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Iminoethers as Carrier Ligands: A Novel trans-Platinum Complex Possessing in Vitro and in Vivo Antitumour Activity

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Abstract

The platinum-based anticancer drug cis-[PtCl2(NH3)2] (cis-DDP) is one of the most effective drugs available for the treatment of human tumours,1 whereas its trans isomer (trans-DDP) is inactive.2–6 The clinical efficacy of cis-DDP is, however, limited by tumour cell resistance present either in the onset of treatment (intrinsic) or after an initial response (acquired)7 Cis-DDP resistance appears to be mediated by factors which reduce platinum-DNA adduct formation, e.g. reduced intracellular accumulation, increased inactivation by intracellular thiols, increased repair8 or tolerance of platinum-DNA adducts.9

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References

  1. P.J. Loehrer and L.H. Einhorn, Cisplatin, Ann. Inter. Med. 100: 704–713 (1984).

    Article  CAS  Google Scholar 

  2. T.A. Connors, M.J. Cleare, and K.R. Harrap, Structure-activity relationships of the antitumour platinum coordination complexes, Cancer Treat. Rep. 63: 1499–1502 (1979).

    CAS  PubMed  Google Scholar 

  3. A. Eastman, The formation, isolation, and characterization of DNA adducts produced by anticancer platinum complexes, Pharmacol. Ther. 34: 155–166 (1987).

    Article  CAS  PubMed  Google Scholar 

  4. J. Reedijk, The mechanism of action of platinum antitumor drugs, Pure Appl. Chem. 59: 181–192(1987).

    Article  CAS  Google Scholar 

  5. S.L. Bruhn, J.H. Toney, and S.J. Lippard, Biological processing of DNA modified by platinum anticancer drugs, Prog. Inorg. Chem. 38: 477–516 (1990).

    Article  CAS  Google Scholar 

  6. M. Sip, A. Schwartz, F. Vovelle, M. Ptak, and M. Leng, Distortion induced in DNA by cis-platinum interstrand adducts, Biochemistry, 31: 2508–2513 (1992).

    Article  CAS  PubMed  Google Scholar 

  7. R.F. Ozols and R.C. Young, Chemotherapy of ovarian cancer, Semin. Oncol. 11: 251–263 (1984).

    CAS  PubMed  Google Scholar 

  8. W. Zhen, C.J. Link, P.M. O’Connor, E. Reed, R. Parker, S.B. Howell, and V. Bohr, Increased gene-specific repair of cisplatin interstrand crosslinks in cisplatin-resistant human ovarian cancer cell lines, mol. Cell. Biol. 12: 3689–3698 (1992).

    CAS  PubMed  Google Scholar 

  9. L.R. Kelland, New platinum antitumor complexes, Crit. Rev. Oncol/Hematol. 15: 191–219 (1993).

    Article  CAS  Google Scholar 

  10. K.M. Comess and S.J. Lippard, Molecular aspects of platinum-DNA interactions, in: “Molecular Aspects of Anticancer Drug-DNA Interactions,” Vol. 1, 134–168. S. Neilde and M. Waring, ed., Macmillan Press Ltd., London (1993).

    Google Scholar 

  11. A. Eastman, M.M. Jennerwein, and D.L. Nagel, Characterization of bifunctional adducts produced in DNA by trans-diamminedichloroplatinum(II), Chem. Biol. Interact 67:71–80(1988).

    Article  CAS  PubMed  Google Scholar 

  12. A.P. Pinto and S.J. Lippard, Sequence-dependent termination of in vitro DNA synthesis by cis- and trans-diamminedichloroplatinum(II), Proc. Natl. Acad. Sci. USA, 82: 4616–4619 (1985).

    Article  CAS  PubMed  Google Scholar 

  13. C.A. Lepre, K.G. Strothkamp, and S.J. Lippard, Synthesis and 1H NMR spectroscopic characterization of trans-[Pt(NH3)2d(AGGCCT) N7-A(1), N7-G(3)], Biochemistry, 26: 5651–5657 (1987).

    Article  CAS  PubMed  Google Scholar 

  14. V. Brabec and M. Leng, DNA interstrand cross-links of trans-diamminedichloro-platinum(II) are preferentially formed between guanine and complementary cytosine residues, Proc. Natl. Acad. Sci. USA, 90: 5345–5349 (1993).

    Article  CAS  PubMed  Google Scholar 

  15. N. Farrell, T.T.B. Ha, J.-P. Souchard, F.L. Wimmer, S. Cros, and N.P. Johnsin, Cytostatic trans-platinum(II) complexes. J. Med. Chem. 32: 2240–2241 (1989).

    Article  CAS  PubMed  Google Scholar 

  16. M. Von Beusichem and N. Farrell, Activation of the trans geometry in platinum antitumor complexes. Synthesis, characterization and biological activity of complexes with planar ligands pyridine, N-methylimidazole, thiazole and quinoline. The crystal and molecular structure of trans-dichloro bis(thiazole) platinum(II). Inorg. Chem. 31: 634–639 (1992).

    Article  Google Scholar 

  17. N. Farrell, L.R. Kelland, J.D. Roberts, and M. Von Beusichem, Activation of the trans geometry in platinum antitumor complexes: a survey of the cytotoxicity of trans compounds containing planar ligands in murine L1210 and human tumor panels and studies on their mechanism of action. Cancer Res. 52: 5065–5072 (1992).

