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Unusual Hairpin-Like Conformations of Oligonucleotides Induced by Platinum Anti-Cancer Drugs

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Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy

Part of the book series: Developments in Oncology ((DION,volume 54))

Abstract

The great efficacy of Pt-anti-cancer drugs1,2 combined with strong The great efficacy of Pt-anti-cancer drugs1,2 combined with strong evidence that these drugs target DNA3 has prompted numerous studies of the binding of Pt complexes to DNA.2,4–7 The principal type of lesion is known to be Pt intrastrand crosslinked GpG moieties.2,4–7 Our finding that active (e.g. cisPt(NH3)2Cl2) but not inactive (e.g. transPt(NH3)2Cl2) compounds induced an unusual downfield 31P NMR signal in DNA8,9 was followed by similar findings for nucleosomes,9 polynucleotides,9,10 and oligonucleotides,11–17 but only for those species with adjacent 6-oxopurine bases. There are well-defined relationships between structural changes and 31P NMR chemical shifts.18 A knowledge of structure is essential for understanding the reason for the potency of this class of drugs.2–16 Indeed, considerable effort has been expended to obtain relevant crystals and only recently has there been some success but with cisPt(NH3)2 adducts of di- and tri-nucleotides.19

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References

  1. Sun, M. Science (1983), 222, 145.

    Article  PubMed  CAS  Google Scholar 

  2. See also: Sun, M. Plat. Met. Rev. (1984), 28, 157.

    Google Scholar 

  3. Pinto, A. L.; Lippard, S. J. Biochim. Biophvs. Acta (1985), 780, 167.

    CAS  Google Scholar 

  4. Roberts, J. J. In “Advances in Inorganic Biochemistry”; Eichhorn, G. L. and Marzilli, L. G., Eds.; Elsevier North Holland, Inc.: New York, 1981; Vol. 3, p 273.

    Google Scholar 

  5. Reedijk, J.; Fichtinger-Schepman, A. M. J.; van Oosterom, A. T.; van de Putte, P. In “Structure and Bonding”; Clarke, M. J., Goodenough, J. B., Jorgensen, C. K., Neilands, J. B., Reinen, D. and Weis, R., Eds.; Springer-Verlag New York, Inc.: New York, in press. van der Veer, J. L.; van den Elst, H.; den Hartog, J. H. J.; Fichtinger-Schepman, A. M. J.; Reedijk, J. Inorg. Chem. (1986), 25, 4657.

    Article  Google Scholar 

  6. ) Marcelis, A. T. M.; Reedijk, J. Recl. Trav. Chim. Pays-Bas (1983), 102, 121.

    Article  CAS  Google Scholar 

  7. ) Sundquist, W. I.; Lippard, S. J.; Stollar, B. D. Biochemistry (1986), 25, 1520.

    Article  PubMed  CAS  Google Scholar 

  8. ) Eastman, A. Biochemistry (1986), 25, 3912.

    Article  PubMed  CAS  Google Scholar 

  9. ) Fichtinger-Schepman, A. M. J.; van der Veer, J. L.; den Hartog, J. H. J.; Lohman, P. H. M.; Reedijk, J. Biochemistry (1985), 24, 707.

    Article  PubMed  CAS  Google Scholar 

  10. ) Brouwer, J.; van de Putte, P.; Fichtinger-Schepman, A. M. J.; Reedijk, J. Proc. Natl. Acad. Sci. USA (1981), 78, 7010.

    Article  PubMed  CAS  Google Scholar 

  11. Lippard, S. J. Science (1982), 218, 1075.

    Article  CAS  Google Scholar 

  12. Ciccarelli, R. B.; Soloman, M. J.; Varshavsky, A.; Lippard, S. J. Biochemistry (1985), 24, 7533.

    Article  PubMed  CAS  Google Scholar 

  13. Reily, M. D.; Marzilli, L. G. manuscript in preparation.

    Google Scholar 

  14. Marzilli, L. G.; Reily, M. D.; Heyl, B. L.; McMurray, C. T.; Wilson, W. D. FEBS Lett. (1984), 176, 389.

    Article  PubMed  CAS  Google Scholar 

  15. Reily, M. D.; Marzilli, L. G. J. Am. Chem. Soc. (1985), 107, 4916.

    Article  CAS  Google Scholar 

  16. Byrd, R. A.; Summers, M. F.; Zon, G.; Fouts, C. S.; Marzilli, L. G. J. Am, Chem, Soc. (1986), 108, 504.

    Article  CAS  Google Scholar 

  17. Fouts, C. S.; Marzilli, L. G.; Summers, M. F.; Zon, G.; Shinozuka, K.; Byrd, R. A. submitted, Inorg. Chem.

    Google Scholar 

  18. den Hartog, J. H. J.; Altona, C.; Chottard, J.-C.; Girault, J.-P.; Lallemand, J.-Y.; deLeeuw, F. A. A. M.; Marcelis, A. T. M.; Reedijk, J. Nucleic Acids Res, (1982), 10, 4715.

    Article  Google Scholar 

  19. den Hartog, J. H. J.; Altona, C.; van der Marel, G. A.; Reedijk, J. Eur, J, Biochem, (1985), 147, 371.

    Google Scholar 

  20. Fouts, C. S.; Reily, M. D.; Zon, G.; Marzilli, L. G. Inorg. Chim. Acta. Bioinorg. Chem., in press.

    Google Scholar 

  21. den Hartog, J. H. J.; Altona, C.; van Boom, J. H.; Reedijk, J. FEBS Lett. (1984), 176, 393.

