Noninvasive measurement of smoking-associated N3-ethyladenine and N7-ethylguanine in human salivary DNA by stable isotope dilution nanoflow liquid chromatography-nanospray ionization tandem mass spectrometry

Toxicology Letters

Volumn 225, Issue 1, 2014, Pages 27-33

  Chen, Hauh Jyun Candy ^a   Lin, Chao Ray ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

3 Ethyladenine; 7 Ethylguanine; DNA adduct; Nanoflow LC MS MS; Saliva

Indexed keywords

3 ETHYLADENINE; 7 ETHYLGUANINE; ADENINE DERIVATIVE; BIOLOGICAL MARKER; DNA; GUANINE DERIVATIVE; NUCLEOTIDE; STABLE ISOTOPE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; ASSAY; DILUTION; DNA DAMAGE; FEMALE; HUMAN; HYDROLYSIS; IONIZATION; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIQUID CHROMATOGRAPHY; MALE; MEASUREMENT; NANOSPRAY IONIZATION; PRIORITY JOURNAL; SALIVA; SMOKING; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY;

3-ETHYLADENINE; 7-ETHYLGUANINE; DNA ADDUCT; NANOFLOW LC-MS/MS; SALIVA;

ADENINE; ADULT; BIOLOGICAL MARKERS; DNA ADDUCTS; FEMALE; GUANINE; HUMANS; HYDROLYSIS; INDICATOR DILUTION TECHNIQUES; LIMIT OF DETECTION; MALE; NANOTECHNOLOGY; REPRODUCIBILITY OF RESULTS; SALIVA; SMOKING; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; YOUNG ADULT;

EID: 84890411077     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2013.11.032     Document Type: Article

References (47)

1. Anna L., Kovacs K., Gyorffy E., Schoket B., Nair J. Smoking-related O4-ethylthymidine formation in human lung tissue and comparisons with bulky DNA adducts. Mutagenesis 2011, 26:523-527.
2. Ashkenazi M., Dennison D.K. A new method for isolation of salivary neutrophils and determination of their functional activity. Journal of Dental Research 1989, 68:1256-1261.
3. Balbo S., Villalta P.W., Hecht S.S. Quantitation of 7-ethylguanine in leukocyte DNA from smokers and nonsmokers by liquid chromatography-nanoelectrospray-high resolution tandem mass spectrometry. Chemical Research in Toxicology 2011, 24:1729-1734.
4. Bessette E.E., Spivack S.D., Goodenough A.K., Wang T., Pinto S., Kadlubar F.F., Turesky R.J. Identification of carcinogen DNA adducts in human saliva by linear quadrupole ion trap/multistage tandem mass spectrometry. Chemical Research in Toxicology 2010, 23:1234-1244.
5. Bronstein S.M., Skopek T.R., Swenberg J.A. Efficient repair of O6-ethylguanine, but not O4-ethylthymine or O2-ethylthymine, is dependent upon O6-alkylguanine-DNA alkyltransferase and nucleotide excision repair activities in human cells. Cancer Research 1992, 52:2008-2011.
6. Chao M.R., Wang C.J., Chang L.W., Hu C.W. Quantitative determination of urinary N7-ethylguanine in smokers and non-smokers using an isotope dilution liquid chromatography/tandem mass spectrometry with on-line analyte enrichment. Carcinogenesis 2006, 27:146-151.
7. Chen H.J. Analysis of DNA adducts in human samples: acrolein-derived exocyclic DNA adducts as an example. Molecular Nutrition and Food Research 2011, 55:1391-1400.
8. Chen H.-J.C., Lee C.-R. Detection and simultaneous quantification of three smoking-related ethylthymidine adducts in human salivary DNA by liquid chromatography tandem mass spectrometry. Toxicology Letters 2014, 224:101-107.
9. Chen H.J., Lin W.P. Quantitative analysis of multiple exocyclic DNA adducts in human salivary DNA by stable isotope dilution nanoflow liquid chromatography-nanospray ionization tandem mass spectrometry. Analytical Chemistry 2011, 83:8543-8551.
10. Chen H.J.C., Lin C.R. Simultaneous quantification of ethylpurine adducts in human urine by stable isotope dilution nanoflow liquid chromatography nanospray ionization tandem mass spectrometry. Journal of Chromatography A 2013, 1322:69-73.
11. Chen H.J., Liu Y.F. Simultaneous quantitative analysis of N(3)-ethyladenine and N(7)-ethylguanine in human leukocyte deoxyribonucleic acid by stable isotope dilution capillary liquid chromatography-nanospray ionization tandem mass spectrometry. Journal of Chromatography A 2013, 1271:86-94.
12. Chen L., Wang M., Villalta P.W., Hecht S.S. Liquid chromatography-electrospray ionization tandem mass spectrometry analysis of 7-ethylguanine in human liver DNA. Chemical Research in Toxicology 2007, 20:1498-1502.
13. Chen H.J., Wang Y.C., Lin W.P. Analysis of ethylated thymidine adducts in human leukocyte DNA by stable isotope dilution nanoflow liquid chromatography-nanospray ionization tandem mass spectrometry. Analytical Chemistry 2012, 84:2521-2527.
14. Chiappin S., Antonelli G., Gatti R., De Palo E.F. Saliva specimen: a new laboratory tool for diagnostic and basic investigation. Clinica Chimica Acta 2007, 383:30-40.
15. Den Engelse L., Menkveld G.J., De Brij R.J., Tates A.D. Formation and stability of alkylated pyrimidines and purines (including imidazole ring-opened 7-alkylguanine) and alkylphosphotriesters in liver DNA of adult rats treated with ethylnitrosourea or dimethylnitrosamine. Carcinogenesis 1986, 7:393-403.
16. Dillon M.C., Opris D.C., Kopanczyk R., Lickliter J., Cornwell H.N., Bridges E.G., Nazar A.M., Bridges K.G. Detection of homocysteine and C-reactive protein in the saliva of healthy adults: comparison with blood levels. Biomark Insights 2010, 5:57-61.
17. Feng S., Roethig H.J., Liang Q., Kinser R., Jin Y., Scherer G., Urban M., Engl J., Riedel K. Evaluation of urinary 1-hydroxypyrene, S-phenylmercapturic acid, trans,trans-muconic acid, 3-methyladenine, 3-ethyladenine, 8-hydroxy-2'-deoxyguanosine and thioethers as biomarkers of exposure to cigarette smoke. Biomarkers 2006, 11:28-52.
18. Godschalk R., Nair J., Kliem H.C., Wiessler M., Bouvier G., Bartsch H. Modified immunoenriched (32)P-HPLC assay for the detection of O(4)-ethylthymidine in human biomonitoring studies. Chemical Research in Toxicology 2002, 15:433-437.
19. Godschalk R., Nair J., van Schooten F.J., Risch A., Drings P., Kayser K., Dienemann H., Bartsch H. Comparison of multiple DNA adduct types in tumor adjacent human lung tissue: effect of cigarette smoking. Carcinogenesis 2002, 23:2081-2086.
20. Goth R., Rajewsky M.F. Persistence of O6-ethylguanine in rat-brain DNA: correlation with nervous system-specific carcinogenesis by ethylnitrosourea. Proceedings of the National Academy of Sciences of the United States of America 1974, 71:639-643.
21. Hecht S.S. Lung carcinogenesis by tobacco smoke. International Journal of Cancer 2012, 131:2724-2732.
22. Himmelstein M.W., Boogaard P.J., Cadet J., Farmer P.B., Kim J.H., Martin E.A., Persaud R., Shuker D.E. Creating context for the use of DNA adduct data in cancer risk assessment: II. Overview of methods of identification and quantitation of DNA damage. Critical Reviews in Toxicology 2009, 39:679-694.
23. Hsu T.M., Zhang Y.J., Santella R.M. Immunoperoxidase quantitation of 4-aminobiphenyl- and polycyclic aromatic hydrocarbon-DNA adducts in exfoliated oral and urothelial cells of smokers and nonsmokers. Cancer Epidemiology, Biomarkers and Prevention 1997, 6:193-199.
24. Hu C.W., Chao M.R. Direct-acting DNA alkylating agents present in aqueous extracts of areca nut and its products. Chemical Research in Toxicology 2012, 25:2386-2392.
25. Hu S., Arellano M., Boontheung P., Wang J., Zhou H., Jiang J., Elashoff D., Wei R., Loo J.A., Wong D.T. Salivary proteomics for oral cancer biomarker discovery. Clinical Cancer Research 2008, 14:6246-6252.
26. IARC Tobacco Smoke and Involuntary Smoking IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 2004, vol. 83:53-119. International Agency for Research on Cancer, Lyon, France.
27. Kopplin A., Eberle-Adamkiewicz G., Glusenkamp K.H., Nehls P., Kirstein U. Urinary excretion of 3-methyladenine and 3-ethyladenine after controlled exposure to tobacco smoke. Carcinogenesis 1995, 16:2637-2641.
28. Lum A., Le Marchand L. A simple mouthwash method for obtaining genomic DNA in molecular epidemiological studies. Cancer Epidemiology, Biomarkers and Prevention 1998, 7:719-724.
29. Osswald K., Mittas A., Glei M., Pool-Zobel B.L. New revival of an old biomarker: characterisation of buccal cells and determination of genetic damage in the isolated fraction of viable leucocytes. Mutation Research 2003, 544:321-329.
30. Pfaffe T., Cooper-White J., Beyerlein P., Kostner K., Punyadeera C. Diagnostic potential of saliva: current state and future applications. Clinical Chemistry 2011, 57:675-687.
31. Prasad M.P., Mukundan M.A., Krishnaswamy K. Micronuclei and carcinogen DNA adducts as intermediate end points in nutrient intervention trial of precancerous lesions in the oral cavity. European Journal of Cancer. Part B, Oral Oncology 1995, 31B:155-159.
32. Prevost V., Shuker D.E. Cigarette smoking and urinary 3-alkyladenine excretion in man. Chemical Research in Toxicology 1996, 9:439-444.
33. Prevost V., Shuker D.E., Friesen M.D., Eberle G., Rajewsky M.F., Bartsch H. Immunoaffinity purification and gas chromatography-mass spectrometric quantification of 3-alkyladenines in urine: metabolism studies and basal excretion levels in man. Carcinogenesis 1993, 14:199-204.
34. Proia N.K., Paszkiewicz G.M., Nasca M.A., Franke G.E., Pauly J.L. Smoking and smokeless tobacco-associated human buccal cell mutations and their association with oral cancer - a review. Cancer Epidemiology, Biomarkers and Prevention 2006, 15:1061-1077.
35. Rogers N.L., Cole S.A., Lan H.C., Crossa A., Demerath E.W. New saliva DNA collection method compared to buccal cell collection techniques for epidemiological studies. American Journal of Human Biology 2007, 19:319-326.
36. Scherer E., Timmer A.P., Emmelot P. Formation by diethylnitrosamine and persistence of O4-ethylthymidine in rat liver DNA in vivo. Cancer Letters 1980, 10:1-6.
37. Shuker D.E., Farmer P.B. Relevance of urinary DNA adducts as markers of carcinogen exposure. Chemical Research in Toxicology 1992, 5:450-460.
38. Singh R., Farmer P.B. Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection. Carcinogenesis 2006, 27:178-196.
39. Singh R., Kaur B., Farmer P.B. Detection of DNA damage derived from a direct acting ethylating agent present in cigarette smoke by use of liquid chromatography-tandem mass spectrometry. Chemical Research in Toxicology 2005, 18:249-256.
40. Streckfus C., Bigler L., Dellinger T., Dai X., Kingman A., Thigpen J.T. The presence of soluble c-erbB-2 in saliva and serum among women with breast carcinoma: a preliminary study. Clinical Cancer Research 2000, 6:2363-2370.
41. Swenberg J.A., Dyroff M.C., Bedell M.A., Popp J.A., Huh N., Kirstein U., Rajewsky M.F. O4-ethyldeoxythymidine, but not O6-ethyldeoxyguanosine, accumulates in hepatocyte DNA of rats exposed continuously to diethylnitrosamine. Proceedings of the National Academy of Sciences of the United States of America 1984, 81:1692-1695.
42. Thomadaki K., Helmerhorst E.J., Tian N., Sun X., Siqueira W.L., Walt D.R., Oppenheim F.G. Whole-saliva proteolysis and its impact on salivary diagnostics. Journal of Dental Research 2011, 90:1325-1330.
43. Thomale J., Huh N.H., Nehls P., Eberle G., Rajewsky M.F. Repair of O6-ethylguanine in DNA protects rat 208F cells from tumorigenic conversion by N-ethyl-N-nitrosourea. Proceedings of the National Academy of Sciences of the United States of America 1990, 87:9883-9887.
44. Verna L., Whysner J., Williams G.M. N-nitrosodiethylamine mechanistic data and risk assessment: bioactivation, DNA-adduct formation, mutagenicity, and tumor initiation. Pharmacology and Therapeutics 1996, 71:57-81.
45. Walsh D.J., Corey A.C., Cotton R.W., Forman L., Herrin G.L., Word C.J., Garner D.D. Isolation of deoxyribonucleic acid (DNA) from saliva and forensic science samples containing saliva. Journal of Forensic Sciences 1992, 37:387-395.
46. Wong D.T. Towards a simple, saliva-based test for the detection of oral cancer 'oral fluid (saliva), which is the mirror of the body, is a perfect medium to be explored for health and disease surveillance'. Expert Review of Molecular Diagnostics 2006, 6:267-272.
47. Zhang Y., Chen S.Y., Hsu T., Santella R.M. Immunohistochemical detection of malondialdehyde-DNA adducts in human oral mucosa cells. Carcinogenesis 2002, 23:207-211.