Predominance of the 1,N2-propano 2′-deoxyguanosine adduct among 4-hydroxy-2-nonenal-induced DNA lesions

Free Radical Biology and Medicine

Volumn 37, Issue 1, 2004, Pages 62-70

  Douki, Thierry ^a   Odin, Francette ^a   Caillat, Sylvain ^a   Favier, Alain ^a   Cadet, Jean ^a  

^a CEA GRENOBLE   (France)

Author keywords

1,N 6 etheno 2 deoxyadenosine; 1,N 6 etheno 2 deoxyguanosine; 1,N2 dGuo; 1,N6 dAdo; Biomarkers; DNA damage; Ethenobases; Free radicals; Lipid peroxidation; Mass spectrometry; Oxidative stress

Indexed keywords

1,N2 PROPANO 2' DEOXYGUANOSINE; 4 HYDROXYNONENAL; GUANOSINE DERIVATIVE; UNCLASSIFIED DRUG; 1,N(2) PROPANODEOXYGUANOSINE; 1,N(2)-PROPANODEOXYGUANOSINE; DEOXYGUANOSINE; DNA; DRUG DERIVATIVE;

ARTICLE; CELL CULTURE; CONTROLLED STUDY; DNA DAMAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIPID PEROXIDATION; MONOCYTE; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; ANIMAL; CATTLE; CHEMISTRY; DNA ADDUCT; GENETICS; MASS SPECTROMETRY; METABOLISM; STEREOISOMERISM;

ANIMALS; CATTLE; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DNA DAMAGE; MASS SPECTROMETRY; STEREOISOMERISM;

EID: 2942538013     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.04.013     Document Type: Article

References (59)

