Loss of ammine from platinum(II) complexes: Implications for cisplatin inactivation, storage, and resistance

Chemistry - A European Journal

Volumn 11, Issue 9, 2005, Pages 2849-2855

  Lau, Justin Kai Chi ^a   Deubel, Dirk V ^a  

^a Computational Science USI Campus ^*  (Switzerland)

Author keywords

Antitumor agents; Cisplatin; Density functional calculation; Platinum

Indexed keywords

COMPLEXATION; DNA; ENTROPY; MATHEMATICAL MODELS; METABOLITES; MOLECULAR DYNAMICS; PROBABILITY DENSITY FUNCTION;

ANTITUMOR AGENTS; CISPLATIN; DENSITY FUNCTIONAL CALCULATIONS; DNA BINDING;

PLATINUM;

ANTINEOPLASTIC AGENT; CISPLATIN; CISPLATIN DNA ADDUCT; CISPLATIN-DNA ADDUCT; GLUTATHIONE;

ARTICLE; BIOTRANSFORMATION; CHEMISTRY; DNA ADDUCT; DRUG RESISTANCE; KINETICS; METABOLISM; QUANTUM THEORY; THERMODYNAMICS;

ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CISPLATIN; DNA ADDUCTS; DRUG RESISTANCE, NEOPLASM; GLUTATHIONE; KINETICS; QUANTUM THEORY; THERMODYNAMICS;

EID: 18544364930     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401053     Document Type: Article

References (85)

