Cisplatin interaction with cysteine and methionine, a theoretical DFT study

Journal of Inorganic Biochemistry

Volumn 99, Issue 11, 2005, Pages 2184-2196

  Zimmermann, Tomáš ^a   Zeizinger, Michal ^a   Burda, Jaroslav V ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Cisplatin; Cysteine; Methionine; Theoretical calculations

Indexed keywords

CHELATE; CISPLATIN; CYSTEINE; METHIONINE; NITROGEN; OXYGEN; PLATINUM COMPLEX; SULFUR; WATER;

ARTICLE; CHELATION; CHEMICAL BINDING; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DISSOCIATION; DRUG PROTEIN BINDING; HYDRATION; MOLECULE; THEORETICAL STUDY;

BIOCHEMISTRY; CISPLATIN; COMPUTATIONAL BIOLOGY; CYSTEINE; ELECTROSTATICS; HYDROGEN SULFIDE; METHIONINE; PLATINUM; THERMODYNAMICS;

EID: 27644543909     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2005.07.021     Document Type: Article

References (101)

1. P.J. O'Dwyer, and J.P. Stevenson B. Lippert Cisplatin 1999 Wiley-VCH Weinheim 31 72
2. E. Wong, and C.M. Giandomenico Chem. Rev. 99 1999 2451 2466
3. B.K. Keppler Metal Complexes in Cancer Therapy 1993 VHC Publishers Weinheim, NY
4. R.L. Kelland R.L. Kelland N. Farrell Platinum-Based Drugs in Cancer Therapy 2000 Humana Press Totowa 299 320
5. D. Fink, and S.B. Howell R.L. Kelland N. Farrell Platinum-Based Drugs in Cancer Therapy 2000 Humana Press Totowa 149 170
6. B. Lippert Cisplatin: Chemistry and Biochemistry of a leading anticancer drug 1999 Wiley-VCH Wienheim, Germany
7. V. Brabec, M. Sip, and M. Leng Biochemistry 32 1993 11676 11681
8. M. Iwamoto, S. Mukundan Jr., and L.G. Marzilli J. Am. Chem. Soc. 116 1994 6238 6244
9. P.M. Takahara, C.A. Frederick, and S.J. Lippard J. Am. chem. Soc. 118 1996 12309 12321
10. J. Malina, O. Novakova, B.K. Keppler, E. Alessio, and V. Brabec J. Biol. Inorg. Chem. 6 2001 435 445
11. S.M. Cohen, Y. Mikata, Q. He, and S.J. Lippard Biochemistry 39 2000 11771 11776
12. K. Hindmarsh, D.A. House, and M.M. Turnbull Inorg. Chim. Acta 257 1997 11 18
13. L.G. Marzilli, S.O. Ano, F.P. Intini, and G. Natile J. Am. Chem. Soc. 121 1999 9133 9142
14. J. Arpalahti, M. Mikola, and S. Mauristo Inorg. Chem. 32 1993 3327 3332
15. M. Mikola, and J. Arpalahti Inorg. Chem. 33 1994 4439 4445
16. S.E. Miller, K.J. Gerard, and D.A. House Inorg. Chim. Acta 190 1991 135 144
17. J.V. Burda, M. Zeizinger, and J. Leszczynski J. Chem. Phys. 120 2004 1253 1262
18. J.V. Burda, M. Zeizinger, and J. Leszczynski J. Comput. Chem. 26 2005 907 914
19. J.-M. Teuben, and J. Reedijk J. Biol. Inorg. Chem. 5 2000 463 468
20. T. Peleg-Shulman, and D. Gibson J. Am. Chem. Soc. 123 2001 3171 3172
21. M. Treskes, U. Holwerda, L.G. Nijtmans, H.M. Pinedo, and W.J.F. van der Vijgh Cancer Chemother. Pharmacol. 29 1992 467 474
22. J. Reedijk Chem. Rev. 99 1999 2499 2510
23. U. Bierbach, and N. Farell J. Biol. Inorg. Chem. 3 1998 570 580
24. M. Beltran, G.B. Onoa, E. Pedroso, V. Moreno, and A. Grandas J. Biol. Inorg. Chem. 4 1999 701 707
25. M. Hahn, M. Kleine, and W.S. Sheldrick J. Biol. Inorg. Chem. 6 2001 556 566
26. V. Saudek, H. Pivcová, D. Nosková, and J. DrobnIÍk J. Inorg. Biochem. 23 1985 55 63
27. T.G. Appleton, F.J. Pescb, M. Wienken, S. Menzer, and B. Lippert Inorg. Chem. 31 1992 4410 4419
