Heavy Metal Nucleotide Interactions. 11. Stereochemical and Electronic Effects in the Electrophilic Attack of cis-and trans-Diammineplatinum(lI) on 5'-Guanosine Monophosphate and Polyguanylate in Aqueous Solution1, 2

Journal of the American Chemical Society

Volumn 100, Issue 2, 1978, Pages 593-606

  Chu, Grace Y H ^a   Mansy, Samir ^a   Duncan, Robert E ^a   Tobias, R Stuart ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947092789     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00470a039     Document Type: Article

References (59)

1. S. Mansy, Ph. D. Thesis, Michigan State University, East Lansing, Mich., 1972.
2. P. J. Stone, A. D. Kelman, and F. M. Sinex, Nature (London), 251, 736
3. P. J. Stone, A. D. Kelman, F. M. Sinex, M. M. Bhargava, and H. O. Halvorson. J. Mol. Biol., 104, 793 (1976).
4. L. L. Munchausen and R. O. Rahn: (a) Cancer Chemother. Rep., 59, 643 (1975);
5. Biochim. Biophys. Acta, 414, 242 (1975).
6. See, for example, the discussions in (a) B. Rosenberg, Naturwissenschaften, 60, 399 (1973);
7. M. J. Cleare and J. D. Hoeschele, Platinum Met. Rev., 17, 2 (1973);
8. M. J. Cleare, Coord. Chem. Rev., 12, 349 (1974);
9. A. J. Thomson, Platinum Met. Rev., 21, 2 (1977).
10. M. H. Grant, K. C. Wu, W. R. Bauer, and S. J. Lippard, Biochemistry, 15, 4339 (1976).
11. D. M. L. Goodgame, I. Jeeves, F. L. Phillips, and A. C. Skapski, Biochim. Biophys. Acta, 378, 153 (1975).
12. M. M. Millard, J. P. Macquet, and T. Theophanides, Biochim. Biophys. Acta, 402, 166 (1975);
13. J. P. Macquet and T. Theophanides, Bioinorg. Chem., 5, 59 (1975).
14. J. Dehand and J. Jordanov, J. Chem. Soc., Chem. Commun., 598 (1976).
15. The evidence against simultaneous N(7), C(6)=O binding has been summarized by G. P. P. Kuntz and G. Kotowycz, Biochemistry, 14, 4144 (1975).
16. D. J. Szalda, T. J. Kistenmacher, and L. G. Marzilli, J. Am. Chem. Soc., 98, 8371 (1976).
17. G. Y. H. Chu and R. S. Tobias, J. Am. Chem. Soc., 98, 2641 (1976).
18. F. B. Howard and H. T. Miles, J. Biol. Chem., 240, 801 (1965);
19. H. T. Miles and J. Frazier, Biochim. Biophys. Acta, 79, 216 (1964).
20. See the discussion in B. Singer, Prog. Nucleic Acid Res. Mol. Biol., 15, 219 (1975).
21. G. Y. H. Chu, R. E. Duncan, and R. S. Tobias, Inorg. Chem., 16, 2625 (1977).
22. G. B. Kauffman and D. O. Cowan, Inorg. Syn., 7, 239 (1963).
23. P. J. Hendra, Spectrochim. Acta, Part A, 23, 1275 (1967).
24. J. D. Hoeschele, “The Preparation, Purification and Analyses of cis-[PtCI2(NH3)2]”, Biophysics Department, Michigan State University, East Lansing, Mich.
25. P. K. Glascoe and F. H. Long, J. Phys. Chem., 64, 188 (1960).
26. S. Mansy and R. S. Tobias, Biochemistry, 14, 2952 (1975).
27. J. C. English, R. W. Chrisman, and R. S. Tobias, Appl. Spectrosc., 30, 168 (1976).
28. S. Mansy and R. S. Tobias, J. Am. Chem. Soc., 96, 6874 (1974).
