Bis(2-methylbenzimidazolyl)amine-derived copper complexes and their antineoplastic activity

European Journal of Inorganic Chemistry

Volumn , Issue 23, 2011, Pages 3454-3460

  Rodríguez Solano, Laura A ^a   Aguiñiga, Itzen ^b   López Ortiz, Manuel ^b   Tiburcio, Reynaldo ^b   Luviano, Axel ^b   Regla, Ignacio ^b   Santiago Osorio, Edelmiro ^b   Ugalde Saldívar, Víctor M ^a   Toscano, Rubén A ^a   Castillo, Ivan ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Copper; Cytotoxicity; N ligands; Sulfur; Voltammetry

Indexed keywords

CELL CULTURE; CELLS; COPPER COMPOUNDS; CYCLIC VOLTAMMETRY; DISEASES; INORGANIC COMPOUNDS; LIGANDS; MASS SPECTROMETRY; REDOX REACTIONS; SPECTROSCOPIC ANALYSIS; X RAY CRYSTALLOGRAPHY;

AMINE LIGAND; ANTINEOPLASTIC ACTIVITY; CELL LINES; COMPLEX 1; COPPER COMPLEXES; CUPRIC IONS; N LIGANDS; N-LIGANDS; SPECTROSCOPIC METHOD; TETRADENTATE;

SULFUR;

EID: 79961160613     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201100301     Document Type: Article

References (43)

