7
Views
20
CrossRef citations to date
0
Altmetric
Part two: Carcinogenesis at the molecular level

Binding of polycyclic aromatic hydrocarbons to DNA: Comparison with mutagenesis and tumorigenesis

, &
Pages 1009-1020 | Published online: 20 Oct 2009

References

  • Andrews , A. W. , Thibault , L. H. and Lijinsky , W. 1978a . The relationship between carcinogenicity and mutagenicity of some polynuclear hydrocarbons . Mutat. Res. , 51 : 311 – 318 .
  • Baird , W. M. and Brookes , P. 1973 . Isolation of the hydrocarbon‐deoxyribonucleoside products from the DNA of mouse embryo cells treated in culture with 7‐methylbenz(a)anthracene‐3 H . Cancer Res. , 33 : 2378 – 2385 .
  • Baird , W. M. and Diamond , L. 1976 . Effect of 7,8‐benzoflavone on the formation of benzo(a)pyrene‐DNA‐bound products in hamster embryo cells . Chem.‐Biol. Interact. , 13 : 67 – 75 .
  • Baird , W. M. , Harvey , R. G. and Brookes , P. 1975 . Comparison of the cellular DNA‐bound products of benzo(a)pyrene with the products formed by the reaction of benzo(a)pyrene‐4,5‐oxide with DNA . Cancer Res. , 35 : 54 – 57 .
  • Barrett , C. and Ts'o , P. O. P. 1978 . Relationship between somatic mutation and neoplastic transformation . Proc. Natl. Acad. Sci. U.S.A. , 75 : 3297 – 3301 .
  • Barrett , C. J. , Tsutsui , T. and Ts'o , P. O. P. 1978 . Neoplastic transformation induced by a direct perturbation of DNA . Nature (Lond.) , 274 : 229 – 232 .
  • Boobis , A. R. and Nebert , D. W. 1977 . Genetic differences in the metabolism of carcinogens and in the binding of benzo(a)pyrene metabolites to DNA . Adv. Enzyme Regul. , 15 : 339 – 362 .
  • Bookes , P. 1966 . Quantitative aspects of the reaction of some carcinogens with nucleic acids and the possible significance of such reactions in the process of carcinogenesis . Cancer Res. , 26 : 1994 – 2003 .
  • Brookes , P. and Lawley , P. D. 1964 . Evidence for the binding of polynuclear aromatic hydrocarbons to the nucleic acids of mouse skin. Relation between carcinogenic power of hydrocarbons and their binding to DNA . Nature (Lond.) , 202 : 781 – 784 .
  • Burdette , W. J. 1955 . The significance of mutation in relation to the origin of tumors: A review . Cancer Res. , 15 : 201 – 226 .
  • Daudel , P. , Duquesne , M. , Vigny , P. , Grover , P. L. and Sims , P. 1975 . Fluorescence spectral evidence that benzo(a)pyrene‐DNA products in mouse skin arise from diol‐epoxides . FEBS Lett. , 57 : 250 – 253 .
  • Deckers‐Schmelzle , B. , Klaus , E. , Kahl , R. and Kahl , G. F. 1978 . Binding of benzo(a)pyrene metabolites to cellular macromolecules in perfused rat lungs . Arch. Pharmacol. , 303 : 303 – 307 .
  • De Serres , F. J. , Fouts , J. R. , Bend , J. R. and Philpot , R. M. , eds. 1976 . In Vitro Metabolic Activation in Mutagenesis Testing , Amsterdam : Elsevier/North‐Holland Biomedical .
  • Eastman , A. , Sweetenham , J. and Bresnick , E. 1978 . Comparison of in vivo and in vitro binding of polycyclic hydrocarbons to DNA . Chem.‐Biol. Interact. , 23 : 345 – 353 .
  • Fahl , W. E. , Shen , A. L. and Jefcoate , C. R. 1978 . UDP‐glucuronosyl transferase and the conjugation of benzo(a)pyrene metabolites to DNA . Biochem. Biophys. Res. Commun. , 85 : 891 – 899 .
  • Gelboin , H. V. 1969 . A microsome‐dependent binding of benzo(a)pyrene to DNA . Cancer Res. , 29 : 1272 – 1276 .
  • Goshman , L. M. and Heidelberger , C. 1967 . Binding of tritium‐labelled polycyclic hydrocarbons to DNA of mouse skin . Cancer Res. , 27 : 1678 – 1688 .
