Analysis of acrolein-derived 1, N 2-propanodeoxyguanosine adducts in human leukocyte DNA from smokers and nonsmokers

Chemical Research in Toxicology

Volumn 24, Issue 1, 2011, Pages 119-124

  Zhang, Siyi ^a   Balbo, Silvia ^a   Wang, Mingyao ^a   Hecht, Stephen S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,N2 PROPANODEOXYGUANOSINE ADDUCT; 3 (2' DEOXYRIBOS 1' YL) 5,6,7,8 TETRAHYDRO 6 HYDROXYPYRIMIDO[1,2 A]PURINE 10(3H)ONE; 3 (2' DEOXYRIBOS 1' YL) 5,6,7,8 TETRAHYDRO 8 HYDROXYPYRIMIDO[1,2 A]PURINE 10(3H)ONE; ACROLEIN; DEOXYGUANOSINE DERIVATIVE; DNA; GLUTATHIONE; GUANOSINE; UNCLASSIFIED DRUG; WATER;

ACCURACY; ADULT; ARTICLE; CLINICAL ARTICLE; CONTROLLED STUDY; DNA ADDUCT; DNA HYDROLYSIS; DNA ISOLATION; ERYTHROCYTE; FEMALE; HUMAN; LEUKOCYTE; LIQUID CHROMATOGRAPHY ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; MALE; POLLUTANT; SMOKING; TANDEM MASS SPECTROMETRY;

ACROLEIN; ADULT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DNA; DNA ADDUCTS; FEMALE; HUMANS; LEUKOCYTES; MALE; MIDDLE AGED; SMOKING; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TUMOR SUPPRESSOR PROTEIN P53;

EID: 78651476372     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100321y     Document Type: Article

References (28)

