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Mechanistic Aspects of Pt Antitumor Chemistry

Structure-activity relationships and the relative importance of platinum binding to nucleic acids and proteins
  • Jan Reedijk
Chapter
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Part of the NATO ASI Series book series (ASEN2, volume 26)

Abstract

Even though simple Platinum compounds, like cis-PtCl2(NH3)2 (abbreviated in literature as CDDP, cis-Pt, cisplatin), have been known for over 150 years, the biological activity of the parent compound has been reported only in the mid-sixties as the result of a serendipitous discovery by Rosenberg [1].

Keywords

Platinum Complex Platinum Compound Amine Compound Amine Ligand Amino Phosphonic Acid 
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.
    Rosenberg, B., Van Camp, L. and Krigas, T. (1965) Inhibition of cell division m Escherichia coli by electrolysis products from a platinum electrode, Nature, 205, 698–699CrossRefGoogle Scholar
  2. 2.
    Reedijk, J. (1992) The Relevance of Hydrogen Bonding in the Mechanism of Action of Platinum Antitumor Compounds, Inorg. Chim. Acta, 198-200, 873–881.CrossRefGoogle Scholar
  3. 3.
    Lippard, S.J. (1987) Chemistry and molecular biology of platinum anticancer drugs, Pure and Appl. Chem., 59, 731–742.CrossRefGoogle Scholar
  4. 4.
    Barnard, C.F.J. (1989) Platinum anti-cancer agents; twenty years of continuing development, Plat. Met. Rev., 33, 162–170.Google Scholar
  5. 5.
    Reedijk, J. (1996) Improved Understanding in Platinum Antitumour Chemistry, Chem. Comm. 801–806Google Scholar
  6. 6.
    Giandomenico, C.M., Abrams, M.J., Murrer, B. A., Vollano, J.F., Rheinheimer, M.I., Wyer, S.B., Bossard G.E. and Higgins III, J.D. (1995) Carboxylation of Kinetically Inert Platinum(IV) Hydroxo Complexes. An entrie into Orally Active Platinum(IV) Antitumor Agents, Inorg. Chem., 34, 1015–1021.CrossRefGoogle Scholar
  7. 7.
    Farrell, N. (1995) DNA binding and chemistry of dinuclear Platinum complexes, Coimn. Inorg. Chem., 16, 373.Google Scholar
  8. 8.
    Hollis, S.L., Amundsen, A.R. and Stern, E.W. (1989) Chemical and biological properties of a new series of cis-diammineplatinum(II) antitumor agents containing three nitrogen donors: cis-[Pt(NH3)2(N-donor)Cl]+, J. Med. Chem., 32, 128–133.CrossRefGoogle Scholar
  9. 9.
    Coluccia, M., Nassi, A., Loseto, F., Bocarelli, A., Mariggio, M.A., Giordano, D., Intini, F.P., Natile, G. (1993) A trans-Platinum Complex Showing Higher Antitumor Activity than the Cis Congeners, J. Med. Chem., 36, 510–512.CrossRefGoogle Scholar
  10. 10.
    Deacon, G.B. (1991) Synthesis and antitumour acitivity of some novel platinum(II) organoamides and organometallics” In Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy, Howell, S.B. (Ed.), Plenum Press, New York, pp 139–Google Scholar
  11. 11.
    Bloemink, M.J., Engelking, H., Karentzopoulous, S., Krebs, B. and Reedijk, J. (1996) Synthesis, crystal structure, antitumor activity, and DNA-binding properties of the new active platinum compound (bis(N-methylimidazol-2-yl)carbino)dichloroplatinum(II), lacking a NH moiety, and of the inactive analog dichloro(N 1, N 1-dimethyl-2, 2′-biimidazole)platinum(II), Inorg. Chem., 35, 619–627.CrossRefGoogle Scholar
  12. 12.
    Martin, R.B. (1963) Deuterated Water Effects on Acid Ionization Constants, Science, 139, 1198–1203.CrossRefGoogle Scholar
  13. 13.
