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The Chemistry of Polycyclic Aromatic Hydrocarbon-DNA Adducts

  • Conference paper
Carcinogenesis: Fundamental Mechanisms and Environmental Effects

Part of the book series: The Jerusalem Symposia on Quantum Chemistry and Biochemistry ((JSQC,volume 13))

Abstract

There is considerable evidence which suggests that modification of DNA by chemical carcinogens is the critical first event in tumor induction. Various methods available for investigation of the chemistry, conformation and consequences of these reactions are discussed using benzo (a) pyrene and 7, 12-dimethylbenzanthracene as examples. Metabolic activation of these hydrocarbons occurs via ‘Bay region’ dihydrodiol epoxide derivatives. The amino group of guanine is the major site of attack in subcellular systems and in cell cultures of human and rodent tissues. We have found that 7-methylbenzo (a) pyrene is metabolized to the 7, 8-dihydrodiol and binding to DNA apparently occurs via a 7, 8-dihydrodiol 9, 10-epoxide. Preliminary evidence on the structure of DMBA-DNA adduct is also presented.

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References

  1. Jeffrey et al.: 1977, Nature 269, pp. 248–360.

    Article  Google Scholar 

  2. Autrup, H., Harris, C.C., Trump, B.F. and Jeffrey, A.M.:2978, Cancer Res., 38, pp. 3689–3696.

    Google Scholar 

  3. Brown, U.S., Jeffrey, A.M. and Weinetein, I.B.: 1979, Cancer Res., 39, pp. 1673–1677.

    CAS  Google Scholar 

  4. Autrup et al.: 1980, Int. J. Cancer, 25, pp. 292–300.

    Google Scholar 

  5. Yiarrie, C.C. et al.: 1979, Cancer Res., 39, pp. 4401–4406.

    Google Scholar 

  6. Ivanowic, V., Geacintov, H.E. and Weinstein, I.B.: 1976, Biochem. Biophys. Ree. Cormun. 70, pp. 1172–1179.

    Article  Google Scholar 

  7. Borgen, A., Darvey, H., Castagnoli, N., Crocker, T.T., Rasmussen, R.E., and Wang, I.Y.: 1973, J. Med. Chem. 16, pp. 502–505.

    Article  CAS  Google Scholar 

  8. McCaustland, D.J. : 1976, In: Carcinogenesis 1, (Freudenthal, R. and Jones, P.W.), Raven Press, Hew York, pp. 349–429.

    Google Scholar 

  9. Harvey, R.G., and Sukwnaran, K.B.: 1977, Tet. Lett., pp. 2387–2390.

    Google Scholar 

  10. Sins, P., Grover, P.L., Swaisland, A., Pal, K., and Hewer, A.: 1974, Nature 252, 326–328.

    Article  Google Scholar 

  11. Jeffrey, A.M., Grzeskowiak, K, Veinstein, I.B., Nakanishi, K., Roller, P. and Harvey, R.G.: 1979, Science 206, pp. 1309–1311.

    Article  CAS  Google Scholar 

  12. Croy, R.G., Essigmann, J.M., Reinhold, V.N. and Wogan, G. N.: 1978, Proc. Natl. Acad. Sci., USA, 75, pp. 1745–1749.

    Article  CAS  Google Scholar 

  13. Weinstein et al.: 1976, Science 292, pp. 592–595.

    Article  Google Scholar 

  14. Prusik, T., Geacintov, N.E., Tobiasz, C., Ivanovic, V. and Weinstein, I.B.: 1975, Photochem. and Photobiol. 29, 223–232.

    Article  Google Scholar 

  15. Grunberger, D. and Weinstein, I.B.: 1975, In: Chemical Carcinogens and DNA, (P.L. Grover, ed.), CRC Press, Boca Raton, Fla. pp. 59–93.

    Google Scholar 

  16. Geacintov, N.E., Gagliano, A., Ivanovic, V. and Weinstein, I.B.: Biochemistry, 17, pp. 5256–5262.

    Google Scholar 

  17. Jennette, K.W., : 1977, Biochemistry 16, pp. 932–938.

    Google Scholar 

  18. Osborne, M.R., Beland, F.A., Harvey, R.G. and Brookes, P.: 1976, Intl. J. Cancer 18, pp. 362–368.

    Article  CAS  Google Scholar 

  19. Fuchs, R. and Daune, M.: 1972, Biochemistry 11, pp. 2656–2666.

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. Santella, R.M., Kriek, E. and Grunberger, D.: 1980, Proc. Am. Assoc. Cancer Res., 21, pp. 70.

    Google Scholar 

  22. Fuchs, R. and Daune, M.: 1973, FEBS Lett. 34, pp. 295–298.

    Article  CAS  Google Scholar 

  23. Wang, A.H., Quigley, G.J., Kolpak, F.J., Cranford, J.L., Van Boon, J. A., Van der Mace I, G., and Rich, A.: 1979, Native 282, pp. 680–686.

