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Z-DNA and Chemical Carcinogenesis

  • Conference paper
Structure, Dynamics, Interactions and Evolution of Biological Macromolecules

Abstract

It is known that ultimate carcinogens bind covalently to DNA and it is generally thought that the chemical modification is an important step in tumorogenic process (1). In general several adducts are formed and it is not yet actually known how these adducts can lead to a mutational event. Among others, the hepatocarcinogen N-hydroxy-2-acetylaminofluorene and some of its derivatives have received great attention. Some of the DNA adducts formed in rat liver after i.p. injection of the carcinogen have been clearly identified as N-(deoxyguanosin-8-yl)-N-acetyl-2-amino-fluorene, 3-(deoxyguanosin-N2-yl)-2-acetylaminofluorene and N-(deoxy-guanosin-8-yl)-2-aminofluorene (2,3), adducts which are also found in vitro after reaction between DNA and metabolites of N-hydroxy-2-acetyl-aminofluorene. The percentages and the persistance of these adducts in in vivo modified DNA of target and not-target tissues vary greatly (2–5). Several physico-chemical studies have been devoted to the in vitro modified DNA and possible explanations of the carcinogen effects have been proposed. For example, the covalent binding of N-acetyl-2-aminofluorene residues to the C(8) of guanine residues in native DNA induces a local denaturation of the double helix, the fluorene residue being inside the helix and stacked with the bases and the guanine residues being outside the helix (insertion-denaturation model (6–8) and base-displacement model (9–11)). On the other hand, the same adduct can induce other conformational changes when bound to long alternated d(GpC) sequences. Acetyl-2-aminofluorene modified poly(dG-dC).poly(dG-dC) (poly(dG-dC)AAF) is in Z-form at low ionic strength (12–15) and does not seem to be in C-form in 3.8 M LiCl (13).

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References

  1. Miller, J.A.:1970, Cancer Res. 30, 559–576.

    CAS  Google Scholar 

  2. Kriek, E.:1979, in Environmental Carcinogenesis, Emmelot, P. and Kriek, E., eds, pp. 143–164.

    Google Scholar 

  3. Kriek, E. and Westra, J.G.:1979, in Chemical Carcinogens and DNA, C.R.C. Press, Vol. 2, pp. 1–28.

    Google Scholar 

  4. Beland, F.A., Dooley, K.L. and Jackson, C.D.:1982, Cancer Res. 42, 1348–1354.

    CAS  Google Scholar 

  5. Poirier, M.C., True, B. and Laishes, B.A.:1982, Cancer Res. 42, 1330–1334.

    Google Scholar 

  6. Fuchs, R.P.P. and Daune, M.P.:1972, Biochemistry 11, 2659–2666.

    Article  CAS  Google Scholar 

  7. Daune, M.P. and Fuchs, R.P.P.:1977, in Reparation du DNA, Mutagenese, Cancerogenese Chimique (C.N.R.S., Paris), pp. 83–97.

    Google Scholar 

  8. Lefèvre, J.P., Fuchs, R.P.P. and Daune, M.P.:1978, Biochemistry 17, 2561–2567.

    Article  Google Scholar 

  9. Nelson, J.H., Grunberger, D., Cantor, R.C. and Weinstein, I.B.:1971, J. Mol. Biol. 62, 331–346.

    Article  CAS  Google Scholar 

  10. Grunberger, D.:1979, NCI Monograph n° 58, pp. 193–199.

    Google Scholar 

  11. Grunberger, D. and Weinstein, I.B.:1979, in Chemical Carcinogens and DNA, C.R.C. Press, vol. 2, pp. 59–93.

    Google Scholar 

  12. Sage, E. and Leng, M.:1980, Proc. Natl. Acad. Sci. USA 77, 4597–4601.

    Article  CAS  Google Scholar 

  13. Sage, E. and Leng, M.:1981, Nucleic Acids Res. 9, 1241–1250.

    Article  CAS  Google Scholar 

  14. Santella, R., Grunberger, D., Weinstein, B.I. and Rich, A.:1981, Proc. Natl. Acad. Sci. USA 78, 1451–1455.

    Article  CAS  Google Scholar 

  15. Santella, R., Grunberger, D., Broyde, S. and Hingerty, B.:1981, Nucleic Acids Res. 9, 5459–5467.

    Article  CAS  Google Scholar 

  16. Wang, A.H.J., Quigley, G.S., Kolpak, F.J., Crawford, J.L., van Boom, J.H., van der Marel, G. and Rich, A.:1979, Nature 282, 680–686.

    Article  CAS  Google Scholar 

  17. Crawford, J.L., Kolpak, F.J. Wang, A.H.J., Quigley, G.J., van Boom, J.H., van der Marel, G. and Rich, A.:1980, Proc. Natl. Acad. Sci. USA 77, 4016–4020.

