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Aqueous Solution Synthesis of Platinum II Polyureas, Polythioureas and Polyamides

  • Charles E. CarraherJr.
  • Tushar A. Manek
  • David J. Giron
  • Mary L. Trombley
  • Kathy M. Casberg
  • William J. Scott
Part of the Polymer Science and Technology book series (POLS, volume 25)

Abstract

Malignant neoplasms are the second leading cause of death in the United States. Until the late 1960’s little effort was made towards the synthesis and characterization of antineoplastic agents except for totally organic compounds. In 1964 Barnett Rosenberg and coworkers discovered by chance that bacteria failed to divide, but continued to grow giving filamentous cells in the presence of platinum electrodes (1). The cause of this inhibition to cell division was eventually traced to small concentrations (about 10 ppm) of cis-dichlorodiamineplatinum II (cis-DDP) and cis-tetrachlorodiamineplatinum IV (cis-TCP). This ability to inhibit bacterial cell division prompted their trial as antitumor agents. Both compounds were found to be active against Sarcoma 180 and Leukemia L1210 test tumors in mice with cis-DDP having greater activity than cis-TCP (2,3). In fact cis-DDP is active against a wide range of tumors in animals (4) and man (5) including several which are particularly resistant to treatment by other techniques such as ovarian and testicular carcinomas.

