Study on potential antitumor mechanism of a novel Schiff Base copper(II) complex: Synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity

Journal of Inorganic Biochemistry

Volumn 105, Issue 5, 2011, Pages 728-737

  Qiao, Xin ^a   Ma, Zhong Ying ^a   Xie, Cheng Zhi ^a   Xue, Fei ^a   Zhang, Yan Wen ^a   Xu, Jing Yuan ^a   Qiang, Zhao Yan ^a   Lou, Jian Shi ^a   Chen, Gong Jun ^b   Yan, Shi Ping ^b  

^a TIANJIN MEDICAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Anticancer activity; Apoptosis; Copper(II) complex; DNA cleavage activity; Schiff base ligand

Indexed keywords

ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 9; COPPER; N 2 PYRIDIYLMETHYLIDENE 2 HYDROXY 5 CHLOROPHENYLAMINE; OXYGEN; SCHIFF BASE; UNCLASSIFIED DRUG; WATER;

AGAR GEL ELECTROPHORESIS; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; ATOM; CELL CYCLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DNA BINDING; DNA CLEAVAGE; DRUG CYTOTOXICITY; DRUG STRUCTURE; FLOW CYTOMETRY; HUMAN; HUMAN CELL; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASE 3; CASPASE 9; CELL LINE, TUMOR; COORDINATION COMPLEXES; COPPER; CRYSTALLOGRAPHY, X-RAY; DNA; HELA CELLS; HUMANS; LIGANDS; MODELS, MOLECULAR; SCHIFF BASES; SPECTROMETRY, FLUORESCENCE;

EID: 79953234182     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2011.01.004     Document Type: Article

References (77)

