Tuning the efficacy of ruthenium(II)-arene (RAPTA) antitumor compounds with fluorinated arene ligands

Organometallics

Volumn 28, Issue 17, 2009, Pages 5061-5071

  Renfrew, Anna K ^a   Phillips, Andrew D ^a   Tapavicza, Enrico ^a   Scopelliti, Rosario ^a   Rothlisberger, Ursula ^a   Dyson, Paul J ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR COMPOUNDS; ARENE LIGANDS; CELLULAR ENVIRONMENT; DFT CALCULATION; MOLECULAR LEVELS; OVARIAN CANCER CELLS; RU(ACAC); TUMOR TARGETING;

OLEFINS; PARAFFINS; RUTHENIUM; SULFUR COMPOUNDS;

HYDROLYSIS;

EID: 69949116777     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900345n     Document Type: Article

References (73)

1. (a) Kostova, I. Curr. Med. Chem. 2006, 13, 1085-1107.
2. (b) Galanski, M.; Arion, V. B.; Jakupec, M. A.; Keppler, B. K. Curr. Pharm. Des. 2003, 9, 2078-2089.
3. Dyson, P. J.; Sava, G. Dalton Trans. 2006, 1929-1933.
4. Smith, C. A.; Sutherland-Smith, A. J.; Keppler, B. K.; Kratz, F.; Baker, E. N. J. Biol. Inorg. Chem. 1996, 1, 424-431.
5. Alessio, E.; Mestroni, G.; Bergamo, A.; Sava, G. Curr. Top. Med. Chem. 2004, 4, 1525-1535.
6. Groessl, M.; Hartinger, C. G.; Egger, A.; Keppler, B. K. Metal Ions Biol. Med. 2006, 9,111-116.
7. (a) Melchart, M.; Sadler, P. J. In Bioorganometallics; Jaouen, G., Ed.; Wiley-VCH: Weinheim, 2006; pp 39-62.
8. (b) Ang, W H.; Dyson, P. J. Eur. J. Inorg. Chem. 2006, 20, 4003-4018.
9. Scolaro, C.; Bergamo, A.; Brescacin, L.; Delfino, R.; Cocchietto, M.; Laurenczy, G.; Geldbach, T. J.; Sava, G.; Dyson, P. J. J. Med. Chem. 2005, 48, 4161-4171.
10. Gerweck, L. E. Semin. Radiât. Oncol. 1998, 8, 176-182.
11. Allardyce, C. S.; Dyson, P. J.; Ellis, D. J.; Heath, S. L. Chem. Commun. 2001, 1396-1397.
12. Groessl, M.; Hartinger, C. G.; Dyson, P. J.; Keppler, B. K. J. Inorg. Biochem. 2008, 102, 1060-1065.
13. Gossens, C.; Dorcier, A.; Dyson, P. J.; Rothlisberger, U. Organometallics 2007, 26, 3969-3975.
14. (a) Koelle, U.; Hoernig, A.; Englert, U. Organometallics 1994, 13, 4064-4066.
15. (b) Fang, X.; Watkin, J. G.; Scott, B. L.; John, K. D.; Kabas, G. J. Organometallics 2002, 21, 2336-2339.
16. (c) Hayashida, T.; Nagashima, H. Organometallics 2002, 21, 3884-3888.
17. (a) Winkhaus, G.; Singer, H. J. Organomet. Chem. 1967, 7, 487-491.
18. (b) Zelonka, R. A.; Baird, M. C. Can. J. Chem. 1972, 50, 3063-3072.
19. (c) Bennett, M. A.; Smith, A. K. Dalton Trans. 1974, 233-241.
20. Bennett, M. A.; Neuman, H.; Thomas, M.; Wang, X.; Pertici, P.; Salvadoři, P.; Vitulli, G. Organometallics 1991, 10, 3237-3245.
21. Bodes, G. F.; Heinemann, W.; Jobi, G.; Klodwig, J.; Neumann, S.; Zenneck, U. Eur. J. Inorg. Chem. 2003, 281-292.
22. Pertici, P.; Vitulli, G.; Lazzaroni, R.; Salvadoři, P.; Barili, P. L. Dalton Trans. 1982, 1019-1022
23. Crocker, M.; Green, M.; Howard, J. A. K.; Norman, N. C.; Thomas, D. M. Dalton Trans. 1990, 2299-2301.
24. (a) Potvin, C.; Manoli, J. M.; Dereigne, A.; Pannetier, G. J. Less Common Met. 1971, 24, 333-334.
25. (b) Potvin, C.; Pannetier, G. J. Less Common Met. 1970, 22, 91-98.
26. Bennett, M. A.; Wilkinson, G. Chem. Ind. 1959,1519.
27. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388.
28. Schmid, M.; Ziegler, M. L. Chem. Ber. 1976, 109, 132-138.
29. Allardyce, C. S.; Dyson, P. J.; Ellis, D. J.; Heath, S. L. Chem. Commun. 2001, 1396-1397.
30. Phillips, A. D.; Gonsalvi, L.; Romerosa, A.; Vizza, F.; Peruzzini, M. Coord. Chem. Rev. 2004, 248, 955.
31. Scolaro, C.; Geldbach, T. J.; Rochat, S.; Dorcier, A.; Gossens, C.; Bergamo, A.; Cocchietto, M.; Tavernelli, I.; Sava, G.; Rothlisberger, U.; Dyson, P. J. Organometallics 2006, 25, 156-165.
32. Chatterjee, S.; Kundu, S.; Bhattacharyya, A.; Hartinger, C G.; Dyson, P. J. J. Biol. Inorg. Chem. 2008, 13, 1149-1155.
