Synthesis of 8-oxo-7,8-dihydro-2'-deoxyguanosine from 2'-deoxyguanosine using Cu(II)/H2O2/ascorbate: A new strategy for an improved yield.
The free nucleoside 2'-deoxyguanosine (dGuo) is the most susceptible to oxidation by reactive oxygen species (ROS) compared to the other free nucleosides, and its oxidation product 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodGuo) has been used as a biomarker to quantify oxidative stress damage. We investigated different reactions using Fe(2+) or Cu(2+) and H2O2 in order to identify the reaction with the best yield. HPLC coupled with a UV detector and micrOTOF mass spectrometry were used to detect and confirm the identity of 8-oxodGuo. The optimized reaction synthesized 8-oxodGuo with a yield of 72.0%, much higher than that previously described in the literature. Our improved method for 8-oxodGuo synthesis could be extremely useful for assays that require the synthesis of internal standards labeled with stable isotopes.
Laboratório de Oxidações Biológicas, Departamento de Bioquímica e Biologia Molecular, Setor de Ciências Biológicas, Universidade Federal do Paraná (UFPR), Curitiba, Brazil.
Patrícia S
PS
Peres
Laboratório de Oxidações Biológicas, Departamento de Bioquímica e Biologia Molecular, Setor de Ciências Biológicas, Universidade Federal do Paraná (UFPR), Curitiba, Brazil.
Andressa
A
Valerio
Laboratório de Oxidações Biológicas, Departamento de Bioquímica e Biologia Molecular, Setor de Ciências Biológicas, Universidade Federal do Paraná (UFPR), Curitiba, Brazil.
Glaucia R
GR
Martinez
D000080242:8-Hydroxy-2'-Deoxyguanosine; D001205:Ascorbic Acid / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003300:Copper / Q000737:chemistry*; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007501:Iron / Q000737:chemistry; D013058:Mass Spectrometry; D008670:Metals / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
D008670:Metals; D003300:Copper; D000080242:8-Hydroxy-2'-Deoxyguanosine; D006861:Hydrogen Peroxide; D007501:Iron; D003849:Deoxyguanosine; D001205:Ascorbic Acid
8-oxodGuo; DNA damage; Fenton reaction; dGuo; synthesis