DNA binding and DNA cleavage studies of a water soluble cobalt(II) complex containing dinitrogen Schiff base ligand: The effect of metal on the mode of binding

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 4239-4245

  Shahabadi, Nahid ^a   Kashanian, Soheila ^a   Darabi, Farivash ^a  

^a RAZI UNIVERSITY   (Iran)

Author keywords

Anticancer drug; Cobalt(II) complex; DNA interaction; Schiff base

Indexed keywords

COBALT COMPLEX; COBALT(II) COMPLEX; SCHIFF BASE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; BINDING AFFINITY; COMPARATIVE STUDY; DNA BINDING; DNA CLEAVAGE; DNA STRUCTURE; FLUORESCENCE SPECTROSCOPY; SOLUBILITY; SYNTHESIS; TITRIMETRY; VISCOSITY;

ANIMALS; CATTLE; COBALT; DNA; LIGANDS; NITROGEN; ORGANOMETALLIC COMPOUNDS; SCHIFF BASES; SOLUBILITY; SPECTRUM ANALYSIS; VISCOSITY; WATER;

EID: 77955560728     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.06.020     Document Type: Article

References (73)

1. A.A.A. Abu-Hussen Synthesis and spectroscopic studies on ternary bis-Schiff base complexes having oxygen and/or nitrogen donors J. Coord. Chem. 59 2006 157 176
2. M.S. Karthikeyan, D.J. Prasal, B. Poojary, K.S. Bhat, B.S. Holla, and N.S. Kumari Synthesis and spectroscopic studies on ternary bis-Schiff-base complexes having oxygen and/or nitrogen donors Bioorg. Med. Chem. 14 2006 7482 7489
3. K. Singh, M.S. Barwa, and P. Tyagi Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate Schiff bases derived by heterocyclic ketone Eur. J. Med. Chem. 41 2006 147 153
4. P. Panneerselvam, R.B. Nair, G. Vijayalakshmi, E.H. Subramanian, and S.K. Sridhar Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents Eur. J. Med. Chem. 40 2005 225 229
5. S.K. Sridhar, M. Saravanan, and A. Ramesh Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives Eur. J. Med. Chem. 36 2001 615 625
6. S.N. Pandeya, D. Sriram, G. Nath, and E. DeClercq Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4′-chlorophenyl)thiazol-2-yl] thiosemicarbazide Eur. J. Pharm. Sci. 9 1999 25 31
7. ® Eur. Polym. J. 38 2002 989 999
8. O.M. Walsh, M.J. Meegan, R.M. Prendergast, and T.A. Nakib Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity Eur. J. Med. Chem. 31 1996 989 1000
9. J.E. Kovacic The CN stretching frequency in the infrared spectra of Schiff's base complexes-I. Copper complexes of salicylidene anilines Spectrochim. Acta 23A 1967 183 187
10. R. Atkins, G. Brewer, E. Kokot, G.M. Mockler, and E. Sinn Copper(II) and nickel(II) complexes of some tetradentate Schiff base ligands Inorg. Chem. 24 1985 127 134
11. A. Sigel H. Sigel, Metal ions in biological systems vol. 32 1996 Marcel Dekker New York
12. K.E. Erkkila, D.T. Odom, and J.K. Barton Recognition and reaction of metallointercalators with DNA Chem. Rev. 99 1999 2777 2796
13. C. Metcalfe, and J.A. Thomas Kinetically inert transition metal complexes that reversibly bind to DNA Chem. Soc. Rev. 32 2003 215 224
14. V. Uma, V.G. Vaidyanathan, and B.U. Nair Synthesis, structure, and DNA binding studies of copper(II) complexes of terpyridine derivatives Bull. Chem. Soc. Jpn. 78 2005 845 850
15. W. Szczepanik, J. Ciesiolka, J. Wrzesinski, J. Skala, and M. Jezowska-Bojczuk Interaction of aminoglycosides and their copper(II) complexes with nucleic acids - implication to the toxicity of these drugs Dalton Trans. 2003 1488 1494
