Copper(II) interacting with the non-steroidal antiinflammatory drug flufenamic acid: Structure, antioxidant activity and binding to DNA and albumins

Journal of Inorganic Biochemistry

Volumn 123, Issue , 2013, Pages 53-65

  Tolia, Charikleia ^a   Papadopoulos, Athanassios N ^b   Raptopoulou, Catherine P ^c   Psycharis, Vassilis ^c   Garino, Claudio ^d   Salassa, Luca ^e   Psomas, George ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b ALEXANDER TECHNOLOGICAL EDUCATIONAL INSTITUTE OF THESSALONIKI   (Greece)

^c NCSR Demokritos   (Greece)

^d UNIVERSITY OF TURIN   (Italy)

^e CIC BIOMAGUNE   (Spain)

Author keywords

Antioxidant activity; Copper complexes; Flufenamic acid; Interaction with DNA; Interaction with serum albumins; Non steroidal antiinflammatory drugs

Indexed keywords

1,10 PHENANTHROLINE; 2,2' BIPYRIDINE; BOVINE SERUM ALBUMIN; CUPRIC ION; ETHIDIUM BROMIDE; FLUFENAMIC ACID; LIPOXYGENASE; N,N DIMETHYLFORMAMIDE; SCAVENGER;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; DNA BINDING; DRUG PROTEIN BINDING; DRUG STRUCTURE; HUMAN; IN VITRO STUDY; INFRARED SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

ALBUMINS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIOXIDANTS; COPPER; DNA; FLUFENAMIC ACID; MODELS, MOLECULAR; PROTEIN BINDING;

BOVINAE; GLYCINE MAX;

EID: 84875133437     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2013.02.009     Document Type: Article

References (100)

