Preparation, 1H NMR Spectrum and Structure of ds-Diamminebis(l-methylcytosine )platinum(II) Nitrate-1-Methylcytosine. Cis Steric Effects in Pyrimidine Ring-Bound di-Bis(nucleic acid base)platinum(II) Compounds

Journal of the American Chemical Society

Volumn 103, Issue 17, 1981, Pages 5126-5133

  Orbell, John D ^a   Kistenmacher, Thomas J ^a   Marzilli, Luigi G ^b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; CYTIDINE; GUANOSINE; HYPOXANTHINE DERIVATIVE; INOSINE; THYMINE; URIDINE;

1 METHYLCYTOSINE; 3' CYTIDYLIC ACID; DRUG ANALYSIS; DRUG COMPARISON; DRUG INTERACTION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; PLATINUM CIS DIAMMINEBIS(1 METHYLCYTOSINE) NITRATE; PROTON NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY; X RAY ANALYSIS;

EID: 0019489762     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00407a029     Document Type: Article

References (59)

1. Rosenberg, B.; Van Camp, L.; Trosko, J. E.; Mansour, V. H. Nature (London) 1969, 222, 385. For a recent review, see: Biochimie 1978, 60, No. 9.
2. Roberts, J. J.; Thomson, A. J. Prog. Nucleic Acid Res. Mol. Biol. 1979, 22, 71.
3. Roberts, J. J. Adv. Inorg. Biochem., in press.
4. de Castro, B.; Kistenmacher, T. J.; Marzilli, L. G. in “Trace Elements in the Pathogenesis and Treatment of Inflammatory Conditions”; Rainsford, K. D., Bruñe, K., Whitehouse, M. W., Eds.; Agents and Actions: Basel, 1981.
5. Marzilli, L. G.; Kistenmacher, T. J.; Eichhorn, G. L. In “Nucleic Acid-Metal Ion Interactions”; Spiro, T. G., Ed.; Wiley: New York, 1980; Chapter 5.
6. Barton, J. K.; Lippard, S. J. Agents and Actions: Basel; Chapter 2.
7. Marzilli, L. G. Adv. Inorg. Biochem., in press.
8. Stone, P. J.; Kelman, A. J.; Sinex, F. M. Nature (London) 1974, 251, 736.
9. Cohen, G. L.; Ledner, J. A.; Bauer, W. R.; Ushay, H. M.; Caravana, C.; Lippard, S. J. J. Am. Chem. Soc. 1980, 102, 2487.
10. Scovell, W. M.; O'Connor, T. J. Am. Chem. Soc. 1977, 99, 120. For a critical update see: Vestues, P. I.; Martin, R. B. J. Am. Chem. Soc. 1981, 102, 806.
11. Robins, A. B. Chem.-Biol. Interact. 1973, 6, 35; 7, 11.
12. Mansy, S.; Chu, G. Y. H.; Duncan, R. E.; Tobias, R. S. J. Am. Chem. Soc. 1978, 100, 607.
13. Inagaki, K.; Kidani, Y. J. Inorg. Biochem. 1979, 11, 39.
14. Jordanov, J.; Williams, R. J. P. Bioinorg. Chem. 1978, 8, 77.
15. Chottard, J. C.; Girault, J. P.; Chottard, G.; Lallemand, J. Y.; Mansuy, D. J. Am. Chem. Soc. 1980, 102, 5565.
16. Marzilli, L. G. Prog. Inorg. Chem. 1977, 23, 255.
17. Kelman, A. D.; Buchbinder, M. Biochimie 1978, 60, 893.
18. Kistenmacher, T. J.; de Castro, B.; Wilkowski, K.; Marzilli, L. G. J. Inorg. Biochem., in press.
19. Gellert, R. W.; Bau, R. J. Am. Chem. Soc. 1975, 97, 7379.
20. Cramer, R. E.; Dahlstrom, P. L. J. Clin. Hematol. Oncol. 1977, 7, 330. Cramer, R. E.; Dahlstrom, P. L.; Seu, M. J. T.; Norton, T.; Kashiwagi, M. Inorg. Chem. 1980, 19, 148.
21. Goodgame, D. M. L.; Jeeves, I.; Phillips, F. L.; Skapski, A. C. Biochim. Biophys. Acta 1975, 378, 153.
22. Bau, R.; Gellert, R. W.; Lehovec, S. M.; Louie, S. J. Clin. Hematol. Oncol. 1977, 7, 51.
