Endogenous formation and significance of 1,N2-propanodeoxyguanosine adducts

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 424, Issue 1-2, 1999, Pages 71-81

  Chung, Fung Lung ^a   Nath, Raghu G ^a   Nagao, Minako ^b   Nishikawa, Akiyoshi ^c   Zhou, Guo Dong ^d   Randerath, Kurt ^d  

^a AMERICAN HEALTH FOUNDATION   (United States)

^b NATIONAL CANCER CENTER RESEARCH INSTITUTE   (Japan)

^c NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^d BAYLOR COLLEGE OF MEDICINE   (United States)

Author keywords

Cyclic adduct; Detection; Endogenous enal formation; F344 rat; Long Evans rat; Mutagenesis and carcinogenesis

Indexed keywords

CARBON TETRACHLORIDE; GLUTATHIONE; GUANOSINE DERIVATIVE;

ARTICLE; CARCINOGENESIS; DNA ADDUCT; HUMAN; LIPID PEROXIDATION; MOUSE; MUTAGENESIS; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; DEOXYGUANOSINE; DNA ADDUCTS; DNA DAMAGE; HUMANS; LIPID PEROXIDATION; LIVER; MICE; RATS; RATS, INBRED F344; RATS, LONG-EVANS;

ANIMALIA; RODENTIA;

EID: 0033535364     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(99)00009-3     Document Type: Article

References (46)