1. G. Crisponi, V.M. Nurchi, D. Fanni, C. Gerosa, S. Nemolato, and G. Faa Coord. Chem. Rev. 254 2010 876 889
2. J.E. Weder, C.T. Dillon, T.W. Hambley, B.J. Kennedy, P.A. Lay, J.R. Biffin, H.L. Regtop, and N.M. Davies Coord. Chem. Rev. 232 2002 95 126
3. J.A. Drewry, and P.T. Gunning Coord. Chem. Rev. 255 2011 459 472
4. B.M. Rode, and Y. Suwannachot Coord. Chem. Rev. 190-192 1999 1085 1099
5. M.E. Katsarou, E.K. Efthimiadou, G. Psomas, A. Karaliota, and D. Vourloumis J. Med. Chem. 51 2008 470 478
6. E.K. Efthimiadou, H. Thomadaki, Y. Sanakis, C.P. Raptopoulou, N. Katsaros, A. Scorilas, A. Karaliota, and G. Psomas J. Inorg. Biochem. 101 2007 64 73
7. F. Dimiza, S. Fountoulaki, A.N. Papadopoulos, C.A. Kontogiorgis, V. Tangoulis, C.P. Raptopoulou, V. Psycharis, A. Terzis, D.P. Kessissoglou, and G. Psomas Dalton Trans. 40 2011 8555 8568
8. F. Dimiza, F. Perdih, V. Tangoulis, I. Turel, D.P. Kessissoglou, and G. Psomas J. Inorg. Biochem. 105 2011 476 489
9. E.K. Efthimiadou, Y. Sanakis, M. Katsarou, C.P. Raptopoulou, A. Karaliota, N. Katsaros, and G. Psomas J. Inorg. Biochem. 100 2006 1378 1388
10. G. Psomas, A. Tarushi, Y. Sanakis, E.K. Efthimiadou, C.P. Raptopoulou, and N. Katsaros J. Inorg. Biochem. 100 2006 1764 1773
11. M. Ruiz, L. Perello, J. Server-Carrio, R. Ortiz, S. Garcia-Granda, M.R. Diaz, and E. Canton J. Inorg. Biochem. 69 1998 231 239
12. A.M. Ramadan J. Inorg. Biochem. 65 1997 183 189
13. C.P. Duffy, C.J. Elliott, R.A. O'Connor, M.M. Heenan, S. Coyle, I.M. Cleary, K. Kavanagh, S. Verhaegen, C.M. O'Loughlin, R. NicAmhlaoibh, and M. Clynes Eur. J. Cancer 34 1998 1250 1259
14. A.R. Amin, P. Vyas, M. Attur, J. Leszczynskapiziak, I.R. Patel, G. Weissmann, and S.B. Abramson Proc. Natl. Acad. Sci. 92 1995 7926 7930
15. D.H. Woo, I. Han, and G. Jung Life Sci. 75 2004 2439 2449
16. K. Kim, J. Yoon, J.K. Kim, S.J. Baek, T.E. Eling, W.J. Lee, J. Ryu, J.G. Lee, J. Lee, and J. Yoo Biochem. Biophys. Res. Commun. 325 2004 1298 1303
17. W.J. Wechter, E.D. Murray, D. Kantoci, D.D. Quiggle, D.D. Leipold, K.M. Gibson, and J.D. McCracken Life Sci. 66 2000 745 753
18. M.L. Smith, G. Hawcroft, and M.A. Hull Eur. J. Cancer 36 2000 664 674
19. L. Klampfer, J. Cammenga, H.G. Wisniewski, and S.D. Nimer Blood 93 1999 2386 2394
20. A. Inoue, S. Muranaka, H. Fujita, T. Kanno, H. Tamai, and K. Utsumi Free Radic. Biol. Med. 37 2004 1290 1299
21. M. Barbaric, M. Kralj, M. Marjanovic, I. Husnjak, K. Pavelic, J. Filipovic-Grcic, D. Zorc, and B. Zorc Eur. J. Med. Chem. 42 2007 20 29
22. T. Zhang, T. Otevrel, Z.Q. Gao, Z.P. Gao, S.M. Ehrlich, J.Z. Fields, and B.M. Boman Cancer Res. 61 2001 8664 8667
23. S. Roy, R. Banerjee, and M. Sarkar J. Inorg. Biochem. 100 2006 1320 1331
24. D. Kovala-Demertzi, A. Theodorou, M.A. Demertzis, C.P. Raptopoulou, and A. Terzis J. Inorg. Biochem. 65 1997 151 157
25. S. Fountoulaki, F. Perdih, I. Turel, D.P. Kessissoglou, and G. Psomas J. Inorg. Biochem. 105 2011 1645 1655
26. S. Lorinc, M. Koman, M. Melnik, J. Moncol, and D. Ondrusova Acta Crystallogr. E60 2004 m590 m592
27. C. Dendrinou-Samara, D.P. Kessissoglou, G.E. Manoussakis, D. Mentzafos, and A. Terzis J. Chem. Soc. Dalton Trans. 1990 959 965
28. A.L. Abuhijleh J. Inorg. Biochem. 55 1994 255 262
29. J.E. Weder, T.W. Hambley, B.J. Kennedy, P.A. Lay, D. MacLachlan, R. Bramley, C.D. Delfs, K.S. Murray, B. Moubaraki, B. Warwick, J.R. Biffin, and H.L. Regtop Inorg. Chem. 38 1999 1736 1744
