Striking difference in antiproliferative activity of ruthenium-and osmium-nitrosyl complexes with azole heterocycles

Inorganic Chemistry

Volumn 52, Issue 11, 2013, Pages 6273-6285

  Büchel, Gabriel E ^a,b   Gavriluta, Anatolie ^a,b   Novak, Maria ^a   Meier, Samuel M ^a   Jakupec, Michael A ^a   Cuzan, Olesea ^c   Turta, Constantin ^c   Tommasino, Jean Bernard ^b   Jeanneau, Erwann ^b   Novitchi, Ghenadie ^d   Luneau, Dominique ^b   Arion, Vladimir B ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITÉ CLAUDE BERNARD LYON 1   (France)

^c INSTITUTE OF CHEMISTRY   (Moldova)

^d GRENOBLE HIGH MAGNETIC FIELD LABORATORY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; HETEROCYCLIC COMPOUND; NITROSO DERIVATIVE; ORGANOMETALLIC COMPOUND; OSMIUM; PYRROLE DERIVATIVE; RUTHENIUM;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; DRUG SCREENING; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; AZOLES; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROSO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; OSMIUM; RUTHENIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84878659481     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic400555k     Document Type: Article

References (72)

1. Grifith, W. P. Adv. Organomet. Chem. 1969, 7, 211-239
2. Johnson, B. F. G.; McCleverty, J. A. Prog. Inorg. Chem. 1966, 7, 277-359
3. Connelly, N. G. Inorg. Chim. Acta, Rev. 1972, 6, 47-89
4. Bottomley, F. Coord. Chem. Rev. 1978, 26, 7-32
5. Enemark, J. H.; Feltham, R. D. Coord. Chem. Rev. 1974, 13, 339-406
6. Swinehart, J. H. Coord. Chem. Rev. 1967, 2, 385-402
7. Eisenberg, R.; Meyer, C. D. Acc. Chem. Res. 1975, 8, 26-34
8. McCleverty, J. A. Chem. Rev. 1979, 7, 53-76
9. Wolak, M.; van Eldik, R. Coord. Chem. Rev. 2002, 230, 263-282
10. Ford, P. C.; Lorkovic, I. M. Chem. Rev. 2002, 102, 993-1017
11. Tfouni, E.; Krieger, M.; McGarvey, B. R.; Franco, D. W. Coord. Chem. Rev. 2003, 236, 57-69
12. Videla, M.; Jacinto, J. S.; Baggio, R.; Garland, M. T.; Singh, P.; Kaim, W.; Slep, L. D.; Olabe, J. A. Inorg. Chem. 2006, 45, 8608-8617
13. Bottomley, F.; White, P. S.; Mukaida, M.; Shimura, K.; Kakihana, H. Dalton Trans. 1988, 2965-2969
14. Hughes, M. N. In The Inorganic Chemistry of Biological Processes, 2 nd ed.; John Wiley & Sons: New York, 1981.
15. Arikawa, Y.; Asayama, T.; Moriguchi, Y.; Agari, S.; Onishi, M. J. Am. Chem. Soc. 2007, 129, 14160-14161
16. McCleverty, J. A. Chem. Rev. 2004, 104, 403-418
17. Pandey, K. K. Coord. Chem. Rev. 1983, 51, 69-98
18. Ang, W. H.; Dyson, P. J. Eur. J. Inorg. Chem. 2006, 20, 4003-4018
19. Ang, W. H.; Daldini, E.; Scopelliti, R.; Juillerat-Jeannerat, L.; Dyson, P. J. Inorg. Chem. 2006, 45, 9006-9013
20. Gossens, C.; Dorcier, A.; Dyson, P. J.; Rothlisberger, U. Organometallics 2007, 26, 3965-3975
21. Dyson, P. J.; Sava, G. Dalton Trans. 2006, 1929-1933
22. Büchel, G. E.; Stepanenko, I. N.; Hejl, M.; Jakupec, M. A.; Arion, V. B.; Keppler, B. K. Inorg. Chem. 2009, 48, 10737-10747
23. Büchel, G. E.; Stepanenko, I. N.; Hejl, M.; Jakupec, M. A.; Keppler, B. K.; Arion, V. B. Inorg. Chem. 2011, 50, 7690-7697
