Sequence distribution of acetaldehyde-derived N2-Ethyl-dG Adducts along Duplex DNA

Chemical Research in Toxicology

Volumn 20, Issue 10, 2007, Pages 1379-1387

  Matter, Brock ^a   Guza, Rebecca ^a   Zhao, Jianwei ^b   Li, Zhong Ze ^a   Jones, Roger ^b   Tretyakova, Natalia ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 METHYLCYTOSINE; ACETALDEHYDE; ACROLEIN; CARCINOGEN; DIHYDROXYBENZO[A]PYRENE OXIDE; DINUCLEOTIDE; DNA BASE; DOUBLE STRANDED DNA; GUANINE NUCLEOTIDE; K RAS PROTEIN; OLIGODEOXYNUCLEOTIDE; PROTEIN P53; SODIUM DERIVATIVE;

ARTICLE; CAPILLARY CHROMATOGRAPHY; DNA ADDUCT; DNA SEQUENCE; ELECTROSPRAY MASS SPECTROMETRY; GENE MUTATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; LABORATORY TEST; LUNG CANCER; ONCOGENE K RAS; TUMOR SUPPRESSOR GENE;

5-METHYLCYTOSINE; ACETALDEHYDE; BASE SEQUENCE; CAPILLARY ELECTROCHROMATOGRAPHY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DNA ADDUCTS; DNA MUTATIONAL ANALYSIS; GENES, P53; GENES, RAS; HUMANS; MOLECULAR SEQUENCE DATA; MUTATION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

ANIMALIA; NICOTIANA TABACUM;

EID: 35848941488     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx7001146     Document Type: Article

References (66)