    CAS  PubMed  Google Scholar 

  18. M. Coluccia, A. Nassi, F. Loseto, A. Boccarelli, M.A. Mariggiò, D. Giordano, F.P. Intini, P.A. Caputo, and G. Natile, A trans-platinum complex showing higher antitumor activity than the cis congeners. J. Med. Chem. 36: 510–512 (1993).

    Article  CAS  PubMed  Google Scholar 

  19. L.R. Kelland, C.F.J. Barnard, K.J. Mellish, M. Jones, P.M. Goddard, M. Valenti, A. Bryant, B.A. Murrer, and K.R. Harrap, A novel trans-platinum coordination complex possessing in vitro and in vivo antitumor activity. Cancer Research, 54: 5618–5622 (1994).

    CAS  PubMed  Google Scholar 

  20. M. Coluccia, M.A. Mariggiò, A. Boccarelli, F. Loseto, N. Cardellicchio, P.A. Caputo, F.P. Intini, and G. Natile, Unpublished results.

    Google Scholar 

  21. R. Cini, P.A. Caputo, F.P. Intini, and G.Natile, Mechanistic and stereochemical investigation of iminoethers formed by alcoholysis of coordinated nitriles: X-ray crystal structure of cis- and trans-[bis(1-imino-1-methoxyethane)dichloroplatinum(II)], Inorg. Chem., in press.

    Google Scholar 

  22. M. Coluccia, M. Correale, F.P. Fanizzi, D. Giordano, L. Maresca, M.A. Mariggiò, G. Natile, and M. Tamaro, Mutagenic activity of some platinum complexes: chemical properties and biological activity, Toxicol. Environm. Chem., 8: 1–8 (1984).

    Article  CAS  Google Scholar 

  23. A. Eastman and M.A. Barry, Interaction of trans-diammine-dichloroplatinum(II) with DNA: formation of monofunctional adducts and their reaction with glutathione. Biochemistry, 26: 3303–3307 (1987).

    Article  CAS  PubMed  Google Scholar 

  24. G.L. Cohen, J.A. Ledner, W.R. Bauer, H.M. Ushay, C. Caravana, and S.J. Lippard, Sequence dependent binding of cis-dichlorodiammineplatinum(II) to DNA, J. Am. Chem. Soc. 102: 2487–2488 (1980).

    Article  CAS  Google Scholar 

  25. R.B. Ciccarelli, M.J. Solomon, A. Varshavsky, and S.J. Lippard, In vivo effects of cis-and trans-diamminedichloroplatinurn(II) on SV40 chromosomes: differential repair, DNA-protein cross-linking, and inhibition of replication. Biochemistry, 24, 7533–7540(1985).

    Article  CAS  PubMed  Google Scholar 

  26. S.W. Johnson, R.P. Perez, A.K. Godwin, A.T. Yeung, L.M. Handel, R.F. Ozols, and T.C. Hamilton, Role of platinum-DNA adduct formation and removal in cisplatin resistance in human ovarian cancer cell lines. Biochem. Pharmacol. 47: 687–697 (1994).

    Article  Google Scholar 

  27. M.A. Lemaire, A. Schwartz, A.R. Rahmouni, and M. Leng, Interstrand crosslinks are preferentially formed at the d(GC) sites in the reaction between cis-diamminedichloroplatinum(II) and DNA. Proc. Natl. Acad. Sci. USA, 88: 1982–1985 (1991).

    Article  CAS  PubMed  Google Scholar 

  28. J. Konopa, J.W. Pawlak, and K. Pawlak, The mode of action of cytotoxic and antitumor 1-nitroacridines. III. In vivo interstrand cross-linking of DNA of mammalian or bacterial cells by 1-nitroacridines. Chem. Biol. Interact. 43: 175–197 (1983).

    Article  CAS  PubMed  Google Scholar 

  29. A. Skladanowski and J. Konopa, Interstrand DNA crosslinking induced by anthracyclines in tumor cells. Biochemical Pharmacology, 47: 2269–2278 (1994).

    Article  CAS  PubMed  Google Scholar 

  30. K. Kohn and C.L. Spears, Stabilization of nitrogen-mustard alkylations and interstrand crosslinks in DNA by alkali. Biochim. Biophys. Acta, 145: 734–741 (1967).

    Article  CAS  PubMed  Google Scholar 

  31. D.C. Gruenert and J.E. Cleaver, Sensitivity of mitomycin C and nitrogen mustard crosslinks to extreme alkaline conditions. Biochem. Biophys. Res. Commun. 123: 549–554 (1984).

    Article  CAS  PubMed  Google Scholar 

  32. J. Konopa, Adriamycin and Daunomycin induce interstrand crosslinks in HeLa S3 cells. Biochem. Biophys. Res. Commun. 110: 819–826 (1983).

    Article  CAS  PubMed  Google Scholar 

  33. P.G. Parson, Dependence on treatment time of melphalan resistance and DNA cross-linking in human melanoma cell lines. Cancer Res. 44: 2773–2778 (1984).

    Google Scholar 

  34. E.P. Geiduschek, “Reversible” DNA. Proc. Natl. Acad. Sci. USA, 47: 950–955 (1961).

    Article  CAS  PubMed  Google Scholar 

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Coluccia, M. et al. (1996). Iminoethers as Carrier Ligands: A Novel trans-Platinum Complex Possessing in Vitro and in Vivo Antitumour Activity. In: Pinedo, H.M., Schornagel, J.H. (eds) Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy 2. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-0218-4_3

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  • DOI: https://doi.org/10.1007/978-1-4899-0218-4_3

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-0220-7

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