Computational Studies on Platinum Antitumor Complexes and Their Adducts with Nucleic Acid Constituents

Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug

Volumn , Issue , 2006, Pages 537-556

  Kozelka, Jiří ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Cancer treatment; Cisplatin; Computational studies; Platinum antitumor complexes; Platinum complexe adducts with nucleic acid constituents

Indexed keywords

BIOMOLECULES; DRUG PRODUCTS; MOLECULAR ORBITALS; NUCLEIC ACIDS; ONCOLOGY; ORBITAL CALCULATIONS;

ANTI-TUMORS; CIS-PLATIN; COMPLEXE; COMPUTATIONAL STUDIES; FORCE FIELD CALCULATIONS;

PLATINUM COMPOUNDS;

EID: 84949188330     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783906390420.ch22     Document Type: Chapter

References (117)

1. M. Peyrone, Ann. Chem. Pharm. 1844, 51, 1.
2. M. Peyrone, Ann. Chem. Pharm. 1845, 55, 205.
3. M. Peyrone, Ann. Chem. Pharm. 1847, 61, 178.
4. A. Werner, Z. anorg. Chem. 1983, 3, 267.
5. I.I. Chernayev, Ann. Inst. Platiny 1927, 5, 109.
6. A. Pidcock, R.E. Richards, L.M. Venanzi, J. Chem. Soc. A 1966, 1707.
7. L.E. Orgel, J. Chem. Phys. 1955, 23, 1819.
8. R.F. Fenske, D.S. Martin, Jr., K. Ruedenberg, Inorg. Chem. 1962, 1, 441.
9. H.B. Gray, C.J. Ballhausen, J. Am. Chem. Soc. 1963, 85, 260.
10. D.S. Martin, Jr., Inorg. Chim. Acta. Rev. 1971, 5, 107.
11. H. Basch, H.B. Gray, Inorg. Chem. 1967, 6, 365.
12. F.A. Cotton, C.B. Harris, Inorg. Chem. 1967, 6, 369.
13. W.T. A.M. van der Lugt, Int.J. Quantum Chem. 1971, 6, 859.
14. R.P. Messmer, L.V. Interrante, K.H. Johnson, J. Am. Chem. Soc. 1974, 96, 3847.
15. B. Rosenberg, L. VanCamp, J.E. Trosko, V.H. Mansoui, Nature 1969, 222, 385.
16. A.S. Dimoglo, Y.M. Chumakov, J.B. Bersuker, Koord. Khim. 1980, 12, 1879.
17. T.P. Carsey, E.A. Boudreaux, Theoret. Chim. Acta 1980, 56, 211.
18. H.H. Patterson, J.C. Tewksbury, M. Martin, M.-B. Krogh-Jespersen, J.A. LoMenzo, H.A. Hooper, A.K. Viswanath, Inorg. Chem. 1981, 20, 2297.
19. M.-B. Krogh-Jespersen, J. Comput. Chem. 1985, 6, 614.
20. M. Martin, M.-B. Krogh-Jespersen, M. Hsu, Tewksbury, M. Laurent, K. Viswanath, H. Patterson, Inorg. Chem. 1983, 22, 647.
21. M. Barber, J.D. Clark, A. Hinchliffe, J. Mol. Struct. 1979, 57, 169.
22. F. Zuolaga, R. Arratia-Pérez, J. Phys. Chem. 1986, 90, 4491.
23. E.A. Boudreaux, in 'Metal-Based Anti-Tumour Drugs', Ed.M.F. Gielen, Freund Publ. House, London, 1988, p. 175.
24. J.C. Slater, in 'Quantum Theory of Molecules and Solids', McGraw-Hill, New York, 1974.
25. J.P. Davidson, P.J. Faber, R.G. Fischer, Jr., S. Mansy, L. VanCamp, B. Rosenberg, Cancer Chemother. Rep., Part 1 1975, 59, 287.
26. B. Lippert, J. Clin. Hemat. Oncol.. 1976, 7, 26.
