Complexes of Peptides and Related Molecules with Diammineplatinum (II) as Models for Platinum-Protein Interactions

  • Trevor G. Appleton
  • John R. Hall
  • Paul D. Prenzler
  • Fraser B. Ross

Abstract

There is ample evidence that the primary target of platinum anti-tumor drugs is DNA, which has caused much interest in the chemistry of platinum complexes of nucleobases.1 If, however, one wishes fully to understand the biological chemistry of the platinum compounds, it is also necessary to consider their interaction with other potential ligands which are present in vivo. Among the more important of these are proteins, peptides, and amino acids. Reaction of platinum drugs with these compounds may have the following effects:2
  1. (i)

    To the extent that the platinum compounds react with such molecules, they are prevented from reacting with the target DNA.

     
  2. (ii)

    Some of the toxic side-effects of platinum drugs are due to platinum-protein interactions.

     
  3. (iii)

    Some forms of resistance of tumor cells toward platinum drugs may be due to enhanced coordination by peptides and proteins.

     

Keywords

Nuclear Magnetic Resonance Imidazole Ring Chelate Ring Platinum Complex Platinum Compound 
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. Lippert, “Platinum Nucleobase Chemistry.”, Prog. Inorg. Chem. 37: 1–97 1989.CrossRefGoogle Scholar
  2. 2.
    A. Eastman, “Cross-Linking of Glutathione to DNA by Cancer Chemotherapeutic Platinum Coordination Complexes.”, Chem.-Biol. Interactions 61: 241–248 1987.CrossRefGoogle Scholar
  3. 3.
    T. G. Appleton, J. R. Hall, and S. F. Ralph, “Reactions of Platinum(II) Aqua Complexes. 3. Multinuclear (15N, 195Pt, 13C, and 1H) NMR study of Aqua and Hydroxo Complexes with Glycine and (Methylimino)diacetic Acid.”, Inorg. Chem. 24: 673–677 1985.CrossRefGoogle Scholar
  4. 4.
    T. G. Appleton, J. R. Hall, and S. F. Ralph, 15N and 195Pt N.M.R. Study of the Effect_of Chain length on the Reactions of the Amino Acids +NH3(CH2)nCO2 (n = 1, 2, 3; with Platinum(II) Ammine Complexes.”, Aust. J. Chem. 39: 1347–1362 1986.CrossRefGoogle Scholar
  5. 5.
    T. G. Appleton, J. R. Hall, and P. D. Prenzler, “Reaction of the cis-Diamminediaquaplatinum(II) Cation with N-Acetylglycine.”, Inorg. Chem. 28: 815–819 1989.CrossRefGoogle Scholar
  6. 6.
    T. G. Appleton, J. R. Hall, T. W. Hambley, and P. D. Prenzler, “Reactions of the cis-Diamminediaquaplatinum(II) Cation with Glycinamide, N-Glycylglycine, and N-(N-Glycylglycyl)glycine. Crystal Structure of a Complex with Two Diammineplatinum(II) Cations Bound to Glycylglycinate.”, Inorg. Chem. 29: 3562–3569 1990.CrossRefGoogle Scholar
  7. 7.
    T. G. Appleton, J. R. Hall, and P. D. Prenzler, to be submitted for publication.Google Scholar
  8. 8.
    T. G. Appleton, J. R. Hall, D. W. Neale, and C. S. M. Thompson, “Reactions of the cis-Diamminediaquaplatinum(II) Cation with 2-Aminomalonic Acid and Its Homologues, Aspartic and Glutamic Acids. Rearrangements of Metastable Complexes with Garboxylate Ligands to N,O-Chelates and Formation of Di-and Trinuclear Complexes.”, Inorg. Chem. 29: 3985–3990 1990.CrossRefGoogle Scholar
  9. 9.
    O. Gandolfi, H. C. Apfelbaum, and J. Blum. “Aminomalonato(1,2-diaminocyclohexane)platinum(II): a Competitive Antitumor Compound within a New Class of Neutral, Chemically Stable, Water Soluble, Functionalized Platinum(II) Complexes.”, Inorg. Chim. Acta. 135: 27 (1987).CrossRefGoogle Scholar
  10. 10.
    T. G. Appleton, J. W. Connor, J. R. Hall, and P. D. Prenzler, “NMR Study of the Reactions of the cis-Diamminediaquaplatinum(II) Cation with Glutathione and Amino Acids Containing a Thiol group.”, Inorg. Chem. 28: 2030–2037 1989.CrossRefGoogle Scholar
  11. 11.
    E. L. M. Lempers, K. Inagaki, and J. Reedijk, “Reactions of [PtCl(dien)]-Cl with Glutathione, Oxidized Glutathione, and S-Methylglutathione. Formation of an S-bridged Dinuclear Unit.”, Inorg. Chim. Acta 152: 201 (1988).CrossRefGoogle Scholar
  12. 12.
    S. J. Berners-Price and P. W. Kuchel, “Reaction of Cis-and Trans-[PtCl2(NH3)2] with Reduced Glutathione Studied by H, C, 195Pt, and 15N-1H DEPT NMR.”, J. Inorg. Biochem. 38: 305–326 1990.CrossRefGoogle Scholar
  13. 13.
    T. G. Appleton, J. W. Connor, and J. R. Hall, “S,O-versus S,N-Chelation in the Reactions of the cis-Diamminediaquaplatinum(II) Cation with Methionine and S-Methylcysteine.”, Inorg. Chem. 27: 130–137 1988.CrossRefGoogle Scholar
  14. 14.
    T. G. Appleton, J. R. Hall, and F. B. Ross, to be submitted for publication.Google Scholar
  15. 15.
    H. M. Brothers and N. M. Kostic, “Noninvasive Tagging of proteins with an Inorganic Chromophore. Selectivity of Chloro(terpyridine)platinum(II) toward Amino Acids, Peptides, and Cytochromes C”, Inorg. Chem. 27: 1761–1767 (1988).CrossRefGoogle Scholar
  16. 16.
    V. Saudek, H. Pivcova, D. Noskova, and J. Drobnik, “The Reaction of Pt-Antitumor Drugs with Selected Nucleophiles. II. Preparation and Characterization of Coordination Compounds of Pt(II) and L-Histidine.” J. Inorg. Biochem. 23: 55–72 (1985).PubMedCrossRefGoogle Scholar
  17. 17.
    P. J. Morris and R. B. Martin, “Tetramer Formation in Tetragonal Transition Metal Ion Complexes of Glycyl-L-Histidine.” J. Inorg. Nucl. Chem. 33: 2913–2918 (1971).CrossRefGoogle Scholar
  18. 18.
    C. J. Hawkins, E. Horn, J. Martin, J. A. L. Palmer, and M. R. Snow, “Synthesis and Characterization of Binuclear and Trinuclear Cobalt(III) Complexes with Imidazolate Bridges.”, Aust. J. Chem. 39: 1213–1220 1986.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • Trevor G. Appleton
    • 1
  • John R. Hall
    • 1
  • Paul D. Prenzler
    • 1
  • Fraser B. Ross
    • 1
  1. 1.Department of ChemistryUniversity of QueenslandBrisbaneAustralia

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