1. American Cancer Society (2007) Cancer Facts and Figures 2007, American Cancer Society, Atlanta.
2. International Agency for Research on Cancer (2004) Tobacco Smoke and Involuntary Smoking, IARC, Lyon, France.
3. Hoffmann, D., and Hoffmann, I. (1997) The changing cigarette, 1950-1995. J. Toxicol. Environ. Health 50, 307-364.
4. Hecht, S. S. (1999) Tobacco smoke carcinogens and lung cancer. J. Natl. Cancer Inst. 91, 1194-1210.
5. Hussain, S. P., and Harris, C. C. (1999) p53 mutation spectrum and load: the generation of hypotheses linking the exposure of endogenous or exogenous carcinogens to human cancer. Mutat. Res. 428, 23-32.
6. Malejka-Giganti, M., and Tretyakova, N. (2006) Molecular mechanisms of carcinogenesis. In Carcinogenic and Anticarcinogenic Food Components (Baer-Dubowska, W., Bartoszek, A., and Malejka-Giganti, D., Eds.) pp 13-36, CRC Press, Boca Raton, FL.
7. Valinluck, V., Liu, P., Kang, J. I., Jr., Burdzy, A., and Sowers, L. C. (2005) 5-halogenated pyrimidine lesions within a CpG sequence context mimic 5-methylcytosine by enhancing the binding of the methyl-CpG-binding domain of methyl-CpG-binding protein 2 (MeCP2). Nucleic Acids Res. 33, 3057-3064.
8. Valinluck, V., Wu, W., Liu, P., Neidigh, J. W., and Sowers, L. C. (2006) Impact of cytosine 5-halogens on the interaction of DNA with restriction endonucleases and methyltransferase. Chem. Res. Toxicol. 19, 556-562.
9. Valinluck, V., Tsai, H. H., Rogstad, D. K., Burdzy, A., Bird, A., and Sowers, L. C. (2004) Oxidative damage to methyl-CpG sequences inhibits the binding of the methyl-CpG binding domain (MBD) of methyl-CpG binding protein 2 (MeCP2). Nucleic Acids Res. 32, 4100-4108.
10. Baskunov, V. B., Subach, F. V., Kolbanovskiy, A., Kolbanovskiy, M., Eremin, S. A., Johnson, F., Bonala, R., Geacintov, N. E., and Gromova, E. S. (2005) Effects of benzo[a]pyrene-deoxyguanosine lesions on DNA methylation catalyzed by EcoRII DNA methyltransferase and on DNA cleavage effected by EcoRII restriction endonuclease. Biochemistry 44, 1054-1066.
11. Hollstein, M., Rice, K., Greenblatt, M. S., Soussi, T., Fuchs, R., Sorlie, T., Hovig, E., Smith-Sorensen, B., Montesano, R., and Harris, C. C. (1994) Database of p53 gene somatic mutations in human tumors and cell lines. Nucleic Acids Res. 22, 3551-3555.
12. Westra, W. H., Baas, I. O., Hruban, R. H., Askin, F. B., Wilson, K., Offerhaus, G. J., and Slebos, R. J. (1996) K-ras oncogene activation in atypical alveolar hyperplasias of the human lung. Cancer Res. 56, 2224-2228.
13. Westra, W. H., Slebos, R. J., Offerhaus, G. J., Goodman, S. N., Evers, S. G., Kensler, T. W., Askin, F. B., Rodenhuis, S., and Hruban, R. H. (1993) K-ras oncogene activation in lung adenocarcinomas from former smokers. Evidence that K-ras mutations are an early and irreversible event in the development of adenocarcinoma of the lung. Cancer 72, 432-438.
14. Pfeifer, G. P. (2000) p53 mutational spectra and the role of methylated CpG sequences. Mutat. Res. 450, 155-166.
15. Denissenko, M. F., Pao, A., Tang, M., and Pfeifer, G. P. (1996) Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in p53. Science 274, 430-432.
16. Denissenko, M. F., Chen, J. X., Tang, M. S., and Pfeifer, G. P. (1997) Cytosine methylation determines hot spots of DNA damage in the human p53 gene. Proc. Natl. Acad. Sci. U.S.A. 94, 3893-3898.
17. Feng, Z., Hu, W., Hu, Y., and Tang, M. S. (2006) Acrolein is a major cigarette-related lung cancer agent: Preferential binding at p53 mutational hotspots and inhibition of DNA repair. Proc. Natl. Acad. Sci. U.S.A. 103, 15404-15409.
18. Obe, G., Natarajan, A. T., Meyers, M., and Hertog, A. D. (1979) Induction of chromosomal aberrations in peripheral lymphocytes of human blood in vitro, and of SCEs in bone-marrow cells of mice in vivo by ethanol and its metabolite acetaldehyde. Mutat. Res. 68, 291-294.
19. Woutersen, R. A., Appelman, L. M., Garderen-Hoetmer, A., and Feron, V. J. (1986) Inhalation toxicity of acetaldehyde in rats. III. Carcinogenicity study. Toxicology 41, 213-231.
20. Department of Health and Human Services (2000) The Ninth Report on Carcinogens, Department of Health and Human Services, U.S. Public Health Service, National Toxicology Program, Research Triangle Park, NC.