    Article  CAS  Google Scholar 

  18. Wang, A.H.J., Quigley, G.S., Kolpak, F.J., van der Marel, G., van Boom, J.H. and Rich, A.:1981, Science 211, 171–176.

    Article  CAS  Google Scholar 

  19. Drew, H., Takano, T., Tanaka, S., Itakura, K. and Dickerson, R.E.: 1980, Nature 286, 567–573.

    Article  CAS  Google Scholar 

  20. Arnott, S., Chandrasekaran, R., Birdsall, D.L., Leslie, A.G.W. and Ratcliff, R.L.: 1980, Nature 283, 743–745.

    Article  CAS  Google Scholar 

  21. Behe, M., Zimmerman, S. and Felsenfeld, G.: 1981, Nature 293, 233–235.

    Article  CAS  Google Scholar 

  22. Pilet, J. and Leng, M.: 1982, Proc. Natl. Acad. Sci. USA 79, 26–30.

    Article  CAS  Google Scholar 

  23. Zbinden, R.: 1964, in Infrared Spectroscopy of High Polymers, (Academie).

    Google Scholar 

  24. Nairn, J.A., Friesner, R., Frank, H.A. and Sauer, K.:1980, Biophys. J. 32, 733–754.

    Article  CAS  Google Scholar 

  25. Thamann, T.J., Lord, R.C., Wang, A.H.J, and Rich, A.:1981, Nucleic Acids Res. 9, 5443–5457.

    Article  CAS  Google Scholar 

  26. Patel, D.J., Canuel, L.L. and Pohl, F.M.:1979, Proc. Natl. Acad. Sci USA 76, 2508–2511.

    Article  CAS  Google Scholar 

  27. Mitra, C.K., Sarma, M.H. and Sarma, R.H.:1981, Biochemistry 20, 2036 2041.

    Article  CAS  Google Scholar 

  28. Wu, H.M., Dattagupta, N. and Crothers, D.M.:1981, Proc. Natl. Acad. Sci USA 78, 6808–6811.

    Article  CAS  Google Scholar 

  29. Patel, D.J., Kozlowski, S.A., Nordheim, A. and Rich, A.:1982, Proc. Ntal. Acad. Sci. USA 79, 1413–1417.

    Article  CAS  Google Scholar 

  30. Pohl, F.M. and Jovin, R.M.:1972, J. Mol. Biol. 67, 375–396.

    Article  CAS  Google Scholar 

  31. Pohl, F.M.: 1976, Nature 260, 365–366.

    Article  CAS  Google Scholar 

  32. Ivanov, V.I. and Minyat, E.E.:1981, Nucleic Acids Res. 9, 4783–4798.

    Article  CAS  Google Scholar 

  33. Englander, S.W. and Englander, J.J.: 1972, in Methods in Enzymology, Hirs, C.H.W. and Timasheff, S.N., eds, XXVI, part C, pp. 406–413.