    Article  Google Scholar 

  22. Unpublished results from this laboratory.

    Google Scholar 

  23. Gorenstein, D. G. In “Phosphorus-31 NMR”; Gorenstein, D. G., Ed.; Academic Press, Inc: New York, 1984; p 7.

    Google Scholar 

  24. Sherman, S. E.; Gibson, D.; Wang, A. H.-J.; Lippard, S. J. Science (1985), 230, 412.

    Article  PubMed  CAS  Google Scholar 

  25. Admiraal, G. A.; van der Veer, J. L.; de Graaff, R. A. G.; den Hartog, J. H. J.; Reedijk, J. J. Am. Chem. Soc. (1987), 109, 592.

    Article  CAS  Google Scholar 

  26. Tsai, M.-D. Biochemistry (1979), 18, 1468.

    Article  PubMed  CAS  Google Scholar 

  27. Cohn, M.; Hu, A. Proc, Natl, Acad, Sci. USA (1978), 75, 200. Lowe, G.; Sproat, B. S. J. Chem. Soc. Chem. Commun. (1978), 565.

    Article  CAS  Google Scholar 

  28. Lutz, D.; Nolle, A.; Staschewski, D. Z. Naturforsch (1978), A33, 380.

    Google Scholar 

  29. den Hartog, J. H. J.; Altona, C.; van Boom, J. J.; van der Marel, G. A.; Haasnoot, C. A. G.; Reedijk, J. J. Biomolecular Structure and Pynamics (1985), 2, 1137.

    Google Scholar 

  30. Wilson, W. D.; Jones, R. L. Nucleic Acids Res. (1982), 10, 1399.

    Google Scholar 

  31. Marzilli, L. G.; Banville, D. L.; Zon, G.; Wilson, W. D. J. Am. Chem. Soc. (1986), 108, 4188.

    Article  CAS  Google Scholar 

  32. Wilson, W. D.; Jones, R. L.; Zon, G.; Scott, E. V.; Banville, D. L.; Marzilli, L. G. J. Am. Chem. Soc. (1986), 108, 7113.

    Article  CAS  Google Scholar 

  33. Marky, L. A.; Blumenfeld, K. S.; Kozlowski, S.; Breslauer, K. J. Biopolymers (1983), 22, 1247.

    Article  PubMed  CAS  Google Scholar 

  34. Gralla, J.; Crothers, D. M. J. Mol. Biol. (1973), 73, 497.

    Article  PubMed  CAS  Google Scholar 

  35. Uhlenbeck, O. C.; Borer, D. N.; Dengler, B.; Tinoco, Jr., I. J. Mol. Biol. (1973), 73, 483.

    Article  PubMed  CAS  Google Scholar 

  36. Scheffler, I. E.; Elson, E.; Baldwin, R. L. J. Mol. Biol. (1968), 36, 291.

    Article  CAS  Google Scholar 

  37. Manning, G. S. Q. Rev, Biophys, (1978), 11, 179.

    Article  CAS  Google Scholar 

  38. Record, M. T.; Anderson, C. F.; Hohman, T. M. Q. Rev. Biophys. (1978), 11, 103.

    Article  PubMed  CAS  Google Scholar 

  39. Summers, M. F.; Byrd, R. A.; Gallo, K. A.; Samson, C. J.; Zon, G.; Egan, W. Nucleic acids Res, (1985), 13, 3675.

    Article  Google Scholar 

  40. Wemmer, D. E.; Benight, A. S. Nucleic Acids Res. (1985), 13, 8611.

    Article  PubMed  CAS  Google Scholar 

  41. Germann, M. W.; Schoenwaelder, K.-H.; van de Sande, J. H. Biochemistry (1985), 24, 5698.

    Article  PubMed  CAS  Google Scholar 

  42. Early, T. A.; Kearns, D. R.; Hillen, W.; Wells, R. D. Biochemistry (1981), 20, 3764.

    Article  PubMed  CAS  Google Scholar 

  43. Haasnoot, C. A. G.; deBruin, S. H.; Berendsen, R. G.; Janssen, H. G. J. M.; Binnendijk, T. J. J.; Hilbers, C. W.; van der Marel, G. A.; van Boom, J. H. J. Biomolecular Structure and Dynamics (1983), 1, 115.

    CAS  Google Scholar 

  44. Patel, D. J.; Kozlowski, S. A.; Hare, D. R.; Reid, B.; Ikuta, S.; Lander, N.; Itakura, K. Biochemistry (1985), 24, 926.

    Article  PubMed  CAS  Google Scholar 

  45. Hare, D. R.; Reid, B. R. Biochemistry (1986), 25, 5341.

    Article  PubMed  CAS  Google Scholar 

  46. Summers, M. F. unpublished observations.

    Google Scholar 

  47. Adams, R. L. P., Knowler, J. T., Leader, D. P. “The Biochemistry of the Nucleic Acids”; Chapman and Hall: New York, 1986; and references contained therein.

    Book  Google Scholar 

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Authors
  1. L. G. Marzilli
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  2. C. Spellmeyer Fouts
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  3. T. Page Kline
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  4. G. Zon
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Editors and Affiliations

  1. University of Padua, Padua, Italy

    Marino Nicolini

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© 1988 Martinus Nijhoff Publishing, Boston

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Marzilli, L.G., Fouts, C.S., Kline, T.P., Zon, G. (1988). Unusual Hairpin-Like Conformations of Oligonucleotides Induced by Platinum Anti-Cancer Drugs. In: Nicolini, M. (eds) Platinum and Other Metal Coordination Compounds in Cancer Chemotherapy. Developments in Oncology, vol 54. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-1717-3_6

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  • DOI: https://doi.org/10.1007/978-1-4613-1717-3_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-8967-8

  • Online ISBN: 978-1-4613-1717-3

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