28. A.H. Talebian, D. Bensely, A. Ghiorghis, C.F. Hammer, P.S. Schein, and D. Green Inorg. Chim. Acta 179 1991 281 287
29. T.G. Appleton, J.R. Hall, D.W. Neale, and C.S.M. Thompson Inorg. Chem. 29 1990 3985 3990
30. S.E. Miller, and D.A. House Inorg. Chim. Acta 187 1991 125 132
31. D. Kushev, G. Gorneva, V. Enchev, E. Naydenova, J. Popova, S. Taxirov, L. Maneva, K. Grancharov, and N. Spassovska J. Inorg. Biochem. 89 2002 203 211
32. P.K. Chattaraj J. Phys. Chem. A 105 2001 511 513
33. R.G. Parr, and R.G. Pearson J. Am. Chem. Soc. 105 1983 7512 7516
34. C.M. Riley, L.A. Sternson, A.J. Repta, and S.A. Slyter Anal. Biochem. 130 1983 203 214
35. R.E. Norman, J.D. Ranford, and P.J. Sadler Inorg. Chem. 31 1992 877 888
36. D.M. Hayes, E. Cvitkovic, R.B. Golbey, E. Scheiiner, L. Helson, and I.H. Krakoff Cancer 39 1979 1372 1381
37. E.L.M. Lempers, and J. Reedijk Inorg. Chem. 29 1990 217 225
38. M.I. Djuran, E.L.M. Lempers, and J. Reedijk Inorg. Chem. 30 1991 2648 2656
39. K.J. Barnham, M.J. Djuran, P.d.S. Murdoch, J.D. Ranford, and P.J. Sadler Inorg. Chem. 36 1996 1065 1072
40. K.J. Barnham, M.J. Djuran, P.d.S. Murdoch, and P.J. Sadler J. Chem. Soc., Chem. Commun. 1994 721 725
41. M. Kleine, D. Wolters, and W.S. Sheldrick J. Inorg. Biochem. 97 2003 354 363
42. D.P. Bancroft, C.A. Lepre, and S.J. Lippard J. Am. Chem. Soc. 112 1990 6860 6871
43. D.V. Deubel J. Am. Chem. Soc. 124 2002 5834 5842
44. D.V. Deubel J. Am. Chem. Soc. 126 2004 5999 6004
45. G.S. Yang, C. Jin, J. Hong, Z.J. Guo, and L.G. Zhu Spectrochim. Acta Part A - Mol. Biomol. Spectrosc. 60 2004 3187 3195
46. L.A. Eriksson, J. Raber, and C. Zhu J. Phys. Chem. 2005 000
47. M.-H. Baik, R.A. Friesner, and S.J. Lippard J. Am. Chem. Soc. 124 2002 4495 4503
48. M.H. Baik, R.A. Friesner, and S.J. Lippard J. Am. Chem. Soc. 125 2003 14082 14092
49. L.A.S. Costa, W.R. Rocha, W.B. De Almeida, and H.F. Dos Santos J. Chem. Phys. 118 2003 10584 10592
50. L.A.S. Costa, W.R. Rocha, W.B. De Almeida, and H.F. Dos Santos Chem. Phys. Lett. 387 2004 182 187
51. J.E. Šponer, J. Leszczynski, F. Glahe, B. Lippert, and J. Šponer Inorg. Chem. 40 2001 3269 3278
52. L. Zhang, Y. Zhang, H.B. Tao, X.J. Sun, Z.J. Guo, and L.G. Zhu J. Mol. Struct. Theochem. 617 2002 87 97
53. K. Spiegel, U. Rothlisberger, and P. Carloni J. Phys. Chem. B 108 2004 2699 2707
54. A. Robertazzi, and J.A. Platts J. Comput. Chem. 25 2004 1060 1067
55. A. Robertazzi, and J.A. Platts Inorg. Chem. 44 2005 267 274
56. M.A. Elizondo-Riojas, and J. Kozelka J. Mol. Biol. 314 2001 1227 1243
57. Z. Chval, and M. ŠIÍp Collect. Czechoslovak Chem. Commun. 68 2003 1105 1118
58. A.P. Silverman, W. Bu, S.M. Cohen, and S.J. Lippard J. Biol. Chem. 277 2002 48751 49743
59. S.T. Sullivan, J.S. Saad, F.P. Fanizzi, and L.G. Marzilli J. Am. Chem. Soc. 124 2002 1558 1565
60. C.J. Ziegler, A.P. Silverman, and S.J. Lippard J. Biol. Inorg. Chem. 5 2000 774 783
61. L.G. Marzilli, J.S. Saad, Z. Kuklenyik, K.A. Keating, and Y. Xu J. Am. Chem. Soc. 123 2001 2764 2770
62. K.M. Williams, T. Scarcia, G. Natile, and L.G. Marzilli Inorg. Chem. 40 2001 445 454
63. M.G. Anorbe, M.S. Luth, M. Roitzch, M.M. Cerda, P. Lax, G. Kampf, H. Sigel, and B. Lippert Chem. A Eur. J. 10 2004 1046 1057
