Development of liquid chromatography electrospray ionization tandem mass spectrometry methods for analysis of DNA adducts of formaldehyde and their application to rats treated with N-nitrosodimethylamine or 4-(methylnitrosamino) -1-(3-pyridyl)-1-butanone

Chemical Research in Toxicology

Volumn 20, Issue 8, 2007, Pages 1141-1148

  Wang, Mingyao ^a   Cheng, Guang ^a   Villalta, Peter W ^a   Hecht, Stephen S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; ADENOSINE DEAMINASE; DIMETHYLNITROSAMINE; FORMALDEHYDE;

ACCURACY; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DNA CROSS LINKING; DNA DETERMINATION; DOSE RESPONSE; ELECTROSPRAY MASS SPECTROMETRY; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MALE; NONHUMAN; RAT; STANDARD;

ADENOSINE DEAMINASE; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIMETHYLNITROSAMINE; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; FORMALDEHYDE; HYDROLYSIS; MALE; MODELS, CHEMICAL; NITROSAMINES; RATS; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TIME FACTORS;

RATTUS;

EID: 34548515774     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700189c     Document Type: Article

References (35)

1. International Agency for Research on Cancer (2006) Formaldehyde, 2-butoxyethanol and 1-tert-butoxypropan-2-ol. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 88, pp 39-325, IARC, Lyon, France.
2. U.S. Department of Health and Human Services (2004) 11th Report on Carcinogens, U.S. Government Printing Office, Washington, DC.
3. Chaw, Y. F., Crane, L. E., Lange, P., and Shapiro, R. (1980) Isolation and identification of cross-links from formaldehyde-treated nucleic acids. Biochemistry 19, 5525-5531.
4. Beland, F. A., Fullerton, N. F., and Heflich, R. H. (1984) Rapid isolation, hydrolysis and chromatography of formaldehyde-modified DNA. J. Chromatogr. 308, 121-131.
5. Huang, H., and Hopkins, P. B. (1993) DNA interstrand cross-linking by formaldehyde: nucleotide sequence preference and covalent structure of the predominant cross-link formed in synthetic oligonucleotides. J. Am. Chem. Soc. 115, 9402-9408.
6. Huang, H., Solomon, M. S., and Hopkins, P. B. (1992) Formaldehyde preferentially interstrand cross-links duplex DNA through deoxyguanosine residues at the sequence 5′-d(AT). J. Am. Chem. Soc. 114, 9240-9241.
7. Cheng, G., Shi, Y., Sturla, S., Jalas, J., McIntee, E. J., Villalta, P. W., Wang, M., and Hecht, S. S. (2003) Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: formation of cyclic deoxyguanosine adducts and formaldehyde cross-links. Chem. Res. Toxicol. 16, 145-152.
8. Preussmann,R., and Stewart, B. W. (1984) N-Nitroso carcinogens. In Chemical Carcinogens, 2nd ed., (Searle,C. E., Ed.) ACS Monograph 182, Vol. 2, pp 643-828, American Chemical Society, Washington, DC.
9. Hecht, S. S. (1998) Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem. Res. Toxicol. 11, 559-603.
10. Shuker, D. E., and Bartsch, H. (1994) DNA adducts of nitrosamines. In IARC Sci. Publ. No. 125. DNA Adducts: Identification and Biological Significance (Hemminki, K.,Dipple, A., Shuker, D. E. G. , Kadlubar, F. F. , Segerback, D., and Bartsch, H., Eds.) pp 73-89, Lyon, France.
11. Kyrtopoulos, S. A., Anderson, L. M., Chhabra, S. K., Souliotis, V. L., Pletsa, V., Valanis, C., and Georgiadis, P. (1997) DNA adducts and the mechanism of carcinogenesis and cytotoxicity of methylating agents of environmental and clinical significance. Cancer Detect. Prevention 21, 391-405.
12. 6-alkylguanine DNA adducts by recombinant human DNA polymerases. J. Biol. Chem. 281, 38244-38256.
13. Lao, Y., Yu, N., Kassie, F., Villalta, P. W., and Hecht, S. S. (2007) Analysis of pyridyloxobutyl DNA adducts in F344 rats chronically treated with (R)- and (S)-N′-nitrosonornicotine. Chem. Res. Toxicol. 20, 246-256.
14. Lao, Y., Yu, N., Kassie, F., Villalta, P. W., and Hecht, S. S. (2007) Formation and accumulation of pyridyloxobutyl DNA adducts in F344 rats chronically treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and enantiomers of its metabolite, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol. Chem. Res. Toxicol. 20, 235-245.