21. Brooks, P. J., and Theruvathu, J. A. (2005) DNA adducts from acetaldehyde: Implications for alcohol-related carcinogenesis. Alcohol 35, 187-193.
22. Vaca, C. E., Fang, J. L., and Schweda, E. K. (1995) Studies of the reaction of acetaldehyde with deoxynucleosides. Chem.-Biol. Interact. 98, 51-67.
23. Wang, M., Mclntee, E. J., Cheng, G., Shi, Y., Villalta, P. W., and Hecht, S. S. (2000) Identification of DNA adducts of acetaldehyde. Chem. Res. Toxicol. 13, 1149-1157.
24. 2-ethyldeoxyguanosine. Chem. Res. Toxicol. 19, 319-324.
25. Chen, L., Wang, M., Villalta, P. W., Luo, X., Feuer, R., Jensen, J., Hatsukami, D. K., and Hecht, S. S. (2007) Quantitation of an acetaldehyde adduct in human leukocyte DNA and the effect of smoking cessation. Chem. Res. Toxicol. 20, 108-113.
26. 2-ethyl-2′- deoxyguanosine triphosphate during DNA synthesis catalyzed by mammalian replicative DNA polymerases. Biochemistry 38, 929-935.
27. Fang, J. L., and Vaca, C. E. (1997) Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis 18, 627-632.
28. 2-ethyl-2′-deoxyguanosine DNA adduct by the exonuclease-free Klenow fragment of Escherichia coli DNA polymerase I. Biochemistry 40, 4106-4114.
29. 6-methylguanine lesions in DNA: Contrasting responses from the "bypass" DNA polymerase η and the replicative DNA polymerase α. Chem. Res. Toxicol. 16, 1616-1623.
30. 2-guanine DNA lesions by human DNA polymerase η. J. Mol. Biol. 352, 72-90.
31. 2-guanine DNA adducts by human DNA polymerase ι. J. Biol. Chem. 281, 12315-12324.
32. 2-ethyldeoxyguanosine DNA adducts in the human embryonic kidney cell line 293. Chem. Res. Toxicol. 19, 960-967.
33. Matter, B., Wang, G., Jones, R., and Tretyakova, N. (2004) Formation of diastereomeric benzo[a]pyrene diol epoxide-guanine adducts in p53 gene-derived DNA sequences. Chem. Res. Toxicol. 17, 731-741.
34. Rajesh, M., Wang, G., Jones, R., and Tretyakova, N. (2005) Stable isotope labeling-mass spectrometry analysis of methyl- and pyridyloxobutyl-guanine adducts of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in p55-derived DNA sequences. Biochemistry 44, 2197-2207.
35. 3]-2′-deoxyguanosine. J. Org. Chem. 62, 7832-7835.
36. 3]adenosine, -guanosine, and their deoxy analogues. J. Org. Chem. 68, 8657-8661.
37. Matter, B., Malejka-Giganti, D., Csallany, A. S., and Tretyakova, N. (2006) Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-(2- deoxy-β-D-erythro-pentofuranosyl)amino]-5(2H)-oxazolone (oxazolone), in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS. Nucleic Acids Res. 34, 5449-5460.
38. Sheskin, D. J. (2000) The between-subjects factorial analysis of variance. In Handbook of Parametric and Nonparametric Statistical Procedures, pp 705-755, CRC Press, New York.
39. Tretyakova, N., Matter, B., Jones, R., and Shallop, A. (2002) Formation of benzo[a]pyrene diol epoxide-DNA adducts at specific guanines within K-ras and p53 gene sequences: Stable isotope-labeling mass spectrometry approach. Biochemistry 41, 9535-9544.
40. Ziegel, R., Shallop, A., Jones, R., and Tretyakova, N. (2003) K-ras gene sequence effects on the formation of 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanone (NNK)-DNA adducts. Chem. Res. Toxicol. 16, 541-550.
41. Hainaut, P., and Pfeifer, G. P. (2001) Patterns of p53 G→T transversions in lung cancers reflect the primary mutagenic signature of DNA-damage by tobacco smoke. Carcinogenesis 22, 367-374.
42. Greenblatt, M. S., Bennett, W. P., Hollstein, M., and Harris, C. C. (1994) Mutations in the p53 tumor suppressor gene: Clues to cancer etiology and molecular pathogenesis. Cancer Res. 54, 4855-4878.
43. Tornaletti, S., and Pfeifer, G. P. (1995) Complete and tissue-independent methylation of CpG sites in the p53 gene: Implications for mutations in human cancers. Oncogene 10, 1493-1499.
44. Ehrlich, M., Gama-Sosa, M. A., Huang, L. H., Midgett, R. M., Kuo, K. C., McCune, R. A., and Gehrke, C. (1982) Amount and distribution of 5-methylcytosine in human DNA from different types of tissues of cells. Nucleic Acids Res. 10, 2709-2721.
45. Newell-Price, J., Clark, A. J., and King, P. (2000) DNA methylation and silencing of gene expression. Trends Endocrinol. Metab. 11, 142-148.
