The multi-channel reaction of the OH radical with 5-hydroxymethylcytosine: a computational study

RSC Advances ◽  
2016 ◽  
Vol 6 (16) ◽  
pp. 13349-13357 ◽  
Author(s):  
Lingxia Jin ◽  
Caibin Zhao ◽  
Cunfang Liu ◽  
Suotian Min ◽  
Tianlei Zhang ◽  
...  

The hydroxyl radical may attack the new cytosine derivative 5-hydroxymethylcytosine (5-hmCyt), causing DNA oxidative damage. Two distinct mechanisms have been explored and our results provide some evidence between 5-hmCyt and tumor development.

2005 ◽  
Vol 70 (11) ◽  
pp. 1769-1786 ◽  
Author(s):  
Luc A. Vannier ◽  
Chunxiang Yao ◽  
František Tureček

A computational study at correlated levels of theory is reported to address the structures and energetics of transient radicals produced by hydrogen atom abstraction from C-1, C-2, C-3, C-4, C-5, O-1, O-3, and O-5 positions in 2-deoxyribofuranose in the gas phase and in aqueous solution. In general, the carbon-centered radicals are found to be thermodynamically and kinetically more stable than the oxygen-centered ones. The most stable gas-phase radical, 2-deoxyribofuranos-5-yl (5), is produced by H-atom abstraction from C-5 and stabilized by an intramolecular hydrogen bond between the O-5 hydroxy group and O-1. The order of radical stabilities is altered in aqueous solution due to different solvation free energies. These prefer conformers that lack intramolecular hydrogen bonds and expose O-H bonds to the solvent. Carbon-centered deoxyribose radicals can undergo competitive dissociations by loss of H atoms, OH radical, or by ring cleavages that all require threshold dissociation or transition state energies >100 kJ mol-1. This points to largely non-specific dissociations of 2-deoxyribose radicals when produced by exothermic hydrogen atom abstraction from the saccharide molecule. Oxygen-centered 2-deoxyribose radicals show only marginal thermodynamic and kinetic stability and are expected to readily fragment upon formation.


2015 ◽  
Vol 10 (2) ◽  
pp. 778-786 ◽  
Author(s):  
DE-HAI YIN ◽  
XIAO-CHUN LIANG ◽  
LI ZHAO ◽  
HONG ZHANG ◽  
QING SUN ◽  
...  

The Analyst ◽  
2021 ◽  
Author(s):  
Jing Zhou ◽  
Dan Yang ◽  
Guohui Liu ◽  
Siying Li ◽  
Wennan Feng ◽  
...  

Guanine (G) oxidation products, such as 8-hydroxy-2′-deoxyguanosine (8-OHdG) and 8-oxo-guanine (8-OXOG), have been widely studied as promising biomarkers for DNA oxidative damage.


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