Skip to main content

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 11))

Abstract

The platinum—pyrimidine blues, derived from cisplatin, are an interesting class of complexes with antitumour activity. They were first discovered as a result of studies on the interaction of cis-[PtCl2(NH3)2] and its aquated products with pyrimidines. The identification of DNA as the target for platinum attack naturally led to a systematic study of the reactions of the complex with nucleic acid constituents. The observation that with polyuridine no immediate reaction took place but that a blue color slowly developed in solution, from which a blue solid could be isolated, led to the preparation of a series of complexes containing substituted uracils and thymines.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J. P. Davidson, P. J. Faber, R. G. Fischer, Jr., S. Mansy, H. J. Peresie, B. Rosenberg, and L. VanCamp: Cancer Chemother Rep. 59 (Part 1), 287 (1975).

    CAS  Google Scholar 

  2. W. Bauer, S. L. Gonias, S. K. Kam, K. C. Wu, and S. J. Lippard: Biochemistry 17, 1060 (1978).

    Article  CAS  Google Scholar 

  3. J. D. Zimbrick, A. Sukrochana, and R. C. Richmond: Int. J. Radiat. Oncol. Biol. Phys. 5, 1351 (1979).

    CAS  Google Scholar 

  4. B. Lippert: J. Clin. Hematol. Oncol. 7, 26 (1977).

    CAS  Google Scholar 

  5. A. J. Thomson, I. A. G. Roos, and R. D. Graham: J. Clin. Hematol. Oncol. 7, 242 (1977).

    CAS  Google Scholar 

  6. K. V. Shooter, R. Howse, R. K. Merrifield, and A. B. Robins: Chem.-Biol. Interactions 5, 289 (1972).

    Article  CAS  Google Scholar 

  7. R. D. MacFarlane and D. F. Torgerson: Science 191, 920 (1976).

    Article  CAS  Google Scholar 

  8. J. D. Woollins and B. Rosenberg: Inorg. Chem. 21, 1280 (1982).

    Article  CAS  Google Scholar 

  9. B.-K. Teo, K. Kijima, and R. Bau: J. Am. Chem. Soc. 100, 621 (1978).

    Article  CAS  Google Scholar 

  10. K. A. Hoffman and G. Bugge: Chem. Ber. 41, 312 (1908).

    Article  Google Scholar 

  11. G. C. Allen and N. S. Hush: Prog. Inorg. Chem. 8, 357 (1967).

    Article  CAS  Google Scholar 

  12. C. A. Chang, R. B. Marcotte, and H. H. Patterson: Inorg. Chem. 20, 1632 (1981).

    Article  CAS  Google Scholar 

  13. T. G. Appleton, R. D. Berry, and J. R. Hall: Inorg. Chim. Acta 64, L229 (1982).

    Article  CAS  Google Scholar 

  14. H. Neubacher, J. Krieger, P. Zaplatynski, and W. Lohmann: Z. Naturforsch. Part B 37, 790 (1982).

    Google Scholar 

  15. D. M. L. Goodgame and I. Jeeves: Z. Naturforsch. Part C 34, 1287 (1979).

    Google Scholar 

  16. H. Neubacher, P. Zaplatynski, A. Haase, and W. Lohmann: Z. Naturforsch. Part B 34, 1015 (1979).

    Google Scholar 

  17. P. Arrizabalaga, P. Castan, and J. P. Laurent: J. Am. Chem. Soc. 106, 1300 (1984).

    Article  CAS  Google Scholar 

  18. P. Arrizabalaga, P. Castan, and J. P. Laurent: Inorg. Chim. Acta 66, L9 (1982).

    Article  CAS  Google Scholar 

  19. P. Arrizabalaga, P. Castan, and J. P. Laurent: Z. Naturforsch. Part B 35, 1508 (1980).

    Google Scholar 

  20. J. P. Laurent, P. Lepage, P. Castan, and P. Arrizabalaga: Inorg. Chim. Acta 67, 31 (1981).

    Article  Google Scholar 

  21. J. H. Burness, M. J. Bandurski, L. J. Passman, and B. Rosenberg: J. Clin. Hematol. Oncol. 7, 508 (1977).

    CAS  Google Scholar 

  22. P. Arrizabalaga, P. Castan, and J. P. Laurent: Transition Met. Chem. 5, 204 (1980).

    Article  CAS  Google Scholar 

  23. R. Ettore: Inorg. Chim. Acta 46, L27 (1980).

    Article  Google Scholar 

  24. J. K. Barton, D. J. Szalda, H. N. Rabinowitz, J. V. Waszczak, and S. J. Lippard: J. Am. Chem. Soc. 101, 1434 (1979).

    Article  CAS  Google Scholar 

  25. T. V. O’Halloran, M. M. Roberts, and S. J. Lippard: J. Am. Chem. Soc. 106, 6427 (1984).

    Article  Google Scholar 

  26. P. K. Mascharak, I. D. Williams, and S. J. Lippard: J. Am. Chem. Soc. 106, 6428 (1984).

    Article  CAS  Google Scholar 

  27. J. K. Barton, S. A. Best, S. J. Lippard, and R. A. Walton: J. Am. Chem. Soc. 100, 3785 (1978).

    Article  CAS  Google Scholar 

  28. J. K. Barton and S. J. Lippard: Ann. N. Y. Acad. Sci. 313, 686 (1978).

    Article  CAS  Google Scholar 

  29. J. D. Woollins and P. F. Kelly: Coord. Chem. Rev. 65, 115 (1985).

    Article  CAS  Google Scholar 

  30. B. Lippert: Inorg. Chem. 20, 4326 (1981).

    Article  CAS  Google Scholar 

  31. B. Lippert: Platinum(II) Complex Formation with Uracil and Thymine (Platinum, Gold, and Other Metal Chemotherapeutic Agents, ACS Symposium Series 209, Ed. S. J. Lippard), p. 147. ACS Washington (1983).

