Mutagenic specificity of N-acetoxy-3-aminobenzanthrone, a major metabolically activated form of 3-nitrobenzanthrone, in shuttle vector plasmids propagated in human cells

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 654, Issue 1, 2008, Pages 82-87

  Nishida, Hiroshi ^a   Kawanishi, Masanobu ^a   Takamura Enya, Takeji ^b   Yagi, Takashi ^a  

^a Frontier Science Innovation Center   (Japan)

^b KANAGAWA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

3 Nitrobenzanthrone; DNA adduct; Polycyclic aromatic hydrocarbons; supF

Indexed keywords

3 NITROBENZANTHRONE; ADENINE; CYTOSINE; DNA POLYMERASE; GUANINE; MUTAGENIC AGENT; N ACETOXY 3 AMINOBENZANTHRONE; PLASMID VECTOR; THYMINE;

AIRBORNE PARTICLE; ARTICLE; CANCER RISK; CELL CULTURE; CELL LINE; CONTROLLED STUDY; CULTURE MEDIUM; DNA ADDUCT; DNA REPAIR; ENZYME ASSAY; EXCISION REPAIR; EXHAUST GAS; GENE; HUMAN; HUMAN CELL; LUNG CANCER; MUTAGENICITY; NUCLEIC ACID BASE SUBSTITUTION; PRIORITY JOURNAL; SHUTTLE VECTOR; STOP CODON; SUPF GENE;

AIR POLLUTANTS; BASE SEQUENCE; BENZ(A)ANTHRACENES; CELL LINE; DNA ADDUCTS; FIBROBLASTS; GENES, SUPPRESSOR; GENETIC VECTORS; HUMANS; MOLECULAR SEQUENCE DATA; MUTAGENS; MUTATION; PLASMIDS; RNA, TRANSFER; SIMIAN VIRUS 40;

EID: 46849112852     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrgentox.2008.05.004     Document Type: Article

References (48)