1. C. Orvig, M. J. Abrams, Chem. Rev. 1999, 99, 2201-2203.
2. Z. Guo, P. J. Sadler, Angew. Chem. Int. Ed. 1999, 38, 1512-1531.
3. B. Rosenberg, Platinum Met. Rev. 1971, 15, 42-51.
4. R. A. Alderden, M. D. Hall, T. W. Hambley, J. Chem. Educ. 2006, 83, 728-734.
5. C. X. Zhang, S. J. Lippard, Curr. Opin. Chem. Biol. 2003, 7, 481-489.
6. L. R. Kelland, Drugs 2000, 59, 1-8.
7. M. Frezza, S. Hindo, D. Chen, A. Davenport, S. Schmitt, D. Tomco, Q. P. Dou, Curr. Pharm. Des. 2010, 16, 1813-1825.
8. T. Wang, Z. Guo, Curr. Med. Chem. 2006, 13, 525-537.
9. M. C. Linder, Biochemistry of Copper, Plenum Press, New York, 1991.
10. S. S. Hindo, M. Frezza, D. Tomco, M. J. Heeg, L. Hryhorczuk, B. R. McGarvey, Q. P. Dou, C. N. Verani, Eur. J. Med. Chem. 2009, 44, 4353-4361.
11. C. Marzano, M. Pellei, F. Tisato, C. Santini, Anti-Cancer Agents Med. Chem. 2009, 9, 185-211.
12. S. Tardito, L. Marchiò, Curr. Med. Chem. 2009, 16, 1325-1348.
13. S. Tardito, I. Bassanetti, C. Bignardi, L. Elviri, M. Tegoni, C. Mucchino, O. Bussolati, R. Franchi-Gazzola, L. Marchiò, J. Am. Chem. Soc. 2011, 133, 6235-6242.
14. B. J. Hathaway in Comprehensive Coordination Chemistry (Eds.:, G. Wilkinson, R. D. Gillard, J. A. McCleverty), Pergamon Press, Oxford, 1987, vol. 5, pp. 533-594.
15. W. E. Antholine, J. M. Knight, D. H. Petering, J. Med. Chem. 1976, 19, 339-341.
16. J. Easmon, G. Puerstinger, G. Heinisch, T. Roth, H. H. Fiebig, W. Holzer, W. Jaeger, M. Jenny, J. Hofmann, J. Med. Chem. 2001, 44, 2164-2171.
17. A. Marzotto, A. Ciccarese, D. A. Clemente, G. Valle, J. Chem. Soc., Dalton Trans. 1995, 1461-1468.
18. M. B. Ferrari, S. Capacchi, G. Pelosi, G. Reffo, P. Tarasconi, R. Albertini, S. Pinelli, P. Lunghi, Inorg. Chim. Acta 1999, 286, 134-141.
19. P. de Hoog, M. J. Louwerse, P. Gamez, M. Pitié, E. J. Baerends, B. Meunier, J. Reedijk, Eur. J. Inorg. Chem. 2008, 612-619.
20. D. S. Sigman, R. Landgraf, D. M. Perrin, L. Pearson, Met. Ions Biol. Syst. 1996, 33, 485-513.
21. P. J. Jansson, P. C. Sharpe, P. V. Bernhardt, D. R. Richardson, J. Med. Chem. 2010, 53, 5759-5769.
22. S. Zhang, Y. Zhu, C. Tu, H. Wei, Z. Yang, L. Lin, J. Ding, J. Zhang, Z. Guo, J. Inorg. Biochem. 2004, 98, 2099-2106.
23. M. Andrzejewska, L. Yepez-Mulia, R. Cedillo-Rivera, A. Tapia, L. Vilpo, J. Vilpo, Z. Kazimierczuk, Eur. J. Med. Chem. 2002, 37, 973-978.
24. S.-T. Huang, L.-J. Hsei, C. Chen, Bioorg. Med. Chem. 2006, 14, 6106-6119.
25. M. Devereaux, M. McCann, D. O. Shea, R. Kelly, D. Egan, C. Deegan, K. Kavanagh, V. McKee, G. Finn, J. Inorg. Biochem. 2004, 98, 1023-1031.
26. M. Devereaux, D. O. Shea, A. Kellett, M. McCann, M. Walsh, D. Egan, C. Deegan, K. Kedziora, G. Rosair, H. Müller-Bunz, J. Inorg. Biochem. 2007, 101, 881-892.
27. P. R. Martínez-Alanis, M. López Ortiz, I. Regla, I. Castillo, Synlett 2010, 423-426.
28. V. O. Rodionov, S. I. Presolski, S. Gardinier, Y.-H. Lim, M. G. Finn, J. Am. Chem. Soc. 2007, 129, 12696-12704.
29. R. Mukherjee in Comprehensive Coordination Chemistry II (Eds.:, J. A. McCleverty, T. J. Meyer), Elsevier, Amsterdam, 2004, vol. 6, pp. 747-910.
30. M. Kodera, T. Kita, I. Miura, N. Nakayama, T. Kawata, K. Kano, S. Hirota, J. Am. Chem. Soc. 2001, 123, 7715-7716.
31. D. Wahnon, R. C. Hynes, J. Chin, J. Chem. Soc., Chem. Commun. 1994, 1441-1442.
32. P. E. Pjura, K. Grzeskoviak, J. Mol. Biol. 1987, 197, 257-271.
33. F. G. Lootiens, P. Regenfuss, A. Zechel, L. Dumortier, R. M. Clegg, Biochemistry 1990, 29, 9029-9039.
34. M. Chikira, Y. Tomizawa, D. Fukita, T. Sugizaki, N. Sugawara, T. Yamazaki, A. Sasano, H. Shindo, M. Palaniandavar, W. E. Antholine, J. Inorg. Biochem. 2002, 89, 163-173.
35. F. Arnesano, G. Natile, Coord. Chem. Rev. 2009, 253, 2070-2081.
36. T. B. Thederahn, M. D. Kuwabara, T. A. Larsen, D. S. Sigman, J. Am. Chem. Soc. 1989, 111, 4941-4946.
37. M. Pitie, C. Boldron, G. Pratviel, Adv. Inorg. Chem. 2006, 58, 77-130.
38. N. Aliaga-Alcalde, P. Marqués-Galleo, M. Kraaijkamp, C. Herranz-Lancho, H. den Dulk, H. Gorner, O. Roubeau, S. J. Teat, T. Weyhermuller, J. Reedijk, Inorg. Chem. 2010, 49, 9655-9663.
39. S. S. Bhat, A. A. Kumbhar, H. Heptullah, A. A. Khan, V. V. Gobre, S. P. Gejji, V. G. Puranik, Inorg. Chem. 2011, 50, 545-558.
40. Bruker AXS, SAINT Software Reference Manual v. 6.23C, Madison, 2002.
41. G. M. Sheldrick, SHELXS-97: Crystal Structure Solution, University of Göttingen, Germany, 1990.
42. G. M. Sheldrick, SHELXL-97: Crystal Structure Refinement, University of Göttingen, Germany, 1997.
43. V. Vichai, K. Kirtikara, Nat. Protoc. 2006, 1, 1112-1116.