Quantification of 3-nitrobenzanthrone-DNA adducts using online column-switching HPLC-electrospray tandem mass spectrometry

Chemical Research in Toxicology

Volumn 22, Issue 11, 2009, Pages 1860-1868

  Da Costa, Gonçalo Gamboa ^a   Singh, Rajinder ^b   Arlt, Volker M ^a   Mirza, Amin ^c   Richards, Meirion ^c   Takamura Enya, Takeji ^d   Schmeiser, Heinz H ^e   Farmer, Peter B ^b   Phillips, David H ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c IMPERIAL CANCER RESEARCH FUND   (United Kingdom)

^d KANAGAWA INSTITUTE OF TECHNOLOGY   (Japan)

^e GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2A2 DEOXYGUANOSIN N 2 YL) 3 AMINOBENZANTHRONE; 2 (2A2 DEOXYGUANOSINE 8 YL) 3 AMINOBENZANTHRONE; 3 AMINOBENZANTHRONE; 3 NITROBENZANTHRONE; DNA; N (2A2 DEOXYGUANOSIN 8 YL) 3 AMINOBENZANTHRONE; N ACETOXY 3 AMINOBENZANTHRONE; N HYDROXY 3 AMINOBENZANTHRONE; N SULFOXY 3 AMINOBENZANTHRONE; NITROGEN 15; PHOSPHORUS 32; POLYCYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LABELING INDEX; NONHUMAN; RAT; SALMON; TANDEM MASS SPECTROMETRY; TESTIS;

ANIMALS; BENZ(A)ANTHRACENES; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; FEMALE; HYDROXYLAMINE; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; SALMON; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY; VEHICLE EMISSIONS;

ANIMALIA; RATTUS;

EID: 72749099767     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900264v     Document Type: Article

References (44)