1. V. Milacic, D. Chen, L. Ronconi, K.R. Landis-Piwowar, D. Fregona, and Q.P. Dou Cancer Res. 66 2006 10478 10486
2. I. Kostova Anticancer Agents Med. Chem. 6 2006 19 32
3. B. Rosenberg, L. VanCamp, J.E. Trosko, and V.H. Mansour Nature 222 1969 385 386
4. E. Wong, and C.M. Giandomenico Chem. Rev. 99 1999 2451 2466
5. D. Chatterjee, A. Mitra, and G.S. De Platinum Met. Rev. 50 2006 2 12
6. P.U. Maheswari, M. Ster, S. Smulders, S. Barends, G.P. Wezel, C. Massera, S. Roy, H. Dulk, P. Gamez, and J. Reedijk Inorg. Chem. 47 2008 3719 3727
7. A.R. Banerjee, J.A. Jaeger, and D.H. Turner Biochemistry 32 1993 153 163
8. Y. Jin, and J.A. Cowan J. Am. Chem. Soc. 127 2005 8408 8415
9. F. Mancin, P. Scrimin, P. Tecilla, and U. Tonellato Chem. Commun. 2005 2540 2548
10. D.R. Green, and J.C. Reed Science 281 1998 1309 1312
11. Y. Ma, L. Cao, T. Kavabata, T. Yoshino, B.B. Yang, and S. Okada Free Radic. Biol. Med. 25 1998 568 575
12. F. Liang, C. Wu, H. Lin, T. Li, D. Gao, Z. Li, J. Wei, C. Zheng, and M. Sun Bioorg. Med. Chem. Lett. 13 2003 2469 2472
13. J. Easmon, G. Pürstinger, G. Heinisch, T. Roth, H.H. Fiebig, W. Holzer, W. Jäger, M. Jenny, and J. Hofmann J. Med. Chem. 44 2001 2164 2171
14. D.S. Sigman, A. Mazumder, and D.M. Perrin Chem. Rev. 93 1993 2295 2316
15. L. Pearson, C.B. Chen, R.P. Gaynor, and D.S. Sigman Nucleic Acids Res. 22 1994 2255 2263
16. J.R. Morrow, and W.C. Trogler Inorg. Chem. 27 1988 3387 3394
17. D.K. Chand, H.J. Schneider, A. Bencini, A. Bianchi, C. Giorgi, S. Ciattini, and B. Valtancoli Chem. Eur. J. 6 2000 4001 4008
18. E.L. Hegg, and J.N. Burstyn Coord. Chem. Rev. 173 1998 133 165
19. S. Dhar, D. Senapati, P.K. Das, P. Chattopadhyay, M. Nethaji, and A.R. Chakravarty J. Am. Chem. Soc. 125 2003 12118 12124
20. S. Dhar, P.A. Reddy, M. Nethaji, S. Mahadevan, M.K. Saha, and A.R. Chakravarty Inorg. Chem. 41 2002 3469 3476
21. B.K. Santra, P.A. Reddy, G. Neelakanta, S. Mahadevan, M. Nethaji, and A.R. Chakravarty J. Inorg. Biochem. 89 2002 191 196
22. S.Y. Tsang, S.C. Tam, I. Bremner, and M.J. Burkitt Biochem. J. 317 1996 13 16
23. J. Bernadou, G. Pratviel, F. Bennis, M. Girardet, and B. Meunier Biochemistry 28 1989 7268 7275
24. F.B. Tamboura, M. Gaye, A.S. Sall, A.H. Barry, and T. Jouini Inorg. Chem. Commun. 5 2002 235 238
25. A.W. Tai, E.J. Lien, M.M. Lai, and T.A. Khwaja J. Med. Chem. 27 1984 236 238
26. P.H. Wang, J.G. Keck, E.J. Lien, and M.M. Lai J. Med. Chem. 33 1990 608 614
27. C.A. Bolos, G.S. Nikolov, L. Ekateriniadou, A. Kortsaris, and D.A. Kyriakidis Met.-Based Drugs 5 1998 323 332
28. A.T. Chaviara, P.J. Cox, K.H. Repana, R.M. Papi, K.T. Papazisis, D. Zambouli, A.H. Kortsaris, D.A. Kyriakidis, and C.A. Bolos J. Inorg. Biochem. 98 2004 1271 1283
29. A.T. Chaviara, P.J. Cox, K.H. Repana, A.A. Pantazaki, K.T. Papazisis, A.H. Kortsaris, D.A. Kyriakidis, G.S. Nikolov, and C.A. Bolos J. Inorg. Biochem. 99 2005 467 476
30. J.R. Sorenson Prog. Med. Chem. 26 1989 437 568
31. S. Roy, P.U. Maheswari, M. Lutz, A.L. Spek, H. Dulk, S. Barends, G.P. van Wezel, F. Hartl, and J. Reedijk Dalton Trans. 2009 10846 10860
32. P. de Hoog, M.J. Louwerse, P. Gamez, M. Pitié, E.J. Baerends, B. Meunier, and J. Reedijk Eur. J. Inorg. Chem. 2008 612 619
33. L.D. Pachon, A. Golobic, B. Kozlevcar, P. Gamez, H. Kooijman, A.L. Spek, and J. Reedijk Inorg. Chem. Acta 357 2004 3697 3702
34. P.U. Maheswari, S. Barends, S. Ozalp-Yaman, P. de Hoog, H. Casellas, S.J. Teat, C. Massera, M. Lutz, A.L. Spek, G.P. van Wezel, B. Kozlevcar, P. Gamez, and J. Reedijk J. Am. Chem. Soc. 128 2006 710 711
35. S.V. Rana J. Trace Elem. Med. Biol. 22 2008 262 284
36. M.D. Pulido, and A.R. Parrish Mutat. Res. 533 2003 227 241
37. H. Shi, L.G. Hudson, and K.J. Liu Free Radic. Biol. Med. 37 2004 582 593
38. K. Salnikow, and A. Zhitkovich Chem. Res. Toxicol. 21 2008 28 44
39. R. Alemon-Medina, M. Brena-Valle, J.L. Munoz-Sanchez, M.I. Gracia-Mora, and L. Ruiz-Azuara Cancer Chemother. Pharmacol. 60 2007 219 228
