Structure and Dynamics of Pt Anticancer Drug Adducts from Nucleotides to Oligonucleotides as Revealed by NMR Methods

Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug

Volumn , Issue , 2006, Pages 247-291

  Ano, Susan O ^a   Kuklenyik, Zsuzsanna ^a   Marzilli, Luigi G ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Cancer treatment; Cisplatin; Dynamics; Pt anticancer drug adducts; Pt biomolecule interaction; Structure

Indexed keywords

AMINES; DYNAMICS; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGONUCLEOTIDES; ONCOLOGY; PLATINUM; POSITIVE IONS; STRUCTURE (COMPOSITION); SUGARS;

ADDUCT STRUCTURES; ANTICANCER DRUG; BIOMOLECULE INTERACTIONS; CIS-PLATIN; DIPOLE INTERACTION; STRUCTURAL MODELS; STRUCTURE AND DYNAMICS; UNUSUAL CONFORMATIONS;

PLATINUM COMPOUNDS;

EID: 84949238298     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783906390420.ch10     Document Type: Chapter

References (125)

1. S. Mansy, G.Y.H. Chu, R.E. Duncan, R.S. Tobias, J. Am. Chem. Soc. 1978, 100, 607.
2. S.E. Sherman, S.J. Lippard, Chem. Rev. 1987, 87, 1153.
3. A.M.J. Fichtinger-Schepman, P.H.M. Lohman, J. Reedijk, Biochemistry 1985, 24, 707.
4. A. Eastman, Biochemistry 1986, 25, 3912.
5. N. Farrell, Met. Ions Biol. Syst. 1996, 32, 603.
6. B. Lippert, Met. Ions Biol. Syst. 1996, 33, 105.
7. A.L. Pinto, S.J. Lippard, Biochim. Biophys. Acta 1985, 780, 167.
8. J.L. van der Veer, J. Reedijk, Chemistry in Britain 1988, 24, 775.
9. P.G. Yohannes, G. Zon, P.W. Doetsch, L.G. Marzilli, J. Am. Chem. Soc. 1993, 115, 5105.
10. M. Iwamoto, S. Mukundan Jr., L.G. Marzilli, J. Am. Chem. Soc. 1994, 116, 6238.
11. X. Jia, G. Zon, L.G. Marzilli, Inorg. Chem. 1991, 30, 228.
12. S.J. Berners-Price, A. Corazza, Z. Guo, K.J. Barnham, P.J. Sadler, Y. Ohyama, M. Leng, D. Locker, Eur.J. Biochem. 1997, 243, 782.
13. C.S. Chow, J.P. Whitehead, S.J. Lippard, Biochemistry 1994, 33, 15124.
14. C.S. Chow, C.M. Barnes, S.J. Lippard, Biochemistry 1995, 34, 2956.
15. P.M. Pil, S.J. Lippard, Science 1992, 256, 234.
16. M.C. Poirier, E. Reed, H. Shamkhani, R.E. Tarone, S. Guptaburt, Environ. Health Perspect. 1993, 99, 149.
17. G. Chu, E. Chang, Science 1988, 242, 564.
18. E.N. Hughes, B.N. Engelsberg, P.C. Billings, J. Biol. Chem. 1992, 267, 564.
19. J. Kasparkova, V. Brabec, Biochemistry 1995, 34, 12379.
20. S.L. Bruhn, P.M. Pil, J.M. Essigmann, D.E. Housman, S.J. Lippard, Proc. Natl. Acad. Sci.U. S.A. 1992, 89, 2307.
21. H. Huang, L. Zhu, B.R. Reid, G.F. Drobney, P.B. Hopkins, Science 1995, 270, 1842.