  • Grover , P. L. and Sims , P. 1969 . Enzyme‐catalyzed reactions of polycyclic hydrocarbons with deoxyribonucleic acid and protein in vitro . Biochem. J. , 110 : 159 – 160 .
  • Grover , P. L. , Hewer , A. , Pal , K. and Sims , P. 1976 . The involvement of a diol‐epoxide in the metabolic activation of benzo(a)pyrene in human bronchial mucosa and in mouse skin . Int. J. Cancer , 18 : 1 – 6 .
  • Heidelberger , C. 1973 . Chemical oncogenesis in culture . Adv. Cancer Res. , 18 : 317 – 366 .
  • Heidelberger , C. 1975 . Chemical carcinogenesis . Annu. Rev. Biochem. , 44 : 79 – 121 .
  • Huberman , E. and Sachs , L. 1976 . Mutability of different genetic loci in mammalian cells by metabolically activated carcinogenic polycyclic hydrocarbons . Proc. Natl. Acad. Sci. U.S.A. , 73 : 188 – 192 .
  • Huberman , E. and Sachs , L. 1977 . DNA binding and its relationship to carcinogenesis by different polycyclic hydrocarbons . Int. J. Cancer , 19 : 122 – 127 .
  • Huberman , E. , Mager , R. and Sachs , L. 1976 . Mutagenesis and transformation of normal cells by chemical carcinogens . Nature (Lond.) , 264 : 360 – 361 .
  • Iball , J. 1939 . The relative potency of carcinogenic compounds . Am. J. Cancer , 35 : 188 – 190 .
  • Jeffrey , A. M. , Weinstein , I. B. , Jennette , K. W. , Grzeskowiak , K. , Nakanishi , K. , Harvey , R. G. , Autrup , H. and Harris , C. 1977 . Structures of benzo(a)pyrene‐nucleic acid adducts formed in human and bovine bronchial explants . Nature (Lond.) , 269 : 348 – 350 .
  • Jollow , D. J. , Mitchell , J. R. , Zampaglione , N. and Gillette , J. R. 1974 . Bromobenzene‐induced liver necrosis. Protective role of glutathione and evidence for 3,4‐bromobenzene oxide as the hepatotoxic metabolite . Pharmacology , 11 : 151 – 169 .
  • Kahl , G. F. , Klaus , E. , Legraverend , C. , Nebert , D. W. and Pelkonen , O. 1979 . Formation of benzo(a)pyrene metabolite‐nucleoside adducts in isolated perfused rat and mouse liver and in mouse lung slices . Biochem. Pharmacol. , 28 : 1051 – 1056 .
  • King , H. W. S. , Thompson , M. H. and Brookes , P. 1975 . The benzo(a)pyrene deoxyribonucleoside products isolated from DNA after metabolism of benzo(a)pyrene by rat liver microsomes in the presence of DNA . Cancer Res. , 35 : 1263 – 1269 .
  • King , H. W. S. , Thompson , M. H. and Brookes , P. 1976 . The role of 9‐hydroxybenzo(a)pyrene in the microsomesmediated binding of benzo(a)pyrene to DNA . Int. J. Cancer , 18 : 339 – 344 .
  • Kuroki , T. and Heidelberger , C. 1971 . The binding of polycyclic aromatic hydrocarbons to the DNA, RNA, and proteins of transformable cells in culture . Cancer Res. , 31 : 2168 – 2176 .
  • Leffler , S. , Pulkrabek , P. , Grunberger , D. and Weinstein , I. B. 1977 . Template activity of calf thymus DNA modified by a dihydrodiol epoxide derivative of benzo(a)pyrene . Biochemistry , 16 : 3133 – 3136 .
  • Levitt , R. , Pelkonen , O. , Okey , A. B. and Nebert , D. W. 1979 . Genetic differences in metabolism of polycyclic aromatic carcinogens and aromatic amines by mouse liver microsomes. Detection by DNA binding of metabolites and by mutagenicity in histidine‐dependent Salmonella typhimurium in vitro . J. Natl. Cancer Inst. , 62 : 947 – 955 .
  • McCann , J. and Ames , B. N. 1976 . Detection of carcinogens as mutagens in Salmonella/microsome test: Assay of 300 chemicals: Discussion . Proc. Natl. Acad. Sci. U.S.A. , 73 : 950 – 954 .