40. C. Trejo-Solis, G. Palencia, S. Zuniga, A. Rodriguez-Ropon, L. Osorio-Rico, S.T. Luvia, I. Gracia-Mora, L. Marquez-Rosado, A. Sanchez, M.E. Moreno-Garcia, A. Cruz, M.E. Bravo-Gomez, L. Ruiz-Ramirez, S. Rodriguez-Enriquez, and J. Sotelo Neoplasia 7 2005 563 574
41. F. Carvallo-Chaigneau, C. Trejo-Solis, C. Gomez-Ruiz, E. Rodriguez-Aguilera, L. Macias-Rosales, E. Cortes-Barberena, C. Cedillo-Pelaez, I. Gracia-Mora, L. Ruiz-Azuara, V. Madrid-Marina, and F. Constantino-Casas Biometals 21 2008 17 28
42. A. De Vizcaya-Ruiz, A. Rivero-Muller, L. Ruiz-Ramirez, G.E. Kass, L.R. Kelland, R.M. Orr, and M. Dobrota Toxicol. In Vitro 14 2000 1 5
43. L. Hernandez-Esquivel, A. Marin-Hernandez, N. Pavon, K. Carvajal, and R. Moreno-Sanchez Toxicol. Appl. Pharmacol. 212 2006 79 88
44. H. Asada, K. Hayashi, S. Negoro, M. Fujiwara, and T. Matsushita Inorg. Chem. Commun. 6 2003 193 196
45. J. Marmur J. Mol. Biol. 3 1961 208 218
46. M.E. Reichmann, S.A. Rice, C.A. Thomas, and P. Doty J. Am. Chem. Soc. 76 1954 3047 3053
47. G.M. Sheldrick SHELXS-97, Program of the Solution of Crystal Structure 1997 University of Göttingen Germany
48. G.M. Sheldrick SHELXL-97, Program of the Refinement of Crystal Structure 1997 University of Göttingen Germany
49. Y. Gultneh, A.R. Khan, D. Blaise, S. Chaudhry, B. Ahvazi, B.B. Marvey, and R.J. Butcher J. Inorg. Biochem. 75 1999 7 18
50. W.H. Armstrong, and S.J. Lippard J. Am. Chem. Soc. 106 1984 4632 4633
51. T. Mosmann J. Immunol. Methods 65 1983 55 63
52. K.W. Yip, E. Ito, X. Mao, P.Y. Au, D.W. Hedley, J.D. Mocanu, C. Bastianutto, A. Schimmer, and F.F. Liu Mol. Cancer Ther. 5 2006 2234 2240
53. T. Frgala, O. Kalous, R.T. Proffitt, and C.P. Reynolds Mol. Cancer Ther. 6 2007 886 897
54. G. Chandrasekher, and D. Sailaja Invest. Ophthalmol. Vis. Sci. 45 2004 3577 3588
55. D. Jain, N. Patel, M. Shelton, A. Basu, R. Roque, and W. Siede Cancer Chemother. Pharmacol. 66 2010 945 952
56. Y. Shi, C.-H. Wang, and X.-G. Gong Biol. Pharm. Bull. 31 2008 1075 1078
57. J.S. Lewis, K. Meeke, C. Osipo, E.A. Ross, N. Kidawi, T. Li, E. Bell, N.S. Chandel, and V.C. Jordan J. Natl Cancer Inst. 97 2005 1746 1759
58. J. Tan, B. Wang, and L. Zhu J. Biol. Inorg. Chem. 14 2009 727 739
59. A.W. Addison, T.N. Rao, J. Reedijk, J. Van Rijn, and G.C. Verschoor J. Chem. Soc., Dalton Trans. 1984 1349 1356
60. V.M. Leovac, M.D. Joksović, V. Divjaković, L.S. Jovanović, Ž. Šaranović, and A. Pevec J. Inorg. Biochem. 101 2007 1094 1097
61. M. Baldini, M. Belicchi-Ferrari, F. Bisceglie, P.P. Dall'aglio, G. Pelosi, S. Pinelli, and P. Tarasconi Inorg. Chem. 43 2004 7170 7179
62. S.A. Tysoe, R.J. Morgan, A.D. Baker, and T.C. Strekas J. Phys. Chem. 97 1993 1707 1711
63. F.J. Meyer-Almes, and D. Porschke Biochemistry 32 1993 4246 4253
64. J.B. Lepecq, and C. Paoletti J. Mol. Biol. 27 1967 87 106
65. B.C. Baguley, and M. Le Bret Biochemistry 23 1984 937 943
66. R.F. Pasternack, M. Caccam, B. Keogh, T.A. Stephenson, A.P. Williams, and E.J. Gibbs J. Am. Chem. Soc. 113 1991 6835 6840
67. J.W. Chen, X.Y. Wang, Y. Chao, J.H. Zhu, Y.G. Zhu, Y.Z. Li, Q. Xu, and Z.J. Guo Inorg. Chem. 46 2007 3306 3312
68. J.R. Lakowicz, and G. Webber Biochemistry 12 1973 4161 4170
69. M. Cory, D.D. McKee, J. Kagan, D.W. Henry, and J.A. Miller J. Am. Chem. Soc. 107 1985 2528 2536
70. M.E. Reichmann, S.A. Rice, C.A. Thomas, and P. Doty J. Am. Chem. Soc. 76 1954 3047 3053
71. T.B. Thederahn, M.D. Kuwabara, T.A. Larsen, and D.S. Sigman J. Am. Chem. Soc. 111 1989 4941 4946
72. D.S. Sigman Acc. Chem. Res. 19 1986 180 186
73. J.L. García-Giménez, M. González-Álvarez, M. Liu-González, B. Macías, J. Borrás, and G. Alzuet J. Inorg. Biochem. 103 2009 923 934
74. D.-D. Li, J.-L. Tian, W. Gu, X. Liu, and S.-P. Yan Eur. J. Inorg. Chem. 33 2009 5036 5045
75. K.J. Kelly, R.M. Sandoval, K.W. Dunn, B.A. Molitoris, and P.C. Dagher Am. J. Physiol. Cell Physiol. 284 2003 1309 1318
76. H. Zhang, R. Thomas, D. Oupicky, and F. Peng J. Biol. Inorg. Chem. 13 2008 47 55
77. I. Budihardjo, H. Oliver, M. Lutter, X. Luo, and X. Wang Annu. Rev. Cell Dev. Biol. 15 1999 269 290