Analysis of DNA-protein crosslinking activity of malondialdehyde in vitro

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 424, Issue 1-2, 1999, Pages 97-106

  Voitkun, Victoria ^a   Zhitkovich, Anatoly ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

DNA adduct; DNA protein crosslink; Endogenous DNA damage; Lipid peroxidation; Malondialdehyde

Indexed keywords

MALONALDEHYDE;

ANIMAL TISSUE; ARTICLE; CROSS LINKING; DNA ADDUCT; DNA DAMAGE; DNA PROTEIN COMPLEX; IN VITRO STUDY; KIDNEY; LIPID PEROXIDATION; LIVER; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; CATTLE; CROSS-LINKING REAGENTS; DNA; DNA ADDUCTS; DNA DAMAGE; LIPID PEROXIDATION; MALE; MALONDIALDEHYDE; PROTEIN BINDING; RATS; RATS, INBRED F344;

BOVINAE;

EID: 0033535440     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(99)00011-1     Document Type: Article

References (44)

1. Ames B.N., Gold L.S. Endogenous mutagens and the causes of aging and cancer. Mut. Res. 250:1991;3-16.
2. Marnett L.J., Burcham P.C. Endogenous DNA adducts: potential and paradox. Chem. Res. Tox. 6:1993;771-785.
3. Nath R.G., Randerath K., Li D., Chung F.-L. Endogenous production of DNA adducts. Regul. Tox. Pharm. 23:1996;22-28.
4. Shibutani S., Takeshita M., Grollman A. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature. 349:1991;431-434.
5. 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.
6. Chiu S.M., Friedman L.R., Oleinick N.L. The fate of DNA-protein crosslinks formed in gamma-irradiated metaphase cells. Int. J. Rad. Biol. 58:1990;235-247.
7. Cress A.E., Kurath K.M., Stea B., Bowden G.T. The crosslinking of nuclear protein to DNA using ionizing radiation. J. Cancer Res. Clin. Oncol. 116:1990;324-330.
8. Dizdaroglu M., Gajewski E., Reddy P., Margolis S.A. Structure of a hydroxyl radical induced DNA-protein cross-link involving thymine and tyrosine in nucleohistone. Biochemistry. 28:1989;3625-3629.
9. Gajewski E., Dizdaroglu M. Hydroxyl radical induced cross-linking of cytosine and tyrosine in nucleohistone. Biochemistry. 29:1990;977-980.
10. Weir Lipton M.S., Fuciarelli A.F., Springer D.L., Edmonds C.G. Characterization of radiation-induced thymine-tyrosine crosslinks by electrospray ionization mass spectrometry. Rad. Res. 145:1996;681-686.
11. H. Esterbauer, Aldehydic products of lipid peroxidation, in: D.C.H. McBrien, T.F. Slater (Eds.), Free Radicals, Lipid Peroxidation and Cancer, Academic Press, NY, 1982, pp. 101-128.
12. Kuykendall J.R., Bogdanffy M.S. Reaction kinetics of DNA-histone crosslinking by vinyl acetate and acetaldehyde. Carcinogenesis. 13:1992;2095-2100.
13. Costa M., Zhitkovich A., Harris M., Paustenbauch D., Gargas M. DNA-protein crosslinks produced by various chemicals in cultured human lymphoma cells. J. Tox. Environ. Health. 50:1997;101-116.
14. Casanova M., Deyo D.F., Heck H.D.'A. Covalent binding of inhaled formaldehyde to DNA in the nasal mucosa of Fisher 344 rats: analysis of formaldehyde and DNA by high-performance liquid chromatography and provisional pharmacokinetic interpretation. Fund. Appl. Pharm. 12:1989;397-417.
15. Casanova M., Morgan K.T., Steinhagen W.H., Everitt J.I., Popp J.A., Heck H.D.'A. Covalent binding of inhaled formaldehyde in the respiratory tract of rhesus monkeys: rat-to-monkey interspecies scaling, and extrapolation to man. Fund. Appl. Pharm. 17:1991;409-428.
16. Lutz W.K. Endogenous formaldehyde does not produce detectable DNA-protein crosslinks in rat liver. Tox. Pathol. 14:1986;462-465.
17. Casanova M., Heck H.D.'A. Lack of evidence for the involvement of formaldehyde in the hepatocarcinogenicity of methyl tertiary-butyl ether in CD-1 mice. Chem.-Biol. Interact. 105:1997;131-143.
18. Sugiyama M., Wang X.-W., Costa M. Comparison of DNA lesions and cytotoxicity induced by calcium chromate in human, mouse, and hamster cell lines. Cancer Res. 46:1986;4547-4551.
19. Costa M., Zhitkovich A., Toniolo P. DNA-protein crosslinks in welders: molecular implications. Cancer Res. 53:1993;460-463.