22. F. Paquet, C. Pérez, M. Leng, G. Lancelot, J.-M. Malinge, J. Biomol. Struct. Dyn. 1996, 14, 67.
23. R. Cramer, P. Dahlstrom, Inorg. Chem. 1985, 24, 3420.
24. A.T.M. Marcelis, C.G. van Kralingen, J. Reedijk, J. Inorg. Biochem. 1980, 13, 213.
25. A.T.M. Marcelis, J.L. van der Veer, J.C.M. Zwetsloot, J. Reedijk, Inorg. Chim. Acta 1983, 78, 195.
26. R.E. Cramer, P.L. Dahlstrom, J. Am. Chem. Soc. 1979, 101, 3679.
27. R.E. Cramer, P.L. Dahlstrom, M.J.T. Seu, T. Norton, M. Kashiwagi, Inorg. Chem. 1980, 19, 148.
28. A.T.M. Marcelis, H.-J. Korte, B. Krebs, J. Reedijk, Inorg. Chem. 1982, 21, 4059.
29. A.T.M. Marcelis, C. Erkelens, J. Reedijk, Inorg. Chim. Acta 1984, 91, 129.
30. F.J. Dijt, G.W. Canters, J.H.J. den Hartog, A.T.M. Marcelis, J. Reedijk, J. Am. Chem. Soc. 1984, 106, 3644.
31. S.K. Miller, L.G. Marzilli, Inorg. Chem. 1985, 24, 2421.
32. M.D. Reily, L.G. Marzilli, J. Am. Chem. Soc. 1986, 108, 6785.
33. Y. Xu, G. Natile, F.P. Intini, L.G. Marzilli, J. Am. Chem. Soc. 1990, 112, 8177.
34. D. Kiser, F.P. Intini, Y. Xu, G. Natile, L.G. Marzilli, Inorg. Chem. 1994, 33, 4149.
35. K.M. Williams, L. Cerasino, F.P. Intini, G. Natile, L.G. Marzilli, Inorg. Chem. 1998, 37, 5260.
36. D. Li, R.N. Bose, J. Chem. Soc., Chem. Commun. 1992, 1596.
37. D. Li, R.N. Bose, J. Chem. Soc., Dalton Trans. 1994, 3717.
38. J.H.J. den Hartog, C. Altona, G.A. van der Marel, J. Reedijk, Eur.J. Biochem. 1985, 147, 371.
39. S.O. Ano, F.P. Intini, G. Natile, L.G. Marzilli, J. Am. Chem. Soc. 1997, 119, 8570.
40. R.W. Gellert, R. Bau, J. Am. Chem. Soc. 1975, 97, 7379.
41. S.K. Miller, D.G. van der Veer, L.G. Marzilli, J. Am. Chem. Soc. 1985, 107, 1048.
42. L.G. Marzilli, P. Chalilpoyil, C.C. Chiang, T.J. Kistenmacher, J. Am. Chem. Soc. 1980, 102, 2480.
43. J.D. Orbell, M.R. Taylor, S.L. Birch, S.E. Lawton, L.M. Vilkins, L.J. Keefe, Inorg. Chim. Acta 1988, 152, 125.
44. K.J. Barnham, C.J. Bauer, M.I. Djuran, M.A. Mazid, T. Rau, P.J. Sadler, Inorg. Chem. 1995, 34, 2826.
45. L.G. Marzilli, M. Iwamoto, E. Alessio, L. Hansen, M. Calligaris, J. Am. Chem. Soc. 1994, 116, 815.
46. E. Alessio, L. Hansen, M. Iwamoto, L.G. Marzilli, J. Am. Chem. Soc. 1996, 118, 7593.
47. L.G. Marzilli, P.A. Marzilli, E. Alessio, Pure Appl. Chem. 1998, 70, 961.
48. J. Kozelka, M.-H. Fouchet, J.-C. Chottard, Eur.J. Biochem. 1992, 205, 895.
49. J. Reedijk, J. Chem. Soc., Chem. Commun. 1996, 801.
50. L.G. Marzilli, F.P. Intini, D. Kiser, H.C. Wong, S.O. Ano, P.A. Marzilli, G. Natile, Inorg. Chem. 1999, in press.