1. Enya T., Suzuki H., Watanabe T., Hirayama T., and Hisamatsu Y. 3-Nitrobenzanthrone, a powerful bacterial mutagen and suspected human carcinogen found in diesel exhaust and airborne particulates. Environ. Sci. Technol. 31 (1997) 2772-2776
2. Murahashi T., Iwanaga E., Watanabe T., and Hirayama T. Determination of the mutagen 3-nitrobenzanthrone in rainwater collected in Kyoto, Japan. J. Health Sci. 49 (2003) 386-390
3. Murahashi T., Watanabe T., Otake S., Hattori Y., Takamura T., Wakabayashi K., and Hirayama T. Determination of 3-nitrobenzanthrone in surface soil by normal-phase high-performance liquid chromatography with fluorescence detection. J. Chromatogr. A 992 (2003) 101-107
4. Watanabe T., Hasei T., Yoshifumi T., Otake S., Murahashi T., Takamura T., Hirayama T., and Wakabayashi K. Mutagenic activity and quantification of nitroarenes in surface soil in the Kinki region of Japan. Mutat. Res. 538 (2003) 121-131
5. Arlt V.M., Zhan L., Schmeiser H.H., Honma M., Hayashi M., Phillips D.H., and Suzuki T. DNA adducts and mutagenic specificity of the ubiquitous environmental pollutant 3-nitrobenzanthrone in Muta Mouse. Environ. Mol. Mutagen. 43 (2004) 186-195
6. Arlt V.M., Cole K.J., and Phillips D.H. Activation of 3-nitrobenzanthrone and its metabolites to DNA-damaging species in human B-lymphoblastoid MCL-5 cells. Mutagenesis 19 (2004) 149-156
7. Lamy E., Kassie F., Gminski R., Schmeiser H.H., and Mersch-Sundermann V. 3-Nitrobenzanthrone (3-NBA) induced micronucleus formation and DNA damage in human hepatoma (HepG2) cells. Toxicol. Lett. 146 (2004) 103-109
8. Nagy E., Johansson C., Zeisig M., and Möller L. Oxidative stress and DNA damage caused by the urban air pollutant 3-NBA and its isomer 2-NBA in human lung cells analyzed with three independent methods. J. Chromatogr. B 827 (2005) 94-103
9. Phousongphouang P.T., Grosovsky A.J., Eastmond D.A., Covarrubias M., and Arey J. The genotoxicity of 3-nitrobenzanthrone and the nitropyrene lactones in human lymphoblasts. Mutat. Res. 472 (2000) 93-103
10. Nagy E., Zeisig M., Kawamura K., Hisamatsu Y., Sugeta A., Adachi S., and Moller L. DNA-adduct and tumor formations in rats after intratracheal administration of the urban air pollutant 3-nitrobenzanthrone. Carcinogenesis 26 (2005) 1821-1828
11. Arlt V.M. 3-Nitrobenzanthrone, a potential human cancer hazard in diesel exhaust and urban air pollution: a review of the evidence. Mutagenesis 20 (2005) 399-410
12. Essigmann J.M., and Wood M.L. The relationship between the chemical structures and mutagenic specifities of the DNA lesions formed by chemical and physical mutagens. Toxicol. Lett. 67 (1993) 29-39
13. 32P-postlabeling. Int. J. Cancer 93 (2001) 450-454
14. Arlt V.M., Glatt H., Muckel E., Pabel U., Sorg B.L., Schmeiser H.H., and Phillips D.H. Metabolic activation of the environmental contaminant 3-nitrobenzanthrone by human acetyltransferases and sulfotransferase. Carcinogenesis 23 (2002) 1937-1945
15. Arlt V.M., Glatt H., Muckel E., Pabel U., Sorg B.L., Seidel A., Frank H., Schmeiser H.H., and Phillips D.H. Activation of 3-nitrobenzanthrone and its metabolites by human acetyltransferases, sulfotransferases and cytochrome P450 expressed in Chinese hamster V79 cells. Int. J. Cancer 105 (2003) 583-592
16. Arlt V.M., Hewer A., Sorg B.L., Schmeiser H.H., Phillips D.H., and Stiborova M. 3-Aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone, forms DNA adducts after metabolic activation by human and rat liver microsomes: evidence for activation by cytochrome P450 1A1 and P450 1A2. Chem. Res. Toxicol. 17 (2004) 1092-1101
17. Arlt V.M., Stiborova M., Henderson C.J., Osborne M.R., Bieler C.A., Frei E., Martinek V., Sopko B., Wolf C.R., Schmeiser H.H., and Phillips D.H. The environmental pollutant and potent mutagen 3-nitrobenzanthrone forms DNA adducts after reduction by NAD(P)H:quinone oxidoreductase and conjugation by acetyltransferases and sulfotransferases in human hepatic cytosols. Cancer Res. 65 (2005) 2644-2652
18. Arlt V.M., Henderson C.J., Wolf C.R., Schmeiser H.H., Phillips D.H., and Stiborova M. Bioactivation of 3-aminobenzanthrone, a human metabolite of the environmental pollutant 3-nitrobenzanthrone: evidence for DNA adduct formation mediated by cytochrome P450 enzymes and peroxidases. Cancer Lett. 234 (2006) 220-231
19. Kawanishi M., Enya T., Suzuki H., Takebe H., Matsui S., and Yagi T. Postlabelling analysis of DNA adducts formed in human hepatoma cells treated with 3-nitrobenzanthrone. Mutat. Res. 470 (2000) 133-139
20. Borlak J., Hansen T., Yuan Z., Sikka H.C., Kumar S., Schmidbauer S., Frank H., Jacob J., and Seidel A. Metabolism andDNA-binding of 3-nitrobenzanthrone in primary rat alveolar type II cells, in human fetal bronchial, rat epithelial and mesenchymal cell lines. Polycyclic Aromat. Compds. 21 (2000) 73-86
21. Arlt V.M., Sorg B.L., Osborne M., Hewer A., Seidel A., Schmeiser H.H., and Phillips D.H. DNA adduct formation by the ubiquitous environmental pollutant 3-nitrobenzanthrone and its metabolites in rats. Biochem. Biophys. Res. Commun. 300 (2003) 107-114
22. Arlt V.M., Stiborova M., Hewer A., Schmeiser H.H., and Phillips D.H. Human enzymes involved in the metabolic activation of the environmental contaminant 3-nitrobenzanthrone: evidence for reductive activation by human NADPH:cytochrome P450 reductase. Cancer Res. 63 (2003) 2752-2761
23. Bieler C.A., Arlt V.M., Wiessler M., and Schmeiser H.H. DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone in V79 cells expressing human cytochrome P450 enzymes. Cancer Lett. 200 (2003) 9-18
