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Experientia

, Volume 28, Issue 10, pp 1129–1149 | Cite as

Arene oxides and the NIH shift: The metabolism, toxicity and carcinogenicity of aromatic compounds

  • J. W. Daly
  • D. M. Jerina
  • B. Witkop
Article

Keywords

Oxide Toxicity Aromatic Compound Carcinogenicity 
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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Literatur

  1. 1.
    D. M. Jerina, J. W. Daly, B. Witkop, P. Zaltzman-Nirenberg andS. Udenfriend, J. Am. chem. Soc.90, 6525 (1968); Biochemistry9, 147 (1970).Google Scholar
  2. 2.
    E. Boyland, Biochem. Soc. Symp.5, 40 (1950).Google Scholar
  3. 3.
    D. R. Boyd, J. W. Daly andD. M. Jerina, Biochemistry11, 1961 (1972).Google Scholar
  4. 4.
    D. M. Jerina, J. W. Daly andB. Witkop, J. Am. chem. Soc.90, 6523 (1968).Google Scholar
  5. 5.
    D. Jerina, N. Kaubisch andJ. W. Daly, Proc. natn. Acad. Sci., USA68, 2545 (1971).Google Scholar
  6. 6.
    N. Kaubisch, J. W. Daly andD. M. Jerina, Biochemistry11, 3080 (1972).Google Scholar
  7. 7.
    J. K. Selkirk, E. Huberman andC. Heidelberger, Biochem. biophys. Res. Commun.43, 1010 (1971).Google Scholar
  8. 8.
    P. L. Grover, A. Hewer andP. Sims FEBS Letters18, 76 (1971).Google Scholar
  9. 9.
    D. M. Jerina, J. W. Daly, B. Witkop, P. Zaltzman-Nirenberg andS. Udenfriend, Arch. Biochem. Biophys.128, 176 (1968).Google Scholar
  10. 10.
    F. Oesch, D. M. Jerina andJ. Daly, Biochim. biophys. Acta227, 685 (1971).Google Scholar
  11. 11.
    D. W. Nebert, W. F. Benedict, J. E. Gielen, F. Oesch andJ. W. Daly, Molec. Pharmac.8, 374 (1972).Google Scholar
  12. 12.
    F. Oesch, D. Jerina, J. Daly, A. H. Lu, R. Kuntzman andA. Conney, Arch. Biochem. Biophys. in press (1972).Google Scholar
  13. 13.
    F. Oesch andJ. Daly, Biochem. biophys. Res. Commun.46, 1713 (1972).Google Scholar
  14. 14.
    D. M. Jerina, H. Ziffer andJ. W. Daly, J. Am. chem. Soc.92, 1056 (1970).Google Scholar
  15. 15.
    F. Oesch, D. M. Jerina andJ. W. Daly, Arch. Biochem. Biophys.144, 253 (1971).Google Scholar
  16. 16.
    H. Pandov andP. Sims, Biochem. Pharmac.19, 299 (1970).Google Scholar
  17. 17.
    P. Sims, Biochem. J.125, 159 (1971).Google Scholar
  18. 18.
    J. W. Daly, D. M. Jerina, H. Ziffer, B. Witkop, F. G. Klärner andE. Vogel, J. Am. chem. Soc.92, 702 (1970).Google Scholar
  19. 19.
    F. Oesch, N. Kaubisch, D. M. Jerina andJ. W. Daly, Biochemistry10, 4858 (1971).Google Scholar
  20. 20.
    F. Oesch andJ. Daly, Biochim. biophys. Acta227, 692 (1971).Google Scholar
  21. 21.
    R. M. De Marinis andG. A. Berchtold J. Am. chem. Soc.91, 6525 (1969).Google Scholar
  22. 22.
    A. Jeffrey andD. M. Jerina, unpublished observations.Google Scholar
  23. 23.
    T. A. Fjellstedt, R. H. Allen, B. Duncan andW. B. Jakoby, in preparation.Google Scholar
  24. 24.
    E. Kuss, Hoppe-Seylers Z. physiol. Chem.352, 817 (1971).Google Scholar
  25. 25.