Keywords

Platinum Complex Platinum Compound Molecular Weight Determination Clinical Hematology Alcaligenes Faecalis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    B. Rosenberg, L. Van Camp and T. Krigas, Nature (London), 205, 698 (1965).ADSCrossRefGoogle Scholar
  2. 2.
    B. Rosenberg, L. Van Camp, J. Trosko, and V. Mansour, Nature (London), 222, 385 (1969).ADSCrossRefGoogle Scholar
  3. 3.
    B. Rosenberg, Plat. Metals Rev., 15, 42 (1971).Google Scholar
  4. 4.
    B. Rosenberg, Cancer Chemother. Rep., Pt. 1, 59, 589 (1975).Google Scholar
  5. 5.
    J. Gottlieb and B. Drewinko, Cancer Chemother. Rep., Pt. 1, 59, 621 (1975).Google Scholar
  6. 6.
    J. Howle, G. Gale and A. B. Smith, Biochem. Pharm., 21, 1465 (1972).CrossRefGoogle Scholar
  7. 7.
    J. Hill, E. Loeb, A. Machellan, N. Hill, A. Khan and J. King, Cancer Chemother. Rep., Pt. 1, 59, 647 (1975).Google Scholar
  8. 8.
    P. Kamalakar, A. Freeman, D. Higby, H. Wallace and L. Sinks, Cancer Treatments. Rep., 61, 835 (1977).Google Scholar
  9. 9.
    J. Ward, D. Young, K. Fauvie, M. Wolpert, R. Davis and A. Guarino, Cancer Treatment. Rep., 60, 1675 (1976).Google Scholar
  10. 10.
    A. Kahan, J. Hill, W. Grater, E. Loeb, A. MacLellan and N. Hill, Cancer Res., 35, 2766 (1975).Google Scholar
  11. 11.
    J. Holland, J. Rowland and M. Plumb, Cancer Res., 37, 2425 (1977).Google Scholar
  12. 12.
    S. Sallan, N. Zinberg and E. Frei, New England J. of Med., 293, 795 (1975).CrossRefGoogle Scholar
  13. 13.
    S. Stadnicki, R. Fleischman, U. Schaeppi and P. Merrimam, Cancer Chemother. Rep., Pt. 1, 59, 467 (1975).Google Scholar
  14. 14.
    J. Ward and K. Fauvie, Tox. and Appl. Pharm., 38, 535 (1976).CrossRefGoogle Scholar
  15. 15.
    C. Litterset, T. Gram, R. Dedrick, A. Leroy and A. Guarino, Cancer Res., 36, 2340 (1966).Google Scholar
  16. 16.
    K.P. Lewis, W.D. Medina, Cancer Treat. Rep., 64 (10–11), 1162 (1980).Google Scholar
  17. 17.
    M.S. Aapro and D.S. Alberts, Cancer Chemother. Pharmacol., 7 (1), 11 (1981).Google Scholar
  18. 18.
    D. Hayes, E. Cvitokovic, R. Golby, E. Scheiner and I. Krakoff, Proceedings of American Assoc. Cancer Res., 17, 169 (1976).Google Scholar
  19. 19.
    K. Chary, D. Higby, E. Henderson and K. Swinerton, Cancer Treat. Rep., 61, 367 (1977).Google Scholar
  20. 20.
    K. Chary, D. Higby, E. Henderson and K. Swingerton, J. Clinical Hematology and Oncology, 7, 633 (1977).Google Scholar
  21. 21.
    C. Merrin, Proceedings American Assoc. Cancer Res., 17, 243 1976 and 18, 298 (1977).ADSGoogle Scholar
  22. 22.
    L. Einhorn and B. Furnas, J. Clinical Hematology and Oncology, 7, 662 (1976).Google Scholar
  23. 23.
    H. Bruckner, C. Cohen, G. Deppe, B. Kabakow, R. Wallach, E. Greenspal, S. Gusberg and J. Holland, J. Clinical Hematology and Oncology, 7, 619 (1977).Google Scholar
  24. 24.
    R. Kwong and B. Kennedy, Proceedings of American Assoc. Cancer Res., 18, 317 (1977).Google Scholar
  25. 25.
    J.A. Mabel, P.C. Merker, M.L. Sturgeon, I. Wodinsky and R.K. Geran, Cancer, 42 (2), 217 (1980).Google Scholar
  26. 26.
    M.H. Amer, R.M. Izbick, V.K. Vaitkerleins and M. AlSarraf, Cancer, 45 (2), 217 (1980).CrossRefGoogle Scholar
  27. 27.
    H. Takita, F. Edgerton, P. Marabella, D. Conway and S. Harguindey, Cancer, 48 (7), 1528 (1981).CrossRefGoogle Scholar
  28. 28.
    M. Cleare, Coord. Chem. Revs., 12, 349 (1974).ADSCrossRefGoogle Scholar
  29. 29.
    R. Speer, H. Ridgway, L. Hall, D. Stewart, K. Howe, D. Lieberman and J. Hill, Wadley Medical Bull., 5, 19 (1975).Google Scholar
  30. 30.
    R. Speer, H. Ridgway, L. Hall, A. Newman, K. Howe, D. Stewart, G. Edwards, and J. Hill, Wadley Medical Bull., 5, 335 (1975).Google Scholar
  31. 31.
    Y. Kidani, K. Indgaki, R. Saito and S. Tsukagoshi, J. Clinical Hematology and Oncology, 7, 197 (1977).Google Scholar
  32. 32.
    E. Loeb, J. Hill, A. Pardue, N. Hill, A. Khan and J. King, J. Clinical Hematology and Oncology, 7, 701 (1977).Google Scholar
  33. 33.
    M. Cleare and J. Hoeschele, Platinum Metals Rev., 17, 2 (1973).Google Scholar
  34. 34.
    M. Cleare and J. Hoeschele, Bioinorg. Chem., 2, 187 (1973).CrossRefGoogle Scholar
  35. 35.
    P. Schwartz, S. Meischen, G. Gale, L. Atkins, A. Smith and E. Walker, Cancer Treat. Rep., 61, 1519 (1977).Google Scholar
  36. 36.
