruthenium(II) complexes of 1,10-phenanthroline family of ligands: DNA binding and photocleavage studies. Proceedings of the Indian Acadamy of Sciences: Chemical Sciences 2000, 112, 1-17. (Pubitemid 30566934)
43. Prabhakar, M.C.; Bhojya Naik, H.S. Binding and photocleavage of DNA by mixed ligand Co(III) and Ni(II) complexes of thiophene[2, 3-b] quinoline and phenanthroline/bipyridine. Biometals 2008, 21, 675-684.
44. Prabhakar, M.C.; Basavaraju, B.; Bhojya Naik,H.S. Co(III) andNi(II) complexes containing bioactive lingands: Synthesis, DNA binding, and photocleavage studies. Bioinorg.Chem. Appl. 2007, 2007. 7-13.
45. Prabhakar, M.C.; Bhojya Naik,H.S.; Krishna, V.; Kumaraswamy,H.M. Binding and oxidative cleavage studies of DNA bymixed ligand Co(III) and Ni(II) complexes of quinolo [3,2-b]benzodiazapine and 1,10-phenanthroline. Nucleosides, Nucleotides, and Nucleic Acids, 2007, 26, 459-471. (Pubitemid 46956928)
46. Yuan, M.; Li, Y.G.; Wang, E.B.; Lu, Y.; Hu, C.W.; Hu,N.H.; Jia, H.Q. Hydrithermal synthesis and crystal structure of a hybrid material based on [Cp(phen)8(HPO3)2]4+ and a highly reduced polyoxoanion. J. Chem. Soc., Dalton Trans. 2002, 2916-2920.
47. Sudhamani, C.N.; Bhojya Naik, H.S.; Sreedhara Pai, K. DNA interaction and antitumor activity of Cu(II) complexes of substituted quinoline containing N, S and N, Se ligands. Ind. J. Chem. Sec A (communicated).