27. J.K. Barton, H.N. Rabinowitz, D.J. Szalda, S.J. Lippard, J. Am. Chem. Soc. 1977, 99, 2827.
28. M. Laurent, M.-B. Krogh-Jespersen, J.C. Tewksbury, H. Patterson, Inorg. Chem. 1980, 19, 1656.
29. A.P. Ginsberg, T.V. O'Halloran, P.E. Fanwick, S.J. Lippard, J. Am. Chem. Soc. 1984, 106, 5430.
30. M.B. Robin, P. Day, Adv. Chem. Radiochem. 1967, 10, 247.
31. C. Mealli, F. Pichierri, L. Randaccio, E. Zangrando, M. Krumm, D. Holtenrich, B. Lippert, Inorg. Chem. 1995, 34, 3418.
32. F. Pichierri, E. Chiarparin, E. Zangrando, L. Randaccio, D. Holtenrich, B. Lippert, Inorg. Chim. Acta 1997, 264, 109.
33. E.A. Boudreaux, T.P. Carsey, Int.J. Quantum Chem. 1980, 18, 469.
34. J. Lipinski, Inorg. Chim. Acta 1988, 152, 151.
35. J. Lipinski, J. Molec. Struct. (Theochem) 1989, 201, 295.
36. U.R. Kim, S.H. Kim, E.A. Boudreaux, Taehan Hwahakhoe Chi 1990, 34, 539.
37. U.R. Kim, S.H. Kim, E.A. Boudreaux, Taehan Hwahakhoe Chi 1990, 34, 331.
38. P.G. Abdul-Ahad, G.A. Webb, Int.J. Quantum Chem. 1982, 21, 1105.
39. K.J. Miller, E.R. Taylor, H. Basch, M. Krauss, W.J. Stevens, J. Biomol. Struct. Dynamics 1985, 2, 1157
40. H. Basch, M. Krauss, W.J. Stevens, D. Cohen, Inorg. Chem. 1986, 25, 684.
41. J. Kozelka, R. Savinelli, G. Berthier, J.P. Flament, R. Lavery, J. Comput. Chem. 1993, 14, 45.
42. J. Kozelka, J. Bergès, J. Chim. Phys. 1998, 95, 2226.
43. M.-A. Elizondo-Riojas, F. Gonnet, P. Augé-Barrere-Mazouat, F. Allain, J. Bergès, R. Attias, J.-C. Chottard, J. Kozelka, in 'Molecular Modeling and Dynamics of Bioinorganic Systems', Eds.L. Banci, P. Comba, Kluwer, Dordrecht, 1997, p. 131.
44. Z. Chval, M. S?íp, J. Phys. Chem. 1998, B 102, 1659.
45. H. Basch, M. Krauss, W.J. Stevens, Inorg. Chem. 1986, 25, 4777.
46. L.S. Hollis, A.R. Amundsen, E.W. Stern, J. Am. Chem. Soc. 1985, 107, 274.
47. T.G. Appleton, H.C. Clark, L.E. Manzer, Coord. Chem. Rev. 1973, 10, 335.
48. G. Frenking, I. Antes, M. Böhme, S. Dapprich, A.W. Ehlers, V. Jonas, A. Neuhaus, M. Otto, R. Stegmann, A. Veldkamp, S.F. Vyboishcikov, Rev. Comput. Chem. 1996, 8, 63.
49. J. Kozelka, G.A. Petsko, G.J. Quigley, S.J. Lippard, J. Am. Chem. Soc. 1985, 107, 4079.
50. J. Kozelka, G.A. Petsko, G.J. Quigley, S.J. Lippard, Inorg. Chem. 1986, 25, 1075.
51. J. Kozelka, S. Archer, G.A. Petsko, S.J. Lippard, G.J. Quigley, Biopolymers 1987, 26, 1245.
52. S.E. Sherman, D. Gibson, A.H.J. Wang, S.J. Lippard, Science 1985, 230, 412.
53. M. Krauss, H. Basch, K.J. Miller, J. Am. Chem. Soc. 1988, 110, 4517.
54. F. Herman, J. Kozelka, V. Stoven, E. Guittet, J.-P. Girault, T. Huynh-Dinh, J. Igolen, J.-Y. Lallemand, J.-C. Chottard, Eur.J. Biochem. 1990, 194, 119.