30. P. Kogerler, P.A.M. Williams, B.S. Parajon-Costa, E.J. Baran, L. Lezama, T. Rojo, and A. Muller Inorg. Chim. Acta 268 1998 239 248
31. A.E. Underhill, S.A. Bougourd, M.L. Flugge, S.E. Gale, and P.S. Gomm J. Inorg. Biochem. 52 1993 139 144
32. F. Dimiza, A.N. Papadopoulos, V. Tangoulis, V. Psycharis, C.P. Raptopoulou, D.P. Kessissoglou, and G. Psomas Dalton Trans. 39 2010 4517 4528
33. H. Yau, G. Baranauskas, and Marco Martina J. Physiol. 588 2010 3869 3882
34. Y. Chi, K. Li, Q. Yan, S. Koizumi, L. Shi, S. Takahashi, Y. Zhu, H. Matsue, M. Takeda, M. Kitamura, and J. Yao J. Pharmacol. Exp. Ther. 339 2011 257 266
35. F. Pena, M.A. Parkis, A.K. Tryba, and J.M. Ramirez Neuron 43 2004 105 117
36. P. Poronnik, M.C. Ward, and D.I. Cook FEBS Lett. 296 1992 245 248
37. M. Ottolia, and L. Toro Biophys. J. 67 1994 2272 2279
38. G. Facchin, M.H. Torre, E. Kremer, O.E. Piro, and E.J. Baran Z. Anorg. Allg. Chem. 624 1998 2025 2028
39. A. Tarushi, F. Kastanias, V. Psycharis, C.P. Raptopoulou, G. Psomas, and D.P. Kessissoglou Inorg. Chem. 51 2012 7460 7462
40. F. Dimiza, A.N. Papadopoulos, V. Tangoulis, V. Psycharis, C.P. Raptopoulou, D.P. Kessissoglou, and G. Psomas J. Inorg. Biochem. 107 2012 54 64
41. S. Tsiliou, L.-A. Kefala, F. Perdih, I. Turel, D.P. Kessissoglou, and G. Psomas Eur. J. Med. Chem. 48 2012 132 142
42. A. Tarushi, X. Totta, C. Raptopoulou, V. Psycharis, G. Psomas, and D.P. Kessissoglou Dalton Trans. 41 2012 7082 7091
43. P. Christofis, M. Katsarou, A. Papakyriakou, Y. Sanakis, N. Katsaros, and G. Psomas J. Inorg. Biochem. 99 2005 2197 2210
44. C. Tan, J. Liu, H. Li, W. Zheng, S. Shi, L. Chen, and L. Ji J. Inorg. Biochem. 102 2008 347 358
45. Rigaku/MSC CrystalClear 2005 Rigaku/MSC Inc. The Woodlands, Texas, USA
46. G.M. Sheldrick SHELXS-97: Structure Solving Program 1997 University of Göttingen Germany
47. G.M. Sheldrick SHELXL-97: Crystal Structure Refinement Program 1997 University of Göttingen Germany
48. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09 Revision B.01 2009 Gaussian, Inc. Wallingford CT
49. M. Casida, C. Jamorski, K.C. Casida, and D.R. Salahub J. Chem. Phys. 108 1998 4439 4449
50. R. Stratmann, G.E. Scuseria, and M.J. Frisch J. Chem. Phys. 109 1998 8218 8224
51. T. Yanai, D. Tew, and N. Handy Chem. Phys. Lett. 393 2004 51 57
52. P. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 270 273
53. A.D. McLean, and G.S. Chandler J. Chem. Phys. 72 1980 5639 5648
54. D.M. York, and M. Karplus J. Phys. Chem. A 103 1999 11060 11079
55. N.M. O'Boyle, A.L. Tenderholt, and K.M. Langner J. Comput. Chem. 29 2008 839 845
56. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605 1612
57. J.R. Lakowicz Principles of Fluorescence Spectroscopy 3rd ed. 2006 Plenum Press New York
58. J.R. Lakowicz, and G. Weber Biochemistry 12 1973 4161 4170
59. S. Wu, W. Yuan, H. Wang, Q. Zhang, M. Liu, and K. Yu J. Inorg. Biochem. 102 2008 2026 2034
60. A.M. Pyle, J.P. Rehmann, R. Meshoyrer, C.V. Kumar, N.J. Turro, and J.K. Barton J. Am. Chem. Soc. 111 1989 3053 3063
61. G. Psomas J. Inorg. Biochem. 102 2008 1798 1811
62. C. Kontogiorgis, and D. Hadjipavlou-Litina J. Enzyme Inhib. Med. Chem. 18 2003 63 69
63. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans Free Radic. Biol. Med. 26 1999 1231 1237
64. K.R. Prabhakar, V.P. Veerapur, P. Bansal, V. Kumar, M. Reddy, A. Barik, B.K. Reddy, P. Reddanna, K.I. Priyadarsini, and M.K. Unnikrishnan Bioorg. Med. Chem. 14 2006 7113 7120
