Photoactivatable organometallic pyridyl ruthenium(II) arene complexes

Organometallics

Volumn 31, Issue 9, 2012, Pages 3466-3479

  Betanzos Lara, Soledad ^a,c   Salassa, Luca ^a   Habtemariam, Abraha ^a   Novakova, Olga ^b   Pizarro, Ana M ^a   Clarkson, Guy J ^a   Liskova, Barbora ^b   Brabec, Viktor ^b   Sadler, Peter J ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b INSTITUTE OF BIOPHYSICS   (Czech Republic)

^c UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,10-PHENANTHROLINE; 1 ,10-PHENANTHROLINE-5 ,6-DIONE; 1 ,2 ,4-TRIAZOLE; 4-METHYLPYRIDINE; 9-ETHYLADENINE; ANTI-CANCER AGENTS; ARENE COMPLEXES; BIPYRIDINES; CALF THYMUS; CELL-FREE; CYTOTOXIC; DISSOCIATION MECHANISMS; DNA BINDING STUDIES; H NMR SPECTROSCOPY; HEXAMETHYLBENZENE; INTERCALATIVE BINDING; LIGHT ACTIVATION; METHYL NICOTINATE; MONODENTATE LIGANDS; MONOFUNCTIONAL; OVARIAN CANCER CELLS; P-CYMENE; PHOTO-IRRADIATION; PHOTOACTIVATABLE; PHOTOCHEMICAL PROCESS; PHOTOPRODUCTS; PHOTOTRIGGERS; PYRIDYL; RU(BPY); RU(PHEN); TRIPLET STATE; UV-VIS ABSORPTIONS; WHITE LIGHT; X RAY CRYSTAL STRUCTURES;

AMIDES; BINDING ENERGY; CELL CULTURE; COMPLEXATION; DENSITY FUNCTIONAL THEORY; DISSOCIATION; LIGANDS; ORGANOMETALLICS; PYRIDINE; RUTHENIUM; RUTHENIUM COMPOUNDS;

SYNTHESIS (CHEMICAL);

EID: 84861162546     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om201177y     Document Type: Article

References (68)