    Chapter  Google Scholar 

  32. D. Neuegebauer and B. Lippert: J. Am. Chem. Soc. 104, 6596 (1982).

    Article  Google Scholar 

  33. B. Lippert: Inorg. Chim. Acta 55, 5 (1981).

    Article  CAS  Google Scholar 

  34. H. Schöllhorn, U. Thewalt, and B. Lippert: Inorg. Chim. Acta 106, 177 (1985).

    Article  Google Scholar 

  35. R. Faggiani, B. Lippert, and C. J. L. Lock: Inorg. Chem. 19, 295 (1980).

    Article  CAS  Google Scholar 

  36. L. S. Hollis and S. J. Lippard: J. Am. Chem. Soc. 103, 1230 (1981).

    Article  CAS  Google Scholar 

  37. L. S. Hollis and S. J. Lippard: J. Am. Chem. Soc. 105, 3494 (1983).

    Article  CAS  Google Scholar 

  38. B. Lippert, D. Neugebauer, and G. Raudaschl: Inorg. Chim. Acta 78, 161 (1983).

    Article  CAS  Google Scholar 

  39. J. F. Britten, B. Lippert, C. J. L. Lock, and P. Pilon: Inorg. Chem. 21, 1936 (1982).

    Article  CAS  Google Scholar 

  40. F. Guay and A. Beauchamp: J. Am. Chem. Soc. 101, 6260 (1979).

    Article  CAS  Google Scholar 

  41. F. Guay and A. Beauchamp: Inorg. Chim. Acta 66, 57 (1982).

    Article  CAS  Google Scholar 

  42. D. M. L. Goodgame, R. W. Rollins, and B. Lippert: Polyhedron 4, 829 (1985).

    Article  CAS  Google Scholar 

  43. D. M. L. Goodgame, M. A. Hitchman, and B. Lippert: Inorg. Chem. 25, 2191 (1986).

    Article  CAS  Google Scholar 

  44. U. Thewalt, D. Neugebauer, and B. Lippert: Inorg. Chem. 23, 1713 (1984).

    Article  CAS  Google Scholar 

  45. H. Schöllhorn, U. Thewalt, and B. Lippert: J. Chem. Soc. Chem. Comm. 769 (1984).

    Google Scholar 

  46. C. J. L. Lock, H. J. Peresie, B. Rosenberg, and G. Turner: J. Am. Chem. Soc. 100, 3371 (1978).

    Article  CAS  Google Scholar 

  47. R. Faggiani, C. J. L. Lock, R. J. Pollock, B. Rosenberg, and G. Turner: Inorg. Chem. 20, 804 (1981).

    Article  CAS  Google Scholar 

  48. R. Faggiani, Lippert, C. J. L. Lock, and R. A. Speranzini: J. Am. Chem. Soc. 103, 1111 (1981).

    Article  CAS  Google Scholar 

  49. L. S. Hollis and S. J. Lippard: Inorg. Chem. 22, 2600 (1983).

    Article  CAS  Google Scholar 

  50. J.-P. Laurent, P. Lepage, and F. Dahan: J. Am. Chem. Soc. 104, 7335 (1982).

    Article  CAS  Google Scholar 

  51. H. Schöllhorn, U. Thewalt, and B. Lippert: Inorg. Chim. Acta 93, 19 (1984).

    Article  Google Scholar 

  52. K. Matsumoto and K. Fuwa: J. Am. Chem. Soc. 104, 897 (1982).

    Article  CAS  Google Scholar 

  53. K Matsumoto, H. Takahashi, and K. Fuwa: J. Am. Chem. Soc. 106, 2049 (1984).

    Article  CAS  Google Scholar 

  54. L. S. Hollis and S. J. Lippard: Inorg. Chem. 21, 2116 (1982).

    Article  CAS  Google Scholar 