20. Taioli E., Zhitkovich A., Toniolo P., Costa M. Normal values of DNA-protein crosslinks in mononuclear cells of a population of healthy controls. Cancer J. 8:1995;76-78.
21. Taioli E., Zhitkovich A., Kinney P., Udasin I., Toniolo P., Costa M. Increased DNA-protein crosslinks in lymphocytes of residents living in chromium contaminated areas. Biol. Trace Element Res. 50:1995;175-180.
22. Zhitkovich A., Lukanova A., Popov T., Taioli E., Cohen H., Costa M., Toniolo P. DNA-protein crosslinks in peripheral lymphocytes of individuals exposed to hexavalent chromium compounds. Biomarkers. 1:1996;86-93.
23. Seto H., Okuda T., Takesue T., Ikemura T. Reaction of malonaldehyde 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. 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.
25. Summerfield F.W., Tappel A.L. Cross-linking of DNA in liver and testes of rats fed 1,3-propanediol. Chem.-Biol. Interact. 50:1984;87-96.
26. Crawford D.L., Yu T.C., Sinnhuber R.O. Reaction of malonaldehyde with protein. J. Food Sci. 32:1967;332-335.
27. Nair V., Cooper C.S., Vietti D.E., Turner G.A. The chemistry of lipid peroxidation metabolites: crosslinking reactions of malondialdehyde. Lipids. 21:1986;6-10.
28. Nair V., Vietti D.E., Cooper C.S. Degenerative chemistry of malondialdehyde. Structure, stereochemistry, and kinetics of formation of enaminals from reaction with amino acids. J. Am. Chem. Soc. 103:1981;3030-3036.
29. 32P-postlabelling Carcinogenesis. 13:1992;593-599.
30. Zhitkovich A., Costa M. A simple, sensitive assay to detect DNA-protein-crosslinks in intact cells and in vivo. Carcinogenesis. 13:1992;1485-1489.
31. Singer V.L., Jones L.J., Yue S.T., Haugland R.P. Characterization of PicoGreen reagent and development of a fluorescence-based solution assay for double-stranded DNA quantitation. Anal. Biochem. 249:1997;228-238.
32. Thoma F., Koller Th., Klug A. Involvement of histone H1 in the organization of the nucleosome and of salt-dependent superstructure of chromatin. J. Cell. Biol. 83:1979;403-427.
33. Ridsdale J.A., Davie J.R. Chicken erythrocyte polynucleosomes which are soluble at physiological ionic strength and contain linker histones are highly enriched in β-globin gene sequences. Nucl. Acids Res. 15:1987;1081-1096.
34. Reiss U., Tappel A.L., Chio K.S. DNA-malonaldehyde reaction: formation of fluorescent products. Biochem. Biophys. Res. Comm. 48:1972;921-926.
35. Kikugawa K., Beppu M. Involvement of lipid oxidation products in the formation of fluorescent and cross-linked proteins. Chem. Phys. Lipids. 44:1987;277-296.
36. Eick S., Nicolai M., Mumberg D., Doenecke D. Human H1 histones: conserved and varied sequence elements in two H1 subtype genes. Eur. J. Cell Biol. 49:1989;110-115.
37. Beppu M., Fukata Y., Kikugawa K. Interaction of malondialdehyde-modified bovine serum albumin and mouse peritoneal macrophages. Chem. Pharm. Bull. 36:1988;4519-4526.
38. Bonnes-Taourel D., Guerin M.-C., Torreilles J. Is malonaldehyde a valuable indicator of lipid peroxidation? Biochem. Pharm. 44:1992;985-988.
39. Niitsu M., Ohya T., Xu X.S., Samejima K. Identification of N4-(2-propenal)spermidine as a major reaction product of malondialdehyde and spermidine. Biol. Pharm. Bull. 18:1995;1162-1164.
40. Chio K.S., Tappel A.L. Synthesis and characterization of the fluorescent products derived from malonaldehyde and amino acids. Biochemistry. 8:1969;2821-2827.
41. L.J. Marnett, DNA adducts of α,β-unsaturated aldehydes and dicarbonyl compounds, in: K. Hemminki, A. Dipple, D.E.G. Shuker, F.F. Kadlubar, D. Segerback, H. Bartsch (Eds.), DNA Adducts: Identification and Biological Significance, IARC scientific publications No 125, IARC, Lyon, 1994, pp. 151-163.
42. 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.
43. 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 gas chromatography/electron capture/negative chemical ionization/mass spectroscopy. Chem. Res. Toxicol. 10:1997;181-188.
44. 32P-postlabelling determination of DNA adducts of malonaldehyde in humans: total white blood cells and breast tissue Carcinogenesis. 16:1995;1847-1851.