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Review
. 2012 Apr;46(4):367-81.
doi: 10.3109/10715762.2012.659248. Epub 2012 Feb 22.

Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids

Jean Cadet  1 , Steffen Loft, Ryszard Olinski, Mark D Evans, Karol Bialkowski, J Richard Wagner, Peter C Dedon, Peter Møller, Marc M Greenberg, Marcus S Cooke
Affiliations
Review

Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids

Jean Cadet et al. Free Radic Res. 2012 Apr.

Abstract

A broad scientific community is involved in investigations aimed at delineating the mechanisms of formation and cellular processing of oxidatively generated damage to nucleic acids. Perhaps as a consequence of this breadth of research expertise, there are nomenclature problems for several of the oxidized bases including 8-oxo-7,8-dihydroguanine (8-oxoGua), a ubiquitous marker of almost every type of oxidative stress in cells. Efforts to standardize the nomenclature and abbreviations of the main DNA degradation products that arise from oxidative pathways are reported. Information is also provided on the main oxidative radicals, non-radical oxygen species, one-electron agents and enzymes involved in DNA degradation pathways as well in their targets and reactivity. A brief classification of oxidatively generated damage to DNA that may involve single modifications, tandem base modifications, intrastrand and interstrand cross-links together with DNA-protein cross-links and base adducts arising from the addition of lipid peroxides breakdown products is also included.

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Conflict of interest statement

Declaration of interest

The authors report no conflicts of interest. The authors alone are responsible for the contents and the writing of the paper. MSC, SL, PM, RO, KB and MDE are partners of ECNIS (Environmental Cancer Risk, Nutrition and Individual Susceptibility), a network of excellence operating within the European Union 6th Framework Program, Priority 5: ‘Food Quality and Safety’ (Contract No 513943). JC is member of EU network COST Action CM0603 ‘Free Radical in Chemical Biology (CHEMBIO-RADICAL)’. MMG is grateful to the National Institute of General Science (GM-054996 and GM-063028) for financial support. MSC is indebted to the UK Medical Research Council for his Research Leader Fellowship CG1001808/1”.

Figures

Figure 1
Figure 1
Structure of oxidatively damaged purine bases that have been detected so far in cellular DNA. (8-oxoGua in dynamic equilibrium with 8-OHGua, 8-oxoAde, FapyGua, FapyAde, Oz).
Figure 2
Figure 2
Structure of oxidatively damaged pyrimidine bases that have been detected so far in cellular DNA (ThyGly, 5-ForUra, 5-HmUra, 5-OHCyt).
Figure 3
Figure 3
Structure of enzymatically 5-methylcytosine oxidation products in cellular DNA (5-HmCyt, 5-ForCyt, 5-CaCyt).
Figure 4
Figure 4
Structure of chlorinated purine and pyrimidine bases that have been detected in cellular DNA (5-ClCyt, 5-ClGua, 5-ClAde).
Figure 5
Figure 5
Structure of the main oxidized a basic sites identified in isolatedDNA(C4-APinequilibriumwiththeacyclic2-deoxypentos-4-ulose abasic site, DOB, 2-deoxyribonolactone or dL).
Figure 6
Figure 6
Structure of oxidatively generated tandem base lesions, 5′,8-cyclo-2′-deoxyadenosine and cytosine-aldehyde interstrand cross-links that have been detected in cellular DNA (G[8 - 5m]T, G[8 - 5]C, (5′R)-cdAdo, cytosine adduct).
Figure 7
Figure 7
Structure of the main ethenobase adducts, MDA and 4HNE guanine adducts that have been detected in cellular DNA. (M1Gua and the open form N2(3-oxo-1-propenyl) Guo (OPD), 1,N2-propanoguanine, 1,N2-εGua, 1,N6-εAde, 1,N4-εCyt).
See this image and copyright information in PMC

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