55. P. Carloni, W. Andreoni, J. Hutter, A. Curioni, P. Giannozzi, M. Parrinello, Chem. Phys. Letters 1995, 234, 50.
56. E. Tornaghi, W. Andreoni, P. Carloni, J. Hutter, M. Parrinello, Chem. Phys. Letters 1995, 246, 469.
57. R.G. Parr, W. Yang, 'Density-Functional Theory of Atoms and Molecules', Oxford University Press, New York, 1989.
58. A.D. Becke, Phys. Rev. A 1988, 38, 3098.
59. J.P. Perdew, Phys. Rev. B 1986, 33, 8822.
60. C.L. Lee, W. Yang, R.G. Parr, Phys. Rev. B 1988, 37, 785.
61. R.N. Barnett, U. Landman, Phys. Bev. B 1993, 48, 2081.
62. P. Carloni, W. Andreoni, J. Phys. Chem. 1996, 100, 17797.
63. T.R. Cundari, W. Fu, E.W. Moody, L.L. Slavin, L.A. Snyder, S.O. Sommerer, T.R. Klinckman, J. Phys. Chem. 1996, 100, 18057.
64. J. Kozelka, Met. Ions Biol. Syst. 1996, 33, 1.
65. T.W. Hambley, Comments Inorg. Chem. 1992, 14, 1.
66. S. Yao, J.P. Plastaras, L.G. Marzilli, Inorg. Chem. 1994, 33, 6061.
67. N. Turkkan, K. Jankowski, W. Brostow, J. Mol. Struct. (Theochem) 1984, 110, 255.
68. K. Jankowski, N. Turkkan, W. Brostow, J. Mol. Struct. (Theochem) 1986, 137, 299.
69. K. Jankowski, N. Turkkan, F. Soler, E. Godin, J. Mol. Struct. (Theochem) 1990, 66, 23.
70. J.A. Rice, D.M. Crothers, A.L. Pinto, S.J. Lippard, Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4158.
71. M.-H. Fouchet, E. Guittet, J.A.H. Cognet, J. Kozelka, C. Gauthier, M. Le Bret, K. Zimmermann, J.-C. Chottard, JBIC 1997, 2, 83.
72. D. Yang, S.S. G.E. van Boom, J. Reedijk, J.H. van Boom, A. H.-J. Wang, Biochemistry 1995, 34, 12912.
73. S.S. G.E. van Boom, D. Yang, J. Reedijk, G.A. van der Marel, A.H.J. Wang, J. Biomol. Struct. Dynamics 1996, 13, 989.
74. M. Iwamoto, S. Mukundan, Jr., L.G. Marzilli, J. Am. Chem. Soc. 1994, 116, 6238.
75. D.A. Pearlman, P.A. Kollman, J. Mol. Biol. 1991, 220, 457.
76. G.M. Crippen, 'Distance Geometry and Conformational Calculations, Chemometrics Research Studies Series 1', Wiley, New York, 1981.
77. G.M. Crippen, T.F. Havel, 'Distance Geometry and Molecular Conformation, Chemometrics Research Studies Series 15', Wiley, New York, 1988.
78. J. Kozelka, M.H. Fouchet, J.C. Chottard, Eur.J. Biochem. 1992, 205, 895.
79. Y. Qu, M.J. Bloemink, J. Reedijk, T.W. Hambley, N. Farrell, J. Am. Chem. Soc. 1996, 118, 9307.
80. M. Ptak, A. Rahmouni, K. Mazeau, N.T. Thuong, M. Leng, Anti-Cancer Drug Design 1989, 4, 53.
81. K. Mazeau, F. Vovelle, A. Rahmouni, M. Leng, M. Ptak, Anti-Cancer Drug Design 1989, 4, 63.
82. C.J. Van Garderen, L.P.A. Van Houte, Eur.J. Biochem. 1994, 225, 1169.
83. C. Prévost, M. Boudvillain, P. Beudaert, M. Leng, R. Lavery, F. Vovelle, J. Biomol. Struct. Dynamics 1997, 14, 703.