1. Esterbauer H., Eckl P., Ortner A. Possible mutagens derived from lipids and lipid precursors. Mutat. Res. 238:1990;223-233
2. Eder E., Scheckenbach S., Deininger C., Hoffman C. The possible role of α, β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis. Toxicol. Lett. 67:1993;87-103
3. Blair I.A. Lipid hydroperoxide-mediated DNA damage. Exp. Gerontol. 36:2001;1473-1481
4. Marnett L.J. Oxy radicals, lipid peroxidation and DNA damage. Toxicology. 181-182:2002;219-222
5. Esterbauer H., Schaur R.J., Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic. Biol. Med. 11:1991;81-128
6. Seto H., Akiyama K., Okuda T., Hashimoto T., Takesue T., Ikemura T. Structure of a new modified nucleoside formed by guanosine-malonaldehyde reaction. Chem. Lett. 1981;707-708
7. Basu A.K., O'Hara S.M., Valladier P., Stone K., Mols O., Marnett L.J. Identification of adducts formed by reaction of guanine nucleosides with malondialdehyde and structurally related aldehydes. Chem. Res. Toxicol. 1:1988;53-59
8. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44:1984;990-995
9. Winter C.K., Segall H.J., Haddon W.F. Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal. Cancer Res. 46:1986;5682-5686
10. Eder E., Hoffman C. Identification and characterization of deoxyguanosine adducts of mutagenic β-alkyl-substituted acrolein congeners. Chem. Res. Toxicol. 6:1993;486-494
11. 2-Ethenoguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48:1988;320-323
12. Sodum R.S., Chung F.-L. Structural characterization of adducts formed in the reaction of 2, 3-epoxy-4-hydroxynonanal with deoxyguanosine. Chem. Res. Toxicol. 2:1989;23-28
13. 4-ethenocytosine by lipid peroxidation products and nucleic acid bases. Chem. Res. Toxicol. 8:1995;278-283
14. Chaudhary A.K., Nokubo M., Reddy G.R., Yeola S.N., Morrow J.D., Blair I.A., Marnett L.J. Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science. 265:1994;1580-1582
15. 32P-Postlabelling determination of DNA adducts of malonaldehyde in humans: total white blood cells and breast tissue. Carcinogenesis. 16:1995;1847-1851
16. Chung F.-L., Nath R.G., Ocando J., Nishikawa A., Zhang L. Deoxyguanosine adducts of t-4-hydroxy-2-nonenal are endogenous DNA lesions in rodents and humans: detection and potential sources. Cancer Res. 60:2000;1507-1511
17. 2- propanodeoxyguanosine adducts of trans-4-hydroxy-2-nonenal after gavage of trans-4-hydroxy-2-nonenal or induction of lipid peroxidation with carbon tetrachloride in F344 rats. Chem.-Biol. Interact. 137:2001;269-283
18. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. USA. 91:1994;7491-7495
19. 32P post labelling. Carcinogenesis. 16:1995;613-617
20. 4-ethenocytosine and 4-amino-5-(imidazol-2-yl)imidazole. Biochemistry. 32:1993;12793-12801
21. 6-ethenodeoxyadenosine, a DNA adduct highly mutagenic in human cells. Biochemistry. 35:1996;11487-11492
22. 2-ethenoguanine in Chinese hamster ovary cell chromosomal DNA. Chem. Res. Toxicol. 12:1999;501-507
23. 6-ethenodeoxyadenosine adduct in human cells. Cancer Res. 60:2000;4098-4104
24. 2-deoxyguanosine adducts of trans-4-hydroxynonenal in mammalian cells. Environ. Mol. Mutagen. 42:2003;68-74
25. Fink S.P., Reddy G.R., Marnett L.J. Mutagenicity in Escherichia coli of the major DNA adduct derived from the endogenous mutagen malondialdehyde. Proc. Natl. Acad. Sci. USA. 94:1997;8652-8657
26. Bartsch H., Barbin A., Marion M.-J., Nair J., Guichard Y. Formation, detection and role in carcinogenesis of ethenobases in DNA. Drug Metab. Rev. 26:1994;349-371
27. Barbin A. Etheno-adduct-forming chemicals: from mutagenicity testing to tumor mutation spectra. Mutat. Res. 462:2000;55-69
28. Canuto R.A., Ferro M., Muzio G., Bassi A.M., Leonarduzzi G., Maggiora M., Adamo D., Poli G., Lindahl R. Role of aldehyde metabolizing enzymes in mediating effects of aldehyde products of lipid peroxidation in liver cells. Carcinogenesis. 15:1994;1359-1364
29. Ullrich O., Grune T., Henke W., Esterbauer H., Siems W.G. Identification of metabolic pathways of the lipid peroxidation product 4-hydroxynonenal by mitochondria isolated from rat kidney cortex. FEBS Lett. 352:1994;84-86
30. Alary J., Bravais F., Cradevi J.-P., Debrauwer L., Rao D., Bories G. Mercapturic acid conjugates as urinary end metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 8:1995;34-39
31. Hartley D.P., Ruth J.A., Petersen D.R. The hepatocellular metabolism of 4-hydroxynonenal by alcohol dehydrogenase, aldehyde dehydrogenase and glutathione S-transferase. Arch. Biochem. Biophys. 316:1995;197-205
