Ultrasensitive simultaneous quantification of 1, N 2-etheno-2'- deoxyguanosine and 1, N 2-propano-2'-deoxyguanosine in DNA by an online liquid chromatography-electrospray tandem mass spectrometry assay

Chemical Research in Toxicology

Volumn 23, Issue 7, 2010, Pages 1245-1255

  Garcia, Camila C M ^a   Freitas, Florêncio P ^a   Di Mascio, Paolo ^a   Medeiros, Marisa H G ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,N2 ETHENO 1' DEOXYGUANOSINE; 1,N2 ETHENO 2' DEOXYGUANOSINE; CIRCULAR DNA; DEOXYGUANOSINE; DNA; STABLE ISOTOPE; UNCLASSIFIED DRUG;

AIR POLLUTION; ARTICLE; CELL CULTURE; DNA ADDUCT; DNA EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIVER; LUNG; NONHUMAN; RAT; TANDEM MASS SPECTROMETRY;

ANIMALS; CATTLE; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYADENOSINES; DEOXYGUANOSINE; DNA; DNA ADDUCTS; HUMANS; MALE; RATS; RATS, WISTAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

ANIMALIA; RATTUS;

EID: 77955404467     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx1001018     Document Type: Article

References (44)

1. Blair, I. A. (2008) DNA adducts with lipid peroxidation products J. Biol. Chem. 283, 15545-15549
2. Medeiros, M. H. G. (2009) Exocyclic DNA adducts as biomarkers of lipid oxidation and predictors of disease. Challenges in developing sensitive and specific methods for clinical studies Chem. Res. Toxicol. 22, 419-425
3. Chung, F. L., Nath, R. G., Nagao, M., Nishikawa, A., Zhou, G. D., and Randerath, K. (1999) Endogenous formation and significance of 1,N 2-propanodeoxyguanosine adducts Mutat. Res. 424, 71-81
4. Minko, I. G., Kozekov, I. D., Harris, T. M., Rizzo, C. J., Lloyd, R. S., and Stone, M. P. (2009) Chemistry and biology of DNA containing 1, N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal Chem. Res. Toxicol. 22, 759-778
5. Golding, B. T., Slaich, P. K., Kennedy, G., Bleasdale, C., and Watson, W. P. (1996) Mechanisms of formation of adducts from reactions of glycidaldehyde with 2'-deoxyguanosine and/or guanosine Chem. Res. Toxicol. 9, 147-157
6. Petrova, K. V., Jalluri, R. S., Kozekov, I. D., and Rizzo, C. J. (2007) Mechanism of 1, N 2-etheno-2'-deoxyguanosine formation from epoxyaldehydes Chem. Res. Toxicol. 20, 1685-1692
7. Akasaka, S. and Guengerich, F. P. (1999) Mutagenicity of site-specifically located 1,N 2-ethenoguanine in Chinese hamster ovary cell chromosomal DNA Chem. Res. Toxicol. 12, 501-507
8. Fernandes, P. H., Kanuri, M., Nechev, L. V., Harris, T. M., and Lloyd, R. S. (2005) Mammalian cell mutagenesis of the DNA adducts of vinyl chloride and crotonaldehyde Environ. Mol. Mutagen. 45, 455-459
9. Zhang, H., Beckman, J. W., and Guengerich, F. P. (2009) Frameshift deletion by Sulfolobus solfataricus P2 DNA polymerase Dpo4 T239W is selective for purines and involves normal conformational change followed by slow phosphodiester bond formation J. Biol. Chem. 284, 35144-35153
10. Nair, U., Bartsch, H., and Nair, J. (2007) Lipid peroxidation-induced DNA damage in cancer-prone inflammatory diseases: a review of published adduct types and levels in humans Free Radical Biol. Med. 43, 1109-1120
11. International Agency for Research on Cancer (1995) Dry Cleaning Some Chlorinated Solvents and Others Chemicals. In Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 63, pp 33 - 477, International Agency for Research on Cancer, Lyon, France.