24. Bieler C.A., Cornelius M., Klein R., Arlt V.M., Wiessler M., Phillips D.H., and Schmeiser H.H. DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone after intratracheal instillation in rats. Int. J. Cancer 116 (2005) 833-838
25. 32P-postlabeling analysis of DNA adducts derived from the environmental contaminant 3-nitrobenzanthrone. Chem. Res. Toxicol. 18 (2005) 1056-1070
26. Kawanishi M., Enya T., Suzuki H., Takebe H., Matsui S., and Yagi T. Mutagenic specificity of a derivative of 3-nitrobenzanthrone in the supF shuttle vector plasmids. Chem. Res. Toxicol. 11 (1998) 1468-1473
27. 6 position of adenine. Int. J. Cancer 118 (2006) 2139-2146
28. 32P-postlabeling method. Mutat. Res. 634 (2007) 184-191
29. Takamura-Enya T., Kawanishi M., Yagi T., and Hisamatsu Y. Structural identification of DNA adducts derived from 3-nitrobenzanthrone, a potent carcinogen present in the atmosphere. Chem. Asian J. 2 (2007) 1174-1185
30. Enya T., Kawanishi M., Suzuki H., Matsui S., and Hisamatsu Y. An unusual DNA adduct derived from the powerfully mutagenic environmental contaminant 3-nitrobenzanthrone. Chem. Res. Toxicol. 11 (1998) 1460-1467
31. Kraemer K.H., and Seidman M.M. Use of supF, an Escherichia coli tyrosine suppressor tRNA gene, as a mutagenic target in shuttle-vector plasmids. Mutat. Res. 220 (1989) 61-72
32. Girardi A.J., Jensen F.C., and Koprowski H. SV40-induced transformation of human diploid cells, crisis and recovery. J. Cell. Comp. Physiol. 62 (1965) 69-84
33. Takebe H., Nii S., Ishii M., and Utsumi H. Comparative studies of host-cell reactivation, colony forming ability and excision repair after UV irradiation of xeroderma pigmentosum, normal human and some other mammalian cells. Mutat. Res. 25 (1974) 383-390
34. Matsuda T., Yagi T., Kawanishi M., Matsui S., and Takebe H. Molecular analysis of mutations induced by 2-chloroacetaldehyde, the ultimate carcinogenic form of vinyl chloride, in human cells using shuttle vectors. Carcinogenesis 16 (1995) 2389-2394
35. Yagi T., Tatsumi-Miyajima J., Sato M., Kraemer K.H., and Takebe H. Analysis of point mutations in an ultraviolet-irradiated shuttle vector plasmid propagated in cells from Japanese xeroderma pigmentosum patients in complementation groups A and F. Cancer Res. 51 (1991) 3177-3182
36. Levy D.D., Groopman J.D., Lim S.E., Seidman M.M., and Kraemer K.M. Sequence specificity of aflatoxin B1-induced mutations in a plasmid replicated in xeroderma pigmentosum and DNA repair proficient human cells. Cancer Res. 52 (1992) 5668-5673
37. Bubley G.J., Ashburner B.P., and Teicher B.A. Spectrum of cis-Diamminedichloroplatinum(II) induced mutations in a shuttle vector propagated in human cells. Mol. Carcinog. 4 (1991) 397-406
38. McLuckie K.I.E., Crookston R.J.R., Gaskell M., Farmer P.B., Routledge M.N., Martin E.A., and Brown K. Mutation spectra induced by R-acetoxytamoxifen-DNA adducts in human DNA repair proficient and deficient (Xeroderma Pigmentosum Complementation Group A) cells. Biochemistry 44 (2005) 8198-8205
39. Boldt J., Mah M.C.-M., Wang Y.-C., Smith B.A., Beland F.A., Maher V.M., and McCormick J.J. Kinds of mutations found when a shuttle vector containing adducts of 1,6-dinitropyrene replicates in human cells. Carcinogenesis 12 (1991) 119-126
40. Mah M.C., Boldt J., Culp S.J., Maher V.M., and McCormick J.J. Replication of acetylaminofluorene-adducted plasmids in human cells: spectrum of base substitutions and evidence of excision repair. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 10193-10197
41. Kohara A., Suzuki T., Honma M., Oomori T., Ohwada T., and Hayashi M. Dinitropyrenes induce gene mutations in multiple organs of the lambda/lacZ transgenic mouse (Muta™ Mouse). Mutat. Res. 515 (2002) 73-83
42. Seidman M.M., Bredberg A., Seetharam S., and Kraemer K.H. Multiple point mutations in a shuttle vector propagated in human cells: evidence for an error-prone DNA polymerase activity. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 4944-4948
43. Courtemanche C., and Anderson A. Multiple mutations in a shuttle vector modified by ultraviolet irradiation (±)-7β, 8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]p yrene, and aflatoxin B1 have different properties than single mutations and may be generated during translesion synthesis. Mutat. Res. 430 (1999) 23-36
44. Bigger C.A.H., Pontén I., Page J.E., and Dipple A. Mutational spectra for polycyclic aromatic hydrocarbons in the supF target gene. Mutat. Res. 450 (2000) 75-93
45. Maher V.M., Yang J.L., and McCormick J.J. Ability of adducts formed in a shuttle vector by reactive metabolites of 1-nitropyrene and benzo(a)pyrene to induce mutations when the plasmid replicates in human cells. Acta Biol. Hung. 41 (1990) 173-186
46. Kanaly R.A., Hanaoka T., Sugimura H., Toda H., Matsui S., and Matsuda T. Development of the adductome approach to detect DNA damage in humans. Antioxid. Redox Signal. 8 (2006) 993-1001
47. Hashimoto A.H., Amanuma K., Hiyoshi K., Sugawara Y., Goto S., Yanagisawa R., Takano H., Masumura K., Nohmi T., and Aoki Y. Mutations in the lungs of gpt delta transgenic mice following inhalation of diesel exhaust. Environ. Mol. Mutagen. 48 (2007) 682-693
48. Healey K., Smith E.C., Wild C.P., and Routledge M.N. The mutagenicity of urban particulate matter in an enzyme free system is associated with the generation of reactive oxygen species. Mutat. Res. 602 (2006) 1-6