Abstract
Modified purine and pyrimidine bases which constitute one of the major classes of oxidative DNA damage are likely to be involved in mutagenesis and carcinogenesis and possibly in aging. In the present survey, the currently available information on the structural aspects of oxidized DNA bases and their mechanism of formation are critically reviewed. A survey of the main approaches (HPLC separations associated with various spectroscopic detections, gas chromatography-mass spectrometry, postlabeling techniques, immunoassays…) involving either initial acid hydrolysis or enzymatic digestion of DNA which were recently developed for monitoring the formation of oxidative DNA base damage in cells, tissues and biological fluids is also presented. The measurement of the above compounds in biological fluids such as urine may be used for assessing oxidative damage to DNA [5]. Other important sources of oxidation processes are provided by physical agents (ionizing radiation, near-ultraviolet/visible light [6,7]). In the latter case, oxidation of DNA would require the presence of endogenous or exogenous photosensitizers including flavins and porphyrins. In this short survey emphasis has been placed on the oxidation reactions of the guanine moiety of DNA and model compounds as the result of one-electron processes and exposure to oxidizing agents including hydroxyl radicals and singlet oxygen. However, it should be mentioned that relevant information on oxidation reactions of adenine, cytosine and thymine, the other DNA bases is available [see for example, 6–10].
To whom correspondence may be addressed
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Ames B.N., Gold L.S. “Endogenous mutagens and the cause of aging and cancer”, Mutat. Res, 250, 3–16 (1991).
Sies H., ed. Oxidative Stress, “Oxidants and Antioxidants”, New York, Academic Press Inc., (1991).
Lindahl T. “Instability and decay of the primary structure of DNA”, Nature, 362, 709–715 (1993).
Srinivasan S., Glauert H.P. “Formation of 5-hydroxymethyl-2’-deoxyuridine in hepatic DNA of rats treated with gamma-irradiation, diethylnitrosamine, 2-acetylaminofluorene or the peroxisome proliferator ciprofibrate”, Carcinogenesis, 11, 2012–2024 (1990).
Shinenaga M.K., Gimeno C.L., Ames B.N. “Urinary 8-hydroxy-2’-deoxyguanosine as a biological marker of in vivo oxidative DNA damage”, Proc. Natl. Acad. Sci. USA, 86, 9697–9701 (1989).
von Sonntag C. ed. “The Chemical Basis of Radiation Biology”, London: Taylor Francis, (1987).
Cadet J., Vigny P. “The photochemistry of nucleic acids”, In: Morrison H, ed. Bioorganic Photochemistry, Vol. 1, New York: Wiley and Sons, 1–272 (1990).
Wagner J.R., van Lier J.E., Decarroz C., Berger M., Cadet J. “Photodynamic methods for oxy radical-induced DNA damage”, Methods Enzym, 186, 502–511 (1990).
Wagner J.R., van Lier J.E., Berger M., Cadet J. “Thymidine hydroperoxides: Structural assignment, conformational features, and thermal decomposition in water”, J. Am. Chem. Soc, 116, 2235–2242 (1994).
Cadet J. “DNA damage caused by oxidation, deamination, ultraviolet radiation and photoexcited psoralens”, In: Hemminki K et al, eds. DNA adducts: Identification and biological significance, Lyon: International Agency for Research on Cancer, IARC Scientific Publications, 125, 245–276 (1994).
Cadet J., Berger M., Buchko G.W., Joshi P.C., Raoul S., Ravanat J.L. “2,2-Diamino-4-[(3,5-di-O-acetyl-2-deoxy-ß-D-erythro-pentofuranosyl)amino]-5-(2H)-oxaz olone: A novel and predominant radical oxidation product of 3′,5′-di-O-acetyl-2′-deoxyguanosine”, J. Am. Chem. Soc, 116, 7403–7404 (1994).
Morin B Cadet J . “Benzophenone photosensitisation of 2′-deoxyguanosine: Characterization of the 2R and 2S diastereoisomers of l-(2-deoxy-ß-D-erythro-pentofuranosyl) -2-methoxy-4, 5-imidazolidinedione. A model system for the investigation of photosensitized formation of DNA-protein crosslinks”, Photochem. Photobiol., 60, 102–109 (1994).