1. Enya, T., Suzuki, H., Watanabe, T., Hirayama, T., and Hisamatsu, Y. (1997) 3-Nitrobenzanthrone, a powerful bacterial mutagen and suspected human carcinogen found in diesel exhaust and airborne particulates. Environ. Sci. Technol. 31, 2772-2776. (Pubitemid 27426108)
2. Takamura-Enya, T., Suzuki, H., and Hisamatsu, Y. (2006) Mutagenic activities and physicochemical properties of selected nitrobenzanthrones. Mutagenesis 21, 399-404. (Pubitemid 44691129)
3. Arlt, V. M., Zhan, L., Schmeiser, H. H., Honma, M., Hayashi, M., Phillips, D. H., and Suzuki, T. (2004) DNA adducts and mutagenic specificity of the ubiquitous environmental pollutant 3-nitrobenzanthrone in Muta Mouse. Environ. Mol. Mutagen 43, 186-195. (Pubitemid 38649734)
4. Nagy, E., Zeisig, M., Kawamura, K., Hisamatsu, Y., Sugeta, A., Adachi, S., and Moller, L. (2005) DNA adduct and tumor formations in rats after intratracheal administration of the urban air pollutant 3-nitrobenzanthrone. Carcinogenesis 26, 1821-1828. (Pubitemid 41487999)
5. Seidel, A., Dahmann, D., Krekeler, H., and Jacob, J. (2002) Biomonitoring of polycyclic aromatic compounds in the urine of mining workers occupationally exposed to diesel exhaust. Int. J. Hyg. Environ. Health 204, 333-338. (Pubitemid 34157882)
6. Murahashi, T., Iwanaga, E., Watanabe, T., and Hirayama, T. (2003) Determination of the mutagen 3-nitrobenzanthrone in rainwater collected in Kyoto, Japan. J. Health Sci. 49, 386-390. (Pubitemid 41289092)
7. Murahashi, T., Watanabe, T., Otake, S., Hattori, Y., Takamura, T., Wakabayashi, K., and Hirayama, T. (2003) Determination of 3-nitrobenzanthrone in surface soil by normal-phase high-performance liquid chromatography with fluorescence detection. J. Chromatogr., A 992, 101-107. (Pubitemid 36349633)
8. Watanabe, T., Hasei, T., Takahashi, Y., Otake, S., Murahashi, T., Takamura, T., Hirayama, T., and Wakabayashi, K. (2003) Mutagenic activity and quantification of nitroarenes in surface soil in the Kinki region of Japan. Mutat. Res. 538, 121-131. (Pubitemid 36776694)
9. Murata, M., Tezuka, T., Ohnishi, S., Takamura-Enya, T., Hisamatsu, Y., and Kawanishi, S. (2006) Carcinogenic 3-nitrobenzanthrone induces oxidative damage to isolated and cellular DNA. Free Radical Biol. Med. 40, 1242-1249.
10. Nagy, E., Johansson, C., Zeisig, M., and Moller, L. (2005) 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, 94-103. (Pubitemid 41551602)
11. Nagy, E., Adachi, S., Takamura-Enya, T., Zeisig, M., and Moller, L. (2007) DNA adduct formation and oxidative stress from the carcinogenic urban air pollutant 3-nitrobenzanthrone and its isomer 2-nitrobenzanthrone, in vitro and in vivo. Mutagenesis 22, 135-145. (Pubitemid 46364520)
12. Hansen, T., Seidel, A., and Borlak, J. (2007) The environmental carcinogen 3-nitrobenzanthrone and its main metabolite 3-aminobenzanthrone enhance formation of reactive oxygen intermediates in human A549 lung epithelial cells. Toxicol. Appl. Pharmacol. 221, 222-234. (Pubitemid 46764807)
13. Arlt, V. M. (2005) 3-Nitrobenzanthrone, a potential human cancer hazard in diesel exhaust and urban air pollution: a review of the evidence. Mutagenesis 20, 399-410.
14. Borlak, J., Hansen, T., Yuan, Z. X., Sikka, H. C., Kumar, S., Schmidbauer, S., Frank, H., Jacob, J., and Seidel, A. (2000) Metabolism and DNA-binding of 3-nitrobenzanthrone in primary rat alveolar type II cells, in human fetal bronchial, rat epithelial and mesenchymal cell lines. Polycyclic Aromat. Compd. 21, 73-86. (Pubitemid 33370178)
15. Bieler, C. A., Wiessler, M., Erdinger, L., Suzuki, H., Enya, T., and Schmeiser, H. H. (1999) DNA adduct formation from the mutagenic air pollutant 3-nitrobenzanthrone. Mutat. Res. 439, 307-311. (Pubitemid 29094823)
16. 32P-postlabeling. Int. J. Cancer 93, 450-454.
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. (2005) 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, 2644-2652. (Pubitemid 40490063)
18. Arlt, V. M., Stiborova, M., Hewer, A., Schmeiser, H. H., and Phillips, D. H. (2003) 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, 2752-2761. (Pubitemid 36667145)
19. Arlt, V. M., Hewer, A., Sorg, B. L., Schmeiser, H. H., Phillips, D. H., and Stiborova, M. (2004) 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, 1092-1101. (Pubitemid 39108677)
20. Arlt, V. M., Henderson, C. J., Wolf, C. R., Schmeiser, H. H., Phillips, D. H., and Stiborova, M. (2006) 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, 220-231.
21. Arlt, V. M., Glatt, H., Muckel, E., Pabel, U., Sorg, B. L., Schmeiser, H. H., and Phillips, D. H. (2002) Metabolic activation of the environmental contaminant 3-nitrobenzanthrone by human acetyltransferases and sulfotransferase. Carcinogenesis 23, 1937-1945. (Pubitemid 35355944)
22. Arlt, V. M., Glatt, H., Muckel, E., Pabel, U., Sorg, B. L., Seidel, A., Frank, H., Schmeiser, H. H., and Phillips, D. H. (2003) Activation of 3-nitrobenzanthrone and its metabolites by human acetyltransferases, sulfotransferases and cytochrome P450 expressed in Chinese hamster V79 cells. Int. J. Cancer 105, 583-592. (Pubitemid 36687724)
23. Arlt, V. M., Schmeiser, H. H., Osborne, M. R., Kawanishi, M., Kanno, T., Yagi, T., Phillips, D. H., and Takamura-Enya, T. (2006) Identification of three major DNA adducts formed by the carcinogenic air pollutant 3-nitrobenzanthrone in rat lung at the C8 and N2 position of guanine and at the N6 position of adenine. Int. J. Cancer 118, 2139-2146.
24. Kanno, T., Kawanishi, M., Takamura-Enya, T., Arlt, V. M., Phillips, D. H., and Yagi, T. (2007) DNA adduct formation in human hepatoma cells treated with 3-nitrobenzanthrone: analysis by the (32)P-postlabeling method. Mutat. Res. 634, 184-191. (Pubitemid 47634000)