1. International Agency for Research on Cancer (1995) Dry Cleaning, Some Chlorinated Solvents and Other Industrial Chemicals. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 63, pp 393 -407, IARC, Lyon, France.
2. Roemer, E., Stabbert, R., Rustemeier, K., Veltel, D. J., Meisgen, T. J., Reininghaus, W., Carchman, R. A., Gaworski, C. L., and Podraza, K. F. (2004) Chemical composition, cytotoxicity and mutagenicity of smoke from US commercial and reference cigarettes smoked under two sets of machine smoking conditions Toxicology 195, 31-52
3. Stevens, J. F. and Maier, C. S. (2008) Acrolein: Sources, metabolism, and biomolecular interactions relevant to human health and disease Mol. Nutr. Food Res 52, 7-25
4. Pan, J. and Chung, F. L. (2002) Formation of cyclic deoxyguanosine adducts from omega-3 and omega-6 polyunsaturated fatty acids under oxidative conditions Chem. Res. Toxicol. 15, 367-372
5. Brock, N., Hilgard, P., Phol, J., Ormstad, K., and Orrenius, S. (1984) Pharmacolkinetics and mechanism of action of detoxifying low-molecular-weight thiols J. Cancer Res. Clin. Oncol. 108, 87-97
6. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde Cancer Res. 44, 990-995
7. Yang, I. Y., Chan, G., Miller, H., Huang, Y., Torres, M. C., Johnson, F., and Moriya, M. (2002) Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells Biochemistry 41, 13826-13832 (Pubitemid 35332721)
8. 2-deoxyguanosine adducts of the alpha, beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal Chem. Res. Toxicol. 22, 759-778
9. 2-Propanodeoxyguanosine adducts: Potential new biomarkers of smoking-induced DNA damage in human oral tissue Cancer Res. 58, 581-584
10. 2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues Cancer Res. 56, 452-456
11. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans Proc. Natl. Acad. Sci. U.S.A. 91, 7491-7495
12. 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
13. Pfeifer, G. P., Denissenko, M. F., Olivier, M., Tretyakova, N., Hecht, S. S., and Hainaut, P. (2002) Tobacco smoke carcinogens, DNA damage and p53 mutations in smoking-associated cancers Oncogene 21, 7435-7451
14. Carmella, S. G., Chen, M., Zhang, Y., Zhang, S., Hatsukami, D. K., and Hecht, S. S. (2007) Quantitation of acrolein-derived 3-hydroxypropylmercapturic acid in human urine by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry: effects of cigarette smoking Chem. Res. Toxicol. 20, 986-990
15. Hecht, S. S., Yuan, J.-M., and Hatsukami, D. K. (2010) Applying tobacco carcinogen and toxicant biomarkers in product regulation and cancer prevention Chem. Res. Toxicol. 23, 1001-1008
16. Carmella, S. G., Chen, M., Han, S., Briggs, A., Jensen, J., Hatsukami, D. K., and Hecht, S. S. (2009) Effects of smoking cessation on eight urinary tobacco carcinogen and toxicant biomarkers Chem. Res. Toxicol. 22, 734-741
17. 2-propanodeoxyguanosine adducts in human lung by liquid chromatography-electrospray ionization-tandem mass spectrometry Chem. Res. Toxicol. 20, 565-571
18. Emami, A., Dyba, M., Cheema, A. K., Pan, J., Nath, R. G., and Chung, F. L. (2008) Detection of the acrolein-derived cyclic DNA adduct by a quantitative 32P-postlabeling/solid-phase extraction/HPLC method: blocking its artifact formation with glutathione Anal. Biochem. 374, 163-172
19. Whitehouse, R. C., Prasad, A. S., Rabbani, P. I., and Cossack, Z. T. (1982) Zinc in plasma, neutrophils, lymphocytes, and erythrocytes as determined by flameless atomic absorption spectrophotometry Clin. Chem. 28, 475-480
20. Tacka, K. A., Dabrowiak, J. C., Goodisman, J., and Souid, A. K. (2002) Kinetic analysis of the reactions of 4-hydroperoxycyclophosphamide and acrolein with glutathione, mesna, and WR-1065 Drug Metab. Dispos. 30, 875-882
21. de los Santos, C., Zaliznyak, T., and Johnson, F. (2001) NMR characterization of a DNA duplex containing the major acrolein-derived deoxyguanosine adduct gamma -OH-1,-N2-propano-2′-deoxyguanosine J. Biol. Chem. 276, 9077-9082
22. Sanchez, A. M., Minko, I. G., Kurtz, A. J., Kanuri, M., Moriya, M., and Lloyd, R. S. (2003) Comparative evaluation of the bioreactivity and mutagenic spectra of acrolein-derived alpha-HOPdG and gamma-HOPdG regioisomeric deoxyguanosine adducts Chem. Res. Toxicol. 16, 1019-1028
23. Kurtz, A. J. and Lloyd, R. S. (2003) 1,N2-deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage J. Biol. Chem. 278, 5970-5976
24. VanderVeen, L. A., Harris, T. M., Jen-Jacobson, L., and Marnett, L. J. (2008) Formation of DNA-protein cross-links between gamma- hydroxypropanodeoxyguanosine and EcoRI Chem. Res. Toxicol. 21, 1733-1738
25. Kozekov, I. D., Turesky, R. J., Alas, G. R., Harris, C. M., Harris, T. M., and Rizzo, C. J. (2010) Formation of deoxyguanosine cross-links from calf thymus DNA treated with acrolein and 4-hydroxy-2-nonenal Chem. Res. Toxicol. 23, 1701-1713
26. Guyton, A. C. and Hall, J. E. (2000) Textbook of Medical Physiology, 10 th ed., Saunders, Philadelphia.
27. 14C]acrolein in Sprague-Dawley rats. II. Identification of urinary and fecal metabolites Toxicol. Sci. 43, 110-120
28. Nath, R. G., Ocando, J. E., Richie, J., and Chung, F. L. (1997) Effect of glutathione depletion on exocyclic adduct levels in the liver DNA of F344 rats Chem. Res. Toxicol. 10, 1250-1253