    P. K. Ayengar, O. Hayaishi, M. Nakajima andJ. Tomida, Biochim. biophys. Acta33, 111 (1959).Google Scholar
  26. 26.
    T. Sato, T. Fukuyama, T. Suzuki andY. Yoshikawa, J. biochem. Tokyo53, 23 (1963).Google Scholar
  27. 27.
    R. H. Knight andL. Young, Biochem. J.70, 111 (1958).Google Scholar
  28. 28.
    W. M. Azouz, D. V. Parke andR. T. Williams, Biochem. J.55, 146 (1953).Google Scholar
  29. 29.
    J. M. Smith, B. Spencer andR. T. Williams, Biochem. J.47, 284 (1950).Google Scholar
  30. 30.
    M. Jaffe, Ber. dt. chem. Ges.12, 1092 (1879).Google Scholar
  31. 31.
    E. Jaffer, Ber. dt. chem. Ges.12, 1092 (1879).Google Scholar
  32. 32.
    G. C. Mills andJ. L. Wood, J. biol. Chem.204, 547 (1953).Google Scholar
  33. 33.
    D. V. Parke, Biochem. J.62, 339 (1956).Google Scholar
  34. 34.
    M. Azouz, D. V. Parke andR. T. Williams, Biochem. J.59, 410 (1955).Google Scholar
  35. 35.
    D. V. Parke andR. T. Williams, Biochem. J.59, 415 (1955).Google Scholar
  36. 36.
    H. D. West, J. R. Lawson, I. H. Miller andG. R. Mathura, Arch. Biochem. Biophys.60, 14 (1956).Google Scholar
  37. 37.
    M. G. Horning, C. Stratton, A. Wilson, E. C. Horning andR. M. Hill, Analyt. Letters4, 537 (1971).Google Scholar
  38. 38.
    T. Chang, A. Savory andA. J. Glazko, Biochem. biophys. Res. Commun.38, 444 (1970).Google Scholar
  39. 39.
    E. D. S. Corner andL. Young, Biochem. J.58, 647 (1954).Google Scholar
  40. 40.
    E. Boyland andP. Sims, Biochem. J.68, 440 (1962).Google Scholar
  41. 41.
    A. J. Grimes andL. Young, Biochem. J.62, 11P (1956).Google Scholar
  42. 42.
    J. Booth andE. Boyland, Biochem. J.44, 361 (1949).Google Scholar
  43. 43.
    E. Boyland andA. A. Levi, Biochem. J.30, 1225 (1936).Google Scholar
  44. 44.
    E. Boyland andG. Wolf, Biochem. J.47, 64 (1950).Google Scholar
  45. 45.
    E. Boyland andP. Sims, Biochem. J.84, 571 (1962).Google Scholar
  46. 46.
    E. Boyland andP. Sims, Biochem. J.84, 564 (1962).Google Scholar
  47. 47.
    E. Boyland andP. Sims, Biochem. J.91, 493 (1964).Google Scholar
  48. 48.
    P. Sims, Biochem. Phramac.19, 795 (1970).Google Scholar
  49. 49.
    D. Gibson, G. Cardini, F. Maseles andR. Kallio, Biochemistry9, 1631 (1970), and cited references.Google Scholar
  50. 50.
    D. M. Jerina, J. W. Daly, A. M. Jeffrey andD. T. Gibson, Arch. Biochem. Biophys.142, 394 (1971).Google Scholar
  51. 51.
    N. Neuss, R. Nagarajan, B. B. Molloy andL. Huckstep, Tetrahedron Lett.42, 4467 (1968).Google Scholar
  52. 52.
    N. Johns andG. W. Kirby, J. chem. Soc. C., chem. Commun.1971, 163.Google Scholar
  53. 53.
    J. D. Bullock andA. P. Ryles, J. chem. Soc. C., chem. Commun.1970, 1404.Google Scholar
  54. 54.
    M. S. Newman andS. Blum, J. Am. chem. Soc.86, 5559 (1964).Google Scholar
  55. 55.
    E. Vogel andH. Günther, Angew. Chem., Int. Edition6, 385 (1967).Google Scholar
  56. 56.
    D. M. Jerina, D. R. Boyd andJ. W. Daly, Tetrahedron Lett.1970, 457.Google Scholar
  57. 57.
