Analysis of glyoxal-induced DNA cross-links by capillary liquid chromatography nanospray ionization tandem mass spectrometry

Chemical Research in Toxicology

Volumn 22, Issue 7, 2009, Pages 1334-1341

  Chen, Hauh Jyun Candy ^a   Chen, Yu Chin ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYRIBONUCLEOSIDE; DOUBLE STRANDED DNA; GLYOXAL;

ARTICLE; CALF (BOVINE); CAPILLARY CHROMATOGRAPHY; CONTROLLED STUDY; DNA CROSS LINKING; DNA DAMAGE; DNA DETERMINATION; HUMAN; HUMAN TISSUE; HYDROLYSIS; NANOSPRAY IONIZATION TANDEM MASS SPECTROMETRY; NONHUMAN; PLACENTA; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; THYMUS;

CHROMATOGRAPHY, LIQUID; CROSS-LINKING REAGENTS; DNA ADDUCTS; DNA DAMAGE; GLYOXAL; HUMANS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 67650999455     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900129e     Document Type: Article

References (39)

1. Sing, R, Barden, A, Mori, T, and Beilin, L. (2001) Advanced glycation end-products: A review. Diabetologia 44, 129-146.
2. Murata-Kamiya, N., Kamiya, H., Iwamoto, N., and Kasai, H. (1995) Formation of a mutagen, glyoxal, from DNA treated with oxygen free radicals. Carcinogenesis 16, 2251-2253.
3. Nagao, M., Fujita, Y., Wakabayashi, K., Nukaya, H., Kosuge, T., and Sugimura, T. (1986) Mutagens in coffee and other beverages. Environ. Health. Perspect. 67, 89-91.
4. Moree-Testa, P., and Saint-Jalm, Y. (1981) Determination of α-dicarbonyl compounds in cigarette smoke. J. Chromatogr. 217, 197-208.
5. 2-glyoxal-deoxyguanosine adduct upon reaction of N-nitroso-2-hydroxymorpholine with deoxyguanosine. Carcinogenesis 6, 1671-1673.
6. Loeppky, R. N., Cui, W., Goelzer, P., Park, M., and Ye, Q. (1999) Glyoxal-Guanine DNA Adducts: Detection, Stability and Formation from Nitrosamines, in Cyclic DNA Adducts II (Singer, B., and Bartsch, H., Eds.) pp 155-168, IARC, Lyon, France.
7. 6-hydroxyethyldeoxyguanosine adducts. Chem. Res. Toxicol. 15, 470-482.
8. Frankel, E. N. (1982) Volatile lipid oxidation products. Prog. Lipid Res. 22, 1-33.
9. Loidl-Stahlhofen, A., and Spiteller, G. (1994) α-Hydroxyaldehydes, products of lipid peroxidation. Biochim. Biophys. Acta 1211, 156-160.
10. Marnett, L. J. (1994) DNA adducts of α,β-unsaturated aldehydes and dicarbonyl compounds. IARC Sci. Publ. 125, 151-163.
11. Thornalley, P. J. (1998) Glutathione-dependent detoxification of α-oxoaldehydes by the glyoxalase system: involvement in disease mechanisms and antiproliferative activity of glyoxalase I inhibitors. Chem.-Biol. Interact. 111-112, 137-151.
12. Raj, D. S. C., Choudhury, D., Welbourne, T. C., and Levi, M. (2000) Advanced glycation end products: A nephrologist's perspective. Am. J. Kidney Dis. 35, 365-380.
13. Ueda, Y., Miyata, T., Goffin, E., Yoshino, A., Inagi, R., Ishibashi, Y., Izuhara, Y., Saito, A., Kurokawa, K., and Van Ypersele De Strihou, C. (2000) Effect of dwell time on carbonyl stress using icodextrin and amino acid peritoneal dialysis fluids. Kidney Int. 58, 2518-2524.
14. Lapolla, A., Flamini, R., Dalla Vedova, A., Senesi, A., Reitano, R., Fedele, D., Basso, E., Seraglia, R., and Traldi, P. (2003) Glyoxal and methyl-glyoxal in diabetic patients: Quantitative determination by a new GC/MS method. Clin. Chem. Lab. Med. 41, 1166-1173.
15. Shapiro, R., and Hachmann, J. (1966) The reaction of guanine derivatives with 1,2-dicarbonyl compounds. Biochemistry 5, 2799-2807.
16. Staehelin, M. (1959) Inactivation of virus nucleic acid with glyoxal derivatives. Biochim. Biophys. Acta 31, 448-454.
17. Shapiro, R., and Hachmann, J. (1966) The reaction of guanine derivatives with 1,2-dicarbonyl compounds. Biochemistry 5, 2799-2807.
18. Kasai, H., Iwamoto-Tanaka, N., and Fukada, S. (1998) DNA modifications by the mutagen glyoxal: adduction to G and C, deamination of C and GC and GA cross-linking. Carcinogenesis 19, 1459-1465.