51. B. van Hemelryck, E. Guittet, G. Chottard, J.-P. Girault, T. Huynh-Dinh, J.-Y. Lallemand, J. Igolen, J.-C. Chottard, J. Am. Chem. Soc. 1984, 106, 3037.
52. H.C. Wong, F.P. Intini, G. Natile, L.G. Marzilli, 1998, in preparation.
53. H.C. Wong, R. Coogan, F.P. Intini, G. Natile, L.G. Marzilli, Inorg. Chem. 1998, submitted.
54. S.O. Ano, F.P. Intini, G. Natile, L.G. Marzilli, J. Am. Chem. Soc. 1998, in press.
55. S.O. Ano, F.P. Intini, G. Natile, L.G. Marzilli, 1998, in preparation.
56. J.-P. Girault, G. Chottard, J.-Y. Lallemand, J.-C. Chottard, Biochemistry 1982, 21, 1352.
57. J.H.J. den Hartog, C. Altona, J.-C. Chottard, J.-P. Girault, J.-Y. Lallemand, F.A. A.M. de Leeuw, A.T.M. Marcelis, J. Reedijk, Nucleic Acids Res. 1982, 10, 4715.
58. J.-C. Chottard, J.-P. Girault, G. Chottard, J.-Y. Lallemand, D. Mansuy, J. Am. Chem. Soc. 1980, 102, 5565.
59. S.E. Sherman, D. Gibson, A. H.-J. Wang, S.J. Lippard, Science 1985, 230, 412.
60. S.E. Sherman, D. Gibson, A. H.-J. Wang, S.J. Lippard, J. Am. Chem. Soc. 1988, 110, 7368.
61. S.J. Berners-Price, K.J. Barnham, U. Frey, P.J. Sadler, Chem. Eur.J. 1996, 2, 1283.
62. T.P. Kline, L.G. Marzilli, D. Live, G. Zon, J. Am. Chem. Soc. 1989, 111, 7057.
63. S. Mukundan Jr., Y. Xu, G. Zon, L.G. Marzilli, J. Am. Chem. Soc. 1991, 113, 3021.
64. S.S. G.E. van Boom, D. Yang, J. Reedijk, G.A. van der Marel, A. H.-J. Wang, J. Biomol. Struct. Dyn. 1996, 13, 989.
65. K. Inagaki, H. Nakahara, M. Alink, Y. Kidani, Inorg. Chem. 1990, 29, 4496.
66. K. Inagaki, H. Nakahara, M. Alink, J. Reedijk, J. Chem. Soc., Dalton Trans. 1991, 1337.
67. C.S. Fouts, L.G. Marzilli, R.A. Byrd, M.F. Summers, G. Zon, K. Shinozuka, Inorg. Chem. 1988, 27, 366.
68. J.L. van der Veer, G.A. van der Marel, H. van den Elst, J. Reedijk, Inorg. Chem. 1987, 26, 2272.
69. S.U. Dunham, S.J. Lippard, J. Am. Chem. Soc. 1995, 117, 10702.
70. T.W. Hambley, E.C.H. Ling, B.A. Messerle, Inorg. Chem. 1996, 35, 4663.
71. J.H.J. den Hartog, C. Altona, J.H. van Boom, G.A. van der Marel, C.A.G. Haasnoot, J. Reedijk, J. Biomol. Struct. Dynamics 1985, 2, 1137.
72. 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.
73. D. Yang, S.S. G.E. van Boom, J. Reedijk, J.H. van Boom, A. H.-J. Wang, Biochemistry 1995, 34, 12912.
74. J.H.J. den Hartog, C. Altona, J.H. van Boom, J. Reedijk, FEBS Lett. 1984, 176, 393.
75. W.D. Wilson, B.L. Heyl, R. Reddy, L.G. Marzilli, Inorg. Chem. 1982, 21, 2527.