    Miller, S.E. and House, D.A. (1990) The hydrolysis products of cis-dichlorodiammineplatinum(II). 3. Hydrolysis kinetics at physiological pH, Inorg. Chim. Acta, 173, 53–56.CrossRefGoogle Scholar
  14. 14.
    Frey, U., Ranford, J.D. and Sadler, P.J. (1993) Ring-opening Reactions of the Anticaner Drug Carboplatin: NMR Characterisation of cis-[Pt(NHr)2(CBDCA-O)(5′-GMP-N7)] in Solution, Inorg. Chem., 32, 1333–1340.CrossRefGoogle Scholar
  15. 15.
    Roberts, J.J., Thomson, A.J. (1979) The mechanism of action of antitumor platinum compounds, Progr. Nucl. Acid Res. Mol. Biol., 22, 71–109.CrossRefGoogle Scholar
  16. 16.
    Bloemink, M.J., Reedijk, J. (1996) Cisplatin and derived anti-cancer drugs, mechanism and current status of DNA binding. In “Metal ions in biological systems” (Eds. H. Sigel and A. Sigel) 32, M. Dekker (New York) pp. 641–685.Google Scholar
  17. 17.
    Chottard, J.C., Girault, J.P., Chottard, G., Lallemand, J.Y., Mansuy, D. (1980) Interaction of cis-[Pt(NH3)2(H2O)2](NO3)2 with ribose dinucleoside monophosphates, J. Am. Chem. Soc., 102, 5566–70CrossRefGoogle Scholar
  18. 18.
    Den Hartog, J.H.J., Altona, C., Chottard, J.C., Girault, J.P., Chottard, G., Lallemand, J.Y., de Leeuw, F.A.A.M., Marcelis, A.T.M., Reedijk, J. (1982) Conformational analysis of the adduct cis-(Pt(NH3)2d(GpG))+ in aqueous soluiton. A high-field (500-300 MHz) nuclear magnetic resonance investigation, Nucl. Acids. Res. 10, 4715–23.CrossRefGoogle Scholar
  19. 19.
    Sherman, S.E., Gibson, D., Wang A.H.-J. and Lippard, S.J. (1985). X-ray structure of the major adduct of the anticancer drug cisplatin with DNA: cis-[Pt(NH3)2], Science, 230, 412–417.CrossRefGoogle Scholar
  20. 20.
    Admiraal, G., van der Veer, J.L., de Graaff, R.A.G., den Hartog, J.H.J., Reedijk, J. (1987) Intrastrand Bis(guanine) Chelation of d(CpGpG) to cis-Platinum: An X-ray Single-Crystal Structure Analysis. J. Am. Chem. Soc., 109, 592–594.CrossRefGoogle Scholar
  21. 21.
    den Hartog, J.H.J., Altona, C., van Boom, J.H., van der Marel, G.A., Haasnoot, C.A.G, Reedijk, J. (1985) Cis-diamminedichloroplatinum(II) Induced Distortion of a Single and Double Stranded Deoxydecanucleosidenonaphosphate Studied by Nuclear Magnetic Resonance, J. Biomol. Struct. Dyn., 2, 1137–1154.CrossRefGoogle Scholar
  22. 22.
    Fichtinger-Schepman, A.M.J., van der Veer, J.L., den Hartog, J.H.J., Lohman, P.H.M., Reedijk, J. (1985) Adducts of the Antitumor Drug cis-Diamrninedichloroplatinum(II) with DNA: Formation, Identification and Quantitation, Biochemistry, 24, 707–713.CrossRefGoogle Scholar
  23. 23.
    Eastman, A. (1987) The formation, isolation and characterisation of DNA adducts produces by anticancer platinum complexes, Pharmacol. Ther. 34, 155–166.CrossRefGoogle Scholar
  24. 24.
    Speelmans, G., Sips, W.H.H.M., Grisel, R.J.H., Stafhorst, R.W.H.M., Fichtinger-Schepman, A.M.J., Reedijk, J., de Kruijff, B. (1996) The interaction of the anti-cancer drugs cisplatin with phospholipids is specific for negatively charged phospholipids, and takes place at low chloride ion concentrations, Biochim. Biophys. Acta, (in press)Google Scholar
  25. 25.
    Speelmans, G., Stafhorst, R.W.H.M., Versluis, K., Reedijk, J., de Kruijff, B. (1996) Cisplatin complexes with phosphatidylserine in membranes, J. Biol. Chem. (submitted).Google Scholar
  26. 26.
    Van Boom, S.S.G.E., Reedijk, J. (1993) Unprecedented Migration of Pt(dien)2+ (dien = l, 5-diamino-3-azapentane) from Sulfur to Guanosine-N7 in S-guanosyl-L-homocysteine (SGH), J. Chem. Soc., Chem. Commun., 1397–1398Google Scholar
