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Original Articles

Microbial transformation of 6‐nitrobenzo[a]pyrene

, &
Pages 519-530 | Received 22 Mar 1986, Accepted 09 Jun 1986, Published online: 20 Oct 2009

References

  • Beland , F. A. , Heflich , R. H. , Howard , P. C. and Fu , P. P. 1985 . “ The in vitro metabolic activation of nitro polycyclic aromatic hydrocarbons ” . In Polycyclic Hydrocarbons and Carcinogenesis , ACS Symposium Series 283 Edited by: Harvey , R. G. 371 – 396 . Washington, D.C. : American Chemical Society .
  • Campbell , J. , Crumplin , G. C. , Garner , J. V. , Garner , R. C. , Martin , C. N. and Rutter , A. 1981 . Nitrated polycyclic aromatic hydrocarbons: Potent bacterial mutagens and stimulators of DNA repair synthesis in cultured human cells . Carcinogenesis , 2 : 559 – 565 .
  • Casy , A. F. 1971 . PMR Spectroscopy in Medicinal and Biological Chemistry , 331 – 334 . New York : Academic .
  • Cerniglia , C. E. 1984 . Microbial metabolism of polycyclic aromatic hydrocarbons . Adv. Appl. Mi‐crobiol. , 30 : 31 – 71 .
  • Cerniglia , C. E. and Gibson , D. T. 1978 . Metabolism of naphthalene by cell extracts of Cunning‐hamella elegans . Arch. Biochem. Biophys. , 186 : 121 – 127 .
  • Cerniglia , C. E. and Gibson , D. T. 1979 . Oxidation of benzo[a]pyrene by the filamentous fungus Cunninghamella elegans . J. Biol. Chem. , 254 : 12174 – 12180 .
  • Cerniglia , C. E. and Gibson , D. T. 1980a . Fungal oxidation of benzo[a]pyrene and ( ±)‐trans‐7,8‐dihydroxy‐7,8‐dihydrobenzo(a)‐pyrene . J. Biol. Chem. , 255 : 5159 – 5163 .
  • Cerniglia , C. E. and Gibson , D. T. 1980b . Fungal oxidation of (±)‐9,10‐dihydroxy‐9,10‐dihydro‐benzo[a]pyrene: Formation of diastereomeric benzo[a]pyrene 9,10‐diol 7,8‐epoxides . Proc. Natl. Acad. Sci. USA , 77 : 4554 – 4558 .
  • Cerniglia , C. E. , Freeman , J. P. and Mitchum , R. K. 1982 . Glucuronide and sulfate conjugation in the fungal metabolism of aromatic hydrocarbons . Appl. Environ. Microbiol. , 43 : 1070 – 1075 .
  • Cerniglia , C. E. , Althaus , J. R. , Evans , F. E. , Freeman , J. P. , Mitchum , R. K. and Yang , S. K. 1983 . Stereochemistry and evidence for an arene oxide‐NIH shift pathway in the fungal metabolism of naphthalene . Chem. Biol. Interact. , 44 : 119 – 132 .
  • Cerniglia , C. E. , Howard , P. C. , Fu , P. P. and Franklin , W. 1984a . Metabolism of nitropolycyclic aromatic hydrocarbons by human intestinal microflora . Biochem. Biophys. Res. Commun. , 123 : 262 – 270 .
  • Cerniglia , C. E. , Miller , D. W. , Yang , S. K. and Freeman , J. P. 1984b . Effects of a fluoro substituent on the fungal metabolism of 1‐fluoronaphthalene . Appl. Environ. Microbiol. , 48 : 294 – 300 .
  • Cerniglia , C. E. , Freeman , J. P. , White , G. L. , Heflich , R. H. and Miller , D. W. 1985 . Fungal metabolism and detoxification of the nitropolycyclic aromatic hydrocarbon, 1‐nitropyrene . Appl. Environ. Microbiol. , 50 : 649 – 655 .
  • Chou , M. W. , Evans , F. E. , Yang , S. K. and Fu , P. P. 1983 . Evidence for a 2,3‐epoxide as an intermediate in the microsomal metabolism of 6‐nitrobenzo[a]pyrene . Carcinogenesis , 4 : 699 – 702 .
  • Chou , M. W. , Heflich , R. H. , Casciano , D. A. , Miller , D. W. , Freeman , J. P. , Evans , F. E. and Fu , P. P. 1984 . Synthesis, spectral analysis, and mutagenicity of 1‐, 3‐, and 6‐nitrobenzo[a]pyr‐ene . J. Med. Chem. , 27 : 1156 – 1161 .