Kasai H., Yamaizumi Z., Berger M., Cadet J. “Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin: a non singlet oxygen mediated reaction”, J. Am. Chem. Soc, 114, 9692–9694 (1992).
Berger M., de Hazen M., Nejjari A., Fournier J., Guignard J., Pezerat H., Cadet J. “Radical oxidation reactions of the purine moiety of 2′-deoxyribo-nucleosides and DNA by iron-containing minerals”, Carcinogenesis, 14, 41–46 (1993).
Cadet J., Berger M., Buchko G.W., Incardona M.F., Morin B., Raoul S., Ravanat J.L. “DNA oxidation: Characterization of the damage and mechanistic aspects”, In: R. Paoletti et al. Oxidative Processes and Antioxidants, New York: Raven Press, 97–115 (1994).
Buchko G.W., Cadet J., Berger M., Ravanat J.L. “Photooxidation of d(TpG) by phthalocyanines and riboflavin. Isolation and characterization of dinucleoside monophosphates containing the 4R* and the 4S* diastereoisomers of 4,8-dihydro-4-hydroxy-8-oxo-2′-deoxyguanosine”, Nucleic. Acids Res., 20, 4847–4851 (1992).
Cadet J., Ravanat J.L., Buchko G.W., Yeo H.C., Ames B.N. “Singlet oxygen DNA damage: Chromatographic and mass spectrometric analysis of damage products”, Methods Enzym, 234, 79–88 (1994).
Cadet J., Weinfeld M. “Detecting DNA damage”, Anal Chem, 65, 675A–682A (1993).
Frenkel K, Klein C.B. Methods used for analyses of environmentally damaged nucleic acids, J. Chromatogr., 618, 289–314 (1993).
Mouret J.F., Odin F., Polverelli M., Cadet J. “32P-Postlabeling measurement of adenine N-l-oxide in cellular DNA exposed to hydrogen peroxide”, Chem. Res. Toxicol., 3, 102–110 (1990).
Cadet J., Odin F., Mouret J.F., Polverelli M., Audic A., Giacomoni P., Favier A., Richard M.J. “Chemical and biochemical postlabeling methods for singling out specific oxidative DNA lesions”, Mutat. Res., 275, 343–354 (1992).
Shigenaga M.K., Aboujaoude E.N., Chen Q., Ames B.N. “Assays of oxidative DNA damage biomarkers 8-oxo-2′-deoxyguanosine and 8-oxoguanine in nuclear DNA and biological fluids by high performance liquid chromatography with electrochemical detection”, Methods Enzym., 234, 16–33 (1994).
Faure H., Incardona M.F., Boujet C., Cadet J., Ducros V., Favier A. “Gas chromato- graphic-mass spectrometric determination of 5-hydroxymethyluracil in human urine by stable isotope dilution”, J. Chromatogr. Biom. Appl., 616, 1–7 (1993).
Boiteux S. “Properties and biological functions of the NTH and FPG proteins of Escherichia coli: two glycosylases that repair oxidative damage in DNA”, J. Photochem. Photobiol. B: Biol., 19, 87–96 (1993).
Hatahet Z., Kow Y.W., Purmal A.A., Cunningham R.P., Wallace S.S. “New substrates from old enzymes”, J. Biol. Chem., 269, 11814–18820 (1994).
Tchou J., Bodepudi V., Shibutani S., Antoshechkin I., Miller J., Grollman A.P., Johnson F. “Substrate specificity of Fpg protein”, J. Biol. Chem., 269, 15318–15324 (1994).
Guy A., Duplaa A.M., Ulrich J., Teoule R. “Incorporation by chemical synthesis and characterization of deoxyribosylformylamine into DNA”, Nucleic. Acids Res., 19, 5815–5820 (1991).
Grollman A.P., Moriya M. “Mutagenesis by 8-oxoguanine: an enemy within”, Trends Genet, 9, 246–249 (1993).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1997 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Cadet, J. et al. (1997). DNA Modifications Due to Oxidative Damage. In: Bardinet, C., Royer, JJ. (eds) Geosciences and Water Resources: Environmental Data Modeling . Data and Knowledge in a Changing World. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-60627-4_29
Download citation
DOI: https://doi.org/10.1007/978-3-642-60627-4_29
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-64483-2
Online ISBN: 978-3-642-60627-4
eBook Packages: Springer Book Archive