  27. 27.
    Van Boom, S.S.G.E. (1995), Ph.D. thesis, Leiden University.Google Scholar
  28. 28.
    Barnham, K.J., Djuran, M.I., del Socorro Murdoch, P., Ranford, J.B., Sadler, P.J. (1995) L-Methionine increases the rate of reaction of 5′-Guanosine monophosphate with the anticancer drug cisplatin: Mixed-ligand adducts and reversible methionine binding, J. Chem. Soc. Dalton Trans. 3721–3726.Google Scholar
  29. 29.
    Eastman, A. (1987) Cross-Linking of Glutathione to DNA by Cancer Chemotherapeutic Platinum Coordination Complexes, Chem. Biol. Interact. 61, 241–248.CrossRefGoogle Scholar
  30. 30.
    Gonnet, F., Reeder, F., Kozelka, J., Chottard, J.-C. 1996. Kinetic analysis of the reactions between GG-containing oligonucleotides and platinum complexes. 1. Reactions of single-stranded oligonucleotides with cis-[Pt(NH3)2(H2O)2]2+ and cis-[Pt(NH3)3(H2O)]2+, Inorg. Chem. 35, 1653–1658.Google Scholar
  31. 31.
    Van Garderen, C.J., van den Elst, H., van Boom, J.H., Reedijk J., van Houte, L.P.A. (1989) A Double-Stranded DNA Fragment Shows a Significant Decrease in Double-Helix Stability After Binding of Monofunctional Platinum Amine Compounds. J. Am. Chem. Soc., 111, 4123–4125.CrossRefGoogle Scholar
  32. 32.
    Brabec, V., Reedijk, J., Leng, M. (1992) Sequence-dependent distortions induced in DNA by monofunctional platinum(II) binding, Biochemistry, 31, 12397–12402CrossRefGoogle Scholar
  33. 33.
    Reeder, F., Kozelka, J., Chottard, J.-C. (1996). Triammineplatinum(II) coordinated to a guanine does not prevent platination of an adjacent guanine in single-stranded oligonucleotides, Inorg. Chem., 35, 1413–1415.CrossRefGoogle Scholar
  34. 34.
    Bloemink, M.J., Heetebrij, R.J., Inagaki, K., Kidani, Y., Reedijk, J. (1992) Reactions of un symmetrically substituted derivatives of cisplatin with short oligodeoxynucleotides containing a — GpG-sequence: H-bonding interactions in pGpG moieties cross-linked by an asymmetric platinum complex enhancing the formation of one geometrical isomer. Inorg. Chem., 31, 4656–4661.CrossRefGoogle Scholar
  35. 35.
    Admiraal, G., Alink, M., Altona, C., Dijt, F.J., van Garderen, C.J., de Graaff, R.A.G., Reedijk, J. (1992) Conformation of Pt(dien)[d(ApGpA)-N7(2)] in the solid state and in aqueous solution, as determined with single-crystal X-ray diffraction and high-resolution NMR spectroscopy in solution, J. Am. Chem. Soc., 114, 930–938.CrossRefGoogle Scholar
  36. 36.
    Takahara, P.M., Rosenzweig, A.C., Frederick, C.A., Lippard, S.J. (1995) Crystal Structure of double-stardned DNA containing the major adduct of the anticancer drug cisplatin, Nature, 377, 649–652.CrossRefGoogle Scholar
  37. 37.
    Bloemink, M.J., Reedijk, J., Farrell, N., Qu, Y., Stetsenko, A.I. (1992) The dinuclear complex[trans-PtCl(NH3)2 2 -H 2N(CH2)6NH2]Cl2 forms a unique macrochelate intrastrand crosslink with d(GpG), J. Chem. Soc., Chem. Commun., 1002–1003.Google Scholar
  38. 38.
    Yang, D., van Boom, S.S.G.E., Reedijk, J., van Boom, J.H., Farrell, N., Wang, A.H.-J. (1992) A novel DNA structure induced by the anticancer bisplatinum compound crosslinked to a GpC site in DNA, Nature Struct. Biol., 2, 577–586.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1997

Authors and Affiliations

  • Jan Reedijk
    • 1
  1. 1.Leiden Institute of Chemistry, Gorlaeus LaboratoriesLeiden UniversityLeidenThe Netherlands

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