32. Candy Chen H.-J., Chung F.-L. Epoxidation of trans-4-hydroxy-2-nonenal by fatty acid hydroperoxides and hydrogen peroxide. Chem. Res. Toxicol. 9:1996;306-312
33. 2, 3-ethenoguanine under peroxidizing conditions. Chem. Res. Toxicol. 13:2000;1243-1250
34. Esterbauer H., Weger W. Über die Wirkungen von Aldehyden auf gesunde und maligne Zellen. Mitt.: Synthese von homologen 4-hydroxy-2-alkenalen, II. Monatsh. Chem. 98:1967;1994-2000
35. 2, 3-ethenoguanine: synthesis and comparison of the electronic spectral properties of these linear and angular three heterocycles related to the Y bases. J. Org. Chem. 42:1977;3292-3296
36. Chapeau C., Marnett L.J. Enzymatic synthesis of purine deoxynucleoside adducts. Chem. Res. Toxicol. 4:1991;636-638
37. Sodum R.S., Chung F.-L. Stereoselective formation of in vitro nucleic acid adducts by 2, 3-epoxy-4-hydroxynonanal. Cancer Res. 51:1991;137-143
38. Ravanat J.L., Douki T., Duez P., Gremaud E., Herbert K., Hofer T., Lasserre L., Saint-Pierre C., Favier A., Cadet J. Cellular background level of 8-oxo-7, 8-dihydro-2′-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up. Carcinogenesis. 23:2002;1911-1918
39. Frelon S., Douki T., Ravanat J.-L., Tornabene C., Cadet J. High performance liquid chromatography-tandem mass spectrometry measurement of radiation-induced base damage to isolated and cellular DNA. Chem. Res. Toxicol. 13:2000;1002-1010
40. 2, 3-ethenoguanosine and their use for quantification of adducts in G12 cells exposed to chloroacetaldehyde. Carcinogenesis. 14:1993;113-116
41. Sevilla C.L., Mahle N.H., Eliezer N., Uzieblo A., O'Hara S.M., Nokubo M., Miller R., Rouzer C.A., Marnett L.J. Development of monoclonal antibodies to the malondialdehyde-deoxyguanosine adduct, pyrimidopurinone. Chem. Res. Toxicol. 10:1997;172-180
42. 32P-postlabelling. Carcinogenesis. 13:1992;593-599
43. 2-(1, 3-propano)-2′-deoxyguanosine 3′-phosphate adducts formed from 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 10:1997;1259-1265
44. Rouzer C.A., Chaudhary A.K., Nokubo M., Ferguson D.M., Reddy G.R., Blair I.A., Marnett L.J. Analysis of the malondialdehyde-2′-deoxyguanosine adduct pyrimidopurinone in human leukocyte DNA by gas chromatography/electron capture/negative chemical ionization/mass spectrometry. Chem. Res. Toxicol. 10:1997;181-188
45. 6- ethenoadenine by gas chromatography/negative ion chemical ionization/mass spectrometry. Chem. Res. Toxicol. 11:1998;1474-1480
46. 2-ethenoguanine with an immunoaffinity/gas chromatography/high resolution mass spectrometry assay. Chem. Res. Toxicol. 14:2001;324-334
47. 2-etheno-2′- deoxyguanosine in DNA. Chem. Res. Toxicol. 15:2002;1302-1308
48. Churchwell M.I., Beland F.A., Doerge D.R. Quantification of multiple DNA adducts formed through oxidative stress using liquid chromatography and electrospray tandem mass spectrometry. Chem. Res. Toxicol. 15:2002;1295-1301
49. 2-propano adducts of 2′-deoxyguanosine with 4-hydroxynonenal and other α, β-unsaturated aldehydes. Chem. Res. Toxicol. 7:1994;511-518
50. Golding B.T., Slaich P.K., Kennedy G., Bleasdale C., Watson W.P. Mechanism of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine. Chem. Res. Toxicol. 9:1996;147-157
51. Lee S.H., Tomoyuki O., Blair I.A. Vitamin C-induced decomposition of lipid hydroperoxides to endogenous genotoxins. Science. 292:2001;2083-2086
52. Dedon P.C., Plastaras J.P., Rouzer C.A., Marnett L.J. Indirect mutagenesis by oxidative DNA damage: formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal. Proc. Natl. Acad. Sci. USA. 95:1998;11113-11116
53. ε-oxopenyllysine. Chem. Res. Toxicol. 13:2000;1235-1242
54. Frelon S., Douki T., Favier A., Cadet J. Comparative study of base damage induced by gamma radiation and Fenton reaction in isolated DNA. J. Chem. Soc. Perkin Trans. 1:2002;2866-2870
55. Candy Chen H.-J., Chung F.-L. Formation of etheno adducts in reactions of enals via autoxidation. Chem. Res. Toxicol. 7:1994;857-860
56. Dosanjh M.K., Chenna A., Kim E., Fraenkel-Conrat H., Samson L., Singer B. All four known cyclic adducts formed in DNA by the vinyl chloride metabolite chloroacetaldehyde are released by a human DNA glycosylase. Proc. Natl. Acad. Sci. USA. 91:1994;1024-1028
57. 6-ethenoadenine when present in DNA. Nucleic Acids Res. 23:1995;3750-3755
58. 4-ethenocytosine are excised by separate human DNA glycosylases. Carcinogenesis. 17:1996;155-157
59. Klungland A., Rosewell I., Hollenbach S., Larsen E., Daly G., Epe B., Seeberg E., Lindahl T., Barnes D.E. Accumulation of premutagenic DNA lesions in mice defective in removal of oxidative base damage. Proc. Natl. Acad. Sci. USA. 96:1999;13300-13305