24. Filak, L. K.; Göschl, S.; Heffeter, P.; Samper, K. G.; Egger, A. E.; Jakupec, M. A.; Keppler, B. K.; Berger, W.; Arion, V. B. Organometallics 2013, 32, 903-914
25. Jakupec, M. A.; Arion, V. B.; Kapitza, S.; Reisner, E.; Eichinger, A.; Pongratz, M.; Marian, B.; Graf von Keyserlingk, N.; Keppler, B. K. Int. J. Clin. Pharmacol. Ther. 2005, 12, 595-596
26. Hartinger, C. G.; Zorbas-Seifried, S.; Jakupec, M. A.; Kynast, B.; Zorbas, H.; Keppler, B. K. J. Inorg. Biochem. 2006, 100, 891-904
27. Heffeter, P.; Böck, K.; Atil, B.; Reza Hoda, M. A.; Körner, W.; Bartel, C.; Jungwirth, U.; Keppler, B. K.; Micksche, M.; Berger, W.; Koellensperger, G. J. Biol. Inorg. Chem. 2010, 15, 737-748
28. Rademaker-Lakhai, J. M.; van den Bongard, D.; Pluim, D.; Beijnen, J. H.; Schellens, J. H. M. Clin. Cancer Res. 2004, 10, 3717-3727
29. Alessio, E.; Mestroni, G.; Bergamo, B.; Sava, G. Curr. Top. Med. Chem. 2004, 4, 1525-1535
30. Berger, M. R.; Garzon, F. T.; Keppler, B. K.; Schmähl, D. Anticancer Res. 1989, 9, 761-765
31. Serli, B.; Zangrado, E.; Iengo, E.; Mestroni, G.; Yellowlees, L.; Alessio, E. Inorg. Chem. 2002, 41, 4033-4043
32. Serli, B.; Zangrado, E.; Gianferrara, T.; Yellowlees, L.; Alessio, E. Coord. Chem. Rev. 2003, 245, 73-83
33. Vacca, A.; Bruno, M.; Boccarelli, A.; Coluccia, M.; Ribatti, D.; Bergamo, A.; Garbisa, S.; Sartor, L.; Sava, G. Br. J. Cancer 2002, 86, 993-998
34. Morbidelli, L.; Donnini, S.; Filippo, S.; Messori, L.; Piccioli, F.; Orioli, P.; Sava, G.; Ziche, M. Br. J. Cancer 2003, 88, 1484-1491
35. Silverman, R. B. Acc. Chem. Res. 2009, 42, 439-445
36. de Mel, A.; Murad, F.; Seifalian, A. M. Chem. Rev. 2011, 111, 5742-5767
37. Furchgott, R. F. Angew. Chem., Int. Ed. 1999, 38, 1870-1880
38. Garthwaite, J.; Charles, S. L.; Chess-Williams, R. Nature 1988, 336, 385-388
39. Dawson, T. M.; Snyder, S. H. J. Neurosci. 1994, 14, 5147-5159
40. Cirino, G.; Distrutti, E.; Wallace, J. L. Inflammation Allergy: Drug Targets 2006, 5, 115-119
41. Laroux, F. S.; Pavlick, K. P.; Hines, I. N.; Kawachi, S.; Harada, H.; Bharwani, S.; Hoffman, J. M.; Grisham, M. B. Acta Phys. Scand. 2001, 173, 113-118
42. Blaise, G. A.; Gauvin, D.; Gangal, M.; Authier, S. Toxicology 2005, 208, 177-192
43. Weigert, A.; Brüne, B. Nitric Oxide 2008, 19, 95-102
44. Brüne, B.; von Knethen, A.; Sandau, K. B. Cell Death Differ. 1999, 6, 969-975
45. Bučinský, L.; Büchel, G. E.; Ponec, R.; Rapta, P.; Breza, M.; Kožíšek, J.; Gall, M.; Biskupič, S.; Fronc, M.; Schiessl, K.; Cuzan, O.; Prodius, D.; Turta, C.; Shova, S.; Zajac, D. A.; Arion, V. B. Eur. J. Inorg. Chem. 2013, 10.1002/ejic.201201526
46. Bhattacharya, R.; Saha, A. M.; Ghosh, P. N.; Mukherjee, M.; Mukherjee, A. K. J. Chem. Soc., Dalton Trans. 1991, 3, 501-510
47. Singh, P.; Sarkar, B.; Sieger, M.; Niemeyer, M.; Fiedler, J.; Zalis, S.; Kaim, W. Inorg. Chem. 2006, 45, 4602-4609
48. Gavriluta, A.; Büchel, G. E.; Freitag, L.; Novitchi, G.; Tommasino, J. B.; Jeanneau, E.; Kuhn, P.-S.; González, L.; Arion, V. B.; Luneau, D. Inorg. Chem. 2013, 10.1021/ic4004824
49. SAINT-Plus, version 7.06a and APEX2; Bruker-Nonius AXS Inc.: Madison, WI, 2004.