16. Q.L. Li, J. Huang, Q. Wang, N. Jiang, C.Q. Xia, H.H. Lin, J. Wu, and X.Q. Yu Monometallic complexes of 1,4,7,10-tetraazacyclododecane containing an imidazolium side: synthesis, characterization, and their interaction with plasmid DNA Bioorg. Med. Chem. 14 2006 4151 4157
17. G.C. Silver, and W.C. Trogler Efficient cleavage of DNA by iron(III) triazacyclononane derivatives J. Am. Chem. Soc. 117 1995 3983 3993
18. Q. Huang, Z. Pan, P. Wang, Z. Chen, X. Zhang, and H. Xu Zinc(II) and copper(II) complexes of β-substituted hydroxylporphyrins as tumor photosensitizers Bioorg. Med. Chem. Lett. 16 2006 3030 3033
19. M.C.B. Oliveira, M.S.R. Couto, P.C. Severino, T. Foppa, G.T.S. Martins, B. Szpoganicz, R. Peralta, A. Neves, and H. Terenzi Nucleic acid cleavage by a Cu(II) polyaza macrocyclic complex Polyhedron 24 2005 495 499
20. R. Hettich, and H.J. Schneider Cobalt(III) polyamine complexes as catalysts for the hydrolysis of phosphate esters and of DNA. A measurable 10 million-fold rate increase J. Am. Chem. Soc. 119 1997 5638 5647
21. N.E. Dixon, R.J. Geue, J.N. Lambert, S. Moghaddas, D.A. Pearce, and A.M. Sargeson DNA hydrolysis by stable metal complexes Chem. Commun. 1996 1287 1288
22. 3+ Trans. Met. Chem. 32 2007 271 277
23. 6 J. Mol. Biol. 144 1980 431 453
24. J. Widom, and R.L. Baldwin Inhibition of cation-induced DNA condensation by intercalating dyes Biopolymers 22 1983 1595
25. R. Gust, I. Ott, D. Posselt, and K. Sommer Development of cobalt (3,4-diarylsalen) complexes as tumor therapeutics J. Med. Chem. 47 2004 5837
26. C.C. Cheng, C.F. Luo, and W.J. Wang A new Co (II) complex as a bulge-specific probe for DNA Angew. Chem. Int. Ed. Engl. 38 1999 1255 1257
27. N. Shahabadi, S. Kashanian, and F. Darabi In vitro study of DNA with a water-soluble dinitrogen Schiff base DNA Cell Biol. 28 2009 1 8
28. A. Silvestri, G. Barone, G. Ruisi, D. Anselmo, S. Riela, and V.T. Liveri The interaction of native DNA with Zn(II) and Cu(II) complexes of 5-triethyl ammonium methyl salicylidene orto-phenylendiimine J. Inorg. Biochem. 101 2007 841 848
29. 4 Biochim. Biophys. Acta 1475 2000 157 162
30. S. Kashanian, M.B. Gholivand, F. Ahmadia, A. Taravati, and A. Hosseinzadeh Colagar DNA Interaction with Al-N,N-bis(salicylidene) 2,2-phenylendiamine complex Spectrochim. Acta A 67 2007 472 478
31. N.H. Khana, N. Pandyaa, R.I. Kureshya, and S.H.R. Abdia Synthesis, characterization, DNA binding and cleavage studies of chiral Ru(II) salen complexes Spectrochim. Acta A 74 2009 113 119
32. X.M. Xu, Z.W. Mao, and L.N. Ji Syntheses, characterization and DNA cleavage studies of acyclic copper(II) complexes Trans. Met. Chem. 29 2004 658 662
33. + Inorg. Chem. 35 1996 4837 4847
34. T. Biver, F. Secco, M.R. Tine, and M. Venturini Kinetics and equilibria for the formation of a new DNA metal-intercalator: the cyclic polyamine Neotrien/copper(II) complex J. Inorg. Biochem. 98 2004 33 40
35. C. Liu, J. Zhou, and H. Xu Interaction of the copper(II) macrocyclic complexes with DNA studied by fluorescence quenching of ethidium J. Inorg. Biochem. 71 1998 1 6
36. S. Mahadevan, and M. Palaniandavar Spectroscopic and voltammetric studies of copper(II) complexes of bis(pyrid-2-yl)-di/trithia ligands bound to calf thymus DNA Inorg. Chim. Acta 254 1997 291 302