    CAS  Google Scholar 

  24. Arnott, S., Chandrasekaron, R., Birdsoll, D.L., Leslie, A.G.W. and Ratliff, R.L.: 1980, Nature 283, 743–745.

    Article  CAS  Google Scholar 

  25. Pohl, P.M. and Jovin, T.M.: 1972, J. Mol. Biol. 67, pp. 374–396.

    Article  Google Scholar 

  26. Pohl., P.M.: 1976, Nature 260, pp. 365–366.

    Article  CAS  Google Scholar 

  27. Patel, D.J., Canuel, L.L., and Pohl, P.M.: 1975, Proc. Natl. Acad. Sci., USA 74, pp. 2508–2511.

    Google Scholar 

  28. Jerina, D.M. et al.: 1976, In: In Vitro Metabolic Activation in Mutagenesis Testing, (J. Pouts, J.R. Bend and R.M. Philipot), Elsevier North Holland Press, Amsterdam, pp. 159–177.

    Google Scholar 

  29. Shipman, L.L.: 1978, In: Carcinogenesis, (Jones P.W. and R. Freudenthal, eds.), Raven Press, N.Y., 3, pp. 139–144.

    Google Scholar 

  30. Harvey, R.G. and Dunnie, F.B.: 1278, Nature 273, pp. 566–568.

    Article  Google Scholar 

  31. Slaga, T.J. et al: 1978, In: Carcinogenesis, (P.W. Jones and R. Preudenthal, J. Raven Press, New York Volume 3, pp. 371–382.

    Google Scholar 

  32. Jerstrom, B. et al.: 1978, Cancer Res. 38, pp. 2600–2607.

    Google Scholar 

  33. Nakanishi, K. et al.: 1977, J. Chem. Soc. 99, pp. 258–260.

    Article  CAS  Google Scholar 

  34. Neman, M.S.: 1976: In: Carcinogenesis, (P.W. Jones and R. Freudenthal), Raven Press, New York, 1, pp. 203–207.

    Google Scholar 

  35. Huggins, C., Grand, L.C. and Brillantes, P.P.: 1961, Nature 189, pp. 204–207.

    Article  CAS  Google Scholar 

  36. Baird, W.M. and Dipple, A.: 1977, Intl. J. Cancer 20, pp. 427–431.

    Article  CAS  Google Scholar 

  37. Ivanovic, V., Geacintov, N., Jeffrey, A.M., Pu, P.P., Harvey, R.G., and Weinstein, I.B.: 1978, Cancer Lett. 4, pp. 131–140.

    Article  CAS  Google Scholar 

  38. Meehan, T. and Straub, K.: 1979, Nature 277, pp. 410–412.

    Article  CAS  Google Scholar 

  39. Westra, J.C., Kriek, E., and Pottenhausen, H.: 1976, Chem. Biol. Interactions 15, pp. 146–164.

    Article  Google Scholar 

  40. Jeffrey, A.M., Weinstein, I.B. and Harvey, R.G.: 1979, Proc. Am. Assoc. Cancer Res. 20, p. 181.

    Google Scholar 

  41. Sage, E., Spodheim-Maurizot, M., Rio, P., Leng, M. and Fuchs, R.P.P.:FEBS Lett. 108, pp. 66–68.

    Google Scholar 

  42. Yamasaki, H., Pulkrabek, P., Grunberger, D. and Weinstein, I.B.: 1977, Cancer Res. 37, pp. 3756–3760.

    CAS  Google Scholar 

  43. Yang, S.K., Chou, M.W., Weiris, H.B. and Fu, P.P.: 1979, Biochem. Biophys. Res. Cormun. 90, pp. 1136–1141.

    Article  CAS  Google Scholar 

  44. Pietropaolo, C. and Weinstein, I.B.: 1975, Cancer Res. 35, pp. 2191–2198.

    CAS  Google Scholar 

  45. Cooper, S. et al.: 1980, Chem.-Biol. Interactions 29, pp. 357–367.

    Article  CAS  Google Scholar 

  46. Schurch, O. and Winsterstein, A.: 1935, Ztschr. physiol. Chem. 236, pp. 79–91.

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Division of Environmental Sciences and Cancer Center/Institute of Cancer Research, Columbia University, New York, New York, 10032, USA

    A. M. Jeffrey, T. Kinoshita, R. M. Santella, D. Grunberger, L. Katz & I. Bernard Weinstein

Authors
  1. A. M. Jeffrey
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  2. T. Kinoshita
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  3. R. M. Santella
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  4. D. Grunberger
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  5. L. Katz
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  6. I. Bernard Weinstein
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Editor information

Editors and Affiliations

  1. Institut de Biologie Physico-Chimique (Fondation Edmond de Rothschild), Université Pierre et Marie Curie (Paris VI), Paris, France

    Bernard Pullman

  2. The Johns Hopkins University, Baltimore, Maryland, USA

    Paul O. P. Ts’o

  3. National Cancer Institute, Bethesda, Maryland, USA

    Harry Gelboin

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© 1980 D. Reidel Publishing Company

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Jeffrey, A.M., Kinoshita, T., Santella, R.M., Grunberger, D., Katz, L., Weinstein, I.B. (1980). The Chemistry of Polycyclic Aromatic Hydrocarbon-DNA Adducts. In: Pullman, B., Ts’o, P.O.P., Gelboin, H. (eds) Carcinogenesis: Fundamental Mechanisms and Environmental Effects. The Jerusalem Symposia on Quantum Chemistry and Biochemistry, vol 13. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-9104-0_47

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  • DOI: https://doi.org/10.1007/978-94-009-9104-0_47

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-009-9106-4

  • Online ISBN: 978-94-009-9104-0

  • eBook Packages: Springer Book Archive

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