Mixed ligand copper(II) complexes of 1,10-phenanthroline with tridentate phenolate/pyridyl/(benz)imidazolyl Schiff base ligands: Covalent vs non-covalent DNA binding, DNA cleavage and cytotoxicity

Journal of Inorganic Biochemistry

Volumn 140, Issue , 2014, Pages 255-268

  Rajarajeswari, Chandrasekaran ^a   Ganeshpandian, Mani ^b   Palaniandavar, Mallayan ^b   Riyasdeen, Anvarbatcha ^a   Akbarsha, Mohammad Abdulkadher ^a,c  

^a BHARATHIDASAN UNIVERSITY   (India)

^b CENTRAL UNIVERSITY OF TAMIL NADU   (India)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Cytotoxicity; DNA binding; Mixed ligand Cu(II) phen complexes; Oxidative DNA cleavage; Tridentate Schiff base ligands

Indexed keywords

(2 PYRIDIN 2 YL ETHYL)PYRIDIN 2 YL METHYLENEAMINE; 1,10 PHENANTHROLINE COPPER; 2 (1H BENZIMIDAZOL 2 YL)ETHYL) PYRIDIN 2 YL METHYLENEAMINE; 2 (1H BENZIMIDAZOL 2 YL)ETHYL)(1H IMIDAZOL 2 YLMETHYLENE)AMINE; 2 (1H BENZIMIDAZOL 2 YL)ETHYL)(4,4A DIHYDROQUINOLIN 2 YL METHYLENE)AMINE; 2 (2 (1H BENZIMIDAZOL 2 YL)ETHYL IMINO)METHYL) 4 METHYLPHENOL; 2 (2 (1H BENZIMIDAZOL 2 YL)ETHYLIMINOMETHYL)PHENOL; CYTOTOXIC AGENT; PLASMID DNA; UNCLASSIFIED DRUG; 1,10-PHENANTHROLINE; COPPER; DNA; HYDROXYBENZOIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; LIGAND; PHENANTHROLINE DERIVATIVE; PHENOLIC ACID; PYRIDINE; PYRIDINE DERIVATIVE; SCHIFF BASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER CELL LINE; COVALENT BOND; CRYSTAL STRUCTURE; DNA CLEAVAGE; DRUG DNA BINDING; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; FLUORESCENCE SPECTROSCOPY; HUMAN; HUMAN CELL; ULTRAVIOLET SPECTROSCOPY; BINDING SITE; CELL SURVIVAL; CHEMISTRY; HYDROLYSIS; METABOLISM; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CELL SURVIVAL; COPPER; CRYSTALLOGRAPHY, X-RAY; DNA; HYDROLYSIS; HYDROXYBENZOATES; IMIDAZOLES; LIGANDS; PHENANTHROLINES; PYRIDINES; SCHIFF BASES;

EID: 84906965540     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2014.07.016     Document Type: Article

References (72)

