Benzo[a]Pyrene Diones are Produced by Photochemical and Enzymatic Oxidation and Induce Concentration-Dependent Decreases in the Proliferative State of Human Pulmonary Epithelial Cells

References

• Bolton , J. L. , Trush , M. A. , Penning , T. M. , Dryhurst , G. and Monks , T. J. 2000 . Role of quinones in toxicology . Chem. Res. Toxicol. , 13 : 135 – 160 .
   PubMed Web of Science ®Google Scholar
• Gerson , C. , Sabater , J. , Scuri , M. , Torbati , A. , Coffey , R. , Abraham , J. W. , Lauredo , I. , Forteza , R. , Wanner , A. , Salathe , M. , Abraham , W. M. and Conner , G. E. 2000 . The lactoperoxidase system functions in bacterial clearance of airways . Am. J. Respir. Cell MoI. Biol. , 22 : 665 – 671 .
   PubMed Web of Science ®Google Scholar
• Kagan , J. , Tuveson , R. W. and Gong , H. H. 1989 . The light-dependent cytotoxicity of benzo[a]pyrene: Effect on human erythrocytes, Escherichia coli cells, and Haemophilus influenzae transforming DNA . Mufat. Res. , 216 : 231 – 242 .
   Google Scholar
• Ke , Y. , Reddel , R. R. , Gerwin , B. I. , Miyashita , M. , McMenamin , M. , Lechner , J. F. and Harris , C C. 1988 . Human bronchial epithelial cells with integrated SV40 virus T antigen genes retain the ability to undergo squamous differentiation . Differentiation , 38 : 60 – 66 .
   PubMed Web of Science ®Google Scholar
• Lesko , S. A. 1984 . Chemical carcinogenesis: Benzopyrene system . Methods Enzymol. , 105 : 539 – 550 .
   PubMed Web of Science ®Google Scholar
• Lorentzen , R. J. , Lesko , S. A. , McDonald , K. and Ts'o , P. O. 1979 . Toxicity of metabolic benzo(a)pyrenediones to cultured cells and the dependence upon molecular oxygen . Cancer Res. , 39 : 3194 – 3198 .
   PubMed Web of Science ®Google Scholar
• Lorentzen , R. J. and Ts'o , P. O. 1977 . Benzo[a]pyrenedione/benzo[a]pyrenediol oxidation-reduction couples and the generation of reactive reduced molecular oxygen . Biochemistry , 16 : 1467 – 1473 .
   PubMed Web of Science ®Google Scholar
• Marnett , L. J. and Reed , G. A. 1979 . Peroxidatic oxidation of benzo[a]pyrene and prostaglandin biosynthesis . Biochemistry , 18 : 2923 – 2929 .
   PubMed Web of Science ®Google Scholar
• Graf , W. and Haller , A. G. 1977 . The phototoxic activity of carcinogenic polycydic hydrocarbons and their degradation products in the biological test Zentralbl . Bakteriol. [Orig. B] , 164 : 250 – 261 [article in German] .
   PubMedGoogle Scholar
• Hoivik , D. J. , Manautou , J. E. , Tveit , A. , Mankowski , D. C. , Khairallah , E. A. and Cohen , S. D. 1996 . Evidence suggesting the 58-kDa acetaminophen binding protein is a preferential target for acetaminophen electrophile . Fundam. Appl. Toxicol. , 32 : 79 – 86 .
   PubMedGoogle Scholar
• Monks , T. J. , Hanzlik , R. P. , Cohen , G. M. , Ross , D. and Graham , D. G. 1992 . Quinone chemistry and toxicity . Toxicol. Appl. Pharmacol. , 112 : 2 – 16 .
   PubMed Web of Science ®Google Scholar
• Ratner , A. J. and Prince , A. 1999 . Lactoperoxidase: New recognition of an "old" enzyme in airway defenses . Am. J. Respir. Cell MoI. Biol. , 20 : 642 – 644 .
   Google Scholar
• Reed , M. and Thompson , D. C. 1997 . lmmunochemical visualization and identification of rat liver proteins adducted by 2,6-di-tert-butyl-4-methylphenol (BHT) . Chem. Res. Toxicol. , 10 : 1109 – 1117 .
   PubMed Web of Science ®Google Scholar
• Shellito , J. , Sniezek , M. and Warnock , M. 1987 . Acquisition of peroxidase activity by rat alveolar macrophages during pulmonary inflammation . Am. J. Pathol. , 129 : 567 – 577 .
   PubMed Web of Science ®Google Scholar
• Shen , A. L. , Fahl , W. E. , Wrighton , S. A. and Jefcoate , C. R. 1979 . Inhibition of benzo(a)pyrene and benzo(a)pyrene 7,8-dihydrodiol metabolism by benzo(a)pyrene quinones . Cancer Res. , 39 : 4123 – 4129 .
   PubMed Web of Science ®Google Scholar
• Sipes, I. G., McQueen, C. A., Candolfi, A. J., and Roth, R. A., eds. (1997). Comprehensive toxicology. Volume 8, Toxicology of the respiratory system. Cambridge, UK: Cambridge University Press.
   Google Scholar
• Skipper , P. L. 1996 . Influence of tertiary structure on nucleophilic substitution reactions of proteins . Chem. Res. Toxicol. , 9 : 918 – 923 .
