Characterization of reaction products between styrene oxide and deoxynucleosides and DNA

Mass spectrometry for the analysis of carcinogen‐DNA adducts

“…The use of tandem MS may be especially helpful when the characteristic base fragment ion is not observed. Such an occurrence, although uncommon, has been reported in a study of the nucleoside adducts isolated from DNA reacted with styrene oxide (44). The absence of the usually prominent [BH,]' ion from DCI spectra of both N4-deoxycytidine (N4-dCyd) (isobutane DCI) and N-3-dThd (ammonia DCI) adducts was noted in this work.…”

Critical review of styrene genotoxicity focused on the mutagenicity/clastogenicity literature and using current organization of economic cooperation and development guidance

“…The numerous available studies using noncellular systems demonstrate convincingly that SO reacts with DNA mainly to form guanine adducts, typically in the following order quantitatively: N7 ‐SO‐G >> N 2 ‐SO‐G > O 6 ‐SO‐G adducts (Savela et al, ; Pongracz et al, , ; Kumar et al, ; Siethoff et al, ); Vodicka and Hemminki, , , a,b; Yang et al, ). These have also been identified in animal and human cells/tissues, with in vitro and in vivo studies.…”

Efficient nonmutagenic replication bypass of DNAs containing β‐adducts of styrene oxide at adenine N6

“…Mutational analysis of styrene oxide-induced mutations in the hprt gene in human T-lymphocytes showed mutations at both GC and AT sites Bastlova and Podlutsky, 1996]. Styrene oxide reacts at many sites in DNA, the ␣or ␤-position of the epoxide, generating a complex array of products [Hemminki and Hesso, 1984;Savela et al, 1986;Latif et al, 1988]. In double-stranded DNA, the major sites of reaction are guanine N7 and adenine N3 [Koskinen et al, 2000]; these adducts are both acid and heat labile and are not expected to persist.…”