Mutagenicity of the 1-nitropyrene-DNA adduct N-(deoxyguanosin-8-yl)-1- aminopyrene in Escherichia coli located in a nonrepetitive CGC sequence

Chemical Research in Toxicology

Volumn 13, Issue 6, 2000, Pages 523-528

  Bacolod, Manny D ^a   Krishnasamy, Ramji ^a   Basu, Ashis K ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 NITROPYRENE; BACTERIAL DNA;

ARTICLE; BACTERIAL GENE; CONTROLLED STUDY; DNA ADDUCT; ESCHERICHIA COLI; GENOTOXICITY; NONHUMAN; TOXICITY TESTING;

BASE COMPOSITION; DEOXYGUANOSINE; DNA REPLICATION; DNA, BACTERIAL; ESCHERICHIA COLI; MUTAGENESIS; MUTAGENICITY TESTS; MUTAGENS; PYRENES; REPETITIVE SEQUENCES, NUCLEIC ACID; SOS RESPONSE (GENETICS); TRANSFORMATION, BACTERIAL;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; PROKARYOTA;

EID: 0034130729     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000023r     Document Type: Article

References (29)

1. Rosenkranz, H. S., McCoy, E. C., Sanders, D. R., Butler, M., Kiriazides, D. K., and Mermelstein, R. (1980) Nitropyrenes: isolation, identification, and reduction of mutagenic impurities in carbon black and toners. Science 209, 1039-1043.
2. 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.
3. Rosenkranz, H. S., and Mermelstein, R. (1985) The genotoxicity, metabolism, and carcinogenicity of nitrated polycyclic hydrocarbons. J. Environ. Sci. Health C3, 221-272.
4. International Agency for Research on Cancer (1989) The genotoxicity, metabolism, and carcinogenicity of nitrated polycyclic hydrocarbons. In IARC Monographs on the Evaluation of Carcinogenic Risk to Humans, Vol. 39, pp 1-458, International Agency for Research on Cancer, Lyon, France.
5. Ohnishi, Y., Kinouchi, T., Manabe, Y., Tsutsui, H., Otsuka, H., Tokiwa, H., and Otofuji, T. (1985) Nitro compunds in environmental mixtures and foods. In Short-Term Genetics Bioassays in the Evaluation of Complex Environmental Mixtures (Waters, M. D., Shandhu, S. S., Lewtas, J., Claxton, L., Strauss, G., and Nesnow, S., Eds.) pp 195-204, Plenum Press, New York.
6. Kinouchi, T., Tsutsui, H., and Ohnishi, Y. (1986) Detection of 1-nitropyrene in yakitori (grilled chicken). Mutat. Res. 171, 105-113.
7. Hirose, M., Lee, M.-S., Wang, C. Y., and King, C. M. (1984) Induction of rat mammary gland tumors by 1-nitropyrene, a recently recognized environmental mutagen. Cancer Res. 44, 1158-1162.
8. El-Bayoumy, K. (1992) Environmental carcinogens that may be involved in human breast cancer etiology. Chem. Res. Toxicol. 5, 585-590.
9. Howard, P. C., and Beland, F. A. (1982) Xanthine oxidase catalyzed binding of 1-nitropyrene to DNA. Biochem. Biophys. Res. Commun. 104, 727-732.
10. Howard, P. C., Heflich, R. H., Evans, F. E., and Beland, F. A. (1983) Formation of DNA adducts in vitro and in Salmonella typhimurium upon metabolic reduction of the environmental mutagen 1-nitropyrene. Cancer Res. 43, 2052-2058.
11. Stanton, C. A., Chow, F. L., Phillips, D. H., Grover, P. L., Garner, R. C., and Martin, C. N. (1985) Evidence for N-(deoxyguanosin-8-yl)-1-aminopyrene as a major DNA adduct in female rats treated with 1-nitropyrene. Carcinogenesis 6, 535-538.
12. Stanton, C. A., Garner, R. C., and Martin, C. N. (1988) The mutagenicity and DNA base sequence changes induced by 1-nitroso-and 1-nitropyrene in the cI gene of lambda prophage. Carcinogenesis 9, 1153-1157.