37. C.A. Mitsopoulou, C.E. Dagas, and C. Makedonas Characterization and DNA interaction of the Pt(II)(pq)(bdt) complex: a theoretical and experimental research Inorg. Chim. Acta 361 2008 1973 1982
38. D.M. Boghaei, E. Askarizadeh, and A. Bezaatpour Synthesis, characterization, spectroscopic and thermodynamic studies of charge transfer interaction of a new water-soluble cobalt(II) Schiff base complex with imidazole derivatives Spectrochim. Acta A 69 2008 624 628
39. B.A. Uzoukwu, K. Gloe, and H. Duddeck 4-Acylpyrazoloneimine Schiff bases and their metal complexes: synthesis and spectroscopic studies Synth. React. Inorg. Met. Org. Chem. 28 1998 819 831
40. N. Saha, and S. Sinha Indian J. Chem. 29A 1990 292
41. 2+ Inorg. Chem. 37 1998 139 141
42. M.J. Waring Complex formation between ethidium bromide and nucleic acids J. Mol. Biol. 13 1965 269 282
43. T.R. Li, Z.Y. Yang, B.D. Wang, and D.D. Qin Synthesis, characterization, antioxidant activity and DNA-binding studies of two rare earth(III) complexes with naringenin-2-hydroxy benzoyl hydrazone ligand Eur. J. Med. Chem. 43 2008 1688 1695
44. P.U. Maheswari, V. Rajendiran, M. Palaniandavar, R. Thomas, and G.U. Kulkarni Mixed ligand ruthenium(II) complexes of 5,6-dimethyl-1,10- phenanthroline: the role of ligand hydrophobicity on DNA binding of the complexes Inorg. Chim. Acta 359 2006 4601 4612
45. J. Sun, S. Wu, Y. An, J. Liu, F. Gao, L.N. Ji, and Z.W. Mao Synthesis, crystal structure and DNA-binding properties of ruthenium(II) polypyridyl complexes with dicationic 2,2′-dipyridyl derivatives as ligands Polyhedron 27 2008 2845 2850
46. S. Sharma, S.K. Singh, M. Chandra, and D.S. Pandey DNA-binding behavior of ruthenium (II) complexes containing both group 15 donors and 2,2′:6′,2″-terpyridine J. Inorg. Biochem. 99 2005 458 466
47. X.L. Wang, H. Chao, H. Li, X.L. Hong, Y.J. Liu, L.F. Tan, and L.N. Ji DNA interactions of cobalt(III) mixed-polypyridyl complexes containing asymmetric ligands J. Inorg. Biochem. 98 2004 1143 1150
48. Q.L. Zhang, J.G. Liu, J. Liu, G.Q. Xue, H. Li, J.Z. Liu, H. Zhou, L.H. Qu, and L.N. Ji 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. 85 2001 291 296
49. S. Satyanarayana, J.C. Dabrowiak, and J.B. Chaires Neither Δ-nor Λ-tris (phenanthroline) ruthenium(II) binds to DNA by classical intercalation Biochemistry 31 1992 9319 9324
50. T.M. Kelly, A.B. Tossi, D.J. McConnell, and T.C.A. Strekas Study of the interactions of some polypyridylruthenium(II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation Nucleic Acids Res. 13 1985 6017 6034
51. P.T. Selvi, and M. Palaniandavar Spectral, viscometric and electrochemical studies on mixed ligand cobalt(III) complexes of certain diimine ligands bound to calf thymus DNA Inorg. Chim. Acta 337 2002 420 428
52. V.G. Vaidyanathan, and B.U. Nair Photooxidation of DNA by cobalt (II) tridentate complex J. Inorg. Biochem. 94 2003 121 126
53. 3+ J. Inorg. Biochem. 83 2001 49 55
54. Q.-L. Zhang, J.-G. Liu, J.-Z. Liu, H. Li, Y. Yang, H. Xu, H. Chao, and L.-N. Ji Effect of intramolecular hydrogen-bond on the DNA-binding and photocleavage properties of polypyridyl cobalt(III) complexes Inorg. Chim. Acta 339 2002 34 40
55. 3+ to DNA J. Am. Chem. Soc. 119 1997 1454 1455
