Formation of tricyclic [4.3.3.0] adducts between 8-oxoguanosine and tyrosine under conditions of oxidative DNA-protein cross-linking.
8-Oxo-7,8-dihydro-2'-deoxyguanosine (OG), a prevalent product of oxidative stress on cellular DNA, is readily further oxidized forming adducts with nucleophiles. In the presence of tyrosine or p-cresol, an unusual tricyclo[4.3.3.0] adduct has been characterized in both nucleoside and oligodeoxynucleotide studies. The adduct is more stable in oligomers than nucleosides and undergoes slow reversion and hydration to spiroiminodihydantoin.
Xu
Xiaoyun
X
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, USA.
Fleming
Aaron M
AM
Muller
James G
JG
Burrows
Cynthia J
CJ
D004247:DNA / Q000737:chemistry*; D018736:DNA Adducts; D004249:DNA Damage; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009838:Oligodeoxyribonucleotides; D018384:Oxidative Stress; D011506:Proteins / Q000737:chemistry*; D013141:Spiro Compounds; D014443:Tyrosine / Q000737:chemistry*
D018736:DNA Adducts; D009838:Oligodeoxyribonucleotides; D011506:Proteins; D013141:Spiro Compounds; C408822:spiroiminodihydantoin; D006151:Guanosine; C046215:8-hydroxyguanosine; D014443:Tyrosine; D004247:DNA