Kinetics and mechanism for reduction of the anticancer prodrug trans, trans, trans-[PtCl2(OH)2(c-C6H11NH2)(NH3)] (JM335) by Thiols

Inorganic Chemistry

Volumn 39, Issue 8, 2000, Pages 1728-1734

  Lemma, Kelemu ^a,c   Shi, Tiesheng ^b   Elding, Lars I ^a  

^a LUND UNIVERSITY   (Sweden)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c ADDIS ABABA UNIVERSITY   (Ethiopia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PLATINUM DERIVATIVE; PRODRUG; TRANS AMMINEDICHLORO(CYCLOHEXYLAMINE)DIHYDROXOPLATINUM; GLUTATHIONE; PLATINUM COMPLEX; THIOL DERIVATIVE;

ARTICLE; CANCER; DRUG EFFECT; DRUG ELIMINATION; NEPHROTOXICITY; OXIDATION REDUCTION REACTION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; PH; STEREOISOMERISM;

ANTINEOPLASTIC AGENTS; GLUTATHIONE; HYDROGEN-ION CONCENTRATION; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; OXIDATION-REDUCTION; PRODRUGS; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 0034678254     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic991351l     Document Type: Article

References (58)

1. For recent general reviews on platinum-based antitumor drugs, see, for example: (a) Wong, E.; Giandomenico, C. M. Chem. Rev. 1999, 99, 2451.
2. (b) Jamieson, E. R.; Lippard, S. J. Chem. Rev. 1999, 99, 2467.
3. (c) Reedijk, J. Chem. Rev. 1999, 99, 2467.
4. von Hoff, D. D.; Schilsky, R.; Reichert, C. M.; Reddick, R. L.; Rozencweig, M.; Young, R. C.; Muggia, F. M. Cancer Treat. Rep. 1979, 63, 1527.
5. Kelland, L. R. Crit. Rev. Oncol. Hematol. 1993, 15, 191.
6. Farrell, N.; Ha, T. T. B.; Souchard, J. P.; Wimmer, F. L.; Cros, S.; Johnson, N. P. J. Med. Chem. 1989, 32, 2240.
7. Van Beusichem, M.; Farrell, N. Inorg. Chem. 1992, 31, 634.
8. Farrell, N.; Kelland, L. R.; Roberts, J. D.; van Beusichem, M. Cancer Res. 1992, 52, 5065.
9. Coluccia, M.; Nassi, A.; Loseto, F.; Boccareli, A.; Mariggio, M. A.; Giordano, D.; Intini, F. P.; Caputo, P.; Natile, G. A. J. Med. Chem. 1993, 36, 510.
10. Kelland, L. R.; Barnard, C. F. J.; Mellish, K. J.; Jones, M.; Goddard, P. M.; Valenti, M.; Bryant, A.; Murrer, B. A.; Harrap, K. R. Cancer Res. 1994, 54, 5618.
11. Natile, G.; Coluccia, M. Top. Biol. Inorg. Chem. 1999, 1, 73.
12. Farrell, N. Met. Ions Biol. Syst. 1996, 32, 603.
13. Mellish, K. J.; Barnard, C. F. J.; Murrer, B. A.; Kelland, L. R. Int. J. Cancer 1995, 62, 717.
14. Roundhill, D. M. Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. 5, p 351.
15. Talman, E. G.; Bruning, W.; Reedijk, J.; Spek, A. L.; Veldman, N. Inorg. Chem. 1997, 36, 854.
16. Poon, G. K.; Raynaud, F. I.; Mistry, P.; Odell, D. E.; Kelland, L. R.; Harrap, K. R.; Barnard, C. F. J.; Murrer, B. A. J. Chromatogr., A 1995, 712, 61.
17. Keck, M. V.; Lippard, S. J. J. Am. Chem. Soc. 1992, 114, 3386.
18. Ellis, L. T.; Er, H. M.; Hambley, T. W. Aust. J. Chem. 1995, 48, 793.
19. Shi, T.; Berglund, J.; Elding, L. I. Inorg. Chem. 1996, 35, 3498.
20. (a) Chen, L.; Lee, P. F.; Ranford, J. D.; Vittal, J. J.; Wong, S. Y. J. Chem. Soc., Dalton Trans. 1999, 1209.
21. (b) Shi, T.; Berglund, J.; Elding, L. I. J. Chem. Soc., Dalton Trans. 1997, 2073.