84. R. Dalbiès, D. Payet, M. Leng, Proc. Natl. Acad. Sci. USA 1994, 91, 8147.
85. H. Huang, L. Zhu, B.R. Reid, G.P. Drobny, P.B. Hopkins, Science 1995, 270, 1842.
86. F. Paquet, C. Pérez, M. Leng, G. Lancelot, J.-M. Malinge, J. Biomol. Struct. Dynamics 1996, 14, 67.
87. D. Yang, S.S. G.E. van Boom, J. Reedijk, J.H. van Boom, N. Farrell, A. H.-J. Wang, Nature Struct. Biol. 1995, 2, 577.
88. J.D. Hoeschele, A.H. Kraker, Y. Qu, B. Van Houten, N. Farrell, in 'Molecular Basis of Specificity in Nucleic Acid-Drug Interactions', Ed.B. Pullman and B. Jortner, Kluwer, Dordrecht, 1990, p. 301.
89. N. Farrell, Y. Qu, L. Feng, B. Van Houten, Biochemistry 1990, 29, 9522.
90. M.-A. Elizondo-Riojas, F. Gonnet, J.-C. Chottard, J.-P. Girault, J. Kozelka, JBIC 1998, 3, 30.
91. F. Herman Ph.D. Thesis, Université Paris VI, 1989.
92. J.C. Chottard, J.P. Girault, J.P. Lallemand, D. Mansuy, J. Am. Chem. Soc. 1980, 102, 5565.
93. J.-P. Girault, J.-C. Chottard, G. Chottard, J.-Y. Lallemand, Biochemistry 1982, 21, 1352.
94. J. Kozelka, in 'Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy', Eds.H.M. Pinedo, J.H. Schornagel, Plenum Press, New York, 1996, p. 37.
95. S.U. Dunham, S.J. Lippard, J. Am. Chem. Soc. 1995, 117, 10702.
96. A.M.J. Fichtinger-Schepman, P.H.M. Lohman, J. Reedijk, Nucleic Acids Res. 1982, 10, 5345.
97. A. Eastman, Biochemistry 1983, 22, 3927.
98. A. Laoui, J. Kozelka, J.-C. Chottard, Inorg. Chem. 1988, 27, 2751.
99. P. Weiner, P. Kollman, J. Comput. Chem. 1981, 2, 287.
100. F. Gonnet, F. Reeder, J. Kozelka, J.C. Chottard, Inorg. Chem. 1996, 35, 1653.
101. T.W. Hambley, Inorg. Chem. 1991, 30, 937.
102. P.J. Hay, W.R. Wadt, J. Chem. Phys. 1985, 82, 270.
103. P.J. Hay, W.R. Wadt, J. Chem. Phys. 1985, 82, 299.
104. J.G. Snijders, E.J. Baerends, Mol. Phys. 1977, 33, 1651.
105. P. Pyykkö, Chem. Rev. 1988, 88, 563.
106. J. Kozelka, W. Ludwig, Helv. Chim. Acta 1983, 66, 902.
107. C. Møller, M.S. Plesset, Phys. Rev. 1934, 46, 618.
108. H. Basch, S. Topiol, J. Chem. Phys. 1979, 71, 802.
109. T.R. Cundari, M.T. Benson, M.L. Lutz, S.O. Sommerer, Rev. Comput. Chem. 1996, 8, 145.
110. T.A. Darden, D. York, L.G. Pedersen, J. Chem. Phys. 1993, 98, 10089.
111. D. York, T.A. Darden, L.G. Pedersen, J. Chem. Phys. 1993, 99, 8345.
112. T.E. Cheatham III, P.A. Kollman, J. Mol. Biol. 1996, 259, 434.
113. R. Car, M. Parrinello, Phys. Rev. Lett. 1985, 55, 2741.
114. J. Hutter, P. Carloni, M. Parrinello, J. Am. Chem. Soc. 1996, 118, 8710.
115. P. Carloni, W. Andreoni, M. Parrinello, Phys. Rev. Lett. 1997, 79, 761.
116. C. Molteni, M. Parrinello, J. Am. Chem. Soc. 1998, 120, 2168.
117. P. Carloni, M. Sprik, W. Andreoni, personal communication.