Cisplatin adducts on a GGG sequence within a DNA duplex studied by NMR spectroscopy and molecular dynamics simulations

Chemistry - A European Journal

Volumn 15, Issue 45, 2009, Pages 12320-12337

  Téletchéa, Stéphane ^a   Skauge, Tormod ^b   Sletten, Einar ^b   Kozelka, Jiří ^a,c  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b UNIVERSITY OF BERGEN   (Norway)

^c MASARYK UNIVERSITY   (Czech Republic)

Author keywords

Antitumor agents; Dna structures; Molecular modeling; Nmr spectroscopy; Platinum

Indexed keywords

ANTI-TUMOR AGENTS; ANTITUMOR DRUGS; CIS-PLATIN; CROSSLINKED; DECANUCLEOTIDE DUPLEX; DNA DUPLEXES; DNA STRUCTURE; DNA STRUCTURES; HOTSPOTS; INTERSTRAND CROSS-LINKS; MOLECULAR DYNAMICS SIMULATIONS; NMR SPECTROSCOPY; NMR SPECTRUM; NO FORMATION; OXALIPLATIN; PHASE ANGLES; PLATINATION; SPECTROSCOPIC DATA; STRUCTURAL PERTURBATION;

BEARINGS (STRUCTURAL); CHELATION; CROSSLINKING; DNA; GENES; MOLECULAR DYNAMICS; MOLECULAR MODELING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACIDS; PLATINUM COMPOUNDS; POSITIVE IONS;

PLATINUM;

ANTINEOPLASTIC AGENT; CISPLATIN; CROSS LINKING REAGENT; DNA; GUANINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; KINETICS; METABOLISM; MOLECULAR DYNAMICS; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PROTEIN BINDING;

ANTINEOPLASTIC AGENTS; BASE SEQUENCE; CISPLATIN; CROSS-LINKING REAGENTS; DNA; GUANINE; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR SEQUENCE DATA; NUCLEIC ACID CONFORMATION; PROTEIN BINDING;

EID: 70849126018     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901158     Document Type: Article

References (71)