1. B. Rosenberg, L. VanCamp, J. E. Trosko, V. H. Mansour, Nature 1969, 222, 385.
2. Books and reviews: a) Cisplatin (Ed.: B. Lippert), Wiley-VCH, Weinheim, 1999;
3. b) Z. J. Quo, P. J. Sadler, Angew. Chem. 1999, 111, 1610
4. ; Angew. Chem. Int. Ed. 1999, 38, 1513;
5. c) E. Wong, C. M. Giandomenico, Chem. Rev. 1999, 99, 2451;
6. d) Platinum-Based Drugs in Cancer Therapy (Eds.: L. R. Kelland, N. Fanell) Humana, Totawa, 2000;
7. e) J. Reedijk, Proc. Nal. Acad. Sci. USA 2003, 100, 3611;
8. f) M. A. Jakupec, M. Galanski, B. K. Keppler, Rev. Physiol. Biochem. Pharmacol. 2003, 146, 1;
9. g) C. X. Zhang, S. J. Lippard, Curr. Opin. Chem. Biol. 2003, 7, 481;
10. h) Y.-P. Ho, S. C. F. Au-Yeung, K. K. W. To, Med. Res. Rev. 2003, 23, 633;
11. Metal Ions in Biological Systems, Vol. 42 (Eds.: A. Sigel, H. Sigel), Dekker, Basel, Switzerland, 2004.
12. S. Ishida, J. Lee, D. J. Thiele, I. Herskowitz, Proc, Natl. Acad. Sci. USA 2002, 99, 14 298.
13. a) S. S. G. E. van Boom, J. Reedijk, J. Chem. Soc. Chem. Commun. 1993, 1397;
14. b) J. Reedijk, Chem. Rev. 1999, 99, 2499, and references therein.
15. a) E. R. Jamieson, S. J. Lippard, Chem. Rev. 1999, 99, 2467;
16. b) U.-M. Ohndorf, M. A. Rould, Q. He, C. O. Pabo, S. J. Lippard, Nature 1999, 399, 708;
17. c) C. X. Zhang, P. V. Chang, S. J. Lippard, J. Am. Chem. Soc. 2004, 126, 6536.
18. M. A. Fuertes, C. Alonso, J. M. Pérez, Chem. Rev. 2003, 103, 645.
19. a) S. Akiyama, Z. S. Chen, T. Sumizawa, T. Furukawa, Anti-Cancer Drug Des. 1999, 14, 143;
20. b) L. R. Kelland, Drugs 2000, 59 Suppl. 4, 1;
21. V. Brabec, J. Kasparkova, Drug Resist. Updates 2002, 5, 147.
22. H. C. Brown, in Determination of Organic Structures by Physical Methods (Eds.: E. A. Braude, F. C. Nacbod), Academic Press, New York, 1955.
23. M. J. Cleare, J. D. Hoeschele, Bioinorg. Chem. 1973, 2, 187.
24. J. Kozelka, G. A. Petsko, S. J. Lippard, G. J. Quigley, J. Am. Chem. Soc. 1985, 107, 4079.
25. S. E. Sherman, D. Gibson, A. H.-J. Wang, S. J. Lippard, Science 1985, 230, 412.
26. J. Reedijk, Inorg. Chim. Acta 1992, 198-200, 873.
27. S.T. Sullivan, A. Ciccarese, F. P. Fanizzi, L. G. Marzilli, J. Am. Chem. Soc. 2001, 123, 9345.
28. D. V. Deubcl, J. Am. Chem. Soc. 2002, 124, 5834.
29. M. H. Baik, R. A. Friesner, S. J. Lippard, J. Am. Chem. Soc. 2003, 125, 14082.
30. a) B. Lippert, C. J. L. Lock, R. A. Speranzini, Inorg. Chem. 1981, 20, 808;
31. b) A. Hegmans, M. Sabat, I. Baxter, E. Freisinger, B. Lippert, Inorg. Chem. 1998, 37, 4921.
32. a) C. M. Riley, L. A. Sternson, A. J. Repta, S. A. Slyter, Anal. Biochem. 1983, 130, 203;
33. b) S. L. Kelley, A. Basu, B. A. Teicher, M. P. Hacker, D. H. Hamer, J. S. Lazo, Science 1988, 241, 1813;
34. T. Ishikawa, F. Aliosman, J. Biol. Chem. 1993, 268, 20116;
35. V. Marchan, V. Moreno, E. Pedroso, A. Grandas, Chem. Eur. J. 2001, 7, 808.
36. Examples: a) Y. Zhang, Z. J. Guo, X. Z. You, J. Am. Chem. Soc. 2001, 123, 9378;
37. b) M. H. Baik, R. A. Friesner, S. J. Lippard, J. Am. Chem. Soc. 2002, 124, 4495;
38. c) J. V. Burda, J. Sponer, J. Hrabadkova, M. Zeizingcr, J. Lcszczynski, J. Phys. Chem. B 2003, 107, 5349;
39. d) K. Spiegel, P. Carloni, U. Röthlisberger, J. Phys. Chem. B 2004, 108, 2699;
40. e) A. Robertazzi, J. A. Platts, J. Comput. Chem. 2004, 25, 1060:
41. f) J. V. Burda, M. Zeizinger, J. Leszczynski, J. Chem. Phys. 2004, 120, 1253.
42. D. V. Deubel, J. Am. Chem. Soc. 2004, 126, 5999.
43. The functional groups of amino acid residues have been used synonymously with their three-letter code, fur example, Met represents the thioether in methionin.
44. For example, see: J. H. Huhcey, E. A. Keiter, R. L. Keiter. Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed., Addison-Wesley, New York, 1997.