12. International Agency for Research on Cancer (1995) Crotonaldehyde. In Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans,Vol. 63, pp 373 - 391, International Agency for Research on Cancer, Lyon, France.
13. Eder, E. and Budiawan. (2001) Cancer risk assessment for the environmental mutagen and carcinogen crotonaldehyde on the basis of TD(50) and comparison with 1, N(2)-propanodeoxyguanosine adduct levels Cancer Epidemiol. Biomarkers Prev. 10, 883-888
14. Eder, E., Schuler, D., and Budiawan. (1999) Cancer risk assessment for crotonaldehyde and 2-hexenal: an approach IARC Sci. Publ. 219-232
15. Chung, F. L., Young, R., and Hecht, S. S. (1984) Formation of cyclic 1,N 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde Cancer Res. 44, 990-995
16. Hecht, S. S., McIntee, E. J., and Wang, M. (2001) New DNA adducts of crotonaldehyde and acetaldehyde Toxicology 166, 31-36
17. 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
18. Wang, M., McIntee, 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
19. International Agency for Research on Cancer (1985) Allyl Compounds, Aldehydes, Epoxides and Peroxides. In Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans,Vol. 36, pp 101 - 132, International Agency for Research on Cancer, Lyon, France.
20. International Agency for Research on Cancer (1999) Re-Evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide (Part Two). In Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 71, pp 319 - 335, International Agency for Research on Cancer, Lyon, France.
21. Jones, A. W. (1995) Measuring and reporting the concentration of acetaldehyde in human breath Alcohol 30, 271-285
22. Salaspuro, V. and Salaspuro, M. (2004) Synergistic effect of alcohol drinking and smoking on in vivo acetaldehyde concentration in saliva Int. J. Cancer 111, 480-483
23. Sako, M., Inagaki, S., Esaka, Y., and Deyashiki, Y. (2003) Histones accelerate the cyclic 1,N 2-propanoguanine adduct-formation of DNA by the primary metabolite of alcohol and carcinogenic crotonaldehyde Bioorg. Med. Chem. Lett. 13, 3497-3498
24. Theruvathu, J. A., Jaruga, P., Nath, R. G., Dizdaroglu, M., and Brooks, P. J. (2005) Polyamines stimulate the formation of mutagenic 1,N 2-propanodeoxyguanosine adducts from acetaldehyde Nucleic Acids Res. 33, 3513-3520
25. Cho, Y. J., Wang, H., Kozekov, I. D., Kurtz, A. J., Jacob, J., Voehler, M., Smith, J., Harris, T. M., Lloyd, R. S., Rizzo, C. J., and Stone, M. P. (2006) Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived alpha-CH3-gamma-OH-1,N 2-propano-2'-deoxyguanosine adducts in the 5'-CpG-3' sequence Chem. Res. Toxicol. 19, 195-208
26. Stein, S., Lao, Y., Yang, I. Y., Hecht, S. S., and Moriya, M. (2006) Genotoxicity of acetaldehyde- and crotonaldehyde-induced 1,N2- propanodeoxyguanosine DNA adducts in human cells Mutat. Res. 608, 1-7
27. Kozekov, I. D., Nechev, L. V., Moseley, M. S., Harris, C. M., Rizzo, C. J., Stone, M. P., and Harris, T. M. (2003) DNA interchain cross-links formed by acrolein and crotonaldehyde J. Am. Chem. Soc. 125, 50-61
28. Kurtz, A. J. and Lloyd, R. S. (2003) 1,N 2-deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage J. Biol. Chem. 278, 5970-5976
29. Arab, K., Pedersen, M., Nair, J., Meerang, M., Knudsen, L. E., and Bartsch, H. (2009) Typical signature of DNA damage in white blood cells: a pilot study on etheno adducts in Danish mother-newborn child pairs Carcinogenesis 30, 282-285
30. Awada, M. and Dedon, P. C. (2001) Formation of the 1,N 2-glyoxal adduct of deoxyguanosine by phosphoglycolaldehyde, a product of 3'-deoxyribose oxidation in DNA Chem. Res. Toxicol. 14, 1247-1253