23. Kistenmacher, T. J.; Chiang, C. C.; Chalilpoyil, P.; Marzilli, L. G. Biochem. Biophys. Res. Commun. 1978, 84, 70.
24. Kistenmacher, T. J.; Chiang, C. C.; Chalilpoyil, P.; Marzilli, L. G. J. Am. Chem. Soc. 1979, 101, 1143.
25. Bau, R.; Gellert, R. W. Biochimie 1978, 60, 1040.
26. Marzilli, L. G.; Chalilpoyil, P.; Chiang, C. C.; Kistenmacher, T. J. J. Am. Chem. Soc. 1980, 102, 2480.
27. Faggiani, R.; Lock, C. J. L.; Lippert, B. J. Am. Chem. Soc. 1980,102, 5419.
28. Wu, S. M.; Bau, R. Biochem. Biophys. Res. Commun. 1979, 88, 1435.
29. Kistenmacher, T. J.; Wilkowski, K.; de Castro, B.; Chiang, C. C.; Marzilli, L. G. Biochem. Biophys. Res. Commun. 1979, 91, 1521.
30. de Castro, B.; Chiang, C. C.; Wilkowski, K.; Marzilli, L. G.; Kistenmacher, T. J. Inorg. Chem. 1981, 20, 1835.
31. Kistenmacher, T. J.; Rossi, M.; Caradonna, J. P.; Marzilli, L. G. Adv. Mol. Relaxation Interact. Processes 1979, 15, 119.
32. Sakai, T. T.; Pogolotti, A. L.; Santi, D. V. J. Heterocyl. Chem. 1968, 5, 849.
33. Dhara, S. C. Indian J. Chem. 1970, 8, 193.
34. Barton, J. K.; Szalda, D. J.; Rabinowitz, H. N.; Waszczak, J. V.; Lippard, S. J. J. Am. Chem. Soc. 1979, 101, 1434 and references therein.
35. Busing, W. R.; Levy, H. A. J. Chem. Phys. 1957, 26, 563.
36. Wilson, A. J. C. Nature (London) 1942, 150, 152.
37. Hanson, H. P.; Herman, F.; Lea, J. D.; Skill man, S. Acta Crystallogr. 1964, 17, 1040.
38. Stewart, R. F.; Davidson, E. R.; Simpson, W. T. J. Chem. Phys. 1965, 42, 3175.
39. Cromer, D. T.; Liberman, D. J. Chem. Phys. 1970, 53, 1891.
40. Lippert, B.; Pfab, R.; Neugebauer, D. Inorg. Chim. Acta 1979, 37, L495.
41. Melanson, R.; Rochon, F. C. Inorg. Chem. 1978, 17, 679.
42. Lock, C. J. L.; Speranzini, R. A.; Powell, J. Can. J. Chem. 1976, 54, 53.
43. Louie, S.; Bau, R. J. Am. Chem. Soc. 1977, 99, 3874.
44. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
45. Rossi, M.; Kistenmacher, T. J. Acta Crystallogr., Sect. B 1977, B33, 3962.
46. Szalda, D. J.; Kistenmacher, T. J.; Marzilli, L. G. Inorg. Chem. 1975, 14, 2623 and references therein.
47. Marzilli, L. G.; Chang, C.-H.; Caradonna, J. P.; Kistenmacher, T. J. Adv. Mol. Relaxation Interact. Processes 1979, 15, 85.
48. Kong, P. C.; Theophanides, T. Inorg. Chem. 1974, 13, 1167.
49. Kong, P. C.; Theophanides, T. Inorg. Chem. 1974, 13, 1981.
50. Chu, G. Y. H.; Duncan, R. E.; Tobias, R. S. Inorg. Chem. 1977,16, 2625.
51. Lallemand, J. Y.; Soulie, J.; Chottard, J. C. J. Chem. Soc., Chem. Commun. 1980, 436.
52. Sorrell, T.; Epps, L. A.; Kistenmacher, T. J.; Marzilli, L. G. J. Am. Chem. Soc. 1978, 100, 5756.
53. Cramer, R. E.; Dahlstrom, P. L. J. Am. Chem. Soc. 1979,101, 3679.
54. Chati, I.; Shaw, B. L. J. Chem. Soc. 1960, 1718.
55. Orchin, M.; Schmidt, P. J. Inorg. Chim. Acta Rev. 1968, 2, 123.
56. Orbell, J. D.; de Castro, B.; Wilkowski, K.; Marzilli, L. G.; Kistenmacher, T. J., to be submitted for publication.
57. Rosenberg, B. Biochimie 1978, 60, 859.
58. Lippert, B.; Lock, C. J. L.; Speranzini, R. A. Inorg. Chem. 1981, 20, 335.
59. Lippert, B.; Lock, C. J. L.; Speranzini, R. A. Inorg. Chem. 1981, 20, 808.