Anticancer activity and DNA binding of a bifunctional Ru(II) arene aqua-complex with the 2,4-diamino-6-(2-pyridyl)-1,3,5-triazine ligand

Inorganic Chemistry

Volumn 52, Issue 17, 2013, Pages 9962-9974

  Busto, Natalia ^a   Valladolid, Jesús ^a   Martínez Alonso, Marta ^a   Lozano, Héctor J ^a   Jalón, Félix A ^b   Manzano, Blanca R ^b   Rodriguez A M ^b   Carrión, M Carmen ^b,c   Biver, Tarita ^d   Leal, José M ^a   Espino, Gustavo ^a   García, Begoña ^a  

^a UNIVERSITY OF BURGOS   (Spain)

^b UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

^c Renewable Energy Research Institute   (Spain)

^d UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4-CYMENE; ANTINEOPLASTIC AGENT; COORDINATION COMPOUND; DNA; INTERCALATING AGENT; PARA CYMENE; RUTHENIUM; TERPENE; TRIAZINE DERIVATIVE;

ANIMAL; ARTICLE; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FEMALE; HUMAN; METABOLISM; OVARY; OVARY TUMOR; PATHOLOGY;

ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; COORDINATION COMPLEXES; DNA; FEMALE; HUMANS; INTERCALATING AGENTS; MODELS, MOLECULAR; MONOTERPENES; OVARIAN NEOPLASMS; OVARY; RUTHENIUM; TRIAZINES;

EID: 84883500309     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic401197a     Document Type: Article

References (67)