  • DiPaolo , J. A. , Demarinis , A. J. , Chou , F. L. , Garner , R. C. , Martin , C. N. and Doniger , J. 1983 . Nitration of carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons results in products able to induce transformation of Syrian hamster cells . Carcinogenesis , 4 : 357 – 359 .
  • Fu , P. P. and Chou , M. W. 1982 . “ In vitro metabolism of 6‐nitro‐benzo[a]pyrene: Effect of the nitro substituent on the regioselectivity of the cytochrome P‐450 mediated drug metabolizing enzyme system ” . In Cytochrome P‐450 Biochemistry, Biophysics and Environmental Implication , Edited by: Hietanen , E. , Laitinen , M. and Hanninen , O. 39 – 42 . Amsterdam : Elsevier Biomédical .
  • Fu , P. P. , Chou , M. W. , Yang , S. K. , Unruh , L. E. , Beland , F. A. , Kadlubar , F. F. , Casciano , D. A. , Heflich , R. H. and Evans , F. E. In vitro metabolism of 6‐nitrobenzo[a]pyrene: Identification and mutagenicity of its metabolites . Polynuclear Aromatic Hydrocarbons: Physical, Biological and Chemistry, Sixth International Symposium . Edited by: Cooke , W. M. , Dennis , A. J. and Fisher , G. L. pp. 287 – 296 . Columbus, Ohio : Battelle .
  • Fu , P. P. , Chou , M. W. , Yang , S. K. , Beland , F. A. , Kalubar , F. F. , Casciano , D. A. , Heflich , R. H. and Evans , F. E. 1982b . Metabolism of the mutagenic environmental pollutant 6‐nitro‐benzo[a]pyrene: Metabolic activation via ring oxidation . Biochem. Biophys. Res. Commun. , 105 : 1037 – 1043 .
  • Fu , P. P. , Heflich , R. H. , Casciano , D. A. , Huang , A. Y. , Trie , W. M. , Kadlubar , F. F. and Beland , F. A. 1982c . Biologically active aromatic amines derived from carcinogenic polycyclic aromatic hydrocarbons: Synthesis and mutagenicity of aminobenzo[a]pyrenes . Mutat. Res. , 94 : 13 – 21 .
  • Howard , P. C. , Beland , F. A. and Cerniglia , C. E. 1983a . Reduction of the carcinogen 1‐nitropyrene to 1‐aminopyrene by intestinal bacteria . Carcinogenesis , 4 : 985 – 990 .
  • Howard , P. C. , Gerrard , J. A. , Milo , G. E. , Fu , P. P. , Beland , F. A. and Kadlubar , F. K. 1983b . Transformation of normal human skin fibroblast by 1‐nitropyrene and 6‐nitrobenzo[a]pyrene . Carcinogenesis , 4 : 353 – 355 .
  • Lofroth , C. , Toftgard , R. , Nilsson , L , Agurell , E. and Gustafsson , J. A. 1984 . Short‐term bioassays of nitro derivatives of benzo[a]pyrene and perylene . Carcinogenesis , 5 : 925 – 930 .
  • Mermelstein , R. , Kiriazides , D. K. , Butler , M. , McCoy , E. C. and Rosenkranz , H. S. 1981 . The extraordinary mutagenicity of nitropyrenes in bacteria . Mutåt. Res. , 89 : 187 – 196 .
  • Nikolaov , K. , Maselet , P. and Mouvier , G. 1984 . Sources and chemical reactivity of polynuclear aromatic hydrocarbons in the atmosphere—A critical review . Sci. Total Environ. , 32 : 103 – 132 .
  • Pitts , J. N. Jr. , Van Cauwenberghe , K. A. , Grosjean , D. , Schmid , J. P. and Fitz , D. R. 1978 . Atmospheric reactions of polycyclic aromatic hydrocarbons: Atmospheric reactions of polycyclic aromatic hydrocarbons: Facile formation of mutagenic nitro derivatives . Science , 202 : 515 – 519 .
  • Rosenkranz , H. S. and Mermelstein , R. 1983 . Mutagenicity and genotoxicity of nitroarenes. All nitro‐containing chemicals were not created equal . Mutat. Res. , 114 : 217 – 267 .
  • Tong , S. and Selkirk , J. K. 1983 . Metabolism of 6‐nitrobenzo[a]‐pyrene by hamster embryonic fibroblasts and its interaction with nuclear macromolecules . Toxicol. Environ. Health , 11 : 381 – 393 .
  • Waller , G. R. 1972 . Biochemical Applications of Mass Spectrometry , 335 – 337 . New York : Wiley .

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