1. B. Singer, H. Bartsch (Eds.), The role of cyclic adducts in carcinogenesis and mutagenesis, IARC Scientific Publication No. 70, Lyon, France, IARC, 1986.
2. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44:1984;990-995.
3. 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 in vitro. Cancer Res. 46:1986;5682-5686.
4. Marnett L.J. DNA adducts of α,β-unsaturated aldehydes and dicarbonyl compounds. IARC Sci. Publ. No. 125:1994;151-163.
5. 2-(1,3-propano)-2-deoxyguanosine 3′-phosphate adducts formed from 4-hydroxy-2-nonenal Chem. Res. Toxicol. 10:1997;1259-1265.
6. Wu H.-Y., Lin J.-K. Determination of aldehydic lipid peroxidation products with dabsylhydrazine by high-performance liquid chromatography. Anal. Chem. 67:1995;1603-1612.
7. 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.
8. 2-(2-Oxoethyl)guanine. Chem. Res. Toxicol. 6:1993;635-648.
9. Park K.-K., Liem A., Stewart B.C., Miller J.A. Vinyl carbamate epoxide, a major strong electrophilic, mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane). Carcinogenesis. 14:1993;441-450.
10. 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.
11. 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.
12. 2-adducts by reaction of deoxyguanosine with α-acetoxy-N-nitrosopyrrolidine, 4-(carbethoxynitrosamino) butanal, and crotonaldehyde. Cancer Res. 43:1983;1230-1235.
13. Chung F.-L., Roy K.R., Hecht S.S. A study of reactions of α,β-unsaturated carbonyl compounds with deoxyguanosine. J. Org. Chem. 53:1988;14-17.
14. 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.
15. 2-ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48:1988;320-323.
16. Chen H.-J.C., Chung F.-L. Formation of etheno adducts in reactions of enals via autoxidation. Chem. Res. Toxicol. 7:1994;857-860.
17. Chen H.-J.C., Chung F.-L. Epoxidation of trans-4-hydroxy-2-nonenal by fatty acid hydroperoxides and hydrogen peroxide. Chem. Res. Toxicol. 9:1996;306-312.
18. 2-propanodeoxyguanosine adducts in DNA of rats treated with N-nitrosopyrrolidine and mice treated with crotonaldehyde. Carcinogenesis. 10:1989;1291-1297.
19. 32P-postlabeling method for simultaneous detection and quantification of exocyclic etheno and propano adducts in DNA Carcinogenesis. 15:1994;979-984.
20. 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. U.S.A. 91:1994;7491-7495.
21. 2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer Res. 56:1996;452-456.
22. Chung F.-L., Chen H.-J.C., Nath R.G. Lipid peroxidation as a potential endogenous source for the formation of exocyclic DNA adducts. Carcinogenesis. 17:1996;2105-2111.
23. 4-ethenocytosine by lipid peroxidation products and nucleic acid bases. Chem. Res. Toxicol. 8:1995;278-283.
24. Klaassen C.D., Plaa G.L. Comparison of the biochemical alterations elicited in livers from rats treated with carbon tetrachloride, chloroform, 1,1,2-trichloroethane and 1,1,1-trichloroethane. Biochem. Pharmacol. 18:1969;2019-2027.
25. Toyokuni S., Uchida K., Okamoto K., Hattori-Nakakuki Y., Hiai H., Stadtman E.R. Formation of 4-hydroxy-2-nonenal-modified proteins in the renal proximal tubules of rats treated with a renal carcinogen, ferric nitrilotriacetate. Proc. Natl. Acad. Sci. U.S.A. 91:1994;2616-2620.
26. M. Mori, M.C. Yoshida, N. Takechi, The LEC Rat, A New Model For Hepatitis And Liver Cancer, Springer-Verlag, Tokyo, 1991, pp. 1-356.
27. Yamada T., Sogawa K., Suzuki Y., Izumi K., Agui T., Matsumoto K. Elevation of the level of lipid peroxidation associated with hepatic injury in LEC mutant rat. Res. Commun. Chem. Pathol. Pharmacol. 77:1992;121-124.
28. Nair J., Sone H., Nagao M., Barbin A., Bartsch H. Copper-dependent formation of miscoding etheno-DNA adducts in the liver of Long-Evans Cinnamon (LEC) rats developing hereditary hepatitis and hepatocellular carcinoma. Cancer Res. 56:1996;1267-1271.
29. Nath R.G., Ocando J.E., Richie J.P. Jr., Chung F.-L. Effect of glutathione depletion on exocyclic adduct levels in the liver DNA of F344 rats. Chem. Res. Toxicol. 10:1997;1250-1253.
30. Kleinman W.A., Richie J.P. Jr. Determination of thiols and disulfides using high-performance liquid chromatography with electrochemical detection. J. Chromatogr. B Biomed. Appl. 672:1995;73-80.
31. Sun J.D., Ragsdale S.S., Benson J.M., Henderson R.F. Effects of the long-term depletion of reduced glutathione in mice administered L-buthionine (S,R)-sulfoximine. Fundam. and Appl. Toxicol. 5:1985;913-919.
32. 32P-postlabeling assay and possible significance for spontaneous tumor induction and aging Carcinogenesis. 7:1986;1615-1617.
33. Randerath K., Lu L.-J.W., Li D. A comparison between different types of covalent DNA modifications (I-compounds, persistent carcinogen adducts and 5-methylcytosine) in regenerating rat liver. Carcinogenesis. 9:1988;1843-1848.
34. 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.
35. Cajelli E., Ferraris A., Brambilla G. Mutagenicity of 4-hydroxynonenal in V79 Chinese hamster cells. Mutat. Res. 190:1987;169-171.
36. Foiles P.G., Akerkar S.A., Chung F.-L. Application of an immunoassay for cyclic acrolein deoxyguanosine adducts to assess their formation in DNA of Salmonella typhimurium under conditions of mutation induction by acrolein. Carcinogenesis. 10:1989;87-90.
37. 4-ethenocytosine, and 4-amino-5-(imidazol-2-yl)imidazole. Biochemistry. 32:1993;12793-12801.
38. 6-ethenodeoxyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry. 35:1996;11487-11492.
39. 2,3-ethenoguanine produces G→A transitions in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 88:1991;9974-9978.
40. Palejwala V.A., Simha D., Humayun M.Z. Mechanisms of mutagenesis by exocyclic DNA adducts. Transfection of M13 viral DNA bearing a site-specific adduct shows that ethenocytosine is a highly efficient recA-independent mutagenic noninstructional lesion. Biochemistry. 30:1991;8736-8743.
41. 4 hot-spot of Salmonella typhimurium his D3052 carried on an M13 vector. J. Biol. Chem. 267:1992;22392-22400.
42. Moriya M., Zhang W., Johnson F., Grollman A.P. Mutagenic potency of exocyclic DNA adducts: marked differences between Escherichia coli and simian kidney cells. Proc. Natl. Acad. Sci. U.S.A. 91:1994;11899-11903.
43. 32P-postlabeling and nucleotide chromatography Carcinogenesis. 12:1991;1483-1490.
44. 2-propanodeoxyguanosine adducts: potential new biomarkers of smoking-induced DNA damage in human oral tissue. Cancer Res. 58:1998;581-584.
45. 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.
46. Nair J., Vaca C.E., Velic I., Mutanen M., Valsta L.M., Bartsch H. High dietary ω-6 polyunsaturated fatty acids drastically increase the formation of etheno-DNA base adducts in white blood cells of female subjects. Cancer Epidemiol. Biomarkers Prev. 6:1997;597-601.