    Google Scholar 

  34. Ramstein, J. and Leng, M.:1980, Nature 288, 413–414.

    Article  CAS  Google Scholar 

  35. Hartmann, B., Pilet, J., Ptak, M., Ramstein, J., Malfoy, B. and Leng M.: 1982, Nucleic Acids Res. 10, 3261–3277.

    Article  CAS  Google Scholar 

  36. Teitelbaum, H. and Englander, S.W.: 1975, J. Mol. Biol. 92, 55–78.

    Article  CAS  Google Scholar 

  37. Teitelbaum, H. and Englander, S.W.: 1975, J. Mol. Biol. 92, 79–92.

    Article  CAS  Google Scholar 

  38. Behe, M. and Felsenfeld, G.:1981, Proc. Natl. Acad. Sci. USA 78, 1619–1623.

    Article  CAS  Google Scholar 

  39. Malfoy, B., Rousseau, N. and Leng, M.: 1982, Biochemistry (in press).

    Google Scholar 

  40. Moller, A., Nordheim, A., Nichols, S.R. and Rich, A.:1981, Proc. Natl. Acad. Sci. USA 78, 4777–4781.

    Article  CAS  Google Scholar 

  41. Malfoy, B., Hartmann, B. and Leng, M.: 1981, Nucleic Acids Res. 9, 5659–5669.

    Article  CAS  Google Scholar 

  42. Ushay, H.M., Santella, R.M., Caradonna, J.P., Grunberger, D. and Lippard, S.J.: 1982, Nucleic Acids Res. (in press).

    Google Scholar 

  43. Mercado, C.M. and Tomasz, M.: 1977, Biochemistry 16, 2040–2046.

    Article  CAS  Google Scholar 

  44. Harvan, D.J., Hass, R.J. and Lieberman, M.W.:1977, Chem. Biol. Interact. 17, 203–210.

    Article  CAS  Google Scholar 

  45. Van de Sande, J.H. and Jovin, T.M.:1982, EMBO J. 1, 115–120.

    Google Scholar 

  46. Zacharias, W., Larson, J.E., Klysik, J., Stirdivant, S.M. and Wells, R.D.: 1982, J. Biol. Chem. 257, 2775–2782.

    CAS  Google Scholar 

  47. Leng, M., Ptak, M. and Rio, P.:1980, Biochim. Biophys. Res. Comm. 96, 1095–1102.

    CAS  Google Scholar 

  48. Evans, F.E., Miller, D.W. and Beland, F.A.:1980, Carcinogenesis 1, 955–959.

    Article  CAS  Google Scholar 

  49. Santella, R., Kriek, E. and Grunberger, D.: 1980, Carcinogenesis 1, 897–902.

    Article  CAS  Google Scholar 

  50. Quadrifoglio, R., Manzini, G., Vasser, M., Dinkelspiel, K. and Crea, R.: 1981, Nucleic Acids Res. 9, 2195–2206.

    Article  CAS  Google Scholar 

  51. Rio, P., Malfoy, B., Sage, E. and Leng, M.:1982, Environmental Health Perspectives (in press).

    Google Scholar 

  52. Volickova, M., Kypr, J., Kleinwächter, V. and Palecek, E.:1980, Nucleic Acids Res. 8, 3965–3973.

    Article  Google Scholar 

  53. Kypr, J., Vorlickova, M., Budesinsky, M. and Sklenar, V.:, Biochem. Biophys. Res. Comm. 99, 1257–1264.

    Article  Google Scholar 

  54. Patel, D.J., Kozlowski, S.A., Suggs, J.W. and Cox, S.D.:1981, Proc. Natl. Acad. Sci. USA 78, 4063–4067.

    Article  CAS  Google Scholar 

  55. Klug, A., Jack, A., Viswamitra, M.A., Kennard, O., Shakked, Z. and Steitz, T.A.:1979, J. Mol. Biol. 131, 669–680.

    Article  CAS  Google Scholar 

  56. Shindo, H., Simpson, R.T. and Cohe, J.S.:1979, J. Biol. Chem. 254, 8125–8128.

    CAS  Google Scholar 

  57. Zimmer, C., Tymer, S., Marek, C. and Guschlbauer, W.:1982, Nucleic Acids Res. 10, 1081–1091.

    Article  CAS  Google Scholar 

  58. Vorlickova, M., Kypr, J., Stokrova, S. and Sponar, J.:1982, Nucleic Acids Res. 10, 1071–1080.

    Article  CAS  Google Scholar 

  59. Lafer, E.M., Möller, A., Nordheim, A., Stollar, B.D. and Rich, A.: Proc. Natl. Acad. Sci. USA 78, 3546–3550.

    Article  Google Scholar 

  60. Malfoy, B. and Leng, M.:1981, FEBS Letters 132, 45–48.

    Article  CAS  Google Scholar 

  61. Leng, M., Guigues, M. and Genest, D.:1978, Biochemistry 17, 3215–3220.

    Article  CAS  Google Scholar 

  62. Lang, M.C., Malfoy, B., Freund, A.M., Daune, M.P. and Leng, M.: EMBO Journal (in press).

    Google Scholar 

  63. Stettier, U.H., Weber, H., Koller, Th. and Weissmann, C.: 1979, J. Mol. Biol. 131, 21–40.

    Article  Google Scholar 

  64. Nordheim, A., Pardue, M.L., Lafer, E.M., Möller, A., Stollar, B.D. and Rich, A.:1981, Nature 294, 417–422.

    Article  CAS  Google Scholar 

  65. Leng, M., Harmann, B., Malfoy, B., Pilet, J., Ramstein, J. and Sage, E.:1982, 47th Symposium on Quantitative Biology, Cold Spring Harbor (in press).

    Google Scholar 

  66. Lemeunier, F., Derbin, C., Taillandier, E., Malfoy, B. and Leng, M.: 1982 (submitted).

    Google Scholar 

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Authors and Affiliations

  1. Centre de Biophysique Moléculaire, C.N.R.S., 1A, avenue de la Recherche Scientifique, 45045, Orléans cedex, France

    Marc Leng

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  1. Marc Leng
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Editors and Affiliations

  1. Centre de Biophysique Moléculaire, CNRS, Orléans, France

    Claude Hélène

  2. Muséum National d’Histoire Naturelle, Paris, France

    Claude Hélène

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© 1983 D. Reidel Publishing Company

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Leng, M. (1983). Z-DNA and Chemical Carcinogenesis. In: Hélène, C. (eds) Structure, Dynamics, Interactions and Evolution of Biological Macromolecules. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-7052-6_3

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  • DOI: https://doi.org/10.1007/978-94-009-7052-6_3

  • Publisher Name: Springer, Dordrecht

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