Modulation of Nucleotide Binding of trans Platinum(II) Complexes by Planar Ligands. A Combined Proton NMR and Molecular Mechanics Study

Inorganic Chemistry

Volumn 36, Issue 17, 1997, Pages 3657-3665

  Bierbach, Ulrich ^a   Farrell, Nicholas ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000992215     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970154o     Document Type: Article

References (48)

1. Kelland, L. R.; Clarke, S. J.; McKeage, M. J. Platinum Met. Rev. 1992, 36, 178.
2. (a) Reedijk, J. Inorg. Chim. Acta 1992, 198-200, 873.
3. (b) Lepre, C. A.; Lippard, S. J. In Nucleic Acids and Molecular Biology, Eckstein, F., Lilley, D. M. J., Eds.; Springer: Berlin, 1990: Vol. 4, pp 9-38.
4. Sherman, S. E.; Lippard, S. J. Chem. Rev. 1987, 87, 1153.
5. Farrell, N. In Transition Metal Complexes as Drugs and Chemotherapeutic Agents; Ugo, R., James, B. R., Eds.; Kluwer: Dordrecht, The Netherlands, 1989: Chapter 3 and literature cited therein.
6. (a) Takahara, P. M.; Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J. Nature 1995, 377, 649.
7. (b) Takahara, P. M.; Frederick. C. A.; Lippard, S. J. J. Am. Chem. Soc. 1996, 118, 12309.
8. Farrell, N. Met. Ions Biol. Syst. 1996, 32, 603.
9. Boudvillain, M.; Dallies, R.; Aussourd, C.; Leng, M. Nucleic Acids Res. 1995, 23, 2381.
10. Brabec, V.; Leng, M. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5345.
11. (a) Hopkins, B. P.; Millard, J. T.; Woo, J.; Weidner, M. F.; Kirchner, J. J.; Sigurdsson, S. T.; Raucher, S. Tetrahedron 1991, 47, 2675.
12. (b) Lemaire, M. A.; Schwartz, A.; Rahmouni, A. R.; Leng, M. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1982.
13. (a) Bancroft, D. P.; Lepre, C. A.; Lippard, S. J. J. Am. Chem. Soc. 1990, 112, 6860.
14. (b) Eastman, A.; Barry, M. A. Biochemists 1987, 26, 3303.
15. Bruhn, S. L.; Toney, J. H.; Lippard, S. J. In Progress in inorganic Chemistry: Bioinorganic Chemistry; Lippard, S. J., Ed.; Wiley: New York. 1990; pp 495-507.
16. Pil, P. M.; Lippard, S. J. Science 1992, 256, 234.
17. Van Beusichem, M.; Farrell, N. Inorg. Chem. 1992, 31, 634.
18. Coluccia, M.; Nassi, A.; Loseto, F.; Boccarelli, A.; Mariggio, M. A.; Giordano, D.; Intini, F. P.; Caputo, P.; Natile G. J. Med. Chem. 1993, 36, 510.
19. Mellish, K. J.; Barnard, C. F. J.; Murrer, B. A.; Kelland, L. R. Int. J. Cancer 1995, 62, 717.
20. Zou, Y.; Van Houten, B.; Farrell, N. Biochemistry 1993, 32, 9632.
21. Kharatishvili, M.; Mathieson, M.; Farrell, N. Inorg. Chim. Acta 1997, 255, 1.
22. Marples, B.; Adomat, H.; Billings, P. C.; Farrell, N. P.; Koch, C. J.; Skov, K. A. Anti- Cancer Drug Des. 1994, 9, 389.
23. Skov, K. A.; Adomat, H.; Doedee, M. J.; Farrell, N. Anti-Cancer Drug Des. 1994, 9, 103.
24. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765.
25. HyperChem, Release 4.5; Hypercube Inc.: Ontario, Canada. 1995.
26. ChemPlus, Extensions for HyperChem, Release 1.0a; Hypercube Inc.: Ontario, Canada, 1994.
27. Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
28. Hambley, T. W. Inorg. Chem. 1988, 27, 1073.
29. Hambley, T. W. Inorg. Chem. 1991, 30, 937.
30. Yao, S.; Plastaras, J. P.; Marzilli, L. G. Inorg. Chem. 1994, 33, 6061.
31. Kozelka, J.; Archer, S.; Petsko, G. A.; Lippard, S. J. Biopolymers 1987, 26, 1245.
32. Hollis, L. S.; Amundsen, A. R.; Stern, E. W. J. Med. Chem. 1989, 32, 128.
33. Marcelis, A. T. M.; van Kralingen, C. G.; Reedijk, J. J. Inorg. Biochem. 1980, 13, 213.
34. 195Pt shifts has been reported before. See, for example: Ismail, I. M.; Sadler, P. J. In Platinum, Gold and Other Metal Chemotherapeutic Agents: ACS Symposium Series 209; American Chemical Society: Washington, DC, 1983; see also literature cited therein.
35. 1H NMR spectra, not explicitly mentioned in this paper, consistently indicate no unplatinated N7 for all the adducts.
36. Schöllhorn, H.; Raudaschl-Sieber, G.; Müller, G.; Thewalt, U.; Lippert, B. J. Am. Chem. Soc. 1985, 107, 5932.
37. Dijt, F. J.; Canters, G. W.; den Hartog, J. H. J.; Marcelis, A. T. M.; Reedijk, J. J. Am. Chem. Soc. 1984, 106, 3644.
38. Arvanitis, G. M.; Gibson, D.; Emge, T. J.; Berman, H. M. Acta Crystallogr., Sect. C 1994, 50, 1217.
39. Scovell, W. M.; O'Connor, T. J. Am. Chem. Soc. 1977, 99, 120.
40. Mansy, S.; Chu, G. J. H.; Duncan, R. E.; Tobias, R. S. J. Am. Chem. Soc. 1978, 100, 607.
41. Cramer, R. E.; Dahlstrom, P. L. J. Am. Chem. Soc. 1979, 101, 3679 .
42. Bose, R. N.; Moghaddas, S.; Weaver, E. L.; Cox, E. H. Inorg. Chem. 1995, 34, 5878.
43. Lambert, B.; Jestin, J.-L.; Bréhin, P.; Oleykowski, C.; Yeung, A. T.; Mailliet, P.; Prétot, C.; Le Pecq, J.-B.; Jacquemin-Sablon, A.; Chottard, J.-C. J. Biol. Chem. 1995, 270, 21251.
44. Drlica, K.; Franco, R. J. Biochemistry 1988, 27, 2253.
45. Osheroff, N. Pharmacol. Ther. 1989, 41, 223.
46. Liu, L. F. In DNA Topology and Its Biological Effects; Wang, J. C., Cozzarelli, N. R., Eds.; CSH Laboratory Press: Cold Spring Harbor, NY, 1990; pp 371-389.
47. Sundquist, W. I.; Bancroft, D. P.; Lippard, S. J. J. Am. Chem. Soc. 1990, 112, 1590.
48. Neidle, S. In DNA Structure and Recognition: Rickwood, D., Ed.; IRL Press: Oxford, England, 1994; pp 71-96 and literature cited therein.