29. R. Faggiani, B. Lippert, C. J. L. Lock, and B. Rosenberg, J. Am. Chem. Soc., 99, 777 (1977).
30. R. M. Izatt, J. J. Christensen, and J. H. Rytting, Chem. Rev., 71, 439 (1971).
31. P-C. Kong and T. Theophanides, Inorg. Chem., 13, 1167 (1974).
32. K. A. Jensen, Z. Anorg. Allg. Chem., 242, 87 (1939).
33. S. C. Erfurth and W. L. Peticolas, Biopolymers, 14, 247 (1975).
34. For GMP, see V. Gramlich, H. Klump, R. Herbeck, and E. D. Schmid, FEBS Lett., 69, 15 (1976).
35. J. Rice, L. Lafleur, G. C. Medeiros, and G. J. Thomas, Jr., J. Raman Spectrosc., 1, 207 (1973).
36. R. C. Lord and G. J. Thomas, Jr., Spectrochim. Acta, Part A, 23, 2551 (1967).
37. S. Mansy, T. E. Wood, J. C. Sprowles, and R. S. Tobias, J. Am. Chem. Soc., 96, 1762 (1974).
38. See M. Tsuboi in “Basic Principles in Nucleic Acid Chemistry”, Vol. 1, P. O. P. Tso, Ed., Academic Press, New York, N. Y., 1974, p 415.
39. H. T. Miles, F. B. Howard, and J. Frazier, Science, 142, 1458 (1963).
40. M. Ogawa and T. Sakaguchi, Chem. Pharm. Bull., 19, 1650 (1971).
41. A. T. Tu and J. A. Reinosa, Biochemistry, 5, 3375 (1966).
42. N. Hadjiliadis and T. Theophanides, Inorg. Chim. Acta, 16, 77 (1976).
43. See M. Tsuboi, S. Takahashi, and I. Harada in “Physico-Chemical Properties of Nucleic Acids”, J. Duchesne, Ed., Vol. 2, Academic Press, New York, N. Y., 1973, p 130.
44. S. Mansy and W. L. Peticolas, Biochemistry, 15, 2650 (1976).
45. R. B. Simpson, J. Am. Chem. Soc., 86, 2059 (1964).
46. R. W. Gellert and R. Bau, J. Am. Chem. Soc., 97, 7379 (1975).
47. P. L. Dahlstrom, R. E. Cramer, and M. Kashiwagi, Abstracts, 172nd National Meeting of the American Chemical Society, San Francisco, Calif., Sept 1976, INOR 124.
48. P. DeMeester, D. M. L. Goodgame, A. C. Skapski, and B. T. Smith, Biochim. Biophys. Acta, 340, 113 (1974).
49. H. Sober, Ed., “Handbook of Biochemistry”, 2nd ed, CRC Press, Cleveland, Ohio, 1970, p G-38.
50. H. Sigel, J. Am. Chem. Soc.,.97, 3209 (1975).
51. D. J. Nelson, P. L. Yeagle, T. L. Miller, and R. B. Martin, Bioinorg. Chem., 5, 353 (1976).
52. H. T. Miles and J. Frazier, Biochem. Biophys. Res. Commun., 49, 199 (1972).
53. See, e.g., F. Basolo and R. G. Pearson, “Mechanisms of Inorganic Reactions”, 2nd ed, Wiley, New York, N. Y., 1967, p 406; M. J. Carter and J. K. Beattie, Inorg. Chem., 9, 1233 (1970).
54. R. M. K. Dale, E. Martin, D. C. Livingston, and D. C. Ward, Biochemistry, 14, 2447 (1975).
55. L. D. Kosturko, C. Folzer, and R. F. Stewart, Biochemistry, 13, 3949 (1974).
56. L. Pauling, “The Nature of the Chemical Bond”, 3rd ed, Cornell University Press, Ithaca, N. Y., 1960, p 262.
57. J. K. Barton, H. N. Rabinowitz, D. J. Szalda, and S. J. Lippard, J. Am. Chem. Soc., 99, 2827 (1977).
58. K. Krogman, Angew. Chem., Int. Ed. Engl., 8, 35 (1969).
59. F. Pochon and A. M. Michelson, Proc. Natl. Acac. Sci. U. S. A., 53, 1425 (1965).