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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.
| Content Provider | Semantic Scholar |
|---|---|
| Author | White, Blánaid Tarun, Maricar C. Gathergood, Nicholas Rusling, James F. Smyth, Malcolm R. |
| Copyright Year | 2005 |
| 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-2'-deoxyguanosine (8-oxodGuo). Oxidised guanidinohydantoin (Gh(ox)) 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, dGh(ox) 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 2'-deoxyribose moiety of the 8-oxodGuo, not whether copper or iron was the metal involved in the oxidation. |
| Starting Page | 34 |
| Ending Page | 40 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | http://doras.dcu.ie/1/2/molecular_biosystems_2005_5-6_373-1.pdf |
| PubMed reference number | 16881006v1 |
| Volume Number | 1 |
| Issue Number | 5-6 |
| Journal | Molecular bioSystems |
| Language | English |
| Access Restriction | Open |
| Subject Keyword | 8-oxo-7-hydrodeoxyguanosine 8-oxoguanine Biological Markers Cations DNA Damage Hydrogen Peroxide National Institute of Environmental Health Sciences (U.S.) Oxidants Pallister-Hall syndrome Peroxides Peroxynitrite Quantity Science Singlet Oxygen United States National Institutes of Health guanidinohydantoin oxaluric acid oxidation spiroiminodihydantoin |
| Content Type | Text |
| Resource Type | Article |
