Lipid peroxidation - DNA damage by malondialdehyde

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 424, Issue 1-2, 1999, Pages 83-95

  Marnett, Lawrence J ^a  

^a VANDERBILT INGRAM CANCER CENTER   (United States)

Author keywords

DNA adduct; Immunochemistry; M1G; Malondialdehyde; Mass spectrometry; Postlabeling; Pyrimidopurinone

Indexed keywords

MALONALDEHYDE; PHOSPHORUS 32;

CANCER; DIET; DNA ADDUCT; DNA DAMAGE; GENOTOXICITY; HUMAN; IMMUNOHISTOCHEMISTRY; LIFESTYLE; LIPID PEROXIDATION; MASS SPECTROMETRY; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL; REVIEW; SITE DIRECTED MUTAGENESIS;

EID: 0033535371     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(99)00010-X     Document Type: Article

References (48)

1. Porter N.A. Mechanisms for the autoxidation of polyunsaturated lipids. Acc. Chem. Res. 19:1986;262-268.
2. Dix T.A., Aikens J. Mechanisms and biological relevance of lipid peroxidation initiation. Chem. Res. Toxicol. 6:1993;2-18.
3. Pryor W.A. Oxy-radicals and related species: their formation, lifetimes and reactions. Annu. Rev. Physiol. 48:1986;657-667.
4. Barclay L.R.C., Locke S.J., MacNeil J.M., VanKessel J., Burton G.W., Ingold K.U. Autoxidation of micelles and model membranes. Quantitative kinetic measurements can be made by using either water-soluble or lipid-soluble chain-breaking antioxidants. J. Am. Chem. Soc. 106:1984;2479-2481.
5. Waldeck A.R., Stocker R. Radical-initiated lipid peroxidation in low density lipoproteins: insights obtained from kinetic modeling. Chem. Res. Toxicol. 9:1996;954-964.
6. Pryor W.A., Stanley J.P. A suggested mechanism for the production of malondialdehyde during the autoxidation of polyunsaturated fatty acids. Non-enzymatic production of prostaglandin endoperoxides during autoxidation. J. Org. Chem. 40:1975;3615-3617.
7. Morrow J.D., Roberts L.J. The isoprostanes - current knowledge and directions for future research. Biochem. Pharmacol. 51:1996;1-9.
8. 1α. J. Biol. Chem. 242:1967;5336-5343.
9. Janero D.R. Malondialdehyde and thiobarbituric acid-reactivity as diagnostic indices of lipid peroxidation and peroxidative tissue injury. Free Radic. Biol. Med. 9:1990;515-540.
10. H. Esterbauer, Lipid peroxidation products: formation, chemical properties and biological activities, in: G. Pli, K.H. Cheeseman, M.U. Dianzani, T.F. Slater (Eds.), Free Radicals in Liver Injury, IRL Press, Oxford, 1985, pp. 29-47.
11. Esterbauer H., Eckl P., Ortner A. Possible mutagens derived from lipids and lipid precursors. Mutat. Res. Rev. Genet. Toxicol. 238:1990;223-233.
12. Hazen S.L., Hsu F.F., d'Avignon A., Heinecke J.W. Human neutrophils employ myeloperoxidase to convert α-amino acids to a battery of reactive aldehydes: a pathway for aldehyde generation at sites of inflammation. Biochemistry. 37:1998;6864-6873.
13. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. U.S.A. 91:1994;7491-7495.
14. Shamberger R.J., Andreone T.L., Willis C.E. Antioxidants and cancer: IV. Initiating activity of malonaldehyde as a carcinogen. J. Natl. Cancer Inst. 53:1974;1771-1773.
15. Fischer S.M., Olge S., Marnett L.J., Nesnow S., Slaga T.J. The lack of initiating and/or promoting activity of sodium malondialdehyde on Sencar mouse skin. Cancer Lett. 19:1983;61-66.
16. Mukai F.H., Goldstein B.D. Mutagenicity of malondialdehyde, a decomposition product of peroxidized polyunsaturated fatty acids. Science. 191:1976;868-869.
17. Marnett L.J., Tuttle M.A. Comparison of the mutagenicities of malondialdehyde and side products formed during its chemical synthesis. Cancer Res. 40:1980;276-282.
18. Basu A.K., Marnett L.J. Unequivocal demonstration that malondialdehyde is a mutagen. Carcinogenesis. 4:1983;331-333.
19. Spalding J.W. Toxicology and carcinogenesis studies of malondialdehyde sodium salt (3-hydroxy-2-propenal, sodium salt) in F344/N rats and B6C3F1 mice. NTP Technical Report. 331:1988;5-13.
20. Marnett L.J., Hurd H.K., Hollstein M.C., Levin D.E., Esterbauer H., Ames B.N. Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat. Res. 148:1985;25-34.
21. E. Schauenstein, H. Esterbauer, H. Zollner, Malondialdehyde, in: E. Schauenstein, H. Esterbauer, H. Zollner (Eds.), Aldehydes in Biological Systems, Pion, London, 1977, pp. 133-140.
22. 6-methylguanine-DNA methyltransferase by various aldehydes in cultured human bronchial fibroblasts. Carcinogenesis. 6:1985;1755-1759.
23. Seto H., Okuda T., Takesue T., Ikemura T. Reaction of malondialdehyde with nucleic acid: I. Formation of fluorescent pyrimido[1,2-a]purin-10(3H)-one nucleosides. Bull. Chem. Soc. Jpn. 56:1983;1799-1802.
