Novel cis- and trans-configured bis(oxime)platinum(II) complexes: Synthesis, characterization, and cytotoxic activity

Inorganic Chemistry

Volumn 49, Issue 12, 2010, Pages 5669-5678

  Scaffidi Domianello, Yulia Yu ^a   Meelich, Kristof ^a   Jakupec, Michael A ^a   Arion, Vladimir B ^a   Kukushkin, Vadim Yu ^b   Galanski, Markus ^a   Keppler, Bernhard K ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PLATINUM COMPLEX;

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

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77953597084     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic100584b     Document Type: Article

References (66)

1. Rosenberg, B., Van Kamp, L., and Crigas, T. Nature 1965, 205, 698-699
2. Jakupec, M. A., Galanski, M., and Keppler, B. K. Rev. Physiol. Biochem. Pharmacol. 2003, 146, 1-54
3. Galanski, M., Jakupec, M. A., and Keppler, B. K. Curr. Med. Chem. 2005, 12, 2075-2094
4. Galanski, M., Arion, V. B., Jakupec, M. A., and Keppler, B. K. Curr. Pharm. Des. 2003, 9, 2078-2089
5. Cleare, M. J. and Hoeschele, J. D. Plat. Met. Rev. 1973, 17, 2-13
6. Cleare, M. J. and Hoeschele, J. D. Bioinorg. Chem. 1973, 2, 187-210
7. Aris, S. M. and Farrell, N. P. Eur. J. Inorg. Chem. 2009, 10, 1293-1302
8. Kalinowska-Lis, U., Ochocki, J., and Matlawska-Wasowska, K. Coord. Chem. Rev. 2008, 252, 1328-1345
9. Natile, G. and Coluccia, M. Coord. Chem. Rev. 2001, 216-217, 383-410
10. Hall, M. D. and Hambley, T. W. Coord. Chem. Rev. 2002, 232, 49-67
11. Farrell, N. In Platinum-Based Drugs in Cancer Therapy; Kelland, L. R. and Farrell, N. P., Eds.; Humana Press: Totowa, NJ, 2000; pp 321 - 338.
12. Liu, Y., Vinje, J., Pacifico, C., Natile, G., and Sletten, E. J. Am. Chem. Soc. 2002, 124, 12854-12862
13. Farrell, N., Ha, T. T. B., Souchard, J. P., Wimmer, F. L., Cros, S., and Johnson, N. P. J. Med. Chem. 1989, 32, 2240-2241
14. Farrell, N., Kelland, L. R., Roberts, J. D., and Van Beusichem, M. Cancer Res. 1992, 52, 5065-5072
15. Van Beusichem, M. and Farrell, N. Inorg. Chem. 1992, 31, 634-639
16. Farrell, N., Povirk, L. F., Dange, Y., DeMasters, G., Gupta, M. S., Kohlhagen, G., Khan, Q. A., Pommier, Y., and Gewirtz, D. A. Biochem. Pharmacol. 2004, 68, 857-866
17. Martinez, A., Lorenzo, J., Prieto, M. J., de Llorens, R., Font-Bardia, M., Solans, X., Aviles, F. X., and Moreno, V. ChemBioChem 2005, 6, 2068-2077
18. Coluccia, M., Nassi, A., Loseto, F., Boccarelli, A., Mariggio, M. A., Giordano, D., Intini, F. P., Caputo, P., and Natile, G. J. Med. Chem. 1993, 36, 510-512
19. Zaludova, R., Zokovska, A., Kasparkova, J., Balcarova, Z., Vrana, O., Coluccia, M., Natile, G., and Brabec, V. Mol. Pharmacol. 1997, 52, 354-361
20. Coluccia, M., Nassi, A., Boccarelli, A., Giordano, D., Cardellicchio, N., Locker, D., Leng, M., Sivo, M., Intini, F. P., and Natile, G. J. Inorg. Biochem. 1999, 77, 31-35
