White, Blánaid ORCID: 0000-0003-2982-8752, Tarun, Maricar C., Gathergood, Nicholas, Rusling, James F. and Smyth, Malcolm R. (2005) Oxidised guanidinohydantoin (Ghox) and spiroiminodihydantoin (Sp) are major products of iron- and copper-mediated 8-oxo-7,8-dihydroguanine and 8-oxo-7,8-dihydro-2-deoxyguanosine oxidation. Molecular BioSystems, 2005 (1). pp. 373-381. ISSN 1742-206X
Abstract
8-Oxo-7,8-dihydroguanine (8-oxoGua), an important biomarker of DNA damage in oxidatively generated stress, is highly reactive towards further oxidation. Much work has been carried out to investigate the oxidation products of 8-oxoGua by one-electron oxidants, singlet oxygen, and
peroxynitrite. This report details for the first time, the iron- and copper-mediated Fenton oxidation of 8-oxoGua and 8-oxo-7,8-dihydro-29-deoxyguanosine (8-oxodGuo). Oxidised
guanidinohydantoin (Ghox) was detected as the major product of oxidation of 8-oxoGua with iron or copper and hydrogen peroxide, both at pH 7 and pH 11. Oxaluric acid was identified as a final product of 8-oxoGua oxidation. 8-oxodGuo was subjected to oxidation under the same
conditions as 8-oxoGua. However, dGhox was not generated. Instead, spiroiminodihydantoin (Sp) was detected as the major product for both iron and copper mediated oxidation at pH 7. It was proposed that the oxidation of 8-oxoGua was initiated by its one-electron oxidation by the
metal species, which leads to the reactive intermediate 8-oxoGua?+, which readily undergoes further oxidation. The product of 8-oxoGua and 8-oxodGuo oxidation was determined by the 29-deoxyribose moiety of the 8-oxodGuo, not whether copper or iron was the metal involved in the oxidation.
Metadata
Item Type: | Article (Published) |
---|---|
Refereed: | Yes |
Subjects: | Physical Sciences > Organic chemistry Physical Sciences > Chemistry |
DCU Faculties and Centres: | DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences Research Institutes and Centres > National Centre for Sensor Research (NCSR) |
Publisher: | RSC Publishing |
Official URL: | http://dx.doi.org/10.1039/b511756a |
Use License: | This item is licensed under a Creative Commons Attribution-NonCommercial-Share Alike 3.0 License. View License |
ID Code: | 1 |
Deposited On: | 25 Oct 2006 by DORAS Administrator . Last Modified 07 Jan 2019 10:23 |
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