  • McCann , J. , Choi , E. , Yamasaki , E. and Ames , B. N. 1975 . Detection of carcinogens as mutagens in the Salmonella/microsome test: Assay of 300 chemicals . Proc. Natl. Acad. Sci. U.S.A. , 72 : 5135 – 5139 .
  • Meehan , T. , Straub , K. and Calvin , M. 1976 . Elucidation of hydrocarbon structure in an enzyme‐catalyzed benzo(a)pyrene poIy(G) covalent complex . Proc. Natl. Acad. Sci. U.S.A. , 73 : 1437 – 1441 .
  • Miller , J. A. 1970 . Carcinogenesis by chemicals: An overview. G. H. A. Clowes memorial lecture . Cancer Res. , 30 : 559 – 576 .
  • Mizusawa , H. and Kakefuda , T. 1979 . Inhibition of DNA synthesis in vitro by binding of benzo(a)pyrene metabolite diol‐epoxide I to DNA . Nature (Lond.) , 279 : 75 – 78 .
  • Montesano , R. , Bartsch , H. and Tomatis , L. , eds. 1976 . Screening Tests in Chemical Carcinogenesis , I ARC Sci. Publ. 12 Lyon : International Agency for Research on Cancer .
  • Nagao , M. , Sugimura , T. and Matsushima , T. 1978 . Environmental mutagens and carcinogens . Annu. Rev. Genet. , 12 : 117 – 159 .
  • Newbold , R. F. , Wigley , C. B. , Thompson , M. H. and Brookes , P. 1977 . Cell‐mediated mutagenesis in cultured Chinese hamster cells by carcinogenic polycyclic hydrocarbons: Nature and extent of the associated hydrocarbon‐DNA reaction . Mutat. Res. , 43 : 101 – 116 .
  • Nordenskjöld , M. , Söderhäll , S. , Moldëus , P. and Jernström , B. 1978 . Differences in the repair of DNA strand breaks induced by 9‐hydroxy‐benzo(a)pyrene and trans‐7,8‐dihydro‐7,8‐dihydroxy‐benzo(a)‐pyrene in cultured human fibroblasts . Biochem. Biophys. Res. Commun. , 85 : 1535 – 1541 .
  • Osborne , M. R. , Thompson , M. H. , Tarmy , E. M. , Beland , F. A. , Harvey , R. G. and Brookes , P. 1976 . The reaction of 7,8‐dihydro‐7,8‐dihydroxy‐benzo(a)pyrene‐9,10‐oxide with DNA in relation to the benzo(a)pyrene‐DNA products isolated from cells . Chem.‐Biol. Interact. , 13 : 343 – 348 .
  • Parodi , S. and Brambilla , G. 1977 . Relationships between mutation and transformation frequencies in mammalian cells treated in vitro with chemical carcinogens . Mutat. Res. , 47 : 53 – 74 .
  • Pelkonen , O. , Boobis , A. R. , Yagi , H. , Jerina , D. and Nebert , D. W. 1978 . The tentative identification of benzo(a)pyrene metabolite‐nucleoside complexes produced in vitro by mouse liver microsomes . Mol. Pharmacol. , 14 : 306 – 322 .
  • Pelkonen , O. , Boobis , A. R. , Levitt , R. C. , Kouri , R. E. and Nebert , D. W. 1979 . Genetic differences in the metabolic activation of benzo(a)pyrene in mice. Attempts to correlate tumorigenesis with binding of reactive intermediates to DNA and with mutagenesis in vitro . Pharmacology , 18 : 281 – 293 .
  • Phillips , D. H. , Grover , P. L. and Sims , P. 1979 . A quantitative determination of the covalent binding of a series of polycyclic hydrocarbons to DNA in mouse skin . Int. J. Cancer , 23 : 201 – 208 .
  • Pitot , H. C. 1974 . Neoplasia: A somatic mutation or a heritable change in cytoplasmic membranes? . J. Natl. Cancer Inst. , 53 : 905 – 911 .
  • Prehn , R. T. 1964 . A clonal selection theory of chemical carcinogenesis . J. Natl. Cancer Inst. , 32 : 1 – 17 .
