Hydroxyl radical reacts with the base and sugar moiety of DNA

Stable Identifier
R-HSA-6789114
Type
Reaction [transition]
Species
Homo sapiens
Compartment
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The hydroxyl radical (•OH) is a highly reactive oxygen species (ROS) that efficiently reacts with nearby biomolecules at diffusion-controlled rates of reaction. The generation of •OH by Fenton type-driven reactions is believed to take place in a site-specific manner, for example, involving metal ions in close proximity or bound to DNA (Cadet J & Wagner JR 2013).

Hydroxyl radical reacts with both the basepairs of DNA and the sugar moiety in the oligonucleotides (Dedon PC 2008; Cadet J & Wagner JR 2014). •OH reacts with 2'-deoxyribose in DNA by H abstraction from all its carbons leading to five C-centered radicals (Dedon PC 2008; Cadet J & Wagner JR 2013). The abstraction at C1' gives 2-deoxyribonolactone, the abstraction at C5′ gives 3′-phosphoglycoaldehyde, and abstraction at C4′ gives an intermediate unsaturated dialdehyde that can couple with cytosine to form a DNA inter- or intrastrand cross-link (Dedon PC 2008; Sczepanski JT et al. 2011; Cadet J & Wagner JR 2013). In addition, the C5′-centered radicals of 2-deoxyribose can react with the purine ring in the same nucleoside to produce 8,5'-cyclo-2′-deoxyguanosine (8,5'-cyclo-dGuo) or 8,5'-cyclo-2′-deoxyadenosine (8,5'-cyclo-dAdo), which are among the major lesions in DNA that are formed by attack of hydroxyl radical (Jaruga P et al. 2002; Chatgilialoglu C et al. 2011).

Literature References
PubMed ID Title Journal Year
22276778 Mechanisms of free radical-induced damage to DNA

Dizdaroglu, M, Jaruga, P

Free Radic. Res. 2012
9707545 DNA strand breaking by the hydroxyl radical is governed by the accessible surface areas of the hydrogen atoms of the DNA backbone

Balasubramanian, B, Pogozelski, WK, Tullius, TD

Proc. Natl. Acad. Sci. U.S.A. 1998
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