21. Casini, A., Gabbiani, C., Mastrobuoni, G., Pellicani, R. Z., Intini, F. P., Arnesano, F., Natile, G., Moneti, G., Francese, S., and Messori, L. Biochemistry 2007, 46, 12220-12230
22. Najajreh, Y., Perez, J. M., Navarro-Ranninger, C., and Gibson, D. J. Med. Chem. 2002, 45, 5189-5195
23. Nguewa, P. A., Fuertes, M. A., Iborra, S., Najajreh, Y., Gibson, D., Martinez, E., Alonso, C., and Perez, J. M. J. Inorg. Biochem. 2005, 99, 727-736
24. Najajreh, Y., Prilutski, D., Ardeli-Tzaraf, Y., Perez, J. M., Khazanov, E., Barenholz, Y., Kasparkova, J., Brabec, V., and Gibson, D. Angew. Chem., Int. Ed. 2005, 44, 2885-2887
25. Najajreh, Y., Khazanov, E., Jawbry, S., Ardeli-Tzaraf, Y., Perez, J. M., Kasparkova, J., Brabec, V., Barenholz, Y., and Gibson, D. J. Med. Chem. 2006, 49, 4665-4673
26. Montero, E. I., Diaz, S., Gonzalez-Vadillo, A. M., Perez, J. M., Alonso, C., and Navarro-Ranninger, C. J. Med. Chem. 1999, 42, 4264-4268
27. Montero, E. I., Perez, J. M., Schwartz, A., Fuertes, M. A., Malinge, J. M., Alonso, C., Leng, M., and Navarro-Ranninger, C. ChemBioChem 2002, 3, 61-67
28. Prokop, R., Kasparkova, J., Novakova, O., Marini, V., Pizarro, A. M., Navarro-Ranninger, C., and Brabec, V. Biochem. Pharmacol. 2004, 67, 1097-1109
29. Kelland, L. R., Barnard, C. F. J., Evans, I. G., Murrer, B. A., Theobald, B. R. C., Wyer, S. B., Goddard, P. M., Jones, M., Valenti, M., Bryant, A., Rogers, P. M., and Harrap, K. R. J. Med. Chem. 1995, 38, 3016-3024
30. Perez, J. M., Kelland, L. R., Montero, E. I., Boxall, F. E., Fuertes, M. A., Alonso, C., and Navarro-Ranninger, C. Mol. Pharmacol. 2003, 63, 933-944
31. Ma, E. S. F., Bates, W. D., Edmunds, A., Kelland, L. R., Fojo, T., and Farrell, N. J. Med. Chem. 2005, 48, 5651-5654
32. Quiroga, A. G., Perez, J. M., Alonso, C., Navarro-Ranninger, C., and Farrell, N. J. Med. Chem. 2006, 49, 224-231
33. van Zutphen, S., Pantoja, E., Soriano, R., Soro, C., Tooke, D. M., Spek, A. L., den Dulk, H., Brouwer, J., and Reedijk, J. Dalton Trans. 2006, 1020-1023
34. Bulluss, G. H., Knott, K. M., Ma, E. S. F., Aris, S. M., Alvarado, E., and Farrell, N. Inorg. Chem. 2006, 45, 5733-5735
35. Ramos-Lima, F. J., Quiroga, A. G., Perez, J. M., Font-Bardia, M., Solans, X., and Navarro-Ranninger, C. Eur. J. Inorg. Chem. 2003, 1591-1598
36. Kalinowska, U., Matlawska, K., Checinska, L., Domagala, M., Kontek, R., Osiecka, R., and Ochocki, J. J. Inorg. Biochem. 2005, 99, 2024-2031
37. Boccarelli, A., Intini, F. P., Sasanelli, R., Sivo, M. F., Coluccia, M., and Natile, G. J. Med. Chem. 2006, 49, 829-837
38. Quiroga, A. G., Cubo, L., de Blas, E., Aller, P., and Navarro-Ranninger, C. J. Inorg. Biochem. 2007, 101, 104-110
39. Zorbas-Seifried, S., Jakupec, M. A., Kukushkin, N. V., Groessl, M., Hartinger, Ch. G., Semenova, O., Zorbas, H., Kukushkin, V. Yu., and Keppler, B. K. Mol. Pharmacol. 2007, 71, 357-365