24. Marnett L.J., Basu A.K., O'Hara S.M., Weller P.E., Rahman A.F.M.M., Oliver J.P. Reaction of malondialdehyde with guanine nucleosides: formation of adducts containing oxadiazabicyclononene residues in the base-pairing region. J. Am. Chem. Soc. 108:1986;1348-1350.
25. Nair V., Turner G.A., Offerman R.J. Novel adducts from the modification of nucleic acid bases by malondialdehyde. J. Am. Chem. Soc. 106:1984;3370-3371.
26. Stone K., Ksebati M., Marnett L.J. Investigation of the adducts formed by reaction of malondialdehyde with adenosine. Chem. Res. Toxicol. 3:1990;33-38.
27. Stone K., Uzieblo A., Marnett L.J. Studies of the reaction of malondialdehyde with cytosine nucleosides. Chem. Res. Toxicol. 3:1990;467-472.
28. 6-oxopropenyl-2′-deoxyadenosine adduct in malondialdehyde-modified DNA using liquid chromatography electrospray ionization tandem mass spectrometry. Carcinogenesis. 17:1996;1167-1170.
29. P.C. Dedon, J.P. Plastaras, C.A. Rouzer, L.J. Marnett, Indirect mutagenesis by oxidative DNA damage: formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal, Proc. Natl. Acad. Sci. U.S.A., 1998, submitted.
30. Benamira M., Johnson K., Chaudhary A., Bruner K., Tibbetts C., Marnett L.J. Induction of mutations by replication of malondialdehyde-modified M13 DNA in Escherichia coli: determination of the extent of DNA modification, genetic requirements for mutagenesis, and types of mutations induced. Carcinogenesis. 16:1995;93-99.
31. Reddy G.R., Marnett L.J. Synthesis of an oligodeoxynucleotide containing the alkaline labile malondialdehyde-deoxyguanosine adduct pyrimido[1,2-a]purin-10(3H)-one. J. Am. Chem. Soc. 117:1995;5007-5008.
32. 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. U.S.A. 94:1997;8652-8657.
33. Johnson K.A., Fink S.P., Marnett L.J. Repair of propanodeoxyguanosine by nucleotide excision repair in vivo and in vitro. J. Biol. Chem. 272:1997;11434-11438.
34. 32P-postlabeling Carcinogenesis. 13:1992;593-599.
35. Kautiainen A., Vaca C.E., Granath F. Studies on the relationship between hemoglobin and DNA adducts of malonaldehyde and their stability in vivo. Carcinogenesis. 14:1993;705-708.
36. Wang M.-Y., Liehr J.G. Induction by estrogens of lipid peroxidation and lipid peroxide-derived malonaldehyde-DNA adducts in male Syrian hamsters: role of lipid peroxidation in estrogen-induced kidney carcinogenesis. Carcinogenesis. 16:1995;1941-1945.
37. Wang M.Y., Liehr J.G. Lipid hydroperoxide-induced endogenous DNA adducts in hamsters: possible mechanism of lipid hydroperoxide-mediated carcinogenesis. Arch. Biochem. Biophys. 316:1995;38-46.
38. 32P-Postlabeling determination of DNA adducts of malonaldehyde in humans: total white blood cells and breast tissue Carcinogenesis. 16:1995;1847-1851.
39. Fang J.L., Vaca C.E., Valsta L.M., Mutanen M. Determination of DNA adducts of malonaldehyde in humans: effects of dietary fatty acid composition. Carcinogenesis. 17:1996;1035-1040.
40. Wang M., Dhingra K., Hittleman W.N., Liehr J.G., de Andrade M., Li D. Lipid peroxidation-induced putative malondialdehyde-DNA adducts in human breast tissues. Cancer Epidemiol. Biomarkers Prev. 5:1996;705-710.
41. 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.
42. 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.
43. 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.
44. Kadlubar F., Anderson K., Lang N., Thompson P., MacLeod S., Mikhailova M., Chou M., Plastaras J., Marnett L., Haussermann S., Bartsch H. Comparison of endogenous DNA adducts levels in human pancreas. Proc. Am. Assoc. Cancer Res. 39:1998;286. Abstract.
45. Chaudhary A.K., Nokubo M., Oglesby T.D., Marnett L.J., Blair I.A. Characterization of endogenous DNA adducts by liquid chromatography/electrospray ionization/tandem mass spectrometry. J. Mass Spectrom. 30:1995;1157-1166.
46. Leuratti C., Singh R., Lagneau C., Farmer P.B., Marnett L.J., Shuker D.E.G. Quantitation of malondialdehyde-DNA damage in human tissues using a sensitive immunoslot blot assay. Proc. Am. Assoc. Cancer Res. 39:1998;286. Abstract.
47. F.F. Kadlubar, K.E. Anderson, N.P. Lang, P.A. Thompson, S.L. MacLeod, M.W. Chou, M. Mikhailova, J. Plastaras, L.J. Marnett, S. Haussermann, J. Nair, I. Velie, H. Bartsch, Comparison of endogenous DNA adduct levels in human pancreas, Mutat. Res., 1998, in press.
48. 32P-Postlabeling determination of DNA adducts of malonaldehyde in humans: total white blood cells and breast tissue Carcinogenesis. 16:1995;1847-1851.