    E. Vogel andR. G. Klärner, Angew. Chem., Int. Edition7, 374 (1968).Google Scholar
  58. 58.
    D. R. Boyd, D. M. Jerina andJ. W. Daly, J. org. Chem.35, 3170 (1970).Google Scholar
  59. 59.
    A. M. Jeffrey andD. M. Jerina, J Am. chem. Soc.94, 4048 (1972) and references therein.Google Scholar
  60. 60.
    G. Guroff, D. Jerina, J. Renson, S. Udenfriend andB. Witkop, Science157, 1524 (1967).Google Scholar
  61. 61.
    J. W. Daly, G. Guroff, D. M. Jerina, S. Udenfriend andB. Witkop, inAdvances in Chemistry, Oxidation of Organic Compounds III (Ed.R. F. Gould, American Chemical Society, Washington, D. C. 1968), vol. 77, p. 279.Google Scholar
  62. 62.
    D. M. Jerina, J. W. Daly andB. Witkop, inBiogenic Amines and Physiological Membranes in Drug Therapy, Part B. (Eds.J. H. Biel andL. G. Abood, Marcel Dekker Inc. New York 1971), p. 413.Google Scholar
  63. 63.
    G. J. Kasperek andT. C. Bruice, J. Am. chem. Soc.94, 198 (1972).Google Scholar
  64. 64.
    G. J. Kasperek, T. C. Bruice, H. Yagi andD. M. Jerina, J. chem. Soc. D., Chem. Commun.784, (1972).Google Scholar
  65. 65.
    H. Yagi, D. M. Jerina, G. J. Kasperek andT. C. Bruice, Proc. natn. Acad. Sci. USA69, 1985 (1972).Google Scholar
  66. 66.
    G. J. Kasperek, T. C. Bruice, H. Yagi, N. Kaubisch andD. M. Jerina, J. Am. chem. Soc., in press (1972).Google Scholar
  67. 67.
    D. Jerina, B. Witkop, C. McIntosh andO. Chapman, in preparation.Google Scholar
  68. 68.
    J. Daly, Biochem. Pharmac.19, 2979 (1970).Google Scholar
  69. 69.
    J. Daly andG. Guroff, Arch. Biochem. Biophys.125, 136 (1968).Google Scholar
  70. 70.
    G. Guroff andJ. Daly, Arch. Biochem. Biophys.122, 212 (1967).Google Scholar
  71. 71.
    G. Guroff, C. A. Reidsnyder andJ. Daly, Biochem. biophys. Res. Commun.24, 720 (1966).Google Scholar
  72. 72.
    L. Nover andM. Luckner, FEBS Letters3, 292 (1969).Google Scholar
  73. 73.
    J. Daly, J. Levitt, G. Guroff andS. Udenfriend, Arch. Biochem. Biophys.126, 593 (1968).Google Scholar
  74. 74.
    G. Guroff, M. Levitt, J. Daly andS. Udenfriend, Biochem. Res. Commun.25, 253 (1966).Google Scholar
  75. 75.
    D. Reed, J. Vimmerstedt, D. M. Jerina andJ. W. Daly, Arch. Biochem. Biophys., submitted.Google Scholar
  76. 76.
    M. H. Zenk, Z. Planzenphysiol.57, 477 (1967).Google Scholar
  77. 77.
    N. Amrhein andM. H. Zenk, Phytochemistry8, 107 (1969).Google Scholar
  78. 78.
    D. W. Russell, E. E. Conn, A. Sutter andH. Grisebach, Biochim. biophys. Acta170, 210 (1968).Google Scholar
  79. 79.
    J. Daly, G. Guroff, S. Udenfriend andB. Witkop Arch. Biochem. Biophys.133, 318 (1967).Google Scholar
  80. 80.
    J. W. Daly, Analyt. Biochem.33, 286 (1970).Google Scholar
  81. 81.
    J. Daly, D. Jerina andB. Witkop, Arch. Biochem. Biophys.128, 517 (1968).Google Scholar
  82. 82.
    J. Daly andD. Jerina, Arch. Biochem. Biophys.134, 266 (1969).Google Scholar
  83. 83.