13. Melchoir, W. B., Jr., Marques, M. M., and Beland, F. A. (1994) Mutations induced by aromatic amine DNA adducts in pBR322. Carcinogenesis 15, 889-899.
14. Malia, S. A., and Basu, A. K. (1995) Mutagenic specificity of reductively activated 1-nitropyrene in Escherichia coli. Biochemistry 34, 96-104.
15. Bell, D. A., Levin, J. G., and DeMarini, D. M. (1991) DNA sequence analysis of revertants of the hisD3052 allele of Salmonella typhimurium TA98 using the polymerase chain reaction and direct sequencing: Application to 1-nitropyrene-induced revertants. Mutat. Res. 252, 35-44.
16. 3 sequence: effects of SOS, proofreading, and mismatch repair. Biochemistry 35, 4568-4577.
17. Mao, B., Vyas, R. R., Hingerty, B. E., Broyde, S., Basu, A. K., and Patel, D. J. (1996) Solution conformation of N-(deoxyguanosin-8-yl)-1-aminopyrene opposite dC in a DNA duplex. Biochemistry 35, 12659-12670.
18. Gu, Z., Gorin, A., Krishnasamy, R., Hingerty, B. E., Basu, A. K., Broyde, S., and Patel, D. J. (1999) Solution structure of the N-(deoxyguanosin-8-yl)-1-aminopyrene ([AP]dG) adduct opposite dA in a DNA duplex. Biochemistry 38, 10843-10854.
19. Nolan, S. J., McNulty, J. M., Krishnasamy, R., McGregor, W. G., and Basu, A. K. (1999) C8-Guanine adduct-induced stabilization of a - 1 frameshift intermediate in a nonrepetitive DNA sequence. Biochemistry 38, 14056-14062.
20. Vyas, R. R., Nolan, S. J., and Basu, A. K. (1993) Synthesis and characterization of oligodeoxynucleotides containing N-(deoxyguanosin-8-yl)-1-aminopyrene. Tetrahedron Lett. 34, 2247-2250.
21. Ramos, L. A., Lipman, R., Tomasz, M., and Basu, A. K. (1998) The Major Mitomycin C-DNA Monoadduct is Cytotoxic but Not Mutagenic in Escherichia coli. Chem. Res. Toxicol. 11, 64-69.
22. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) In Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NT.
23. Banerjee, S. K., Christensen, R. B., Lawrence, C. W., and LeClerc, J. E. (1988) Frequency and spectrum of mutations produced by a single cis-syn thymine-thymine cylobutane dimer in a single-stranded vector. Proc. Natl. Acad. Sci. U.S.A. 85, 8141-8145.
24. Hanrahan, C. J., Bacolod, M. D., Vyas, R. R., Liu, T.-M., Geacintov, N. E., Loechler, E. L., and Basu, A. K. (1997) Sequence specific mutagenesis of the major (+)-anti-benzo[a]pyrene diol epoxide-DNA adduct at a mutational hotspot in vitro and in Escherichia coli cells. Chem. Res. Toxicol. 10, 369-377.
25. Streisinger, G., Okada, Y., Emrich, J., Newton, J., Tsugita, A., Terzaghi, E., and Inouye, M. (1966) Frameshift mutations and the genetic code. Cold Spring Harbor Symp. Quant. Biol. 31, 77-84.
26. Wood, R. D., and Hutchinson, F. (1987) Ultraviolet light-induced mutagenesis in the Escherichia coli chromosome: sequences of mutants in the cI gene of a lambda lysogen. J. Mol Biol. 193, 637-641.
27. Moriya, M., Zhang, W., Johnson, F., and Grollman, A. P. (1994) Mutagenic potency of exocyclic DNA adducts: marked difference between Escherichia coli and simian kidney cells. Proc. Natl. Acad. Sci. U.S.A. 91, 11899-11903.
28. 6-Ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry 35, 11487-11492.
29. Moriya, M., Spiegel, S., Fernandas, A., Amin, S., Liu, T., Geacintov, N., and Grollman, A. P. (1996) Fidelity of translesional synthesis past benzo[a]pyrene diol epoxide-2′-deoxyguanosine DNA adducts: marked effects of host cell, sequence context, and chirality. Biochemistry 35, 16646-16651.