56. B. Norden, and F. Tjerneld Structure of methylene-blue DNA complexes studied by linear and circular-dichroism spectroscopy Biopolymers 21 1982 1713 1734
57. C.F. Jordan, L.S. Lerman, and J.H. Venable Structure and circular dichroism of DNA in concentrated polymer solutions Nature New Biol. 236 1982 67 70
58. J.A. Pachter, C.H. Huang, V.H. DuVernay Jr., A.W. Prestayko, and S.T. Crooke Viscometric and fluorometric studies of DNA interactions of several new anthracyclines Biochemistry 21 1982 1541 1547
59. E. Nyarko, N. Hanada, A. Habib, and M. Tabata Fluorescence and phosphorescence spectra of Au(III), Pt(II) and Pd(II) porphyrins with DNA at room temperature Inorg. Chim. Acta 357 2004 739 745
60. V.G. Vaidyanathan, and B.U. Nair Synthesis, characterization and DNA binding studies of a ruthenium (II) complex J. Inorg. Biochem. 91 2002 405 412
61. J.M. Kelly, D.J. McConnel, C. Ohuigin, A.B. Tossi, A.K.D. Mesmaeker, A. Masschelein, and J. Nasielski Ruthenium polypyridyl complexes; their interaction with DNA and their role as sensitisers for its photocleavage J. Chem. Soc. Chem. Commun. 1987 1821 1823
62. A.K. De-Mesmaeker, G. Orellana, J.K. Barton, and N. Turro Ligand-dependent interaction of ruthenium(II)polypyridyl complexes with DNA probed by emission spectroscopy J. Photochem. Photobiol. 52 1990 461 472
63. B.F. Ye, Z.J. Zhang, and H.X. Ju Fluorescence study on the interaction between naproxen and yeast DNA Chin. J. Chem. 23 2005 58 62
64. I.H. Bhat, and S. Tabassum Synthesis of new piperazine derived Cu(II)/Zn(II) metal complexes, their DNA binding studies, electrochemistry and anti-microbial activity: validation for specific recognition of Zn(II) complex to DNA helix by interaction with thymine base Spectrochim. Acta A 72 2009 1026 1033
65. B.D. Wang, Z.Y. Yang, Q. Wang, T.K. Cai, and P. Crewdson Synthesis, characterization, cytotoxic activities and DNA-binding properties of the La(III) complex with Naringenin Schiff-base Bioorg. Med. Chem. 14 2006 1880 1888
66. A.G. Krishna, D.V. Kumar, B.M. Khan, S.K. Rawal, and K.N. Ganesh Taxol-DNA interactions: fluorescence and CD studies of DNA groove binding properties of taxol Biochim. Biophys. Acta 1381 1998 104 112
67. R. Bera, B.K. Sahoo, K.S. Ghosh, and S. Dasgupta Studies on the interaction of isoxazolcurcumin with calf thymus DNA Int. J. Biol. Macromol. 42 2008 14 21
68. A.K. Parta, S. Dhar, M. Nethaji, and A.R. Chakravarty Metal-assisted red light-induced DNA cleavage by ternary l-methionine copper(II) complexes of planar heterocyclic bases Dalton Trans. 2005 896 902
69. E. Gao, Y. Sun, Q. Liu, and L. Duan An anticancer metallobenzylmalonate: crystal structure and anticancer activity of a palladium complex of 2,2′-bipyridine and benzylmalonate J. Coord. Chem. 59 2006 1295 1300
70. E.M. Hodnett, and P.D. Mooney Antitumor activities of some Schiff bases J. Med. Chem. 13 1970 786
71. E.M. Hodnett, and W.J. Dunn Cobalt derivatives of Schiff bases of aliphatic amines as antitumor agents J. Med. Chem. 15 1972 339
72. S.D. Kennedy, and R.C. Bryant Manganese-deoxyribonucleic acid binding modes. Nuclear magnetic relaxation dispersion results Biophys. J. 50 1986 669 676
73. V.A. Bloomfield, D.M. Crothers, and I. Tioco Physical Chemistry of Nucleic Acids 1974 Harper and Row New York pp. 432