25. Nagy, E., Adachi, S., Takamura-Enya, T., Zeisig, M., and Moller, L. (2006) DNA damage and acute toxicity caused by the urban air pollutant 3-nitrobenzanthrone in rats: characterization of DNA adducts in eight different tissues and organs with synthesized standards. Environ. Mol. Mutagen 47, 541-552. (Pubitemid 44291167)
26. Phillips, D. H., and Arlt, V. M. (2007) The 32P-postlabeling assay for DNA adducts. Nat. Protoc. 2, 2772-2781.
27. Phillips, D. H., and Castegnaro, M. (1999) Standardization and validation of DNA adduct postlabelling methods: report of interlaboratory trials and production of recommended protocols. Mutagenesis 14, 301-315.
28. Farmer, P. B., and Singh, R. (2008) Use of DNA adducts to identify human health risk from exposure to hazardous environmental pollutants: the increasing role of mass spectrometry in assessing biologically effective doses of genotoxic carcinogens. Mutat. Res. 659, 68-76.
29. Enya, T., Kawanishi, M., Suzuki, H., Matsui, S., and Hisamatsu, Y. (1998) An unusual DNA adduct derived from the powerfully mutagenic environmental contaminant 3-nitrobenzanthrone. Chem. Res. Toxicol. 11, 1460-1467. (Pubitemid 29013619)
30. Osborne, M. R., Arlt, V. M., Kliem, C., Hull, W. E., Mirza, A., Bieler, C. A., Schmeiser, H. H., and Phillips, D. H. (2005) Synthesis, characterization, and 32P-postlabeling analysis of DNA adducts derived from the environmental contaminant 3-nitrobenzanthrone. Chem. Res. Toxicol. 18, 1056-1070. (Pubitemid 40880895)
31. Bieler, C. A., Cornelius, M. G., Klein, R., Arlt, V. M., Wiessler, M., Phillips, D. H., and Schmeiser, H. H. (2005) DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone after intratracheal instillation in rats. Int. J. Cancer 116, 833-838. (Pubitemid 41209187)
32. Bieler, C. A., Cornelius, M. G., Stiborova, M., Arlt, V. M., Wiessler, M., Phillips, D. H., and Schmeiser, H. H. (2007) Formation and persistence of DNA adducts formed by the carcinogenic air pollutant 3-nitrobenzanthrone in target and non-target organs after intratracheal instillation in rats. Carcinogenesis 28, 1117-1121. (Pubitemid 47072199)
33. Arlt, V. M., Glatt, H., Gamboa da Costa, G., Reynisson, J., Takamura- Enya, T., and Phillips, D. H. (2007) Mutagenicity and DNA adduct formation by the urban air pollutant 2-nitrobenzanthrone. Toxicol. Sci. 98, 445-457. (Pubitemid 47244814)
34. Gamboa da Costa, G., Marques, M. M., Beland, F. A., Freeman, J. P., Churchwell, M. I., and Doerge, D. R. (2003) Quantification of tamoxifen DNA adducts using on-line sample preparation and HPLC-electrospray ionization tandem mass spectrometry. Chem. Res. Toxicol. 16, 357-366.
35. Singh, R., Teichert, F., Verschoyle, R. D., Kaur, B., Vives, M., Sharma, R. A., Steward, W. P., Gescher, A. J., and Farmer, P. B. (2009) Simultaneous determination of 8-oxo-2′-deoxyguanosine and 8-oxo- 2′- deoxyadenosine in DNA using online column-switching liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 23, 151-160.
36. Singh, R., Gaskell, M., Le Pla, R. C., Kaur, B., Azim-Araghi, A., Roach, J., Koukouves, G., Souliotis, V. L., Kyrtopoulos, S. A., and Farmer, P. B. (2006) Detection and quantitation of benzo[a]pyrene-derived DNA adducts in mouse liver by liquid chromatography-tandem mass spectrometry: comparison with 32P-postlabeling. Chem. Res. Toxicol. 19, 868-878. (Pubitemid 43939066)
37. Gamboa da Costa, G., Churchwell, M. I., Hamilton, L. P., Von Tungeln, L. S., Beland, F. A., Marques, M. M., and Doerge, D. R. (2003) DNA adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice. Chem. Res. Toxicol. 16, 1328-1337.
38. Takamura-Enya, T., Kawanishi, M., Yagi, T., and Hisamatsu, Y. (2007) Structural identification of DNA adducts derived from 3-nitrobenzanthrone, a potent carcinogen present in the atmosphere. Chem. Asian J. 2, 1174-1185.
39. vom Brocke, J., Krais, A., Whibley, C., Hollstein, M. C., and Schmeiser, H. H. (2009) The carcinogenic air pollutant 3-nitrobenzanthrone induces GC to TA transversion mutations in human p53 sequences. Mutagenesis 24, 17-23.
40. Arlt, V. M., Suzuki, T., Zhan, L., Schmeiser, H. H., Honma, M., Hayashi, M., and Phillips, D. H. (2004) DNA adducts and mutagenic specificity of the ubiquitous environmental pollutant 3-nitrobenzanthrone in Muta Mouse. Mutagenesis 19, 511-511
41. Arlt, V. M., Gingerich, J., Schmeiser, H. H., Phillips, D. H., Douglas, G. R., and White, P. A. (2008) Genotoxicity of 3-nitrobenzanthrone and 3-aminobenzanthrone in MutaMouse and lung epithelial cells derived from MutaMouse. Mutagenesis 23, 483-490.
42. Schild, L. J., Phillips, D. H., Osborne, M. R., Hewer, A., Beland, F. A., Churchwell, M. I., Brown, K., Gaskell, M., Wright, E., and Poirier, M. C. (2005) Hepatic DNA adduct dosimetry in rats fed tamoxifen: a comparison of methods. Mutagenesis 20, 115-124. (Pubitemid 40637811)
43. Wang, J. J., Marshall, W. D., Frazer, D. G., Law, B., and Lewis, D. M. (2003) Characterization of DNA adducts from lung tissue of asphalt fume-exposed mice by nanoflow liquid chromatography quadrupole time-of-flight mass spectrometry. Anal. Biochem. 322, 79-88. (Pubitemid 37188559)
44. Vanhoutte, K., Van Dongen, W., Hoes, I., Lemiere, F., Esmans, E. L., Van Onckelen, H., Van den Eeckhout, E., van Soest, R. E., and Hudson, A. J. (1997) Development of a nanoscale liquid chromatography/ electrospray mass spectrometry methodology for the detection and identification of DNA adducts. Anal. Chem. 69, 3161-3168. (Pubitemid 127698299)