1. S. O. Ano, Z. Kuklenyik, L. G. Marzilli in Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug (Ed.: B. Lippert), Verlag Helvetica Chimica Acta, Zürich, 1999, pp. 247-291.
2. M.-A. Elizondo-Riojas, J. Kozelka, J. Mol. Biol. 2001, 314, 1227-1243.
3. Y. Wu, D. Bhattacharyya, C. L. King, I. Baskerville-Abraham, S.-H. Hu, G. Boysen, J. A. Swenberg, B. Temple, S. L. Campbell, S. G. Chaney, Biochemistry 2007, 46, 6477-6487.
4. S. Sharma, P. Gong, B. Temple, D. Bhattacharyya, N. V. Dokholyan, S. G. Chaney, J. Mol. Biol. 2007, 373,1123-1140.
5. V. Murray, H. Motyka, P.R. England, G. Wickham, H.H. Lee, W. A. Denny, W. D. McFadyen, J. Biol. Chem. 1992, 267, 18805-18809.
6. S. M. Cohen, Y. Mikata, Q. He, S. J. Lippard, Biochemistry 2000, 39, 11771-11776.
7. V. Monjardet-Bas, J.-C. Chottard, J. Kozelka, Chem. Eur. J. 2002, 8, 1144-1150.
8. 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, 119-133.
9. a) J. Falbe, M. Regitz, Römpp Chemie-Lexikon, 9th ed., Georg Thieme Verlag, Stuttgart, 1995, p. 4871;
10. b) G. Job, R. Rüffler, Physikalische Chemie-Eine Einführung nach neuem Konzept mit zahlreichen Experimenten, Teubner Studienbücher Chemie, Wiesbaden, 2008.
11. S. S. Wijmenga, M. M. W. Mooren, C. W. Hilbers in NMR of Macromolecules: A Practical Approach (Ed.: G.C.K. Roberts), Oxford University Press, New York, 1993, pp. 218-283.
12. S. S. Wijmenga, B. N. M. van Buuren, Prog. Nucl. Magn. Reson. Spectrosc. 1998, 32, 287-387.
13. R. M. Scheek, R. Boelens, N. Russo, J. H. van Boom, R. Kaptein, Biochemistry 1984, 23,1371-1376.
14. E.J. M. van de Ven, C.W. Hilbers, Nucleic Acids Res. 1988, 16, 5713-5726.
15. C Giessner-Prettre, B. Pullman, Biopolymers 1976, 15, 2277-2286.
16. R. Lavery, H. Sklenar, J. Biomol. Struct. Dyn. 1988, 6, 63-91.
17. R. Lavery, H. Sklenar, J. Biomol. Struct. Dyn. 1989, 7, 655-667.
18. L. J. Rinkel, C. Altona, J. Biomol. Struct. Dyn. 1987, 5, 621-651.
19. M. R. Conte, C. J. Bauer, A. N. Lane, J. Biomol. NMR 1996, 7, 190-206.
20. S. Teletchéa and J. Kozelka, unpublished results.
21. S. Teletchéa, S. Komeda, J.-M. Teuben, M.-A. Elizondo-Riojas, J. Reedijk, J. Kozelka, Chem. Eur. J. 2006, 12, 3741-3753.
22. K. Grzeskowiak, K. Yanagi, G. G. Privé, R. E. Dickerson, J. Biol. Chem. 1991, 266, 8861-8883.
23. S. A. Schroeder, V. Roongta, J. M. Fu, C. R. Jones, D. Gorenstein, Biochemistry 1989, 28, 8292-8303.
24. C Castagné, E. C Murphy, A. M. Gronenborn, M. Delepierre, Eur. J. Biochem. 2000, 267,1223-1229.
25. K. Wecker, M. C Bonnet, E. F. Meurs, M. Delepierre, Nucleic Acids Res. 2002, 30, 4452-4459.
26. S. Teletchéa, B. Hartmann, J. Kozelka, J. Biomol. Struct. Dyn. 2004, 22, 489-494.
27. B. Hartmann, D. Piazzola, R. Lavery, Nucleic Acids Res. 1993, 21, 561-568.
28. A. Lefebvre, O. Mauffret, E. Lescot, B. Hartmann, S. Fermandjian, Biochemistry 1996, 35,12560-12569.
29. H.-O. Bertrand, T. Ha-Duong, S. Fermandjian, B. Hartmann, Nucleic Acids Res 1998, 26,1261-1267.
30. D. Over, G Bertho, M.-A. Elizondo-Riojas, J. Kozelka, J. Biol. Inorg. Chem. 2006, 11,139-152.
31. D. G. Gorenstein, Phosphorus-31 NMR: Principles and Applications, Academic Press, New York, 1984.
32. E. J. M. van de Ven, C. W. Hilbers, Eur. J. Biochem. 1988, 178,1-38.
33. P. Varnai, D. Djuranovic, R. Lavery, B. Hartmann, Nucleic Acids Res. 2002, 30, 5398-5406.
34. D. Svozil, J. E. Sponer, I. Marchan, A. Pérez, T. E. Cheatham, III, F. Forti, E. J. Luque, M. Orozco, J. Sponer, J. Phys. Chem. B 2008, 112, 8188-8197.