45. a's: a)cysteine: 8.3. J. M. Berg, J. L. Tymoczko, L. Stryer, Biochemistry, 5th ed., Freeman, New York, 2002;
46. b) MeSH: 10.3. J. J. Klicic, R. A. Friesner, S.-Y. Liu, W. C. Guida, J. Phys. Chem. A 2002, 106, 1327.
47. G. Archontis, T. Simonson, J. Am. Chem. Soc. 2001, 123, 11047, and references therein. The dielectric constant of proteins is typically estimated to be lower than 10 and might be as low as 3 if the site of interest is buried in the protein interior.
48. 6, but this aqua ligand would be a better leaving group than thiolate or thioether.
49. Examples: a) P. D. Murdoch, N. A. Kratochwil, J. A. Parkinson, M. Patriarca, P. J. Sadler, Angew. Chem. 1999, 111, 3062:
50. Angew. Chem. Int. Ed. 1999, 38, 2949;
51. b) J.-M. Teuben, J. Reedijk, J. Biol. Inorg. Chem. 2000, 5, 463;
52. M. Hahn, M. Kleine, W. S. Shcldrick, J. Biol. Inorg. Chem. 2001, 6, 556;
53. S. Fakih, V. P. Munk, M. A. Shipman, P. D. Murdoch, J. A. Parkinson, P. J. Sadler, Eur. J. Inorg. Chem. 2003, 1206.
54. A. D. Becke, J. Chem. Phys. 1993, 98. 5648.
55. C. T. Lee, W. T. Yang, R. G. Parr. Phys. Rev. B 1988, 37, 785.
56. Gaussian 98, Revision A.11, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, O. Cui, K. Morukuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombc, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
57. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299.
58. a) J. S. Binkley, J. A. Pople, W. J. Hehre, J. Am. Chem. Soc. 1980, 102, 939:
59. b) W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257.
60. A. W. Ehlers, M. Böhme, S. Dapprich, A. Gobbi, A. Höllwarth, V. Jonas, K. F. Köhler, R. Stegmann, A. Veldkamp, G. Frenking, Chem. Phys. Lett. 1993, 208, 111.
61. a) D. V. Dcubel, G. Frenking, J. Am. Chem. Soc. 1999, 121, 2021;
62. b) D. V. Dcubel, J. Sundermeyer, G. Frenking, J. Am. Chem. Soc. 2000, 122, 10101:
63. c) D. V. Deubel, S. Schlecht, G. Frenking, J. Am. Chem. Soc. 2001, 123, 10085;
64. d) D. V. Deubel, Angew. Chem. 2003. 115, 2019;
65. Angew. Chem. Int. Ed. 2003, 42, 1974;
66. e) D. V. Deubel, G. Frenking, Acc. Chem. Res. 2003, 36, 645;
67. f) D. V. Deubel, J. Am. Chem. Soc. 2003, 125, 15308;
68. g) D. V. Deubel, J. Am. Chem. Soc. 2004, 126, 996;
69. h) D. V. Deubel, G. Frenking, P. Gisdakis, W. A. Hermann, N. Rösch, J. Sundermeyer, Acc. Chem. Res. 2004, 37, 645.
70. Jaguar 5.0; Schrodinger, Inc.: Portland, OR. 2000.
71. See: G. Vacek, J. K. Perry, J.-M. Langlois, Chem. Phys. Lett. 1999, 310, 189.
72. -1.
73. Compare with: a) A. A. Rashin, B. Honig, J. Phys. Chem. 1985, 89, 5588;
74. b) T. M. Gilbert, I. Hristov, T. Ziegler. Organometallics 2001, 20, 1183;
75. J. Cooper, T. Ziegler, Inorg. Chem. 2002, 41, 6614;
76. M. H. Baik, R. A. Friesner, J. Phys. Chem. A 2002, 106, 7407.
77. a) W. L. Jorgensen, J. M. Briggs, J. Gao, J. Am. Chem. Soc. 1987, 109, 6857. Note that this approach does not consider the heterogeneity of the cell, for example, the possibility of a charge separation involving different environments, as do not experimental studies carried out homogeneously in a less polar solvent; see:
78. b) M. L. Guo, Z. J. Guo, P. J. Sadler, J. Biol. Inorg. Chem. 2001, 6, 698.
79. a) C. C. Chambers, G. D. Hawkins, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. 1996, 100, 16385;
80. b) G. J. Tawa, I. A. Topol, S. K. Burt, R. A. Caldwcll, A. A. Rashin, J. Chem. Phys. 1998, 109, 4852;
81. c) J. A. Mejias, S. Lago, J. Chem. Phys. 2000, 113, 7306.
82. a) J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027;
83. b) C. J. Cramer, D. G. Truhlar, Chem. Rev. 1999, 99, 2161.
84. a) D. H. Wertz, J. Am. Chem. Soc. 1980, 102, 5316;
85. b) M. H. Abraham, J. Am. Chem. Soc. 1981, 103, 6742.