46. Momparler, R. L., and Bovenzi, V. (2000) DNA methylation and cancer. J. Cell Physiol. 183, 145-154.
47. Hausheer, F. H., Rao, S. N., Gamcsik, M. P., Kollman, P. A., Colvin, O. M., Saxe, J. D., Nelkin, B. D., McLennan, I. J., Barnett, G., and Baylin, S. B. (1989) Computational analysis of structural and energetic consequences of DNA methylation. Carcinogenesis 10, 1131-1137.
48. Norberg, J., and Vihinen, M. (2001) Molecular dynamics simulation of the effects of cytosine methylation on structure of oligonucleotides. J. MoI. Structure (THEOCHEM) 546, 51-62.
49. Zacharias, W., O'Connor, T. R., and Larson, J. E. (1988) Methylation of cytosine in the 5-position alters the structural and energetic properties of the supercoil-induced Z-helix and of B-Z junctions. Biochemistry 27, 2970-2978.
50. Mathison, B. H., Said, B., and Shank, R. C. (1993) Effect of 5-methylcytosine as a neighboring base on methylation of DNA guanine by N-methyl-N-nitrosourea. Carcinogenesis 14, 323-327.
51. Weisenberger, D. J., and Romano, L. J. (1999) Cytosine methylation in a CpG sequence leads to enhanced reactivity with benzo[a]pyrene diol epoxide that correlates with a conformational change. J. Biol. Chem. 274, 23948-23955.
52. 6 alkylation by the N-nitroso carcinogens N-methyl-and N-ethyl-N-nitrosourea. Mutat. Res. 250, 153-160.
53. 2-dG adduct formation in 5′-d(CGT), 5′-d(CGA), and 5′-d(CGC) sequence contexts of single- and double-stranded oligonucleotides. Chem. Res. Toxicol. 12, 816-821.
54. Mathur, P., Xu, J., and Dedon, P. C. (1997) Cytosine methylation enhances DNA damage produced by groove binding and intercalating enediynes: Studies with esperamicins A1 and C. Biochemistry 36, 14868-14873.
55. Das, A., Tang, K. S., Gopalakrishnan, S., Waring, M. J., and Tomasz, M. (1999) Reactivity of guanine at m5CpG steps in DNA: Evidence for electronic effects transmitted through the base pairs. Chem. Biol. 6, 461-471.
56. Ross, M. K., Mathison, B. H., Said, B., and Shank, R. C. (1999) 5-Methylcytosine in CpG sites and the reactivity of nearest neighboring guanines toward the carcinogen aflatoxin B1-8,9-epoxide. Biochem. Biophys. Res. Commun. 254, 114-119.
57. Chen, J. X., Zheng, Y., West, M., and Tang, M. S. (1998) Carcinogens preferentially bind at methylated CpG in the p53 mutational hot spots. Cancer Res. 58, 2070-2075.
58. Li, V. S., Reed, M., Zheng, Y., Kohn, H., and Tang, M. (2000) C5 cytosine methylation at CpG sites enhances sequence selectivity of mitomycin C-DNA bonding. Biochemistry 39, 2612-2618.
59. 6-pyridyloxobutylation by the tobacco carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Biochemistry 43, 540-549.
60. Harris, C. C. (1996) Structure and function of the p53 tumor suppressor gene: Clues for rational cancer therapeutic strategies. J. Natl. Cancer Inst. 88, 1442-1455.
61. Cloutier, J. F., Drouin, R., and Castonguay, A. (1999) Treatment of human cells with N-nitroso(acetoxymethyl)methylamine: Distribution patterns of piperidine-sensitive DNA damage at the nucleotide level of resolution are related to the sequence context. Chem. Res. Toxicol. 12, 840-849.
62. Cloutier, J. F., Drouin, R., Weinfeld, M., O'Connor, T. R., and Castonguay, A. (2001) Characterization and mapping of DNA damage induced by reactive metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) at nucleotide resolution in human genomic DNA. J. Mol. Biol. 313, 539-557.
63. Smith, L. E., Denissenko, M. F., Bennett, W. P., Li, H., Amin, S., Tang, M., and Pfeifer, G. P. (2000) Targeting of lung cancer mutational hotspots by polycyclic aromatic hydrocarbons. J. Natl. Cancer Inst. 92, 803-811.
64. Wurdeman, R. L., and Gold, B. (1988) The effect of DNA sequence, ionic strength, and cationic DNA affinity binders on the methylation of DNA by N-methyl-N-nitrosourea. Chem. Res. Toxicol. 1, 146-147.
65. Gold, B., Marky, L. M., Stone, M. P., and Williams, L. D. (2006) A review of the role of the sequence-dependent electrostatic landscape in DNA alkylation patterns. Chem. Res. Toxicol. 19, 1402-1414.
66. Margolin, Y., Cloutier, J. F., Shafirovich, V., Geacintov, N. E., and Dedon, P. C. (2006) Paradoxical hotspots for guanine oxidation by a chemical mediator of inflammation. Nat. Chem. Biol. 2, 365-366.