    D. Jerina, G. Guroff andJ. Daly, Arch. Biochem. Biophys.124, 612 (1968).Google Scholar
  84. 84.
    J. Daly, D. Jerina, J. Farnsworth andG. Guroff Arch. Biochem. Biophys.131, 238 (1969).Google Scholar
  85. 85.
    D. M. Jerina, J. W. Daly andB. Witkop, Biochemistry10, 366 (1971).Google Scholar
  86. 86.
    J. Renson, J. Daly, H. Weissbach, B. Witkop andS. Udenfriend, Biochem. biophys. Res. Commun.25, 504 (1966).Google Scholar
  87. 87.
    T. Nambara, M. Numazawa andS. Akiyama, Chem. Pharma. Bull., Tokyo17, 2394 (1969).Google Scholar
  88. 88.
    S. Udenfriend, P. Zaltzman-Nirenberg, J. Daly, G. Guroff, C. Chidsey andB. Witkop, Arch. Biochem. Biophys.120, 413 (1967).Google Scholar
  89. 89.
    W. R. Bowman, I. T. Bruce andG. W. Kirby, J. chem. Soc. D,1969, 1075.Google Scholar
  90. 90.
    J. Daly andD. Jerina, unpublished results.Google Scholar
  91. 91.
    A. R. Battersby andE. E. Hall, Chem. Commun.1969, 793.Google Scholar
  92. 92.
    B. J. Auret, D. R. Boyd, P. M. Robinson, C. G. Watson, J. W. Daly andD. M. Jerina, J. chem. Soc. D., Chem. Commun.1971, 1585.Google Scholar
  93. 93.
    J. P. Ferris, M. Fasco, F. Stylianopoulou, D. M. Jerina, J. W. Daly andA. M. Jeffrey, Biochemistry, submitted.Google Scholar
  94. 94.
    M. Tanabe, D. Yasuda, J. Tagg andC. Mitoma, Biochem. Pharmac.16, 2230 (1967).Google Scholar
  95. 95.
    B. E. Ellis andN. Amrhein, Phytochemistry10, 3069 (1971).Google Scholar
  96. 96.
    T. Nagatsu, M. Levitt andS. Udenfriend, Analyt. Biochem.9, 122 (1964).Google Scholar
  97. 97.
    S. H. Pomerantz, Biochem. biophys. Res. Commun.16, 188 (1964).Google Scholar
  98. 98.
    T. Nambara, S. Akiyama andS. Honma, Chem. pharm. Bull., Tokyo19, 1727 (1971).Google Scholar
  99. 99.
    J. Fishman, H. Guzit andL. Hellman, Biochemistry9, 1593 (1970).Google Scholar
  100. 100.
    A. I. Scott andM. Yalpani, Chem. Commun.1967, 945.Google Scholar
  101. 101.
    A. Sutter andH. Grisebach, Phytochemistry8, 101 (1969).Google Scholar
  102. 102.
    H. Kindl, Hoppe-Seyler's Z. physiol. Chem.350, 1289 (1969).Google Scholar
  103. 103.
    E. Leete, R. M. Bowman andM. F. Manuel, Phytochemistry10, 3029 (1971).Google Scholar
  104. 104.
    C. Poupat andM. G. Kunesch, C. r. Acad. Sci., Paris C273, 433 (1971).Google Scholar
  105. 105.
    J. Lundström, Acta pharm. suécica8, 275 (1971).Google Scholar
  106. 106.
    C. R. Hall andR. H. Prager, Aust. J. Chem.22, 2437 (1969).Google Scholar
  107. 107.
    G. Guroff andA. Abramowitz, Analyt. Biochem.19, 548 (1967).Google Scholar
  108. 108.
    J. W. Daly andB. Witkop, J. Am. chem. Soc.89, 1032 (1967).Google Scholar
  109. 109.
    W. Lovenberg, R. E. Bensinger, R. L. Jackson andJ. W. Daly, Analyt. Biochem.43, 269 (1971).Google Scholar
  110. 110.
    J. W. Daly, Analyt. Biochem.33, 286 (1970).Google Scholar
  111. 111.
