Oxidation of a biomarker for phenol carcinogen exposure: expanding the redox chemistry of 2'-deoxyguanosine.
A biomarker for phenolic carcinogen exposure, 8-(4''-hydroxyphenyl)-2'-deoxyguanosine, has been found to undergo oxidative coupling in the presence of Na2IrCl6 to afford ortho-ortho C-C-coupled polyphenols through the intermediacy of a phenoxyl radical. One can envision using such unique chemistry to oxidatively couple strands of DNA for the generation of new biomaterials. Our results also demonstrate the potential for phenolic adducts of DNA to undergo further oxidation reactions that may contribute to phenol-mediated cytotoxicity and genotoxicity.
Weishar
Jennifer L
JL
Department of Chemistry, University of Guelph, Guelph, Ontario, Canada.
McLaughlin
Christopher K
CK
Baker
Michael
M
Gabryelski
Wojciech
W
Manderville
Richard A
RA
D015415:Biomarkers / Q000737:chemistry*; D002273:Carcinogens / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D003849:Deoxyguanosine / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry*; D010084:Oxidation-Reduction; D019800:Phenol / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D059808:Polyphenols
D015415:Biomarkers; D002273:Carcinogens; D003432:Cross-Linking Reagents; D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols; C042329:phenoxy radical; D019800:Phenol; D004247:DNA; D003849:Deoxyguanosine