19. Olsen, R., Molander, P., Øvrebø, S., Ellingsen, D. G., Thorud, S., Thomassen, Y., Lundanes, E., Greibrokk, T., Backman, J., Sjöholm, R., and Kronberg, L. (2005) Reaction of glyoxal with 2′-deoxyguanosine, 2′-deoxyadenosine, 2′-deoxycytidine, cytidine, thymidine, and calf thymus DNA: Identification of DNA adducts. Chem. Res. Toxicol. 18, 730-739.
20. Bidmon, C., Frischmann, M., and Pischetsrieder, M. (2007) Analysis of DNA-bound advanced glycation end-products by LC and mass spectrometry. J. Chromatogr., B 855, 51-58.
21. Pluskota-Karwatka, D., Paw?owicz, A. J., Tomas, M., and Kronberg, L. (2008) Formation of adducts in the reaction of glyoxal with 2′- deoxyguanosine and with calf thymus DNA. Bioorg. Chem. 36, 57-64.
22. Murata-Kamiya, N., Kamiya, H., Kaji, H., and Kasai, H. (1997) Mutational specificity of glyoxal, a product of DNA oxidation, in the lacI gene of wild-type Escherichia coli W3110. Mutat. Res. 377, 255-262.
23. Murata-Kamiya, N., Kamiya, H., Kaji, H., and Kasai, H. (1997) Glyoxal, a major product of DNA oxidation, induces mutation at G:C sites on a shuttle vector plasmid replicated in mammalian cells. Nucleic Acids Res. 25, 1897-1902.
24. Brock, A. K., Kozekov, I. D., Rizzo, C. J., and Harris, T. M. (2004) Coupling products of nucleosides with the glyoxal adduct of deoxyguanosine. Chem. Res. Toxicol. 17, 1047-1056.
25. Singh, R., and Farmer, P. B. (2006) Liquid chromatography-electrospray ionization-mass spectrometry: The future of DNA adduct detection. Carcinogenesis 27, 178-196.
26. Zeng, Y., and Wang, Y. (2007) UVB-induced formation of intrastrand cross-link products of DNA in MCF-7 cells treated with 5-bromo-2′- deoxyuridine. Biochemistry 46, 8189-8195.
27. 2/ascorbate. Chem. Res. Toxicol. 19, 614-621.
28. 7-(2-[pentafluorobenzyloxy]ethyl)xanthine, a product derived from an ethylene oxide DNA adduct. J. Chromatogr. 629, 35-40.
29. Bianchini, F., Donato, F., Faure, H., Ravanat, J. L., Hall, J., and Cadet, J. (1998) Urinary excretion of 5-(hydroxymethyl) uracil in healthy volunteers: effect of active and passive tobacco smoke. Int. J. Cancer 77, 40-46.
30. Ravanat, J. L., Guicherd, P., Tuce, Z., and Cadet, J. (1999) Simultaneous determination of five oxidative DNA lesions in human urine. Chem. Res. Toxicol. 12, 802-808.
31. Vanhoutte, K., Van Dongen, W., Hoes, I., Lemiere, F., Esmans, E. L., Van Onckelen, H., Van den Eeckhout, E., van Soest, R. E., and Hudson, A. J. (1997) Development of a nanoscale liquid chromatography/electrospray mass spectrometry methodology for the detection and identification of DNA adducts. Anal. Chem. 69, 3161-3168.
32. Embrechts, J., Lemiere, F., Van Dongen, W., and Esmans, E. L. (2001) Equilenin-2′-deoxynucleoside adducts: analysis with nano-liquid chromatography coupled to nano-electrospray tandem mass spectrometry. J. Mass Spectrom. 36, 317-328.
33. Embrechts, J., Lemiere, F., Van Dongen, W., Esmans, E. L., Buytaert, P., Van Marck, E., Kockx, M., and Makar, A. (2003) Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 14, 482-491.
34. Liu, X., Lovell, M. A., and Lynn, B. C. (2005) 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. 77, 5982-5989.
35. Liu, X., Lovell, M. A., and Lynn, B. C. (2006) 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. 19, 710-718.
36. 6-ethenoadenine in human placental DNA by mass spectrometry. Chem. Res. Toxicol. 12, 1119-1126.
37. Barth, A., Peiker, G., Gross, W., Schroder, S., and Michels, W. (1997) Peroxidative and glutathione status in uterus and placenta after normal and pathological pregnancy. Exp. Toxicol. Pathol. 49, 497-500.
38. Walsh, S. W. (1998) Maternal-placental interactions of oxidative stress and antioxidants in preeclampsia. Semin. Reprod. Endocrinol. 16, 93-104.
39. Chen, H.-J. C., Row, S.-W., and Hong, C.-L. (2002) Detection and quantification of 5-chlorocytosine in DNA by isotope dilution gas chromatography/negative ion chemical ionization/mass spectrometry. Chem. Res. Toxicol. 15, 262-268.