PMID: 8448342Jan 1, 1993Paper

Bis(hydroxyphenylethyl)deoxyguanosine adducts identified by [32P]-postlabeling and four-sector tandem mass spectrometry: unanticipated adducts formed upon treatment of DNA with styrene 7,8-oxide

Chemical Research in Toxicology
S KaurA L Burlingame

Abstract

Calf thymus DNA was incubated with [8-14C]styrene oxide in vitro, and six covalent xenobiotic-DNA adducts were detected using the [32P]-postlabeling procedure. Adducts 1-3 were purified by HPLC and identified as bis-substituted-2'-deoxyguanosine 3'-phosphate derivatives using four-sector tandem mass spectrometry. These adducts represented less than 2% of the total adducts detected by [14C]-radioactivity. Adducts 1-3 were also detected when styrene oxide was allowed to react with the mononucleotide, 2'-deoxyguanosine 3'-phosphate only. The elemental compositions of these adducts (C26H30N5O9P) were determined by measurement of their accurate masses by high-resolution mass spectrometry and revealed the unusual incorporation of 2 mol of hydroxyphenylethyl moieties. The structures of these bis(phenylethyl) adducts were established by interpretation of high-energy collision-induced dissociation (CID) mass spectra, together with UV/visible and fluorescence spectrophotometry as N2-(2-hydroxy-1-phenylethyl)-O6-(2-hydroxy-2-phenylethyl)-2'-deoxygua nos ine 3'-phosphate (adduct 1), N2-(2-hydroxy-1-phenylethyl)-O6-(2-hydroxy-1-phenylethyl)-2'-deoxygua nos ine 3'-phosphate (adduct 2), and N1,N2-bis(2-hydroxy-1-phenylethyl)-2'-deoxyguanosine...Continue Reading

Citations

Jan 4, 2001·Chemico-biological Interactions·M Koskinen, K Plná
Jan 1, 2001·Biomarkers : Biochemical Indicators of Exposure, Response, and Susceptibility to Chemicals·M KoskinenK Hemminki
Feb 6, 2009·Emerging Infectious Diseases·Nalaka KanakaratneMaya Gunasekera
Aug 2, 2003·Emerging Infectious Diseases·Pallavi GargO Colin Stine
Jan 1, 1994·Critical Reviews in Toxicology·D H Phillips, P B Farmer
Jan 1, 1996·Chemical Research in Toxicology·R R Selzer, A A Elfarra

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