    G. Guroff, K. Kondo andJ. Daly, Biochem. biophys. Res. Commun.25, 622 (1966).Google Scholar
  112. 112.
    R. E. Counsell, P. S. Chan andP. A. Weinhold, Biochim. biophys. Acta215, 187 (1970).Google Scholar
  113. 113.
    J. W. Daly, G. Guroff, S. Udenfriend andB. Witkop, Biochem. Pharmac.17, 31 (1968).Google Scholar
  114. 114.
    G. Guroff, personal communication.Google Scholar
  115. 115.
    E. W. Thomas, B. C. Longhman andR. G. Powell, Nature, Lond.204, 884 (1964).Google Scholar
  116. 116.
    J. K. Faulkner andD. Woodcock, J. chem. Soc.1965, 1187.Google Scholar
  117. 117.
    D. M. Foulkes, Nature, Lond.221, 582 (1969).Google Scholar
  118. 118.
    D. M. Foulkes, J. Pharmac. exp. Ther.172, 115 (1970).Google Scholar
  119. 119.
    D. M. Bowker andJ. E. Casida, J. agric. Food. Chem.17, 956 (1969).Google Scholar
  120. 120.
    V. Ullrich, J. Wolfe, E. Amadori andHj. Staudinger, Hoppe-Seyler's Z. physiol. Chem.349, 85 (1968).Google Scholar
  121. 121.
    J. Renson andV. Bourdon, Archs int. Pharmacodyn.171, 240 (1968).Google Scholar
  122. 122.
    H. Kindl, Europ. J. Biochem.7, 340 (1969).Google Scholar
  123. 123.
    K. Taniguchi, T. Kappe andM. D. Armstrong, J. biol. Chem.239, 3389 (1964).Google Scholar
  124. 124.
    B. Schepartz andG. Gurin, J. biol. Chem.186, 663 (1949).Google Scholar
  125. 125.
    E. Holme, G. Lindstedt, S. Lindstedt andM. Tofft, Biochim. biophys. Acta212, 50 (1970).Google Scholar
  126. 126.
    R. E. Rhoads andS. Udenfriend, Proc. natn. Acad. Sci., USA60, 1473 (1968).Google Scholar
  127. 127.
    B. Lindblad, G. Lindstedt, S. Lindstedt andM. Tofft, J. Am. chem. Soc.91, 4604 (1969).Google Scholar
  128. 128.
    B. Lindblad, G. Lindstedt andS. Lindstedt, J. Am. chem. Soc.92, 7446 (1970).Google Scholar
  129. 129.
    B. Witkop andS. Goodwin, Experientia8, 377 (1952).Google Scholar
  130. 130.
    J. W. Daly, inPhenolic Compounds and Metabolic Regulation (Ed.B. J. Finkle andV. C. Runeckles, Appleton-Century-Crefts New York 1967), p. 280.Google Scholar
  131. 131.
    R. W. Estabrook, inHandbook of Experimental Phyrmacology (Eds.B. B. Brodie andJ. R. Gillette: Springer-Verlag, New York 1971), vol. 28, part2, p. 264.Google Scholar
  132. 132.
    H. W. Strobel andM. J. Coon, J. biol. Chem.246, 7826 (1971).Google Scholar
  133. 133.
    J. W. Daly, inHandbook of Experimental Pharmacology (EdsB. B. Brodie andJ. R. Gillette: Springer-Verlag, New York 1971), vol. 28, part2, p. 285.Google Scholar
  134. 134.
    M. Tanabe, D. Yasuda, J. Tagg andC. Mitoma, Biochem. Pharmac.16, 2230 (1967).Google Scholar
  135. 135.
    J. M. Perel, P. G. Dayton, C. L. Tauriello, L. Brand andL. C. Mark, J. med. Chem.10, 371 (1967).Google Scholar
  136. 136.
    M. Tanabe, J. Tagg, D. Yasuda, S. E. LeValley andC. Mitoma, J. med. Chem.13, 30 (1970).Google Scholar
  137. 137.
    S. Udenfriend, C. T. Clark, J. Axelrod andB. B. Brodie, J. biol. Chem.208, 731 (1954).Google Scholar
  138. 138.