  • Pulkrabek , P. , Leffler , S. , Weinstein , I. B. and Grunberger , D. 1977 . Conformation of DNA modified with a dihydrodiol epoxide derivative of benzo(a)pyrene . Biochemistry , 16 : 3127 – 3132 .
  • Purchase , I. F. H. , Longstaff , E. , Ashby , J. , Styles , J. A. , Anderson , D. , Lefevre , P. A. and Westwood , F. R. 1976 . Evaluation of six short term tests for detecting organic chemical carcinogens and recommendations for their use . Nature (Lond.) , 264 : 624 – 627 .
  • Setlow , R. B. 1978 . Repair deficient human disorders and cancer . Nature (Lond.) , 271 : 713 – 717 .
  • Sims , P. , Grover , P. L. , Swaisland , A. , Pal , K. and Hewer , A. 1974 . Metabolic activation of benzo(o)pyrene proceeds by a diol‐expoxide . Nature (Lond.) , 252 : 326 – 328 .
  • Straub , K. M. , Meehan , T. , Burlingarne , A. L. and Calvin , M. 1977 . Identification of the major adducts formed by reaction of benzo(a)pyrene diol epoxide with DNA in vitro . Proc. Natl. Acad. Sci. U.S.A. , 74 : 5285 – 5289 .
  • Sugimura , T. , Sato , S. , Nagao , M. , Yahagi , T. , Matsushima , T. , Seino , Y. , Takeuchi , M. and Kawachi , T. 1976 . “ Overlapping of carcinogens and mutagens ” . In Fundamentals in Cancer Prevention , Edited by: Magee , P. N. , Takayama , S. , Sugimura , T. and Matsushima , T. 191 – 215 . Baltimore : University Park .
  • Temin , H. M. 1974 . On the origin of the genes for neoplasia: G. H. A. Clowes memorial lecture . Cancer Res. , 34 : 2835 – 2841 .
  • Thompson , M. H. , King , H. W. S. , Osbome , M. R. and Brookes , P. 1976 . Rat liver microsome‐mediated binding of benzo(a)pyrene metabolites to DNA . Int. J. Cancer , 17 : 270 – 274 .
  • Vähäkangas , K. , Nebert , D. W. and Pelkonen , O. 1979 . The DNA binding of benzo(a)pyrene metabolites catalyzed by rat lung microsomes in vitro and in isolated perfused rat lung . Chem.‐Biol. Interact. , 24 : 167 – 176 .
  • Weinstein , I. B. , Jeffrey , A. M. , Jennette , K. W. , Blobstein , S. H. , Harvey , R. G. , Harris , C. , Autrup , H. , Kasai , H. and Nakanishi , K. 1976a . Benzo(a)pyrene diol expoxides as intermediates in nucleic acid binding in vitro and in vivo . Science , 193 : 592 – 595 .
  • Weinstein , I. B. , Wigler , M. and Stadler , U. 1976b . “ Analysis of the mechanism of chemical carcinogenesis in epithelial cell cultures ” . In Screening Tests in Chemical Carcinogenesis , Edited by: Montesano , R. , Bartsch , H. and Tomatis , L. 355 – 381 . Lyon : International Agency for Research on Cancer .
  • Wigley , C. B. , Thompson , M. H. and Brookes , P. 1976 . The nature of benzo(a)pyrene binding to DNA in an epithelial cell culture system . Eur. J. Cancer , 12 : 743 – 745 .
  • Wigley , C. B. , Newbold , R. F. , Amos , J. and Brookes , P. 1979 . Cell‐mediated mutagenesis in cultured Chinese hamster cells by polycyclic hydrocarbons: Mutagenicity and DNA‐reaction related to carcinogenicity in a series of compounds . Int. J. Cancer , 23 : 691 – 696 .
  • Yamasaki , H. , Roush , T. W. and Weinstein , I. B. 1978 . Benzo(a)pyrene 7,8‐dihydrodiol‐9,10‐oxide modification of DNA: Relation to chromatin structure and reconstitution . Chem.‐Biol. Interact. , 23 : 201 – 213 .
  • Zytkovicz , T. H. , Moses , H. L. and Spelsberg , T. C. 1977 . The binding of benzo(a)pyrene and N‐methyl‐N‐nitro‐nitrosoguanidine to subnuclear fractions of AKR mouse embryo cells in culture . Int. J. Cancer , 20 : 408 – 417 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.