1. Rosenberg, B.; van Camp, L.; Trosko, J. E.; Mansour, V. H. Nature 1969, 222, 385-386
2. Ahmad, S. Chem. Biodiversity 2010, 7, 543-566
3. Kelland, L. Nat. Rev. Cancer 2007, 7, 573-584
4. Jamieson, E. R.; Lippard, S. J. Chem. Rev. 1999, 99, 2467-2498
5. Rosenberg, B. Adv. Exp. Med. Biol. 1977, 91, 129-50
6. Bruijnincx, P. C. A.; Sadler, P. J. Curr. Opin. Chem. Biol. 2008, 12, 197-206
7. Georgiades, S. N.; Vilar, R. Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem. 2010, 106, 481-503
8. Suntharalingam, K.; Vilar, R. Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem. 2011, 107, 339-358
9. Thompson, K. H.; Orvig, C. Dalton Trans. 2006, 761-764
10. Bergamo, A.; Gaiddon, C.; Schellens, J. H. M.; Beijnen, J. H.; Sava, G. J. Inorg. Biochem. 2012, 106, 90-99
11. Antonarakis, E.; Emadi, A. Cancer Chemother. Pharmacol. 2010, 66, 1-9
12. Bergamo, A.; Sava, G. Dalton Trans. 2007, 1267-1272
13. Bergamo, A.; Masi, A.; Peacock, A. F. A.; Habtemariam, A.; Sadler, P. J.; Sava, G. J. Inorg. Biochem. 2010, 104, 79-86
14. Ang, W.-H.; Casini, A.; Sava, G.; Dyson, P. J. J. Organomet. Chem. 2011, 696, 989-998
15. Aliende, C.; Pérez-Manrique, M.; Jalón, F. A.; Manzano, B. R.; Rodriguez, A. M.; Cuevas, J. V.; Espino, G.; Martinez, M. A.; Massaguer, A.; Gonzalez-Bartulos, M.; de Llorens, R.; Moreno, V. J. Inorg. Biochem. 2012, 117, 171-188
16. Busto, N.; Valladolid, J.; Aliende, C.; Jalon, F. A.; Manzano, B. R.; Rodriguez, A. M.; Gaspar, J. F.; Martins, C.; Biver, T.; Espino, G.; Leal, J. M.; García, B. Chem.-Asian J. 2012, 7, 788-801
17. Novakova, O.; Chen, H.; Vrana, O.; Rodger, A.; Sadler, P. J.; Brabec, V. Biochemistry 2003, 42, 11544-11554
18. Wang, F.; Chen, H.; Parsons, S.; Oswald, I. D. H.; Davidson, J. E.; Sadler, P. J. Chem.-Eur. J. 2003, 9, 5810-5820
19. Chen, H.; Parkinson, J. A.; Morris, R. E.; Sadler, P. J. J. Am. Chem. Soc. 2003, 125, 173-186
20. García, B.; Ibeas, S.; Muñoz, A.; Leal, J. M.; Ghinami, C.; Secco, F.; Venturini, M. Inorg. Chem. 2003, 42, 5434-5441
21. Geary, W. J. Coord. Chem. Rev. 1971, 7, 81-122
22. Domingo, P. L.; Garcia, B.; Leal, J. M. Can. J. Chem. 1987, 65, 583-589
23. García, B.; Ibeas, S.; Leal, J. M. J. Phys. Org. Chem. 1996, 9, 593-597
24. Peacock, A. F. A.; Habtemariam, A.; Moggach, S. A.; Prescimone, A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2007, 46, 4049-4059
25. Betanzos-Lara, S.; Novakova, O.; Deeth, R.; Pizarro, A.; Clarkson, G.; Liskova, B.; Brabec, V.; Sadler, P.; Habtemariam, A. J. Biol. Inorg. Chem. 2012, 17, 1033-1051
26. Scheller, K. H.; Scheller-Krattiger, V.; Martin, R. B. J. Am. Chem. Soc. 1981, 103, 6833-6839
27. Peacock, A. F. A.; Habtemariam, A.; Fernández, R.; Walland, V.; Fabbiani, F. P. A.; Parsons, S.; Aird, R. E.; Jodrell, D. I.; Sadler, P. J. J. Am. Chem. Soc. 2006, 128, 1739-1748
28. Bugarcic, T.; Habtemariam, A.; Stepankova, J.; Heringova, P.; Kasparkova, J.; Deeth, R. J.; Johnstone, R. D. L.; Prescimone, A.; Parkin, A.; Parsons, S.; Brabec, V.; Sadler, P. J. Inorg. Chem. 2008, 47, 11470-11486
29. Hanif, M.; Henke, H.; Meier, S. M.; Martic, S.; Labib, M.; Kandioller, W.; Jakupec, M. A.; Arion, V. B.; Kraatz, H.-B.; Keppler, B. K.; Hartinger, C. G. Inorg. Chem. 2010, 49, 7953-7963
30. Zobi, F.; Hohl, M.; Zimmermann, I.; Alberto, R. Inorg. Chem. 2004, 43, 2771-2772
31. Burgess, J. Metal Ions in Solution; Ellis Horwood Ltd.: Chichester: New York, 1978; p 481.
32. Diebler, H.; Secco, F.; Venturini, M. Biophys. Chem. 1987, 26, 193-205
33. Lepecq, J. B.; Paoletti, C. J. Mol. Biol. 1967, 27, 87-106
34. García, B.; Leal, J. M.; Ruiz, R.; Biver, T.; Secco, F.; Venturini, M. J. Phys. Chem. B 2010, 114, 8555-8564
35. Biver, T.; Secco, F.; Venturini, M. Coord. Chem. Rev. 2008, 252, 1163-1177