    M. Tobe and A. Khokhar, J. Clinical Hematology and Oncology, 7, 114 (1977).Google Scholar
  37. 37.
    H. Allcock, R. Allen and J. O’Brien, Chem. Comm., 717 (1976).Google Scholar
  38. 38.
    H. Allcock, Science, 193, 1214 (1976).ADSCrossRefGoogle Scholar
  39. 39.
    H. Allcock, Polymer Preprints, 18, 857 (1977).Google Scholar
  40. 40.
    H. Allcock, Organometallic Polymers (C. Carraher, J. Sheats and C. Pittman, Editors), Academic Press, N.Y. (1978), pgs. 283–288.Google Scholar
  41. 41.
    H. Allcock, R. Allen and J. O’Brien, J. Amer. Chem. Soc., 99, 3984 (1977).CrossRefGoogle Scholar
  42. 42.
    C. Carraher, C. Admu-John and J. Fortman, unpublished results.Google Scholar
  43. 43.
    C. Carraher, D.J. Giron, I. Lopez, D.R. Cerutis and W.J. Scott, Organic Coatings and Plastics Chemistry, 44, 120 (1981).Google Scholar
  44. 44.
    C. Carraher, W.J. Scott, J.A. Schroeder and D.J. Giron, J. Macromol. Sci.-Chem. A15 (4), 625 (1981).CrossRefGoogle Scholar
  45. 45.
    C. Carraher, Organic Coatings and Plastics Chemistry, 42, 428 (1980).Google Scholar
  46. 46.
    C. Carraher, T. Manek, D. Giron, D.R. Cerutis and M. Trombley, Polymer Preprints, 23 (2), 77 (1982).Google Scholar
  47. 47.
    C. Carraher and A. Gasper, Polymer Preprints, 23 (2), 75 (1982).Google Scholar
  48. 48.
    C. Carraher, Biomedical and Dental Applications of Polymers (G. Gebelein and F. Koblitz, editors), Plenum Press, N.Y., 1981, Chpt. 16.Google Scholar
  49. 49.
    C. Carraher, D.J. Giron, T. Manek and D. Blair, unpublished results.Google Scholar
  50. 50.
    C. Carraher, H.M. Molloy, M.L. Taylor, T.O. Tiernan and W.J. Scott, unpublished results.Google Scholar
  51. 51.
    R. Speer, H. Ridgway, L. Hall, D. Stewart, K. Howe, D. Lieberman, D.A. Newman and J. Hill, Cancer Chemother. Rep., Pt. 1, 59, 629 (1975).Google Scholar
  52. 52.
    M. Tucker, C. Colvin and D. Martin, Inorganic Chem., 3, 1373 (1964).CrossRefGoogle Scholar
  53. 53.
    C. Colvin, R. Gunther, L. Hunter, J. McLean, M. Tucker and D. Martin, Inorganic Chimica Acta, 3, 487 (1968).Google Scholar
  54. 54.
    T. Conners, M. Jones, W. Ross, P. Braddock, A. Khokharard, M. Tobe, Chemico-Biological Interactions, 5, 415 (1972).CrossRefGoogle Scholar
  55. 55.
    K. Inagaki, Y. Kidani, K. Suzuki and T. Tashiro, Chem. Pharm. Bull. (Tokyo), 28 (8), 2286 (1980).CrossRefGoogle Scholar
  56. 56.
    K. Okamoto, M. Noji, T. Tashiro and Y. Kidani, Chem. Pharm. Bull. (Tokyo), 29 (4), 929 (1981).CrossRefGoogle Scholar
  57. 57.
    P. Ribaud, D.P. Kelsen, N. Alcock, G.E. Garcia, P. Dubouch, C.C. Young, F. Muggin, J. Burchenal and G. Mathe, Recent Results Cancer Res., 74, 156 (1980).CrossRefGoogle Scholar
  58. 58.
    C. Carraher, W.J. Scott and D.J. Giron, “Bioactive Polymers,” (Edited by C. Gebelein and C. Carraher) Plenum, 1983.Google Scholar
  59. 59.
    G. Rowland, G. O’Neil and D. Davis, Nature, 255, 487 (1975).ADSCrossRefGoogle Scholar
  60. 60.
    H. Ringsorf, Middland Macromolecules Meeting (Edited by H. Elias ), Marcel Dekker, N.Y., 1978.Google Scholar
  61. 61.
    H.J. Ryser, Nature, 215, 934 (1967).ADSCrossRefGoogle Scholar
  62. 62.
    J.H. Burchenal, K. Kalaher, K. Dew, L. Lokys and G. Gale, Biochimie, 60, 961 (1978).CrossRefGoogle Scholar
  63. 63.
    L.A. Zwelling, J. Filipski and K.W. Kohn, Cancer Research, 39, 4989 (1979).Google Scholar
  64. 64.
    J. Filipski, K.W. Kohn, R. Prather and W.M. Bonner, Science, 204 (13), 182 (1979).ADSGoogle Scholar
  65. 65.
    F. Basolo and R.G. Pearson, Prog. Inorg. Chem., 4, 381 (1962).CrossRefGoogle Scholar
  66. 66.
    A.A. Grinberg, M. Serator and M.I. Gel’fman, Russian J. Inorg. Chem., 13 1695 (1968).Google Scholar
  67. 67.
    G. Barrow, R. Krueger and F. Basolo, J. Inorganic and Nuclear Chemistry, 2, 340 (1956).CrossRefGoogle Scholar
  68. 68.
    C. Carraher and J. Schroeder, Polymer Letters, 13, 215 (1975).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1984

Authors and Affiliations

  • Charles E. CarraherJr.
  • Tushar A. Manek
    • 1
  • David J. Giron
    • 2
  • Mary L. Trombley
    • 1
    • 2
  • Kathy M. Casberg
    • 2
  • William J. Scott
    • 1
  1. 1.Departments of ChemistryWright State UniversityDaytonUSA
  2. 2.Department of Microbiology and ImmunologyWright State UniversityDaytonUSA

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