40. Kukushkin, V. Yu., Tudela, D., and Pombeiro, A. J. L. Coord. Chem. Rev. 1996, 156, 333-362
41. Reedijk, J. Inorg. Chim. Acta 1992, 198-200, 873-881
42. Vetrovsky, P., Boucher, J.-L., Schott, C., Beranova, P., Chalupsky, K., Callizot, N., Muller, B., Entlicher, G., Mansuy, D., and Stoclet, J.-C. J. Pharm. Exp. Ther. 2002, 303, 823-830
43. Hambley, T. W., Ling, E. C. H., OMara, S., McKeage, M. J., and Russell, P. J. J. Biol. Inorg. Chem. 2000, 5, 675-681
44. Saglam, N., Colak, A., Serbest, K., Duelger, S., Guener, S., Karaboecek, S., and Belduez, A. O. BioMetals 2002, 15, 357-365
45. Portela-Cubillo, F., Lymer, J., Scanlan, E. M., Scott, J. S., and Walton, J. C. Tetrahedron 2008, 64, 11908-11916
46. Alcalde, E., Mesquida, N., Alvarez-Rua, C., Cuberes, R., Frigola, J., and Garcia-Granda, S. Molecules 2008, 13, 301-318
47. Wang, K., Fu, X., Liu, J., Liang, Y., and Dong, D. Org. Lett. 2009, 11, 1015-1018
48. SAINT-Plus, version 7.06a, and APEX2; Bruker-Nonius AXS Inc.: Madison, WI, 2004.
49. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Solution; University of Göttingen: Göttingen, Germany, 1997.
50. Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
51. Johnson, C. K. Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
52. International Tables for X-ray Crystallography; Kluwer Academic Press: Dordrecht, The Netherlands, 1992; Vol. C, Tables 4.2.6.8 and 6.1.1.4.
53. Kukushkin, V. Yu., Tudela, D., Izotova, Y. A., Belsky, V. K., and Stash, A. I. Polyhedron 1998, 17, 2455-2461
54. Dhara, S. C. Indian J. Chem. 1970, 8, 193-194
55. Kauffman, G. B. and Cowan, D. O. Inorg. Synth. 1963, 7, 239-245
56. Chval, Z., Sip, M., and Burda, J. V. J. Comput. Chem. 2008, 29, 2370-2381
57. Kukushkin, V. Yu., Nishioka, T., Tudela, D., Isobe, K., and Kinoshita, I. Inorg. Chem. 1997, 36, 6157-6165
58. Kukushkin, N. V., Ketrush, P. M., and Haukka, M. Acta Crystallogr. 2007, E63, m1286
59. Manivannan, V., Kumar, B., Chandan Kumar Pal, D., and Chakravorty, A. Inorg. Chem. 1997, 36, 1526-1528
60. Ebeling, G., Gruber, A. S., Burrow, R. A., Dupont, J., Lough, A. J., and Farrar, D. H. Inorg. Chem. Commun. 2002, 5, 552-554
61. Berger, I., Nazarov, A. A., Hartinger, Ch. G., Groessl, M., Valiahdi, S.-M., Jakupec, M. A., and Keppler, B. K. ChemMedChem. 2007, 2, 505-514
62. Rochon, F. D. and Bonnier, C. Inorg. Chim. Acta 2007, 360, 461-472
63. Rochon, F. D. and Buculei, V. Inorg. Chim. Acta 2004, 357, 2218-2230
64. Scaffidi-Domianello, Yu., Nazarov, A. A., Haukka, M., Galanski, M., Keppler, B. K., Schneider, J., Du, P., Eisenberg, R., and Kukushkin, V. Yu. Inorg. Chem. 2007, 46, 4469-4482
65. Scaffidi-Domianello, Yu., Haukka, M., Kelly, P. F., Galanski, M., Keppler, B. K., and Kukushkin, V. Yu. Z. Kristallogr.-New Cryst. Struct. 2006, 221, 226-228
66. Llewellyn, D. R., OConnor, C. J., and Odell, A. L. J. Chem. Soc. 1964, 196-200