    B. B. Brodie, J. Axelrod, P. A. Shore andS. Udenfriend, J. biol. Chem.208, 741 (1954).Google Scholar
  139. 139.
    B. B. Brodie, P. A. Shore, J. Axelrod andS. Udenfriend, Fedn. Proc.11, 326 (1952).Google Scholar
  140. 140.
    R. O. C. Norman andJ. R. Lindsay-Smith inOxidases and Related Redox Systems (Eds.T. E. King, H. S. Mason andM. Morrison; Wiley, New York 1965), vol. 1, p. 131.Google Scholar
  141. 141.
    A. Bobst andM. Viscontini, Helv. chim. Acta49, 884 (1966).Google Scholar
  142. 142.
    M. Viscontini, H. Leidner, C. Mattern andT. Okada, Helv. chim. Acta49, 1911 (1966).Google Scholar
  143. 143.
    V. Ullrich, Z. Naturforsch.24b, 699 (1969).Google Scholar
  144. 144.
    G. A. Hamilton andJ. P. Friedman, J. Am. chem. Soc.85, 1008 (1963).Google Scholar
  145. 145.
    D. Jerina, J. Daly, W. Landis, B. Witkop andS. Udenfriend, J. Am. chem. Soc.89, 3347 (1967).Google Scholar
  146. 146.
    A. M. Jeffrey, D. M. Jerina, J. W. Daly andD. T. Gibson, Fedn. Proc.31, 869 Abs tr. (1972).Google Scholar
  147. 147.
    J. W. Daly andD. M. Jerina, Biochim biophys. Acta208, 340 (1970).Google Scholar
  148. 148.
    H. Kindl, Phytochemistry10, 1475 (1971).Google Scholar
  149. 149.
    H. Hart, Acct. chem. Research4, 337 (1971).Google Scholar
  150. 150.
    T. Kumazi andR. Wolffenstein, Chem. Ber.41, 297 (1908).Google Scholar
  151. 151.
    V. Ullrich andH. Staudinger, inMicrosomes and Drug Oxidation (Eds.J. Gillette, A. Conney, G. Cosmides, R. Estabrook, J. Fouts andG. Mannering Academic Press. New York 1969), p. 199.Google Scholar
  152. 152.
    V. Ullrich andH. Staudinger, Z. Naturforsch.24b, 583 (1969).Google Scholar
  153. 153.
    W. A. Butte Jr. andC. C. Price, J. Am. chem. Soc.84, 3567 (1962).Google Scholar
  154. 154.
    K. B. Sharpless andT. C. Flood, J. Am chem. Soc.93, 2316 (1971).Google Scholar
  155. 155.
    L. Shuster A. Rev. Biochem.33, 584 (1964).Google Scholar
  156. 156.
    J. A. Miller andE. C. Miller, Lab. Invest.15, 217 (1966).Google Scholar
  157. 157.
    J. R. Debaun, E. C. Miller andJ. A. Miller, Cancer Res.30, 577 (1970).Google Scholar
  158. 158.
    P. D. Lotlikar andL. Luha, Molec. Pharmac.7, 381 (1971).Google Scholar
  159. 159.
    P. N. Magee andK. Y. Kee, Ann. N. Y. Acad. Sci.104 916 (1963).Google Scholar
  160. 160.
    S. S. Mirvish andH. Sidransky, Biochem. Pharmac.20, 3493 (1971).Google Scholar
  161. 161.
    M. V. Jago, J. A. Edgar, L. W. Smith andC. C. J. Culvenor, Molec. Pharmac.6, 1402 (1970).Google Scholar
  162. 162.
    R. Schoental, Nature. Lond.227 401 (1970).Google Scholar
  163. 163.
    B. L. Van Duuren, L. Langseth, B. M. Goldschmidt andL. Orris, J. natn. Cancer Inst.39, 1217 (1967).Google Scholar
  164. 164.
    F. De Matteis, FEBS Letters,6, 343 (1970).Google Scholar
  165. 165.
    W. Levin, M. Jacobson andR. Kuntzman, Archs. Biochem. Biophys.148, 262 (1972).Google Scholar
  166. 166.