22. Choi, S.; Filotto, C.; Bisanzo, M.; Delaney, S.; Lagasee, D.; Witworth, J. L.; Jusko, A.; Li, C.; Wood, N. A.; Willingham, J.; Schwenker, A.; Spaulding, K. Inorg. Chem. 1998, 37, 2500.
23. Lemma, K.; Sargeson, A. M.; Elding, L. I. J. Chem. Soc., Dalton Trans. 2000, 1167.
24. Lemma, K.; Berglund, J.; Farrell, N.; Elding, L. I. J. Biol. Inorg. Chem. 2000, 5, in press.
25. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70.
26. Riddles, P. W.; Blakeley, R. L.; Zerner, B. Anal. Biochem. 1979, 94, 75.
27. Taylor, J. E.; Van, J. F.; Wang, J.-L. J. Am. Chem. Soc. 1966, 88, 1663.
28. Bridgart, G. J.; Wilson, I. R. J. Chem. Soc., Dalton Trans. 1973, 1281.
29. York, M. J.; Beilharz, G. R.; Kuchel, P. W. Int. J. Pept. Protein Res. 1987, 29, 638.
30. Ehrenberg, L.; Harms-Ringdahl, M.; Fedorcak, I.; Granath, F. Acta Chem. Scand. 1989, 43, 177.
31. Applied Photophysics Bio Sequential SX-18 MV, Sequential Stopped-Flow ASVD Spectrofluorimeter software, Applied Photophysics Ltd., Leatherhead, Surrey, U.K.
32. 30-32 The reaction conditions chosen here (i.e., pseudo-first-order with excess of thiol) suggest that similar reactions will occur.
33. Appleton, T. G.; Connor, J. W.; Hall, J. R.; Prenzler, P. D. Inorg. Chem. 1989, 28, 2030.
34. Berners-Price, S. J.; Kuchel, P. W. J. Inorg. Biochem. 1990, 38, 305.
35. Odenheimer, B.; Wolf, W. Inorg. Chim. Acta 1982, L41-L43.
36. Connet, P. H.; Wetterhahn, K. E. J. Am. Chem. Soc. 1986, 108, 1842.
37. Reid, R. S.; Rabenstein, D. L. Can. J. Chem. 1981, 59, 1505.
38. Reuben, D. M. E.; Bruice, T. C. J. Am. Chem. Soc. 1976, 98, 114.
39. Smith, R. M.; Martell, A. E. Critical Stability Constants - Other Organic Ligands; Plenum Press: New York, 1977.
40. Rabenstein, D. L. J. Am. Chem. Soc. 1973, 95, 2797.
41. Mason, W. R. Coord. Chem. Rev. 1972, 7, 241.
42. Wilmarth, W. K.; Fanchiang, Y.-T.; Byrd, J. E. Coord. Chem. Rev. 1983, 51, 141.
43. Wilmarth, W. K.; Dooly, M. M.; Byrd, J. E. Coord. Chem. Rev. 1983, 51, 125.
44. Chandayot, P.; Fanchiang, Y.-T. Inorg. Chem. 1985, 24, 3532.
45. Chandayot, P.; Fanchiang, Y.-T. Inorg. Chem. 1985, 24, 3535.
46. (a) Elding, L. I.; Gustafson, L. Inorg. Chim. Acta 1976, 19, 165.
47. (b) Elding, L. I.; Gustafson, L. Inorg. Chim. Acta 1977, 24, 239.
48. (c) Drougge, L.; Elding, L. I. Inorg. Chim. Acta 1986, 121, 175.
49. (d) Berglund, J.; Voigt, R.; Fronaeus, S.; Elding, L. I. Inorg. Chem. 1994, 33, 3346.
50. (e) Shi, T.; Elding, L. I. Inorg. Chim. Acta 1998, 282, 55.
51. Kratochwil, N. A.; Guo, Z.; del Socco Murdoch, P.; Parkinson, J. A.; Bednarski, P. J.; Sadler, P. J. J. Am. Chem. Soc. 1998, 120, 8253.
52. Kratochwil, N. A.; Ivanov, A. I.; Patriarca, M.; Parkinson, J. A.; Gouldsworthy, A. M.; del Socco Murdoch, P.; Sadler, P. J. J. Am. Chem. Soc. 1999, 121, 8193.
53. Allison, W. S. Acc. Chem. Res. 1976, 9, 293.
54. Shi, T.; Elding, L. I. Inorg. Chem. 1996, 35, 5941.
55. Beattie, J. K.; Basolo, F. Inorg. Chem. 1967, 6, 2069.
56. Lempers, E. L. M.; Inagaki, K.; Reedijk, J. Inorg. Chim. Acta 1988, 152, 201.
57. Goddard, P. M.; Orr, R. M.; Valenti, M. R.; Barnard, C. F. J.; Murrer, B. A.; Kelland, L. R.; Harrap, K. R. Anticancer Res. 1996, 16, 33.
58. Appleton, T. G.; Bailey, A. J.; Bamham, K. J.; Hall, J. R. Inorg. Chem. 1992, 31, 3077.