76. L.G. Marzilli, M.D. Reily, B.L. Heyl, C.T. McMurray, W.D. Wilson, FEBS Lett. 1984, 176, 389.
77. A. Gelasco, S.J. Lippard, Biochemistry 1998, 37, 9230.
78. M. Iwamoto, Ph.D. Thesis, Emory University, 1993.
79. Y. Qu, M.J. Bloemink, J. Reedijk, T.W. Hambley, N. Farrell, J. Am. Chem. Soc. 1996, 118, 9307.
80. J. Kaspárková, K.J. Mellish, Y. Qu, V. Brabec, N. Farrell, Biochemistry 1996, 35, 16705.
81. K.J. Mellish, Y. Qu, N. Scarsdale, N. Farrell, Nucleic Acids Res. 1997, 25, 1265.
82. D. Norman, P. Abuaf, B.E. Hingerty, D. Live, D. Grunberger, S. Broyde, D.J. Patel, Biochemistry 1989, 28, 7462.
83. B. Mao, M. Cosman, B.E. Hingerty, S. Broyde, D.J. Patel, Biochemistry 1995, 34, 6226.
84. B. van Hemelryck, J.-P. Girault, G. Chottard, P. Valadon, A. Laoui, J.-C. Chottard, Inorg. Chem. 1987, 26, 787.
85. F. Dijt, J.-C. Chottard, J.-P. Girault, J. Reedijk, Eur.J. Biochem. 1989, 179, 333.
86. D. Lemaire, M.-H. Fouchet, J. Kozelka, J. Inorg. Biochem. 1994, 53, 261.
87. F. Gonnet, F. Reeder, J. Kozelka, J.-C. Chottard, Inorg. Chem. 1996, 35, 1653.
88. W.I. Sundquist, S.J. Lippard, Coord. Chem. Rev. 1990, 100, 293.
89. K.M. Comess, S.J. Lippard, In 'Molecular Aspects of Anticancer Drug-DNA Interactions' Eds.S. Neidle, M. Waring, Macmillan, London, 1993, p. 134.
90. K. Inagaki, C. Ninomiya, Y. Kidani, Chem. Lett. 1986, 233.
91. A.T.M. Marcelis, J.H.J. den Hartog, G.A. van der Marel, G. Wille, J. Reedijk, Eur.J. Biochem. 1983, 135, 343.
92. J.-M. Neumann, S. Tran-Dinh, J.-P. Girault, J.-C. Chottard, T. Huynh-Dinh, Eur.J. Biochem. 1984, 141, 465.
93. R.A. Byrd, M.F. Summers, G. Zon, C.S. Fouts, L.G. Marzilli, J. Am. Chem. Soc. 1986, 108, 504.
94. M.J. Bloemink, R.J. Heetebrij, K. Inagaki, Y. Kidani, J. Reedijk, Inorg. Chem. 1992, 31, 4656.
95. C.J. van Garderen, M.J. Bloemink, E. Richardson, J. Reedijk, J. Inorg. Biochem. 1991, 42, 199.
96. S.J. Berners-Price, J.D. Ranford, P.J. Sadler, Inorg. Chem. 1994, 33, 5842.
97. D.P. Bancroft, C.A. Lepre, S.J. Lippard, J. Am. Chem. Soc. 1990, 112, 6860.
98. J.-P. Girault, J.-C. Chottard, E.R. Guittet, J.-Y. Lallemand, T. Huynh-Dinh, J. Ingolen, Biochem. Biophys. Res. Commun. 1982, 109, 1157.
99. J.P. Caradonna, S.J. Lippard, M.J. Gait, M. Singh, J. Am. Chem. Soc. 1982, 104, 5793.
100. J.P. Caradonna, S.J. Lippard, Inorg. Chem. 1988, 27, 1454.
101. D.G. Gorenstein, In 'Phosphorus-31 NMR. Principles and Applications', Ed.D.G. Gorenstein, Academic Press, Inc., Orlando, FL, 1984, p. 7.