64. R.K.O. Sigel, E. Freisinger, and B. Lippert J. Biol. Inorg. Chem. 5 2000 287 299
65. V. Brabec, K. Neplechova, J. Kasparkova, and N. Farell J. Biol. Inorg. Chem. 5 2000 364 368
66. J. Kašparková, F.S. Mackay, V. Brabec, and P.J. Sadler J. Biol. Inorg. Chem. 8 2003 741 745
67. M.J. Bloemink, J.M.J. Perez, R.J. Heetebrij, and J. Reedijk J. Biol. Inorg. Chem. 4 1999 554 567
68. S. Komeda, M. Lutz, L. Spek, Y. Yamanaka, T. Sato, M. Chikuma, and J. Reedijk J. Am. Chem. Soc. 124 2002 4738 4746
69. J.V. Burda, M. Zeizinger, J. Šponer, and J. Leszczynski J. Chem. Phys. 113 2000 2224 2232
70. M. Zeizinger, J.V. Burda, J. Šponer, V. Kapsa, and J. Leszczynski J. Phys. Chem. A 105 2001 8086 8092
71. J.V. Burda, J. Šponer, and J. Leszczynski J. Biol. Inorg. Chem. 5 2000 178 188
72. J.V. Burda, J. Šponer, and J. Leszczynski Phys. Chem. Chem. Phys. 3 2001 4404 4411
73. J.V. Burda, and J. Leszczynski Inorg. Chem. 42 2003 7162 7172
74. J.V. Burda, J. Šponer, J. Hrabáková, M. Zeizinger, and J. Leszczynski J. Phys. Chem. B 107 2003 5349 5356
75. M. Zeizinger, J.V. Burda, and J. Leszczynski Phys. Chem. Chem. Phys. 6 2004 3585 3590
76. A.D. Becke Phys. Rev. A 38 1988 3098 3100
77. A.D. Becke Yarkoni Modern Electronic Structure Theory 1995 World Scientific Pub. Co. Singapore
78. C. Adamo, and V. Barone Chem. Phys. Lett. 274 1997 242 250
79. C. Adamo, and V. Barone J. Chem. Phys. 108 1998 664 674
80. A.D. Boese, N.L. Doltsinis, N.C. Handy, and M. Sprik J. Chem. Phys. 112 2000 1670 1677
81. J.P. Perdew, K. Burke, and M. Ernzerhof Phys. Rev. Lett. 78 1997 1396 1400
82. J.P. Perdew, K. Burke, and M. Ernzerhof Phys. Rev. Lett. 77 1996 3865 3868
83. D. Andrae, U. Haussermann, M. Dolg, H. Stoll, and H. Preuss Theor. Chim. Acta 77 1990 123 141
84. A. Bergner, M. Dolg, W. Kuechle, H. Stoll, and H. Preuss Mol. Phys. 80 1993 1431 1443
85. S.F. Boys, and F. Bernardi Mol. Phys. 19 1970 553 566
86. J.E. Carpenter, and F. Weinhold J. Mol. Struct. (Theochem.) 169 1988 41 62
87. A.E. Reed, R.B. Weinstock, and F. Weinhold J. Chem. Phys. 83 1985 735 746
88. U.C. Singh, and P.A. Kollman J. Comput. Chem. 5 1984 129 138
89. B.H. Besler, J. Merz, and K.M.P.A. Kollman J. Comput. Chem. 11 1990 431 438
90. C.M. Breneman, and K.B. Wiberg J. Comput. Chem. 11 1990 361 370
91. Y.A. Borisov, Y.A. Zolotarev, E.V. Laskatelev, and N.F. Myasoedov Russ. Chem. Bull. 47 1998 1442 1445
92. X.L. Cao, and G. Fischer J. Phys. Chem. A 106 2002 41 50
93. T. Dudev, and C. Lim J. Am. Chem. Soc. 124 2002 6759 6766
94. M.L. Huang, and A. Rauk J. Phys. Chem. A 108 2004 6222 6230
95. C. Pepe, S. Rochut, J.P. Paumard, and J.C. Tabet Rapid Commun. Mass Spectrom. 18 2004 307 312
96. M.A. Zamora, H.A. Baldoni, J.A. Bombasaro, M.L. Mak, A. Perczel, O. Farkas, and R.D. Enriz J. Mol. Struct. Theochem. 540 2001 271 283
97. M. Strajbl, J. Florian, and A. Warshel J. Phys. Chem. B 105 2001 4471 4484
98. R. Bonaccorsi, P. Palla, and J. Tomasi J. Am. Chem. Soc. 106 1984 1945 1950
99. V. Barone, L. Orlandini, and C. Adamo Int. J. Quantum Chem. 56 1995 697 705
100. A. Bondi J. Phys. Chem. 68 1964 441 451
101. P. Pyykkö Chem. Rev. 97 1997 597 636