  55. H. Schöllhorn, P. Eisenmann, U. Thewalt, and B. Lippert: Inorg. Chem. 25, 3384 (1986).

    Article  Google Scholar 

  56. B. Lippert and D. Neugebauer: Inorg. Chem. 21, 451 (1981).

    Article  Google Scholar 

  57. L. S. Hollis, M. M. Roberts, and S. J. Lippard: Inorg. Chem. 22, 3637 (1983).

    Article  CAS  Google Scholar 

  58. E. B. Boyar and S. D. Robinson: Coord. Chem. Rev. 50, 109 (1983).

    Article  CAS  Google Scholar 

  59. T. R. Felthouse: Prog. Inorg. Chem. 29, 73 (1982).

    Article  CAS  Google Scholar 

  60. T. V. O’Halloran and S. J. Lippard: Isr. J. Chem. 25, 130 (1985).

    Google Scholar 

  61. T. Ramstad, J. D. Woollins, and M. J. Weaver: Inorg. Chim. Acta 124, 187 (1986).

    Article  CAS  Google Scholar 

  62. T. V. O’Halloran, M. M. Roberts, and S. J. Lippard: Inorg. Chem. 25, 957 (1986).

    Article  Google Scholar 

  63. B. Lippert, H. Schöllhorn, and U. Thewalt: J. Am. Chem. Soc. 108, 525 (1986).

    Article  CAS  Google Scholar 

  64. B. Lippert, H. Schöllhorn, and U. Thewalt: Inorg. Chem. 25, 407 (1986).

    Article  CAS  Google Scholar 

  65. J. K. Barton, C. Caravana, and S. J. Lippard: J. Am. Chem. Soc. 101, 7269 (1979).

    Article  CAS  Google Scholar 

  66. J. K. Barton, S. A. Best, S. J. Lippard, and R. A. Walton: J. Am. Chem. Soc. 100, 3785 (1978).

    Article  CAS  Google Scholar 

  67. A. P. Ginsberg, T. V. O’Halloran, P. E. Fanwick, L. S. Hollis, and S. J. Lippard: J. Am. Chem. Soc. 106, 5430 (1984).

    Article  CAS  Google Scholar 

  68. M. B. Robin and P. Day: Adv. Inorg. Chem. Radiochem. 10, 247 (1967).

    Article  CAS  Google Scholar 

  69. C. C. F. Blake, S. J. Oatley, and R. J. P. Williams: J. Chem. Soc. Chem. Comm. 1043 (1976).

    Google Scholar 

  70. J. D. Woollins and B. Rosenberg: J. Inorg. Biochem. 19, 41 (1983).

    Article  CAS  Google Scholar 

  71. S. K. Aggarwal, R. W. Wagner, P. K. McAllister, and B. Rosenberg: Proc. Nat. Acad. Sci. U.S.A. 72, 928 (1975).

    Article  CAS  Google Scholar 

  72. P. K. McAllister, B. Rosenberg, S. K. Aggarwal, and R. W. Wagner: J. Clin. Hematol. Oncol. 7, 717 (1977).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1989 Kluwer Academic Publishers

About this chapter

Cite this chapter

Farrell, N. (1989). The Platinum—Pyrimidine Blues. In: Transition Metal Complexes as Drugs and Chemotherapeutic Agents. Catalysis by Metal Complexes, vol 11. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-7568-5_6

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-7568-5_6

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-011-7570-8

  • Online ISBN: 978-94-011-7568-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics