Analysis of DNA adducts in human samples: Acrolein-derived exocyclic DNA adducts as an example

Molecular Nutrition and Food Research

Volumn 55, Issue 9, 2011, Pages 1391-1400

  Chen, Hauh Jyun Candy ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

32P postlabeling; Acrolein; DNA adduct; MS; Nanoflow LC

Indexed keywords

1,N(2) PROPANODEOXYGUANOSINE; 1,N(2)-PROPANODEOXYGUANOSINE; ACROLEIN; DEOXYGUANOSINE; DRUG DERIVATIVE; PHOSPHORUS;

CHEMISTRY; DNA ADDUCT; HUMAN; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; REVIEW; SENSITIVITY AND SPECIFICITY; SMOKING;

ACROLEIN; DEOXYGUANOSINE; DNA ADDUCTS; HUMANS; MASS SPECTROMETRY; PHOSPHORUS RADIOISOTOPES; SENSITIVITY AND SPECIFICITY; SMOKING;

NICOTIANA TABACUM;

EID: 80052551528     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.201100185     Document Type: Review

References (72)

1. Izard, C., Libermann, C., Acrolein. Mutat. Res. 1978, 47, 115.
2. Esterbauer, H., Schaur, R. J., Zollner, H., Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic. Biol. Med. 1991, 11, 81-128.
3. O'Brien, P. J., Siraki, A. G., Shangari, N., Aldehyde sources, metabolism, molecular toxicity mechanisms, and possible effects on human health. Crit. Rev. Toxicol. 2005, 35, 609-662.
4. Sakata, K., Kashiwagi, K., Sharmin, S., Ueda, S., Igarashi, K., Acrolein produced from polyamines as one of the uraemic toxins. Biochem. Soc. Trans. 2003, 31, 371-374.
5. Stevens, J. F., Maier, C. S., Acrolein: sources, metabolism, and biomolecular interactions relevant to human health and disease. Mol. Nutr. Food Res. 2008, 52, 7-25.
6. Kozekov, I. D., Nechev, L. V., Moseley, M. S., Harris, C. M. et al., DNA interchain crosslinks formed by acrolein and crotonaldehyde. J. Am. Chem. Soc. 2003, 125, 50-61.
7. 2-Deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage. J. Biol. Chem. 2003, 278, 5970-5976.
8. Carmella, S. G., Chen, M., Zhang, Y., Zhang, S. et al., Quantitation of acrolein-derived 3-hydroxypropylmercapturic acid in human urine by liquid chromatographyatmospheric pressure chemical ionization-tandem mass spectrometry: effects of cigarette smoking. Chem. Res. Toxicol. 2007, 20, 986-990.
9. Lutz, D., Eder, E., Neudecker, T., Henschler, D., Structure-mutagenicity relationship in α, β-unsaturated carbonylic compounds and their corresponding allylic alcohols. Mutat. Res. 1982, 93, 305-315.
10. Marnett, L. J., Hurd, H. K., Hollstein, M. C., Levin, D. E. et al., Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA 104. Mutat. Res. 1985, 148, 25-34.
11. Curren, R. D., Yang, L. L., Conklin, P. M., Grafstrom, R. C., Harris, C. C., Mutagenesis of xeroderma pigmentosum fibroblasts by acrolein. Mutat. Res. Lett. 1988, 209, 17-22.
12. Yang, I. Y., Chan, G., Miller, H., Huang, Y. et al., Mutagenesis by acrolein-derived propanodeoxyguanosine adducts in human cells. Biochemistry 2002, 41, 13826-13832.
13. Feng, Z., Hu, W., Hu, Y., Tang, M.-S., Acrolein is a major cigarette-related lung cancer agent: preferential binding at p53 mutational hotspots and inhibition of DNA repair. Proc. Natl. Acad. Sci. USA 2006, 103, 15404-15409.
14. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 1984, 44, 990-995.
15. Liu, X., Lovell, M. A., Lynn, B. C., Development of a method for quantification of acrolein-deoxyguanosine adducts in DNA using isotope dilution-capillary LC/MS/MS and its application to human brain tissue. Anal. Chem. 2005, 77, 5982-5989.
16. 2-Propano-2'-deoxyguanosine adducts derived from acrolein and crotonaldehyde in human placenta and leukocytes by isotope dilution nanoflow LC nanospray ionization tandem mass spectrometry. Anal. Chem. 2009, 81, 9812-9818.
17. 32P-postlabeling method for simultaneous detection and quantification of exocyclic etheno and propano adducts in DNA. Carcinogenesis 1994, 15, 979-984.
18. Liu, X., Lovell, M. A., Lynn, B. C., Detection and quantification of endogenous cyclic DNA adducts derived from trans-4-hydroxy-2-nonenal in human brain tissue by isotope dilution capillary liquid chromatography nanoelectrospray tandem mass spectrometry. Chem. Res. Toxicol. 2006, 19, 710-718.
19. 2-propanodeoxyguanosine adducts in DNA from human tissues using liquid chromatography-electrsopray ionization-tandem mass spectrometry. Chem. Res. Toxicol. 2006, 19, 1386-1392.
20. Pfeifer, G. P., Denissenko, M. F., Olivier, M., Tretyakova, N. et al., Tobacco smoke carcinogens, DNA damage and p53 mutations in smoking-associated cancers. Oncogene 2002, 21, 7435-7451.
21. Hecht, S. S., Smoking and lung cancer - a new role for an old toxicant? Proc. Natl. Acad. Sci. USA 2006, 103, 15725-15726.
22. Cohen, S. M., Garland, E. M., St. John, M., Okamura, T., Smith, R. A., Acrolein initiates rat urinary bladder carcinogenesis. Cancer Res. 1992, 52, 3577-3581.
23. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. USA 1994, 91, 7491-7495.
24. 2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer Res. 1996, 56, 452-456.
25. 2-Propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue. Cancer Res. 1998, 58, 581-584.
26. 2-propanodeoxyguanosine adducts in human lung by liquid chromatography-electrospray ionization-tandem mass spectrometry. Chem. Res. Toxicol. 2007, 20, 565-571.
27. Bessette, E. E., Goodenough, A. K., Langouët, S., Yasa, I. et al., Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer. Anal. Chem. 2009, 81, 809-819.
28. 2-propanodeoxyguanosine adducts derived from enals. Anal. Biochem. 2006, 348, 15-23.
29. 32P-postlabeling/solid-phase extraction/HPLC method: blocking its artifact formation with glutathione. Anal. Biochem. 2008, 374, 163-172.
30. Turteltaub, K. W., Dingley, K. H., Application of accelerated mass spectrometry (AMS) in DNA adduct quantification and identification. Toxicol. Lett. 1998, 102-103, 435-439.
31. Ciccimaro, E., Blair, I. A., Stable-isotope dilution LC-MS for quantitative biomarker analysis. Bioanalysis 2010, 2, 311-341.
32. Wang, M., McIntee, E. J., Cheng, G., Shi, Y., et al., A Schiff base is a major DNA adduct of crotonaldehyde. Chem. Res. Toxicol. 2001, 14, 423-430.
33. Hoberg, A.-M., Otteneder, M., Marnett, L. J., Poulsen, H. E., Measurement of the malondialdehyde-2'-deoxyguanosine adduct in human urine by immuno-extraction and liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry. J. Mass Spectrom. 2004, 39, 38-42.
34. 6-etheno-2'-deoxyadenosine in human urine by column-switching LC/APCI-MS/MS. Free Radic. Biol. Med. 2004, 36, 1383-1392.
35. 2-etheno-2'-deoxyguanosine adducts. Chem. Res. Toxicol. 2005, 18, 780-786.
36. Hillestrom, P. R., Weimann, A., Poulsen, H. E., Quantification of urinary etheno-DNA adducts by column-switching LC/APCI-MS/MS. J. Am. Soc. Mass Spectrom. 2006, 17, 605-610.
37. Kanaly, R. A., Matsui, S., Hanaoka, T., Matsuda, T., Application of the adductome approach to assess intertissue DNA damage variations in human lung and esophagus. Mutat. Res. 2007, 625, 83-93.
38. Wang, J. J., Marshall, W. D., Law, B., Lewis, D. M., Fragmentation patterns of DNA-benzo[a]pyrene diol epoxide adducts characterized by nanoflow LC/quadrupole time-of-flight mass spectrometry. Int. J. Mass Spectrom. 2003, 230, 45-55.
39. Wang, J. J., Marshall, W. D., Frazer, D. G., Law, B., Lewis, D. M., Characterization of DNA adducts from lung tissue of asphalt fume-exposed mice by nanoflow liquid chromatography quadrupole time-of-flight mass spectrometry. Anal. Biochem. 2003, 322, 79-88.
40. n method for the characterization and quantification of 2'-deoxyguanosine adducts of the dietary carcinogen 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine by 2-D linear quadrupole ion trap mass spectrometry. Chem. Res. Toxicol. 2007, 20, 263-276.
41. Giese, R. W., Detection of DNA adducts by electron capture mass spectrometry. Chem. Res. Toxicol. 1997, 10, 255-270.
42. 4-ethenocytosine in DNA and in human urine by isotope dilution gas chromatography/negative ion chemical ionization/mass spectrometry. Chem. Res. Toxicol. 2001, 14, 1612-1619.
43. 6-ethenoadenine in human urine by stable isotope dilution capillary gas chromatography/negative ion chemical ionization/mass spectrometry. Chem. Res. Toxicol. 2003, 16, 1099-1106.
44. 4-ethenocytosine levels measured by gas chromatography/mass spectrometry. Toxicol. Sci. 2003, 76, 321-327.
45. Chen, H.-J. C., Kao, C.-F., Effect of gender and cigarette smoking on urinary excretion of etheno DNA adducts in humans measured by isotope dilution gas chromatography/mass spectrometry. Toxicol. Lett. 2007, 169, 72-81.
46. Niessen, W. M. A., Advances in instrumentation in liquid chromatography-mass spectrometry and related liquid-introduction techniques. J. Chromatogr. A, 1998, 794, 407-435.
47. Niessen, W. M. A., State-of-the-art in liquid chromatography-mass spectrometry. J. Chromatogr. A 1999, 856, 179-197.
48. Singh, R., Farmer, P. B., Liquid chromatography-electrospray ionization-mass spectrometry: the future of DNA adduct detection. Carcinogenesis 2006, 27, 178-196.
49. Vanhoutte, K., Van Dongen, W., Hoes, I., Lemiere, F. et al., Development of a nanoscale liquid chromatography/electrospray mass spectrometry methodology for the detection and identification of DNA adducts. Anal. Chem. 1997, 69, 3161-3168.
50. Lovell, M. A., Xie, C., Markesbery, W. R., Acrolein is increased in Alzheimer's disease brain and is toxic to primary hippocampal cultures. Neurobiol. Aging 2001, 22, 187-194.
51. Chen, H.-J. C., Chen, Y.-C., Analysis of glyoxal-induced DNA cross-links by capillary liquid chromatography nanospray ionization tandem mass spectrometry. Chem. Res. Toxicol. 2009, 22, 1334-1341.
52. 32P-post-labelling analysis of DNA adducts formed by food-derived heterocyclic amines: evidence for incomplete hydrolysis and a procedure for adduct pattern simplification. Carcinogenesis 1994, 15, 877-882.
53. 32P-postlabeling method. Jpn. J. Cancer Res. 1994, 85, 113-117.