1. I.S. Ahuja, and I. Prasad Inorg. Nucl. Chem. Lett. 12 1976 777 784
2. A.S. Mildvan, and M. Cohm J. Biol. Chem. 241 1966 1178 1193
3. E. Bouwman, W.L. Driessen, and J. Reedijk Coord. Chem. Rev. 104 1990 143 172
4. I. Kostova, and S. Balkansky Curr. Med. Chem. 20 2013 4508 4539
5. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893 930
6. H. Kucukbay, R. Durmaz, E. Orhan, and S. Gunal Il Farmaco 58 2003 431 437
7. V.K. Limesova, J. KocI, K. Waisser, and J. Kaustova Il Farmaco 57 2002 259 265
8. Y. He, B. Wu, J. Yang, D. Robinson, L. Risen, R. Ranken, L. Blyn, S. Sheng, and E.E. Swayze Bioorg. Med. Chem. Lett. 13 2003 3253 3256
9. G. Ayhan, and N. Altanlar Il Farmaco 58 2003 1345 1350
10. N.S. Pawar, D.S. Dalal, S.R. Shimpi, and P.P. Mahulikar Eur. J. Pharm. Sci. 21 2004 115 118
11. N. Bharti, M.T. Shailendra, G. Garza, D.E. Cruz-Vega, J. Castro-Garza, K. Saleem, F. Naqvi, M.R. Maurya, and A. Azam Bioorg. Med. Chem. Lett. 12 2002 869 871
12. S. Ozden, D. Atabey, S. Yildiz, and H. Goker Bioorg. Med. Chem. 13 2005 1587 1597
13. G. Navarrete-Vazquez, R. Cedillo, A. Hernandez-Campos, J. Yepez, F. Hernndez-Luis, J. Valldez, R. Morales, R. Cortes, M. Hernandez, and R. Castillo Bioorg. Med. Chem. Lett. 11 2001 187 190
14. A.A. Spasov, I.N. Yozhitsa, L.I. Bugavea, and V.A. Anisimova Pharm. Chem. J. 33 1999 232 243
15. T.A. Kabanos, A.D. Keramidas, D. Mentzafos, U. Russo, A. Terzis, and J.M. Tsangaris J. Chem. Soc. Dalton Trans. 1992 2729 2733
16. C. Marzanol, M. Pellei, F. Tisato, and C. Santini Anti-Cancer Agents in Medicinal Chemistry 9 2009 185 211
17. C.H. Ng, K.C. Kong, S.T. Von, P. Balraj, P. Jensen, E. Thirthagiri, H. Hamada, and M. Chikira Dalton Trans. 2008 447 454
18. A. Barve, A. Kumbhar, M. Bhat, B. Joshi, R. Butcher, U. Sonawane, and R. Joshi Inorg. Chem. 48 2009 9120 9132
19. S. Zhang, Y. Zhu, C. Tu, H. Wei, Z. Yang, L. Lin, J. Ding, J. Zhang, and Z. Guo J. Inorg. Biochem. 98 2004 2099 2106
20. S. Cardaci, G. Filomeni, G. Rotilio, and M.R. Ciriolo Int. J. Cancer 112 2004 596 606
21. D.S. Sigman, D.R. Graham, V.D. Aurora, and A.M. Stern J. Biol. Chem. 254 1979 12269 12272
22. A. Spassky, and D.S. Sigman Biochemistry 24 1985 8050 8056
23. P.U. Maheswari, S. Roy, H.D. Dulk, S. Barends, G.V. Wezel, B. Kozlevcar, P. Gamez, and J. Reedijk J. Am. Chem. Soc. 128 2006 710 711
24. J.D. Ranford, P.J. Sadler, and D.A. Tocher J. Chem. Soc. Dalton Trans. 1993 3393 3399
25. E.L. Hegg, and J.N. Burstyn Coord. Chem. Rev. 173 1998 133 165
26. S. Roy, S. Saha, R. Majumdar, R.R. Dighe, and A.R. Chakravarty Inorg. Chem. 48 2009 9501 9509
27. A. Raja, V. Rajendiran, P. Uma Maheswari, R. Balamurugan, C.A. Kilner, M.A. Halcrow, and M. Palaniandavar J. Inorg. Biochem. 99 2005 1717 1732
28. S. Ramakrishnan, and M. Palaniandavar J. Chem. Sci. 117 2005 179 186
29. B. Selvakumar, V. Rajendiran, P. Uma Maheswari, H.S. Evans, and M. Palaniandavar J. Inorg. Biochem. 100 2006 316 330
30. V. Rajendiran, R. Karthik, M. Palaniandavar, H.S. Evans, V.S. Periasamay, M.A. Akbarsha, B.S. Srinag, and H. Krishnamurthy Inorg. Chem. 46 2007 8208 8221
31. S. Ramakrishnan, V. Rajendiran, M. Palaniandavar, V.S. Periasamay, M.A. Akbarsha, B.S. Srinag, and H. Krishnamurthy Inorg. Chem. 48 2009 1309 1322
32. S. Ramakrishnan, D. Shakthipriya, E. Suresh, V.S. Periasamy, M.A. Akbarsha, and M. Palaniandavar Inorg. Chem. 50 2011 6458 6471
33. R. Loganathan, S. Ramakrishnan, E. Suresh, A. Riyasdeen, M.A. Akbarsha, and M. Palaniandavar Inorg. Chem. 51 2012 5512 5532
34. P. Vidhya, R. Dhivya, M.A. Akbarsha, and M. Palaniandavar J. Inorg. Biochem. 114 2012 94 105
35. M. Ganeshpandian, R. Loganathan, S. Ramakrishnan, A. Riyasdeen, M.A. Akbarsha, and M. Palaniandavar Polyhedron 52 2013 924 938