1. Farrer, N. J.; Salassa, L.; Sadler, P. J. Dalton Trans. 2009, 10690-10701
2. Sutin, N.; Creutz, C. Pure Appl. Chem. 1980, 52, 2717-2738
3. Balzani, V.; Moggi, L.; Manfrin, M. F.; Bolletta, F.; Laurence, G. S. Coord. Chem. Rev. 1975, 15, 321-433
4. Hager, G. D.; Crosby, G. A. J. Am. Chem. Soc. 1975, 97, 7031-7037
5. Fernández-Moreira, V.; Thorp-Greenwood, F.; Coogan, M. P. Chem. Commun. 2010, 46, 186-202
6. Puckett, C. A.; Barton, J. K. Biochemistry 2008, 47, 11711-11716
7. Zhang, C. X.; Lippard, S. J. Curr. Opin. Chem. Biol. 2003, 7, 481-489
8. Cosgrave, L.; Devocelle, M.; Forster, R. J.; Keyes, T. E. Chem. Commun. 2010, 46, 103-105
9. Gill, T. P.; Mann, K. R. Organometallics 1982, 1, 485-488
10. Schrenk, J. L.; Palazzotto, M. C.; Mann, K. R. Inorg. Chem. 1983, 22, 4047-4049
11. McNair, A. M.; Schrenk, J. L.; Mann, K. R. Inorg. Chem. 1984, 23, 2633-1640
12. Weber, W.; Ford, P. C. Inorg. Chem. 1986, 25, 1088-1092
13. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233-241
14. Magennis, S. W.; Habtemariam, A.; Nováková, O.; Henry, J. B.; Meier, S.; Parsons, S.; Oswald, I. D. H.; Brabec, V.; Sadler, P. J. Inorg. Chem. 2007, 46, 5059-5068
15. Aird, R.; Cummings, J.; Ritchie, A.; Muir, M.; Morris, R.; Chen, H.; Sadler, P.; Jodrell, D. Br. J. Cancer 2002, 86, 1652-1657
16. 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, 3616-3621
17. Nováková, O.; Kašpárková, J.; Bursova, V.; Hofr, C.; Vojtiskova, M.; Chen, H.; Sadler, P. J.; Brabec, V. Chem. Biol. 2005, 12, 121-129
18. Pizarro, A. M.; Habtemariam, A.; Sadler, P. J. In Topics in Organometallic Chemistry; Jaouen, G.; Metzler-Nolte, N., Eds.; Springer-Verlag: Berlin, 2010; Vol. 32, pp 21-56.
19. Wang, F.; Habtemariam, A.; van der Geer, E. P. L; Fernández, R.; Melchart, M.; Deeth, R. J.; Aird, R.; Guichard, S.; Fabbiani, F. P. A; Lozano-Casal, P.; Oswald, I. D. H.; Jodrell, D. I.; Parsons, S.; Sadler, P. J. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 18269-18274
20. Peacock, A. F. A.; Habtemariam, A.; Moggach, S. A.; Prescimone, A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2007, 46, 4049-4059
21. Betanzos-Lara, S.; Salassa, L.; Habtemariam, A.; Sadler, P. J. Chem. Commun. 2009, 6622-6624
22. Salassa, L.; Phillips, H. I. A.; Sadler, P. J. Phys. Chem. Chem. Phys. 2009, 11, 10311-10316
23. Salassa, L.; Garino, C.; Salassa, G.; Nervi, C.; Gobetto, R.; Lamberti, C.; Gianolio, D.; Bizzarri, R.; Sadler, P. J. Inorg. Chem. 2009, 48, 1469-1481
24. Salassa, L.; Garino, C.; Salassa, G.; Gobetto, R.; Nervi, C. J. Am. Chem. Soc. 2008, 130, 9590-9597
25. Cubo, L.; Pizarro, A. M.; Gómez Quiroga, A.; Salassa, L.; Navarro-Ranninger, C.; Sadler, P. J. J. Inorg. Biochem. 2010, 104, 909-918
26. Govindaswamy, P.; Canivet, J.; Therrien, B.; Süss-Fink, G.; Štěpnička, P.; Ludvík, J. J. Organomet. Chem. 2007, 692, 3664-3675
27. Sheldrick, G. M. SHELXL97; University of Göttingen, Göttingen, Germany, 1997.
28. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473
29. Sheldrick, G. M. Acta Crystallogr. 2008, 64, 12-122
30. Krezel, A.; Bal, W. J. Inorg. Biochem. 2004, 98, 161-166
31. Frisch, M. J., Gaussian 03, revision D0.1; Gaussian Inc., Wallingford, CT, 2004.
32. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
33. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
34. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283
35. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648
36. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681
37. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449
38. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224
39. Browne, W. R.; O'Boyle, N. M.; McGarvey, J. J.; Vos, J. G. Chem. Soc. Rev. 2005, 34, 641-663
40. O'Boyle, N. M.; Vos, J. G., GaussSum; Dublin City University, available at http://gausssum.sourceforge.net., 2005.
41. Brabec, V.; Palecek, E. Biophysik 1970, 6, 290-300
42. Brabec, V.; Palecek, E. Biophys. Chem. 1976, 4, 79-92
43. Brabec, V.; Leng, M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5345-5349
44. Lemaire, M. A.; Schwartz, A.; Rahmouni, A. R.; Leng, M. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1982-1985
45. Keck, M. V.; Lippard, S. J. J. Am. Chem. Soc. 1992, 114, 3386-3390
46. Loskotova, H.; Brabec, V. Eur. J. Biochem. 1999, 266, 392-402
47. Butour, J. L.; Macquet, J. P. Eur. J. Biochem. 1977, 78, 455-463
48. Butour, J. L.; Alvinerie, P.; Souchard, J. P.; Colson, P.; Houssier, C.; Johnson, N. P. Eur. J. Biochem. 1991, 202, 975-980
49. Butour, J. L.; Macquet, J. P. Eur. J. Biochem. 1977, 78, 455-463
50. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107-1112
51. Mann, K. R.; Blough, A. M.; Schrenk, J. L.; Koefod, R. S.; Freedman, D. A.; Matachek, J. R. Pure Appl. Chem. 1995, 67, 95-101
52. Wagenknecht, P. S.; Ford, P. C. Coord. Chem. Rev. 2011, 591-616
53. Yan, Y. K.; Melchart, M.; Habtemariam, A.; Sadler, P. J. Chem. Commun. 2005, 4764-4776
54. Lavalle, R. J.; Kutal, C. J. Organomet. Chem. 1998, 562, 97-104
55. Pinnick, D. V.; Durham, B. Inorg. Chem. 1984, 23, 1440-1445
56. Durham, B.; Wilson, S. R.; Hodgson, D. J.; Meyer, T. J. J. Am. Chem. Soc. 1980, 102, 600-607
57. Collin, J. P.; Jouvenot, D.; Koizumi, M.; Sauvage, J. P. Inorg. Chem. 2005, 44, 4693-4698
58. Moucheron, C.; Kirsch-De Mesmaeker, A.; Kelly, J. M. J. Photochem. Photobiol. B 1997, 40, 91-106
59. Pinnick, D. V.; Durham, B. Inorg. Chem. 1984, 23, 1440-1445
60. Durham, B.; Wilson, S. R.; Hodgson, D. J.; Meyer, T. J. J. Am. Chem. Soc. 1980, 102, 600-607
61. Collin, J. P.; Jouvenot, D.; Koizumi, M.; Sauvage, J. P. Inorg. Chem. 2005, 44, 4693-4698
62. Watts, R. J. J. Chem. Educ. 1983, 60, 834-842
63. Baerends, E. J.; Rosa, A. Coord. Chem. Rev. 1998, 177, 97-125
64. Vos, J. G.; Kelly, J. M. Dalton Trans. 2006, 4869-4883
65. Betanzos-Lara, S. Ph.D. Thesis, University of Warwick, Warwick, U.K., 2010.
66. Bancroft, D. P.; Lepre, C. A.; Lippard, S. J. J. Am. Chem. Soc. 1990, 112, 6860-6871
67. Chen, H. M.; Parkinson, J. A.; Nováková, O.; Bella, J.; Wang, F. Y.; Dawson, A.; Gould, R.; Parsons, S.; Brabec, V.; Sadler, P. J. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 14623-14628
68. Kemp, S.; Wheate, N. J.; Wang, S.; Collins, J. G.; Ralph, S. F.; Day, A. I.; Higgins, V. J.; Aldrich-Wright, J. R. J. Biol. Inorg. Chem. 2007, 12, 969-979