15. Lao, Y., Villalta, P. W., Sturla, S. J., Wang, M., and Hecht, S. S. (2006) Quantitation of pyridyloxobutyl DNA adducts of tobacco-specific nitrosamines in rat tissue DNA by high performance liquid chromatography- electrospray ionization-tandem mass spectrometry. Chem. Res. Toxicol. 19, 674-682.
16. Jones, J. W., and Robins, R. K. (1963) Purine nucleosides. III. Methylation studies of certain naturally occurring purine nucleosides. J. Am. Chem. Soc. 85, 193-201.
17. Murphy, S. E., Palomino, A., Hecht, S. S., and Hoffmann, D. (1990) Dose-response study of DNA and hemoglobin adduct formation by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in F344 rats. Cancer Res. 50, 5446-5452.
18. Devereux, T. R., Anderson, M. W., and Belinsky, S. A. (1988) Factors regulating activation and DNA alkylation by 4-(N-methyl-N-nitrosamino)-1-(3- pyridyl)-1-butanone and nitrosodimethylamine in rat lung and isolated lung cells, and their relationship to carcinogenicity. Cancer Res. 48, 4215-4221.
19. Hecht, S. S., Trushin, N., Castonguay, A., and Rivenson, A. (1986) Comparative tumorigenicity and DNA methylation in F344 rats by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N-nitrosodimethylamine. Cancer Res. 46, 498-502.
20. 2-ethyldeoxyguanosine. Chem. Res. Toxicol. 19, 319-324.
21. Singer, B., and Grunberger, D. (1983) Molecular Biology of Mutagens and Carcinogens, pp 45-96, Plenum Press, New York.
22. Feldman, M. Y. (1973) Reactions of nucleic acids and nucleoproteins with formaldehyde. Prog. Nucleic Acid. Res. Mol. Biol. 13, 1-49.
23. Auerbach, C., Moutschen-Dahmen, M., and Moutschen, J. (1977) Genetic and cytogenetical effects of formaldehyde and related compounds. Mutat. Res. 39, 317-361.
24. McGhee, J. D., and von Hippel, P. H. (1975) Formaldehyde as a probe of DNA structure. I. Reaction with exocyclic amino groups of DNA bases. Biochemistry 14, 1281-1296.
25. McGhee, J. D., and von Hippel, P. H. (1975) Formaldehyde as a probe of DNA structure. II. Reaction with endocyclic imino groups of DNA bases. Biochemistry 14, 1297-1303.
26. McGhee, J. D., and von Hippel, P. H. (1977) Formaldehyde as a probe of DNA structure. 3. Equilibrium denaturation of DNA and synthetic polynucleotides. Biochemistry 16, 3267-3276.
27. McGhee, J. D., and von Hippel, P. H. (1977) Formaldehyde as a probe of DNA structure. Mechanism of the initial reaction of formaldehyde with DNA. Biochemistry 16, 3276-3293.
28. Zhong, W., and Hee, S. S. (2005) Comparison of UV, fluorescence, and electrochemical detectors for the analysis of formaldehyde-induced DNA adducts. J. Anal. Toxicol. 29, 182-187.
29. Zhong, W., and Que Hee, S. S. (2004) Formaldehyde-induced DNA adducts as biomarkers of in vitro human nasal epithelial cell exposure to formaldehyde. Mutat. Res. 563, 13-24.
30. 6-Methylguanine is a critical determinant of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumorigenesis in A/J mouse lung. Cancer Res. 51, 5557-5564.
31. 6-[4-oxo-4-(3-pyridyl)butylguanine] in Escherichia coli and human cells. Chem. Res. Toxicol. 15, 165-169.
32. Loeppky, R. N., and Goelzer, P. (2002) Microsome-mediated oxidation of N-nitrosodiethanolamine (NDELA), a bident carcinogen. Chem. Res. Toxicol. 15, 457-469.
33. Liu, X., Lao, Y., Yang, I.-Y., Hecht, S. S., and Moriya, M. (2006) Replication-coupled repair of crotonaldehyde/acetaldehyde induced guanine-guanine interstrand cross-links and their mutagenicity. Biochemistry 45, 12898-12905.
34. Nudelman, A., Levovich, I., Cutts, S. M., Phillips, D. R., and Rephaeli, A. (2005) The role of intracellularly released formaldehyde and butyric acid in the anticancer activity of acyloxyalkyl esters. J. Med. Chem. 48, 1042-1054.
35. Trocho, C., Pardo, R., Rafecas, I., Virgili, J., Remesar, X., Fernandez-Lopez, J. A., and Alemany, M. (1998) Formaldehyde derived from dietary aspartame binds to tissue components in vivo. Life Sci. 63, 337-349.