102. W. Saenger, In 'Principles of Nucleic Acid Structure' Springer, New York, 1984, p. 1.
103. D.G. Gorenstein, In 'Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis', Eds.L.D. Quin, J.G. Verkade, VCH, Weinheim, 1994, p. 267.
104. D.G. Gorenstein, S.A. Schroeder, J.M. Fu, J.T. Metz, V. Roongta, C.R. Jones, Biochemistry 1988, 27, 7223.
105. J.H.J. den Hartog, C. Altona, J.H. van Boom, G.A. van der Marel, C.A.G. Haasnoot, J. Reedijk, J. Am. Chem. Soc. 1984, 106, 1528.
106. B. van Hemelryck, E. Guittet, G. Chottard, J.-P. Girault, F. Herman, T. Huynh-Dinh, J.-Y. Lallemand, J. Igolen, J.-C. Chottard, Biochem. Biophys. Res. Commun. 1986, 138, 758.
107. Z. Kuklenyik, K.A. Keating, Y. Xu, L.G. Marzilli, 1998, manuscript in preparation.
108. K.J. Barnham, S.J. Berners-Price, T.A. Frenkiel, U. Frey, P.J. Sadler, Angew. Chem., Int. Ed. Engl. 1995, 34, 1874.
109. I.M. Ismail, P.J. Sadler, In 'Platinum, Gold, and Other Metal Chemotherapeutic Agents', Ed.S.J. Lippard, American Chemical Society, Washington, D. C., 1983, Vol. 209; p. 171.
110. L.G. Marzilli, Y. Hayden, M.D. Reily, Inorg. Chem. 1986, 25, 974.
111. C.S. Fouts, M.D. Reily, L.G. Marzilli, G. Zon, Inorg. Chim. Acta 1987, 137, 1.
112. T.P. Kline, L.G. Marzilli, D. Live, G. Zon, Biochem. Pharmacol. 1990, 40, 97.
113. M.D. Reily, L.G. Marzilli, J. Am. Chem. Soc. 1985, 107, 4916.
114. M.-H. Fouchet, E. Guittet, J.A.H. Cognet, J. Kozelka, C. Gauthier, M. Le Bret, K. Zimmermann, J.-C. Chottard, J. Biol. Inorg. Chem. 1997, 2, 83.
115. S.S. Wijmenga, M. Kruithof, C.W. Hilbers, J. Biomol. NMR 1997, 10, 337.
116. C. Giessner-Prettre, B. Pullman, P.N. Borer, L.-S. Kan, P.O.P. Ts'o, Biopolymers 1976, 15, 2277.
117. K. Wüthrich, In 'NMR of Proteins and Nucleic Acids', Wiley, New York, 1986, p. 1.
118. H. Shindo, S. Okhubo, U. Matsumoto, C. Giessner-Prettre, G. Zon, J. Biomol. Struct. Dyn. 1988, 5, 913.
119. T.A. Early, D.R. Kearns, W. Hillen, R.D. Wells, Biochemistry 1981, 20, 3764.
120. J.L. Leroy, M. Kochoyan, T. Huynh-Dinh, M. Gueron, J. Mol. Biol. 1988, 200, 233.
121. J. Kozelka, G.A. Petsko, S.J. Lippard, G.J. Quigley, J. Am. Chem. Soc. 1985, 107, 4079.
122. J. Kozelka, G.A. Petsko, G.J. Quigley, S.J. Lippard, Inorg. Chem. 1986, 25, 1075.
123. J. Kozelka, S. Archer, G.A. Petsko, S.J. Lippard, G.J. Quigley, Biopolymers 1987, 26, 1245.
124. P.M. Takahara, A.C. Rosenzweig, C.A. Frederick, S.J. Lippard, Nature 1995, 377, 649.
125. P.M. Takahara, C.A. Frederick, S.J. Lippard, J. Am. Chem. Soc. 1996, 118, 12309.