36. S. Ramakrishnan, E. Suresh, A. Riyasdeen, M.A. Akbarsha, and M. Palaniandavar Dalton Trans. 40 2011 3524 3536
37. C. Rajarajeswari, R. Loganathan, M. Palaniandavar, E. Suresh, A. Riyasdeen, and M.A. Akbarsha Dalton Trans. 42 2013 8347 8363
38. M.E. Reichman, S.A. Rice, C.A. Thomas, and P. Poty J. Am. Chem. Soc. 76 1954 3047 3053
39. SMART & SAINT Software Reference manuals, version 5.0 1998 Bruker AXS Inc. Madison, WI
40. G.M. Sheldrick SADABS Software for Empirical Absorption Correction 2000 University of Gottingen Gottingen, Germany
41. SHELXTL Reference Manuals, version 5.1 1998 Bruker AXS Inc. Madison, WI
42. J. Bernadou, G. Prativiel, F. Bennis, M. Girardet, and B. Meunier Biochemistry 28 1989 7268 7275
43. M. Blagosklonny, and W.S. E1-Diery Int. J. Cancer 67 1996 386 392
44. A.W. Addison, T.N. Rao, J. Reedijk, J. Van Rijn, and G.C. Veschoor J. Chem. Soc. Dalton Trans. 1984 1349 1356
45. M. Duggan, N. Ray, B. Hathaway, G. Tomlinson, P. Brint, and K. Pelin J. Chem. Soc. Dalton Trans. 1980 1342 1348
46. A.W. Addison Inorg. Chim. Acta 162 1989 217 220
47. S. Usha, and M. Palaniandavar J. Chem. Soc. Dalton Trans. 1994 2277 2283
48. M. Palaniandavar, T. Pandiyan, M. Lakshminarayanan, and H. Manohar J. Chem. Soc. Dalton Trans. 1995 455 461
49. G. Murphy, P. Nagle, B. Murphy, and B. Hathaway J. Chem. Soc. Dalton Trans. 1997 2645 2652
50. G. Murphy, C. Murphy, B. Murphy, and B. Hathaway J. Chem. Soc. Dalton Trans. 1997 2653 2660
51. P. Nagle, E. Osullivan, and B. Hathaway J. Chem. Soc. Dalton Trans. 1990 3399 3406
52. G. Huang, C. Su, S. Wang, F. Liao, and K. Lin J. Coord. Chem. 49 2000 211 226
53. B.J. Hathaway, G. Wilkinsons, R.G. Gillard, and J.A. McCleverty Comprehensive Coordination Chemistry vol. 5 1987 861 (Pergamon. Oxford)
54. A.W. Addison Copper coordination chemistry K.D. Karlin, J. Zubieta, Biohemical and Inorganic Perspectives 109 1983 Adenine Guilderland, New York
55. U. Sakaguchi, and A.W. Addison J. Chem. Soc. Dalton Trans. 1979 600 608
56. D.X. West, and M. Palaniandavar Inorg. Chim. Acta 76 1983 L149
57. A.W. Addison, P.J. Burke, K. Henrick, T.N. Rao, and E. Sinn Inorg. Chem. 22 1983 3645
58. M. Palaniandavar, I. Somasundaram, M. Lakshminarayanan, and H. Manohar J. Chem. Soc. Dalton Trans. 1996 1333 1340
59. M. Murali, M. Palaniandavar, and T. Pandiyan Inorg. Chim. Acta 224 1994 19 25
60. R. Loganathan, S. Ramakrishnan, E. Suresh, M. Palaniandavar, A. Riyasdeen, and M.A. Akbarsha Dalton Trans. 43 2014 6177
61. J.E. Huheey, E.A. Keiter, R.L. Keiter, and O.K. Medhu Inorganic Chemistry Principles of Structure and Reactivity 2006 Pearson Education Upper Saddle River, NJ 425
62. N. Grover, T.W. Welch, T.A. Fairely, M. Cory, and H.H. Throp Inorg. Chem. 33 1994 3544 3548
63. V. Rajendiran, M. Murali, E. Suresh, S. Sinha, K. Somasundaram, and M. Palaniandavar Dalton Trans. 2008 148 163
64. S.A. Tysoe, R.J. Morgan, A.D. Baker, and T.C. Strekas J. Phys. Chem. 97 1993 1707 1711
65. J.M. Kelly, A.B. Tossi, D.J. McConnell, and C. OhUigin Nucleic Acids Res. 13 1985 6017 6034
66. I.S. Haworth, A.H. Elcock, J. Freemann, A. Rodger, and W.G.J. Richards J. Biomol. Struct. Dyn. 9 1991 23 43
67. P.E. Pjura, K. Grzeskowiak, and R.E. Dickerson J. Mol. Biol. 197 1987 257 271
68. V. Rajendiran, M. Murali, E. Suresh, S. Sinha, K. Somasundaram, and M. Palaniandavar Dalton Trans. 2008 2157 2170
69. B.C. Baguley, and M. LeBret Biochemistry 23 1984 937 943
70. M. Lee, A.L. Rhodes, M.D. Wyatt, S. Forrow, and J.A. Hartley Biochemistry 32 1993 4237 4245
71. S. Satyanarayana, J.C. Dabrowiak, and J.B. Chaires Biochemistry 31 1992 9319 9324
72. C.T. Dillon, P.A. Lay, A.M. Bonin, M. Cholewa, and G.J.F. Legge Chem. Res. Toxicol. 13 2000 742 748