    R. Kuntzjan, E. Sernatinger, M. Jacobson andW. Levin, Fedn. Proc.31, 548 Abstr. (1972).Google Scholar
  167. 167.
    D. J. Doedens, Diss. Abstr.32, 295 1B (1971).Google Scholar
  168. 168.
    R. L. Foreman andE. W. Maynert, Pharmacologist12, 306 Abstr. (1970).Google Scholar
  169. 169.
    H. V. Gelboin, F. Wiebel andL. Diamond, Science170, 169 (1970).Google Scholar
  170. 170.
    E. Calvalieri andM. Calvin, Proc. natn. Acad. Sci., USA68, 1251 (1971).Google Scholar
  171. 171.
    P. Sims, J. Cancer Inst.2, 505 (1967);E. Boyland andP. Sims, J. Cancer Inst.2, 500 (1967).Google Scholar
  172. 172.
    E. C. Miller andJ. A. Miller, Proc. Soc. exp. biol. Med.124, 915 (1967).Google Scholar
  173. 173.
    B. B. Brodie, W. D. Reid, A. K. Cho, G. Sipes, G. Krishna andJ. R. Gillette, Proc. natn. Acad. Sci., USA68, 160 (1971).Google Scholar
  174. 174.
    J. R. Mitchell, Fedn. Proc.30, 651 Abstr. (1971).Google Scholar
  175. 175.
    H. V. Gelboin, E. Huberman andL. Sachs, Proc. natn. Acad. Sci., USA64, 1188 (1969).Google Scholar
  176. 176.
    G. Krishna, M. Eichelbaum andW. D. Reid, Pharmacologist13, 196 (1971), abstract.Google Scholar
  177. 177.
    J. R. Mitchell, W. D. Reid, B. Christie, J. Moskowitz, G. Krishna andB. B. Brodie, Res. Commun. Chem. path. Pharmac.2, 877 (1971).Google Scholar
  178. 178.
    D. Jollow, N. Zampaglione andJ. R. Gillette, Pharmacologist13, 288 (1971), abstract.Google Scholar
  179. 179.
    W. D. Reid, B. Christie, M. Eichelbaum andG. Krishna, Expl. molec. Path.15, 363 (1971).Google Scholar
  180. 180.
    P. L. Grover, P. Sims, E. Huberman, H. Marquardt, T. Kuroki andC. Heidelberger, Proc. natn. Acad. Sci., USA68, 1098 (1971).Google Scholar
  181. 181.
    H. Marquardt, T. Kuroki, E. Huberman, J. K. Selkirk, C. Heidelberger, P. O. Grover andP. Sims, Cancer Res.32, 716 (1972).Google Scholar
  182. 182.
    H. Marquardt andC. Heidelberger, Cancer Res32, 721 (1972).Google Scholar
  183. 183.
    P. L. Grover andP. Sims, Biochem. Pharmac.19, 2251 (1970).Google Scholar
  184. 184.
    P. L. Grover, J. A. Forrester andP. Sims, Biochem. Pharmac.20, 1297 (1971).Google Scholar
  185. 185.
    T. Kuroki andC. Heidelberger, Biochemistry11, 2119 (1972).Google Scholar
  186. 186.
    T. Kuroki, E. Huberman, H. Marquardt, J. K. Selkirk, C. Heidelberger, P. L. Grover andP. Sims, Chem. biol. Interactions4, 389 (1971/72).Google Scholar
  187. 187.
    B. N. Ames, P. Sims andP. L. Grover, Science176, 47 (1972).Google Scholar
  188. 188.
    M. J. Cookson, P. Sims andP. L. Grover, Nature, New Biol.234, 186 (1971).Google Scholar
  189. 189.
    E. Huberman, L. Aspiras, C. Heidelberger, P. L. Grover andP. Sims, Proc. natn. Acad. Sci. USA68, 3195 (1971).Google Scholar

Copyright information

© Birkhäuser Verlag 1972

Authors and Affiliations

  • J. W. Daly
    • 1
  • D. M. Jerina
    • 1
  • B. Witkop
    • 1
  1. 1.National Institute of Arthritis, Metabolism and Digestive DiseasesNational Institutes of HealthBethesdaUSA

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