54. Gangl, E. T., Turesky, R. J., Vouros, P., Determination of in vitro- and in vivo-formed DNA adducts of 2-amino-3-methylimidazo[4, 5-f]quinoline by capillary liquid chromatography/microelectrospray mass spectrometry. Chem. Res. Toxicol. 1999, 12, 1019-1027.
55. Phillips, D. H., Castegnaro, M., Standardization and validation of DNA adduct postlabelling methods: report of interlaboratory trials and production of recommended protocols. Mutagenesis 1999, 14, 301-315.
56. 2-propanodeoxyguanosine adducts in human leukocyte DNA from smokers and nonsmokers. Chem. Res. Toxicol. 2011, 24, 119-124.
57. Sancar, A., Lindsey-Boltz, L. A., Unsal-Kacmaz, K., Linn, S., Molecular mechanisms of mammalian DNA repair and the DNA damage checkpoints. Annu. Rev. Biochem. 2004, 73, 39-85.
58. Baute, J., Depicker, A., Base excision repair and its role in maintaining genome stability. Crit. Rev. Biochem. Mol. Biol. 2008, 43, 239-276.
59. 2-ethenoguanine, a mutagenic DNA adduct, is a primary substrate of Escherichia coli mismatch-specific uracil-DNA glycosylase and human alkylpurine-DNA-N-glycosylase. J. Biol. Chem. 2002, 277, 26987-26993.
60. 2-ethenoguanine measured by isotope dilution liquid chromatography/electrospray ionization-tandem mass spectrometry. Chem. Res. Toxicol. 2005, 18, 1593-1599.
61. Chang, W. C. L., Chapkin, R. S., Lupton, J. R., Fish oil blocks azoxymethane-induced rat colon tumorigenesis by increasing cell differentiation and apoptosis rather than decreasing cell proliferation. J. Nutr. 1998, 128, 491-497.
62. Fernandez, E., Chatenoud, L., La Vecchia, C., Negri, E., Franceschi, S., Fish consumption and cancer risk. Am. J. Clin. Nutr. 1999, 70, 85-90.
63. Rao, C. V., Hirose, Y., Indranie, C., Reddy, B. S., Modulation of experimental colon tumorigenesis by types and amounts of dietary fatty acids. Cancer Res. 2001, 61, 1927-1933.
64. Pan, J., Chung, F. L., Formation of cyclic deoxyguanosine adducts from ω-3 and ω-6 polyunsaturated fatty acids under oxidative conditions. Chem. Res. Toxicol. 2002, 15, 367-372.
65. Pan, J., Keffer, J., Emami, A., Ma, X. et al., Acrolein-derived DNA adduct formation in human colon cancer cells: its role in apoptosis induction by docosahexaenoic acid. Chem. Res. Toxicol. 2009, 22, 798-806.
66. 2-propano-2'-deoxyguanosine. J. Biol. Chem. 2001, 276, 9077-9082.
67. 2-propano-2'-deoxyguanosine adduct in the 5'-CpG-3' DNA sequence. J. Am. Chem. Soc. 2009, 131, 8416-8424.
68. Chen, H.-J. C., Lin, G.-J., Lin, W.-P., Simultaneous quantification of three lipid peroxidation-derived etheno adducts in DNA by stable isotope dilution nanoflow liquid chromatography nanospray ionization tandem mass spectrometry. Anal. Chem. 2010, 82, 4486-4493.
69. Ricicki, E. M., Luo, W., Fan, W., Zhao, L. P. et al., Quantification of N-(deoxyguanosin-8-yl)-4-aminobiphenyl adducts in human lymphoblastoid TK6 cells dosed with N-hydroxy-4-acetylaminobiphenyl and their relationship to mutation, toxicity, and gene expression profiling. Anal Chem. 2006, 78, 6422-6432.
70. Brown, S. C., Kruppa, G., Dasseux, J. L., Metabolomics applications of FT-ICR mass spectrometry. Mass Spectrom. Rev. 2005; 24, 223-231.
71. Dettmer, K., Aronov, P. A., Hammock, B. D., Mass spectrometry-based metabolomics. Mass Spectrom. Rev. 2007, 26, 51-78.
72. 6-ethenoadenine in human placental DNA by mass spectrometry. Chem. Res. Toxicol. 1999, 12, 1119-1126.