33. For example see: (a) Nguyen, A.; Top, S.; Pigeon, P.; Vessieres, A.; Hillard, E. A.; Plamont, M.; Huche, M.; Rigamonti, C.; Jaouen, G. Chem. Eur. J. 2009, 15, 684-696.
34. (b)Top, S.; Thibaudeau, C.; Vessieres, A.; Brule, E.; Le Bideau, F.; Joerger, J.; Plamont, M.; Samreth, S.; Edgar, A.; Marrot, J.; Herson, P.; Jaouen, G. Organometallics 2009, 28 (5), 1414-1424.
35. (c) Strohfeldt, K.; Tacke, M. Chem. Soc. Rev. 2008, 37, 1174-1187.
36. (d) Hogan, M.; Claffey, J.; Pampillon, C.; Tacke, M. Med. Chem. 2008, 4,9199.
37. (e) Kirin, S. I.; Ott, I.; Gust, R.; Mier, W.; Weyhermueller, T.; MetzlerNolte, N. Angew. Chem. 2008, 47, 955-959.
38. (f) Gross, A.; Metzler-Nolte, N. J. Organomet. Chem. 2009, 694, 1185-1188.
39. (g) Zobi, F.; Blacque, O.; Sigel, R. K. O.; Alberto, R. Inorg. Chem. 2007, 46, 10458-10460.
40. (h)Xavier, C.; Giannini, C.; Dall'Angelo, S.; Gano, L.; Maiorana, S.; Alberto, R.; Santos, I. J. Biol. Inorg. Chem. 2008, 13, 1335-1344.
41. (i) Hartinger, C G.; Dyson, P. J. Chem. Soc. Rev. 2009, 38, 391-401.
42. (a) Romerosa, A.; Saoud, M.; Campos-Malpartida, T.; Lidrissi, C.; Serrano-Ruiz, M.; Peruzzini, M.; Garrido, J. A.; Garcia-Maroto, F. Eur. J. Inorg. Chem. 2007, 18, 2803-2812.
43. (b) Schmid, W F.; John, R. O.; Arion, V B.; Jakupec, M. A.; Keppler, B. K. Organometallics 2007, 26, 6643-6652.
44. (c) Habtemariam, A.; Melchart, M.; Fernandez, R.; Parsons, S.; Oswald, I. D. H.; Parkin, A.; Fabbiani, F. P. A.; Davidson, J. E.; Dawson, A.; Aird, R. E.; Jodrell, D. I.; Sadler, P. J. J. Med. Chem. 2006, 49, 6858-6868.
45. (a) Fish, R. H. Coord. Chem. Rev. 1999, 185-186, 569-584.
46. (b) Chen, H.; Maestre, M. F.; Fish, R. H. J. Am. Chem. Soc. 1995, 117,3631-3632.
47. Albers, M. O.; Ashworth, T. V.; Oosthuizen, H. E.; Singleton, E. Inorg. Synth. 1989, 26, 249-258.
48. Daigle, D. J. Inorg. Synth. 1998, 52,40-45.
49. Dyson, P. J.; McIndoe, J. S. Inorg. Chim. Acta 2003, 354, 68-74.
50. Powell, P. J. Organomet. Chem. 1974, 65, 89-92.
51. Mikkelesen, K.; Nielsen, S. O. J. Phys. Chem. 1960, 64, 632-637.
52. Liptak, M. D.; Gross, K. C.; Seybold, P. G.; Feldgus, S.; Shields, G. C J. Am. Chem. Soc. 2002, 124, 6421-6421
53. McQuarrie, D. M. Statistical Mechanics; Harper and Row: New York, 1970.
54. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
55. Gaussian 03, Revision B.03; Gaussian, Inc.: Wallingford, CT, 2004.
56. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995-2001.
57. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V J. Comput. Chem. 2003, 24,669-681.
58. Halvani, S.; Noorbala, M. R. THEOCHEM 2004, 711, 13-18.
59. Andrae, D.; Haeussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-141
60. (a) Dorcier, A.; Dyson, P. J.; Gossens, C.; Rothlisberger, U.; Scopelliti, R.; Tavernelli, I. Organometallics 2005, 24, 2114-2123.
61. (b) Rallies, B.; Mitzner, R. J. Phys. Chem. B 1997, 101, 2959-2967.
62. (c) De Abreu, H. A.; De Almeida, W B.; Duarte, H. A. Chem. Phys. Lett. 2004, 383,47-52.
63. Duisenberg, A. J. M. J. Appl. Crystallogr. 1992, 25, 92-96.
64. CrysAlis CCD and CrysAlis RED, version 1.71; Oxford Diffraction Ltd: Abingdon, 2006.
65. COLLECT: data collection software; Bruker AXIS B.V: Delft, 1999.
66. Automar, version 1.8; Marresearch G.m.b.H.: Norderstedt, 2005.
67. Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M. J. Appl. Crystallogr. 2003, 36, 220-229.
68. Sheldrick, G. M. SADABS: Area detector absorption and other corrections, version 2.06; Bruker-AXS: Madison, 2003.
69. XPREP: Reciprocal Space Exploration, version 6.14; BrukerAXS: Madison, 2003.
70. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University Göttingen: Germany, 1997.
71. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University Göttingen: Germany, 1997.
72. Nardelli, M. J. Appl. Crystallogr. 1999, 32, 563-571.
73. Diamond: Crystal and Molecular Structure Visualization, version 3.1e; Crystal Impact: Bonn, 2007.