   PubMed Web of Science ®Google Scholar
• Sun , J. D. , Wolff , R. K. , Kanapilly , G. M. and McClellan , R. O. 1984 . Lung retention and metabolic fate of inhaled benzo(a)pyrene associated with diesel exhaust particles . Toxicol. Appl. Pharmacol. , 73 : 48 – 59 .
   PubMed Web of Science ®Google Scholar
• Thannickal , V. J. and Fanburg , B. L. 2000 . Reactive oxygen species in cell signaling . Am. J. Physiol. Lung Cell MoI. Physiol. , 279 : L1005 – L1028 .
   PubMed Web of Science ®Google Scholar
• U.S. Environmental Protection Agency . 2000 . Health assessment document for diesel exhaust, chaps. 6-9.EPA/600/8-90/057E , Washington, DC : Office of Research and Development, U.S. Environmental Protection Agency .
   Google Scholar
• Environmental Protection Agency , U.S. 2001 . National-scale air toxics assessment for 7996. EPA-453/R-01 -003 , Research Triangle Park, NC : Office of Air Quality Planning and Standards, U.S. Environmental Protection Agency .
   Google Scholar
• U.S. Environmental Protection Agency . 2002 . Third external review draft of air quality criteria for paniculate matter , Vol. 1 , Research Triangle Park, NC : Office of Research and Development, EPA 600/P-99/002aC. U.S. Environmental Protection Agency .
   Google Scholar
• Van Cauwenberghe , K. A. 1985 . “ Atmospheric reactions of PAH ” . In Handbook of polycyclic aromatic hydrocarbons , Edited by: BjØrseth , A. and Ramdahl , T. 351 – 384 . New York : Marcel Dekker .
   Google Scholar
• Weyand , E. H. and Bevan , D. R. 1986 . Benzo(a)pyrene disposition and metabolism in rats following intratracheal instillation . Cancer Res. , 46 : 5655 – 5661 .
   PubMed Web of Science ®Google Scholar
• Winston , G. W. , Church , D. F. , Cueto , R. and Pryor , W. A. 1993 . Oxygen consumption and oxyradical production from microsomal reduction of aqueous extracts of cigarette tar . Arch. Biochem. Biophys. , 304 : 371 – 378 .
   PubMed Web of Science ®Google Scholar
• Wislocki , P. C. , Wood , A. W. , Chang , R. L. , Levin , W. , Yagi , H. , Hemandez , O. , Dansette , P. M. , Jerina , D. M. and Conney , A. H. 1976 . Mutagenicity and cytotoxicity of benzo(a)pyrene arene oxides, phenols, quinones, and dihydrodiols in bacterial and mammalian cells . Cancer Res. , 36 : 3350 – 3357 .
   PubMed Web of Science ®Google Scholar
• Yang , S. K. , Selkirk , J. K. , Plotkin , E. V. and Gelboin , H. V. 1975 . Kinetic analysis of the metabolism of benzo(a)pyrene to phenols, dihydrodiols, and quinones by high-pressure chromatography compared to analysis by aryl hydrocarbon hydroxylase assay, and the effect of enzyme induction . Cancer Res. , 35 : 3642 – 3650 .
   PubMed Web of Science ®Google Scholar
• Zhu , H. , Li , Y. and Trush , M. A. 1995 . Characterization of benzo[a]pyrene quinone-induced toxicity to primary cultured bone marrow stromal cells from DBA/2 mice: Potential role of mitochondrial dysfunction . Toxicol. Appl. Pharmacol. , 130 : 108 – 120 .
   PubMed Web of Science ®Google Scholar
• Cavalieri , E. L. , Devanesan , P. D. and Rogan , E. G. 1988 . Radical cations in the horseradish peroxidase and prostaglandin H synthase mediated metabolism and binding of benzo[a]pyrene to deoxyribonudeic acid . Biochem. Pharmacol. , 37 : 2183 – 2187 .
   PubMed Web of Science ®Google Scholar
• Cavalieri , E. L. and Rogan , E. G. 1995 . Central role of radical cations in metabolic activation of poly cyclic aromatic hydrocarbons . Xenobiotica , 25 : 677 – 688 .
   PubMed Web of Science ®Google Scholar
• Chesis , P. L , Levin , D. E. , Smith , M. T. , Ernster , L and Ames , B. N. 1984 . Mutagenicity of quinones: Pathways of metabolic activation and detoxification . Proc. Natl. Acad. Sci. USA , 81 : 1696 – 1700 .
   PubMed Web of Science ®Google Scholar
• de Mendez , I. , Young , K. R. Jr , Bignon , J. and Lambre , C. R. 1991 . Biochemical characteristics of alveolar macrophage-specific peroxidase activities in the rat . Arch. Biochem. Biophys. , 289 : 319 – 323 .
   PubMed Web of Science ®Google Scholar
• Finlayson-Pitts , B. J. and Pitts , J. N. Jr . 1999 . “ Airborne polycydic aromatic hydrocarbons and their derivatives: Atmospheric chemistry and toxicological implications ” . In Chemistry of the upper and lower atmosphere: Theory, experiments, and applications , 436 – 546 . San Diego, CA : Academic Press .
   Google Scholar