Polycyclic aromatic hydrocarbon o-quinones mutate p53 in human lung adenocarcinoma (A549) cells

Polycyclic Aromatic Compounds

Volumn 24, Issue 4-5, 2004, Pages 583-596

  Penning, Trevor M ^a   Shen, Yu Min ^a   Mick, Rosemarie ^a   Shults, Justine ^a   Field, Jeffrey M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Aldo keto reductase; ortho quinones; Polycyclic aromatic hydrocarbon; Reactive oxygen species

Indexed keywords

COMPLEMENTARY DNA; EPOXIDE; METHYLNITRONITROSOGUANIDINE; MUTAGENIC AGENT; MUTANT PROTEIN; OXIDOREDUCTASE; POLYCYCLIC AROMATIC COMPOUND; PROTEIN P53; PYRENE DERIVATIVE; QUINONE DERIVATIVE; SOLVENT;

CANCER CELL; CONFERENCE PAPER; CONTROLLED STUDY; HUMAN; HUMAN CELL; LUNG ADENOCARCINOMA; METABOLITE; MUTATION; OXIDATION REDUCTION REACTION; PROTEIN EXPRESSION; REPORTER GENE; YEAST;

EID: 4844229240     PISSN: 10406638     EISSN: None     Source Type: Journal    
DOI: 10.1080/10406630490471717     Document Type: Conference Paper

References (27)