35. Y Wu, P. Pradhan, J. Havener, G. Boysen, J. A. Swenberg, S. L. Campbell, S. G. Chaney, J. Mol. Biol. 2004, 341,1251-1269.
36. 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. Dyn. 1985, 3,1137-1155.
37. J. A. Parkinson, Y Chen, Z. Guo, S. J. Berners-Price, T. Brown, P. J. Sadler, Chem. Eur. J. 2000, 6, 3636-3644.
38. X. Jia, G. Zon, L. G. Marzilli, Inorg. Chem. 1991, 30, 228-235.
39. P. G Yohannes, G. Zon, P. W. Doetsch, L. G Marzilli, J. Am. Chem. Soc. 1993, 115, 5105-5110.
40. J. M. Villanueva, X. Jia, P. G. Yohannes, P. W. Doetsch, L. G Marzilli, Inorg. Chem. 1999, 38, 6069-6080.
41. V. Monjardet-Bas, M.-A. Elizondo-Riojas, J.-C. Chottard, J. Kozelka, Angew. Chem. 2002, 114, 3124-3127;
42. Angew. Chem. Int. Ed. 2002, 41, 2998-3001.
43. E Reeder, F. Gonnet, J. Kozelka, J. C. Chottard, Chem. Eur. J. 1996, 2,1068-1076.
44. J. Kozelka, Inorg. Chim. Acta 2009, 362, 651-668.
45. J. Kozelka, J.-C. Chottard, Biophys. Chem. 1990, 35,165-178.
46. J. Reedijk, Inorg. Chim. Acta 1992, 198-200, 873-881.
47. S. T. Sullivan, A. Ciccarese, F. P. Fanizzi, L. G. Marzilli, J. Am. Chem. Soc. 2001, 123, 9345-9355.
48. P. M. Takahara, A. C Rosenzweig, C. A. Frederick, S. J. Lippard, Nature 1995, 377, 649-652.
49. P. M. Takahara, C. A. Frederick, S. J. Lippard, J. Am. Chem. Soc. 1996, 225, 12309-12321.
50. B. Spingler, D. A. Whittington, S. J. Lippard, Inorg. Chem. 2001, 40, 5596-5602.
51. J. Malina, C Hofr, L. Maresca, G. Natile, V. Brabec, Biophys. J. 2000, 78, 2008-2021.
52. O. Delalande, J. Malina, V Brabec, J. Kozelka, Biophys. J. 2005, 88, 1-11.
53. A. Lefebvre, S. Fermandjian, B. Hartmann, Nucleic Acids Res. 1997, 25, 3855-3862.
54. D. Djuranovic, B. Hartmann, J. Biomol. Struct. Dyn. 2003, 21, 771-788.
55. M. Krauss, H. Basch, K.J. Miller, J. Am. Chem. Soc. 1988, 110, 4517-4521.
56. B. Hartmann, M. R. Sullivan, L. F. Harris, Biopolymers 2003, 68, 250-264.
57. L. G. Marzilli, J. S. Saad, Z. Kuklenyik, K. A. Keating, Y. Xu, J. Am. Chem. Soc. 2001, 123, 2764-2770.
58. M.-A. Elizondo-Riojas, F. Gonnet, P. Augé-Barrere-Mazouat, F. Allain, J. Berges, R. Attias, J.-C. Chottard, J. Kozelka in Molecular Modeling and Dynamics of Bioinorganic Systems (Eds.: L. Banci, P. Comba), Kluwer Academic Publishers, Dordrecht, 1997, pp. 131-160.
59. Z. Chval, M. Sip, J. Phys. Chem. B 1998, 102, 1659-1661.
60. U. M. Ohndorf, M. A. Rould, Q. He, C. O. Pabo, S. J. Lippard, Nature 1999, 399, 708-712.
61. S. U. Dunham, S. J. Lippard, Biochemistry 1997, 36,11428-11436.
62. J. S. Kerrison, P. J. Sadler, J. Chem. Soc. Chem. Commun. 1977, 861-863.
63. C R. Cantor, M. M. Warshaw, Biopolymers 1970, 9, 1079-1103.
64. S. Redon, S. Bombard, M.-A. Elizondo-Riojas, J.-C. Chottard, Biochemistry 2001, 40, 8463-8470.
65. V Sklenar, A. Bax, J. Am Chem. Soc. 1987, 109, 7525-7526.
66. H. Green, R. Freeman, J. Magn. Reson. (1969-1992) 1991, 93, 93-141.
67. T. D. Goddard, D. G. Kneller, SPARKY 3 (version 3.112), University of California, San Fransisco (USA), 2006.
68. D.A. Case, D.A. Pearlman, J.W. Caldwell, T.E. Cheatham, III, W. S. Ross, C.L. Simmerling, T.A. Darden, K.M. Merz, Jr., R. V. Stanton, A.L. Cheng, J.J. Vincent, M. Crowley, V. Tsui, R.J. Radmer, Y Duan, J. Pitera, I. Massova, G. L. Seibel, U. C Singh, P. K. Weiner, P. A. Kollman, AMBER 6, University of California, San Francisco (USA), 1999.
69. XmGrace, a 2D plotting tool: http://plasma-gate.weizmann.ac.il/ Grace/.
70. www.steletch.org.
71. A. Dalke, W. Humphrey, J. Ulrich, VMD (version 1.2bl), Theoretical Biophysics Group, University of Illinois and Beckman Institute, Urbana (USA), 1997.