31. Barbin, A. (2000) Etheno-adduct-forming chemicals: from mutagenicity testing to tumor mutation spectra Mutat. Res. 462, 55-69
32. Langouet, S., Mican, A. N., Muller, M., Fink, S. P., Marnett, L. J., Muhle, S. A., and Guengerich, F. P. (1998) Misincorporation of nucleotides opposite five-membered exocyclic ring guanine derivatives by escherichia coli polymerases in vitro and in vivo: 1, N2-ethenoguanine, 5,6,7,9-tetrahydro-9- oxoimidazo[1,2-a]purine, and 5,6,7,9-tetrahydro-7-hydroxy-9-oxoimidazo[1, 2-a]purine Biochemistry 37, 5184-5193
33. Langouet, S., Muller, M., and Guengerich, F. P. (1997) Misincorporation of dNTPs opposite 1, N2-ethenoguanine and 5,6,7,9-tetrahydro-7-hydroxy-9- oxoimidazo[1,2-a]purine in oligonucleotides by Escherichia coli polymerases I exo- and II exo-, T7 polymerase exo-, human immunodeficiency virus-1 reverse transcriptase, and rat polymerase beta Biochemistry 36, 6069-6079
34. Wang, L., Hirayasu, K., Ishizawa, M., and Kobayashi, Y. (1994) Purification of genomic DNA from human whole blood by isopropanol-fractionation with concentrated Nal and SDS Nucleic Acids Res. 22, 1774-1775
35. Loureiro, A. P. M., Di Mascio, P., Gomes, O. F., and Medeiros, M. H. G. (2000) trans,trans-2,4-decadienal-induced 1,N2-etheno-2'-deoxyguanosine adduct formation Chem. Res. Toxicol. 13, 601-609
36. Loureiro, A. P. M., Marques, S. A., Garcia, C. C. M., Di Mascio, P., and Medeiros, M. H. G. (2002) Development of an on-line liquid chromatography- electrospray tandem mass spectrometry assay to quantitatively determine 1,N2-etheno-2'-deoxyguanosine in DNA Chem. Res. Toxicol. 15, 1302-1308
37. Nath, R. G. and Chung, F. L. (1994) Detection of exocyclic 1,N2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans Proc. Natl. Acad. Sci. U.S.A. 91, 7491-7495
38. Nath, R. G., Ocando, J. E., and Chung, F. L. (1996) Detection of 1, N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues Cancer Res. 56, 452-456
39. Budiawan and Eder, E. (2000) Detection of 1, N(2)-propanodeoxyguanosine adducts in DNA of Fischer 344 rats by an adapted (32)P-post-labeling technique after per os application of crotonaldehyde Carcinogenesis 21, 1191-1196
40. Schuler, B. D. and Eder, E. (2000) Development of a 32P-postlabelling method for the detection of 1, N2-propanodeoxyguanosine adducts of crotonaldehyde in vivo Arch. Toxicol. 74, 404-414
41. Pan, J., Davis, W., Trushin, N., Amin, S., Nath, R. G., Salem, N., Jr., and and Chung, F. L. (2006) A solid-phase extraction/high-performance liquid chromatography-based (32)P-postlabeling method for detection of cyclic 1, N2-propanodeoxyguanosine adducts derived from enals Anal. Biochem. 348, 15-23
42. Nath, R. G., Ocando, J. E., Guttenplan, J. B., and Chung, F. L. (1998) 1, N2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue Cancer Res. 58, 581-584
43. Zhang, S., Villalta, P. W., Wang, M., and Hecht, S. S. (2006) Analysis of crotonaldehyde- and acetaldehyde-derived 1, N 2-propanodeoxyguanosine adducts in DNA from human tissues using liquid chromatography electrospray ionization tandem mass spectrometry Chem. Res. Toxicol. 19, 1386-1392
44. Pang, B., Zhou, X., Yu, H., Dong, M., Taghizadeh, K., Wishnok, J. S., Tannenbaum, S. R., and Dedon, P. C. (2007) Lipid peroxidation dominates the chemistry of DNA adduct formation in a mouse model of inflammation Carcinogenesis 28, 1807-1813