1. A. H. Conney, Induction of Microsomal Enzymes by Foreign Chemicals and Carcinogenesis by Polycyclic Aromatic Hydrocarbons: G. H. A. Clowes Memorial Lecture, Cancer Research 42 (1982):4875-4917.
2. H. V. Gelboin, Benzo[a]pyrene Metabolism, Activation and Carcinogenesis: Role and Regulation of Mixed Function Oxidases and Related Enzymes, Physiological Reviews 60 (1980):1107-1166.
3. T. R. Sutter, Y. M. Tang, C. L. Hayes, Y.-Y. P. Wo, W. Jabs, X. Li, H. Yin, C. W. Cody, and W. F. Greenlee, Complete cDNA Sequence of a Human Dioxin-Inducible mRNA Identifies a New Gene Subfamily of Cytochrome P450 that Maps to Chromosome 2, Journal of Biological Chemistry 269 (1994):13092-13099.
4. T. Shimada, C. L. Hayes, H. Yamazaki, S. Amin, S. S. Hecht, F. P. Guengerich, and T. R. Sutter, Activation of Chemically Diverse Procarcinogens by Human Cytochrome P450 1B1, Cancer Research 56 (1996):2979-2984.
5. T. M. Penning, M. E. Burczynski, C.-F. Hung, K. D. McCoull, N. T. Palackal, and L. S. Tsuruda, Dihydrodiol Dehydrogenases and Polycyclic Aromatic Hydrocarbon Activation: Generation of Reactive and Redox-Active o-Quinones, Chemical Research in Toxicology 12 (1999):1-18.
6. p53 Mutation in Lung Cancer, http://perso.curie.fr/Thierry.Soussi/ p53_mutation_in_ %20lung.html
7. K. W. Jennette, A. M. Jeffery, S. H. Blobstein, F. A. Beland, R. G. Harvey, and I. B. Weinstein, Nucleoside Adducts from the In Vitro Reaction of Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide or Benzo[a]pyrene-4,5-oxide with Nucleic Acids, Biochemistry 16 (1977):932-938.
8. A. M. Jeffrey, K. W. Jennette, S. H. Blobstein, I. B. Weinstein, F. A. Beland, R. G. Harvey, H. Kasai, I. Miura, and K. Nakanishi, Benzo[a]pyrene- Nucleic Acid Derivative Found In Vivo: Structure of a Benzo[a]pyrene- Tetrahydrodiol Epoxide-Guanosine Adduct, Journal of American Chemical Society 98 (1976):5714-5715.
9. M. Koreeda, P. D. Moore, P. G. Wislocki, W. Levin, A. H. Conney, H. Yagi, and D. M. Jerina, Binding of Benzo[a]pyrene-7,8-diol-9,10-epoxides to DNA, RNA and Protein of Mouse Skin Occurs with High Stereoselectivity, Science 199 (1978):778-781.
10. M. R. Osborne, F. A. Beland, R. G. Harvey, and P. Brookes, The Reaction of (±)-7α,8β-dihydroxy-9β,10β-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene with DNA, International Journal of Cancer 18 (1976):362-368.
11. M. Shou, R. G. Harvey, and T. M. Penning, Reactivity of Benzo[a]pyrene-7,8-dione with DNA: Evidence for the Formation of Deoxyguanosine Adducts, Carcinogenesis 14 (1993):475-482.
12. K. D. McCoull, D. Rindgen, I. A. Blair, and T. M. Penning, Synthesis and Characterization of Polycyclic Aromatic Hydrocarbon o-Quinone Depurinating N7-Guanine Adducts, Chemical Research in Toxicology 12 (1999):237-246.
13. P. D. Devanesan, N. V. S. RamaKrishna, R. Todorovic, E. G. Rogan, E. L. Cavalieri, H. Jeong, R. Jankowiak, and G. J. Small, Identification and Quantitation of Benzo[a]pyrene-DNA Adducts Formed by Rat Liver Microsomes In Vitro, Chemical Research in Toxicology 5 (1992):302-309.
14. L. Chen, P. D. Devanesan, S. Higginbotham, F. Ariese, R. Jankowiak, G. J. Small, E. G. Rogan, and E. Cavalieri, Expanded Analysis of Benzo[a]pyrene-DNA Adducts Formed In Vitro and In Mouse Skin: Their Significance in Tumor Initiation, Chemical Research in Toxicology 9 (1996):897-903.
15. D. Yu, T. M. Penning, and J. M. Field, Benzo[a]pyrene-7,8-dione Is More Mutagenic than anti-BPDE on p53 and Is Dependent upon the Generation of ROS, Polycyclic Aromatic Compounds 22 (2002):881-891.
16. D. Yu, J. A. Berlin, T. M. Penning, and J. M. Field, Reactive Oxygen Species Generated by PAH o-Quinones Cause Change-in-Function Mutations in p53, Chemical Research in Toxicology 15 (2002):832-842.
17. Q. A. Khan and L. M. Anderson, Hydrocarbon Carcinogens Evade Cellular Defense Mechanism of G1 Arrest in Nontransformed and Malignant Lung Cell Lines, Toxicology and Applied Pharmacology 173 (2001):105-113.
18. N. T. Palackal, S. H. Lee, R. G. Harvey, I. A. Blair, and T. M. Penning, Activation of Polycyclic Aromatic Hydrocarbon trans-Dihydrodiol Proximate Carcinogens by Human Aldo-Keto Reductase (AKR1C) Enzymes and Their Functional Overexpression in Human Lung Carcinoma (A549) Cells, Journal of Biological Chemistry 277 (2002):24799-24808.
19. K. B. Sukamaran and R. G. Harvey, Synthesis of o-Quinones and Dihydrodiols of Polycyclic Aromatic Hydrocarbons from the Corresponding Phenols, Journal of Organic Chemistry 45 (1980):4407-4413.
20. C. Ishioka, T. Frebourg, Y.-X. Yan, M. Vidal, S. H. Friend, S. Schmidt, and R. Iggo, Screening Patients for Heterozygous p53 Mutations Using a Functional Assay in Yeast, Nature Genetics 5 (1993):124-129.
21. C. Guthrie and G. R. Fink, Guide to Yeast Genetics and Molecular Biology, in Methods in Enzymol, 194 (New York: Academic Press, 1991).
22. S. J. Wei, R. L. Chang, N. Bhachech, X. X. Cui, K. A. Merkler, C. Q. Wong, E. Hennig, H. Yagi, D. M. Jerina, and A. H. Conney, Dose-Dependent Differences in the Profile of Mutations Induced by (+)-7R,8S-dihydroxy-9S,10R- epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in the Coding Region of the Hypoxanthine (Guanine) Phosphoribosyltransferase Gene in Chinese Hamster V-79 Cells, Cancer Research 53 (1993):3294-3301.
23. H. Khalili, F.-J. Zhang, R. G. Harvey, and A. Dipple, Mutagenicity of Benzo[a]-pyrene-Deoxyadenosine Adducts in a Sequence Context Derived from the p53 Gene, Mutation Research 465 (2000):39-44.
24. P. Chary, G. J. Latham, D. L. Robberson, S. J. Kim, S. Han, C. M. Harris, T. M. Harris, and R. S. Lloyd, In Vivo and In Vitro Replication Consequences of Stereoisomeric Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide Adducts on Adenine N6 at the Second Position of N-ras Codon 61, Journal of Biological Chemistry 270 (1995):4990-5000.
25. J. R. Mitchell, H. J. L. Hoeijmakers, and L. J. Niedernhofer, Divide and Conquer: Nucleotide Excision Repair Battles Cancer and Ageing, Curr. Opinion Cell Biol. 15 (2003):232-240.
26. R. W. Sobol, D. E. Watson, J. Nakamura, F. M. Yakes, E. Hou, J. K. Horton, J. Ladapo, B. van Houten, J. A. Swenberg, K. R. Tindall, L. D. Samson, and S. H. Wilson, Mutations Associated with Base Excision Repair Deficiency and Methylation-Induced Genotoxic Stress, Proceedings of the National Academy of Science USA 99 (2002):6860-6865.
27. R. K. Brachman, M. Vidal, and J. D. Boeke, Dominant-Negative p53 Mutations Selected in Yeast Hit Cancer Hot-Spots, Proceedings of the National Academy of Science USA 93 (1996):4091-4095.