65. K. Nakamoto Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry 6th ed. 2009 Wiley New Jersey
66. B.J. Hathaway G. Wilkinson, Comprehensive Coordination Chemistry vol. 5 1987 Pergamon Press Oxford 533 773
67. P. Zivec, F. Perdih, I. Turel, G. Giester, and G. Psomas J. Inorg. Biochem. 117 2012 35 47
68. B.J. Hathaway Struct. Bond. (Berlin) 14 1973 49 67
69. A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn, and G.C. Verchoor J. Chem. Soc. Dalton Trans. 1984 1349 1356
70. C. Castellari, G. Feroci, and S. Ottani Acta Crystallogr. C 55 1999 907 910
71. S. Youngme, K. Chinnakali, S. Chantrapromma, and H. Fun Acta Crystallogr. C55 1999 899 901
72. R.E. Marsh Acta Crystallogr. B61 2005 359
73. Y. Wang, and N. Okabe Inorg. Chim. Acta 358 2005 3407 3416
74. F. Ugozzoli, A.M.M. Lanfredi, N. Marsich, and A. Camus Inorg. Chim. Acta 256 1997 1 7
75. N. Okabe, A. Tsuji, and M. Yodoshi Acta Crystallogr. E63 2007 m2162
76. N. Okabe, A. Tsuji, and M. Yodoshi Acta Crystallogr. E63 2007 m2108 m2109
77. Y. Wang, G. Lin, J. Hong, T. Lu, L. Li, N. Okabe, and M. Odoko Inorg. Chim. Acta 362 2009 377 384
78. N. Okabe, A. Tsuji, and M. Yodoshi Acta Crystallogr. E63 2007 m1756 m1757
79. S. Youngme, A. Cheansirisomboon, C. Danvirutai, N. Chaichit, C. Pakawatchai, G.A. van Albada, and J. Reedijk Inorg. Chem. Commun. 9 2006 973 977
80. R. Carballo, B. Covelo, N. Fernandez-Hermida, A.B. Lago, and E.M. Vazquez-Lopez Z. Anorg. Allg. Chem. 633 2007 1791 1795
81. C. Tan, J. Liu, H. Li, W. Zheng, S. Shi, L. Chen, and L. Ji J. Inorg. Biochem. 102 2008 347 358
82. Y. Wang, H. Zhang, G. Zhang, W. Tao, and S. Tang J. Lumin. 126 2007 211 218
83. V. Rajendiran, R. Karthik, M. Palaniandavar, H. Stoeckli-Evans, V.S. Periasamy, M.A. Akbarsha, B.S. Srinag, and H. Krishnamurthy Inorg. Chem. 46 2007 8208 8221
84. Q. Zhang, J. Liu, H. Chao, G. Xue, and L. Ji J. Inorg. Biochem. 83 2001 49 55
85. E.C. Long, and J.K. Barton Acc. Chem. Res. 23 1990 271 273
86. A. Jancso, L. Nagy, E. Moldrheim, and E. Sletten J. Chem. Soc. Dalton Trans. 1999 1587 1594
87. G. Pratviel, J. Bernadou, and B. Meunier Adv. Inorg. Chem. 45 1998 251 262
88. M.T. Carter, M. Rodriguez, and A.J. Bard J. Am. Chem. Soc. 111 1989 8901 8911
89. J.L. Garcia-Gimenez, M. Gonzalez-Alvarez, M. Liu-Gonzalez, B. Macias, J. Borras, and G. Alzuet J. Inorg. Biochem. 103 2009 923 934
90. J. Liu, H. Zhang, C. Chen, H. Deng, T. Lu, and L. Li Dalton Trans. 2003 114 119
91. W.D. Wilson, L. Ratmeyer, M. Zhao, L. Strekowski, and D. Boykin Biochemistry 32 1993 4098 4104
92. S. Dhar, M. Nethaji, and A.R. Chakravarty J. Inorg. Biochem. 99 2005 805 812
93. R. Cini, G. Giorgi, A. Cinquantini, C. Rossi, and M. Sabat Inorg. Chem. 29 1990 5197 5200
94. K. Muller Arch. Pharm. 327 1994 3 19
95. J. Van der Zee, T.E. Eling, and R.P. Mason Biochemistry 28 1989 8363 8367
96. S.B. Bukhari, S. Memona, M.M. Tahir, and M.I. Bhanger J. Mol. Struct. 892 2008 39 46
97. Z.D. Petrovic, D. Hadjipavlou-Litina, and V.P. Petrovic J. Mol. Liq. 144 2009 55 58
98. E. Pontiki, D. Hadjipavlou-Litina, A.T. Chaviara, and C.A. Bolos Bioorg. Med. Chem. Lett. 16 2006 2234 2237
99. Z. Liu, B. Wang, Z. Yang, Y. Li, D. Qin, and T. Li Eur. J. Med. Chem. 44 2009 4477 4484
100. K.C. Skyrianou, F. Perdih, A.N. Papadopoulos, I. Turel, D.P. Kessissoglou, and G. Psomas J. Inorg. Biochem. 105 2011 1273 1285