36. Zimmer, C.; Luck, G. Use of circular dichroism to probe DNA structure and drug binding to DNA. In Advances in DNA Sequence-specific Agents; Hurley, L. H., Ed. Elsevier: Amsterdam, 1992; Vol. 1.
37. Busto, N.; García, B.; Leal, J. M.; Secco, F.; Venturini, M. Org. Biomol. Chem. 2012, 10, 2594-2602
38. Cohen, G.; Eisenberg, H. Biopolymers 1969, 8, 45-55
39. Leszczynski, T.; Dunski, H. Zesz. Nauk.-Politech. Lodz., Chem. Spozyw. Biotechnol. 2006, 70, 13-22
40. Cantor, C. R.; Schimmel, P. R. Biophysical Chemistry.: W.H. Freeman: San Francisco, 1985.
41. Graves, D. E.; Velea, L. M. Curr. Org. Chem. 2000, 4, 915-929
42. Busto, N.; García, B.; Leal, J. M.; Gaspar, J. F.; Martins, C.; Boggioni, A.; Secco, F. Phys. Chem. Chem. Phys. 2011, 13, 19534-19545
43. Liu, H.-K.; Sadler, P. J. Metal Complexes as DNA Intercalators Acc. Chem. Res. 2011, 44, 349-359
44. Bugarcic, T.; Novakova, O.; Halamikova, A.; Zerzankova, L.; Vrana, O.; Kasparkova, J.; Habtemariam, A.; Parsons, S.; Sadler, P. J.; Brabec, V. J. Med. Chem. 2008, 51, 5310-5319
45. Morris, R. E.; Aird, R. E.; Murdoch, P. D.; Chen, H. M.; Cummings, J.; Hughes, N. D.; Parsons, S.; Parkin, A.; Boyd, G.; Jodrell, D. I.; Sadler, P. J. J. Med. Chem. 2001, 44 (22) 3616-3621
46. Renfrew, A. K.; Phillips, A. D.; Egger, A. E.; Hartinger, C. G.; Bosquain, S. S.; Nazarov, A. A.; Keppler, B. K.; Gonsalvi, L.; Peruzzini, M.; Dyson, P. J. Organometallics 2009, 28 (4) 1165-1172
47. Renfrew, A. K.; Phillips, A. D.; Tapavicza, E.; Scopelliti, R.; Rothlisberger, U.; Dyson, P. J. Organometallics 2009, 28 (17) 5061-5071
48. Ang, W. H.; Grote, Z.; Scopelliti, R.; Juillerat-Jeanneret, L.; Severin, K.; Dyson, P. J. J. Organomet. Chem. 2009, 694 (6) 968-972
49. Mahoney, B. P.; Raghunand, N.; Baggett, B.; Gillies, R. J. Biochem. Pharmacol. 2003, 66, 1207-1218
50. Pizarro, A. M.; Melchart, M.; Habtemariam, A.; Salassa, L.; Fabbiani, F. P. A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2010, 49, 3310-3319
51. Romero-Canelón, I.; Salassa, L.; Sadler, P. J. J. Med. Chem. 2013, 56, 1291-1300
52. Webb, B. A.; Chimenti, M.; Jacobson, M. P.; Barber, D. L. Nat. Rev. Cancer 2011, 11, 671-677
53. Lo, K. K.-W.; Lee, T. K.-M.; Lau, J. S.-Y.; Poon, W.-L.; Cheng, S.-H. Inorg. Chem. 2008, 47, 200-208
54. Neugebauer, U.; Pellegrin, Y.; Devocelle, M.; Forster, R. J.; Signac, W.; Moran, N.; Keyes, T. E. Chem. Commun. 2008, 5307-5309
55. Puckett, C. A.; Barton, J. K. Biochemistry 2008, 47, 11711-11716
56. Gallagher, F. A.; Kettunen, M. I.; Day, S. E.; Hu, D.-E.; Ardenkjaer-Larsen, J. H.; Zandt, R. i. t.; Jensen, P. R.; Karlsson, M.; Golman, K.; Lerche, M. H.; Brindle, K. M. Nature 2008, 453, 940-943
57. Gillies, R. J.; Raghunand, N.; Karczmar, G. S.; Bhujwalla, Z. M. J. Magn. Reson. Imaging 2002, 16, 430-450
58. Ginzinger, W.; Mühlgassner, G.; Arion, V. B.; Jakupec, M. A.; Roller, A.; Galanski, M.; Reithofer, M.; Berger, W.; Keppler, B. K. J. Med. Chem. 2012, 55, 3398-3413
59. Zelonka, R. A.; Baird, M. C. Can. J. Chem. 1972, 50, 3063-3072
60. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233-241
61. Case, F. H.; Koft, E. J. Am. Chem. Soc. 1959, 81, 905-906
62. Reichmann, M. E.; Rice, S. A.; Thomas, C. A.; Doty, P. J. Am. Chem. Soc. 1954, 76, 3047-3053
63. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176-2179
64. SAINT Area-Detector Integration Program, SAINT+ v7.12a.; Bruker AXS: Madison, Wisconsin, USA, 2004.
65. Sheldrick, G. M. SADABS A Program for Empirical Absorption Correction, version 2004/1; University of Göttingen: Göttingen, Germany, 2004.
66. SHELXTL-NT Structure Determination Package, version 6.12; Bruker AXS: Madison, Wisconsin, USA, 2001.
67. Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Cancer Res. 1987, 47, 943-946