©2011 JCBN JCBNournal of Clinical Biochemistry and Nutrition0912-00091880 5 86the Society for Free Radical Rese rch JapanKyot, Japanjcbn11-003FR0.3 64/jcb.11-003FRR viewNucleotides function as endogenous chemical sensors for oxidative stress signaling

Copyright © 2011 JCBN2011This is an open access article distributed under the terms of theCreat ve Commons Attribution Licens, which permit unre-st icted use, distribution, and reproduction i any medium, p ovided the original work is prop rly cit d.Oxidized and nitrated nucleo id s in l ing 8oxogunanine and 8 nitroguanine derivatives such as 8nitroguanosine 3',5'cyclic mono phosphate were generated by reactive nitrogen oxides and reac tive oxygen species in cultured cells and in tissues. 8oxoguanine and 8nitroguanine in DNA and RNA are potentially mutagenic, and the former also induces cell death. Some derivative, 8 nitroguanosine 3',5'cyclic monophosphate a major nitrated guanine nucleotide, was identified as a novel second messenger. Surprisingly, the amount of 8nitroguanosine 3',5'cyclic mono phosphate generated was found to be higher than that of guano sine 3',5'cyclic monophosphate in cells expressing inducible nitric oxide synthase. More important, 8nitroguanosine 3',5'cyclic monophosphate is electrophilic and reacted efficiently with sulf hydryls of proteins to produce a novel posttranslational modifica tion (named Sguanylation) via guanosine 3',5'cyclic mon