50. CrysAlis RED, version 1.171.35.15 (release 03-08-2011 CrysAlis171.NET); Oxford Diffracttion Ltd., 2011.
51. Sheldrick, G. M. Acta Crystallogr. 2008, A46, 112-122
52. Burnett, M. N.; Johnson, G. K. ORTEPIII. Report ORNL-6895; OAK Ridge National Laboratory: Oak Ridge, TN, 1996.
53. Davies, J. A.; Hockensmith, C. M.; Kukushkin, V. Yu.; Kukushkin, Yu. N. Synthetic Coordination Chemistry-Principles and Practice; World Scientific: Hackensack, NJ, 1995; pp 392-396.
54. Meier, S. M.; Hanif, M.; Kandioller, W.; Keppler, B. K.; Hartinger, C. G. J. Inorg. Biochem. 2012, 108, 91-95
55. Schmid, W. F.; John, R. O.; Mühlgassner, G.; Heffeter, P.; Jakupec, M. A.; Galanski, M.; Berger, W.; Arion, V. B..; Keppler, B. K. J. Med. Chem. 2007, 50, 6343-6355
56. Schuecker, R.; John, R. O.; Jakupec, M. A.; Arion, V. B.; Keppler, B. K. Organometallics 2008, 27, 6587-6595
57. Filak, L. K.; Mühlgassner, G.; Jakupec, M. A.; Heffeter, P.; Berger, W.; Arion, V. B.; Keppler, B. K. J. Biol. Inorg. Chem. 2010, 15, 903-918
58. Filak, L. K.; Mühlgassner, G.; Bacher, F.; Roller, A.; Galanski, M.; Jakupec, M. A.; Keppler, B. K.; Arion, V. B. Organometallics 2011, 30, 273-283
59. Hanif, M.; Nazarov, A. A.; Hartinger, C. G.; Kandioller, W.; Jakupec, M. A.; Arion, V. B.; Dyson, P. J.; Keppler, B. K. Dalton Trans. 2010, 39, 7345-7352
60. Mühlgassner, G.; Bartel, C.; Schmid, W. F.; Jakupec, M. A.; Arion, V. B.; Keppler, B. K. J. Inorg. Biochem. 2012, 116, 180-187
61. Stepanenko, I. N.; Novak, M. S.; Mühlgassner, G.; Roller, A.; Hejl, M.; Arion, V. B.; Jakupec, M. A.; Keppler, B. K. Inorg. Chem. 2011, 50, 11715-11728
62. Cebrián-Losantos, B.; Krokhin, A. A.; Stepanenko, I. N.; Eichinger, R.; Jakupec, M. A.; Arion, V. B.; Keppler, B. K. Inorg. Chem. 2007, 46, 5023-5033
63. Dorcier, A.; Ang, W. H.; Bolaño, S.; Gousalvi, L.; Juillerat-Jeannerat, L.; Laurenczy, G.; Peruzzini, M.; Phillips, A. D.; Zanobini, F.; Dyson, P. J. Organometallics 2006, 25, 4090-4096
64. Peacock, A. F. A.; Melchart, M.; Deeth, R. J.; Habtemariam, A.; Parsons, S.; Sadler, P. J. Chem.-Eur. J. 2007, 13, 2601-2613
65. Peacock, A. F. A.; Habtemariam, A.; Moggach, S. A.; Prescimone, A.; Parsons, S.; Sadler, P. J. Inorg. Chem. 2007, 46, 4049-4059
66. Maksimoska, J.; Williams, D. S.; Atilla-Gokcumen, G. E.; Smalley, K. S. M.; Carroll, P. J.; Webster, R. D.; Filippakopoulos, P.; Knapp, S.; Meggers, E. Chem.-Eur. J. 2008, 14, 4816-4822
67. Stepanenko, I. N.; Krokhin, A. A.; John, R. O.; Roller, A.; Arion, V. B.; Jakupec, M. A.; Keppler, B. K. Inorg. Chem. 2008, 47, 7338-7347
68. Bonavida, B.; Khineche, S.; Huerta-Yepez, S.; Garbán, H. Drug Resist. Updates 2006, 9, 157-173
69. Brüne, B.; Knethen, A.; Sandau, K. B. Eur. J. Pharmacol. 1998, 351, 261-272
70. Heinrich, T. A.; Von Poelhsitz, G.; Reis, R. I.; Castellano, E. E.; Neves, A.; Lanznaster, M.; Machado, S. P.; Batista, A. A.; Costa-Neto, C. M. Eur. J. Med. Chem. 2011, 46, 3616-3622
71. Mocellin, S.; Bronte, V.; Nitti, D. Med. Res. Rev. 2007, 27, 317-352
72. Cleare, M. J. Platinum Met. Rev. 1968, 12, 131-133