Laboratoire Chimie Provence, Aix-Marseille Universités-CNRS (UMR 6264), 3 Place Victor Hugo, 13331 Marseille Cedex 3, France.
Chemosphere. 2010 Aug;80(9):1081-7. doi: 10.1016/j.chemosphere.2010.04.075.
This work is an attempt to investigate the chemical stability of 1,N2-propano-2'-deoxyguanosine (pdG-HNE) and 1,N2-etheno-2'-deoxyguanosine (epsilondG) DNA adducts against hydrolysis and upon oxidation reactions. It includes both kinetic issues together with proposed degradation pathways. While both chemicals are stable in the 3.5-9 pH range, the results suggest that pdG-HNE adduct is less prone to in vitro oxidative transformation than epsilondG adduct. EpsilondG and pdG-HNE behave differently upon hydroxyl radical and one electron oxidation reactions. The exocyclic ring of epsilondG is mainly affected by oxidative processes leading to the regeneration of 2'-deoxyguanosine (dG) while the integrity of the exocyclic ring is preserved for pdG-HNE. Consequently, pdG-HNE might be a better biomarker than epsilondG for monitoring oxidative stress during environmental or occupational exposures to chemicals. Understanding the in vitro routes of etheno and propano DNA adduct degradation would probably help to guide the development of analytical methodologies for the reliable detection of these endogenous adducts.
本工作旨在研究 1,N2-丙烷-2'-脱氧鸟苷（pdG-HNE）和 1,N2-乙烯-2'-脱氧鸟苷（epsilondG）DNA 加合物在水解和氧化反应中的化学稳定性。其中包括动力学问题和提出的降解途径。虽然这两种化学物质在 3.5-9 的 pH 值范围内稳定，但结果表明 pdG-HNE 加合物比 epsilondG 加合物不易发生体外氧化转化。epsilondG 和 pdG-HNE 在羟基自由基和单电子氧化反应中的行为不同。epsilondG 的环外碱基主要受到氧化过程的影响，导致 2'-脱氧鸟苷（dG）的再生，而 pdG-HNE 的环外碱基保持完整。因此，pdG-HNE 可能是监测环境或职业暴露于化学物质时氧化应激的更好的生物标志物，比 epsilondG 更适合。了解乙撑和丙烷 DNA 加合物的体外降解途径可能有助于指导用于可靠检测这些内源性加合物的分析方法的开发。
