Health & Environmental Research Online (HERO)


Print Feedback Export to File
10173 
Journal Article 
Styrene oxide-induced 2'-deoxycytidine adducts: implications for the mutagenicity of styrene oxide 
Koskinen, M; Calebiro, D; Hemminki, K 
2000 
Yes 
Chemico-Biological Interactions
ISSN: 0009-2797
EISSN: 1872-7786 
126 
3 
201-213 
English 
10862818 
WOS:000087738200003 
The reaction between 2'-deoxycytidine and styrene 7,8-oxide (SO) resulted in alkylation at the 3-position and at the 02-position through the "alpha"- and "beta"-carbons of the epoxide but at the N4-position only through the "alpha"-carbon. The 3-alkylated adducts were found to deaminate to the corresponding 2'-deoxyuridine adducts (37 degrees C, pH 7.4) with half-lives of 6 min and 2.4 h for the "alpha"- and "beta"-isomers, respectively. The N4-alkylated products were stable at neutral pH. The 02-alkylated products were unstable being prone to depyrimidation and to isomerisation between "alpha"- and "beta"-isomers. In SO-treated double-stranded DNA, enzymatic hydrolysis allowed the identification of the "beta"3-deoxyuridine and "alpha"N4-deoxycytidine adducts (1.9 and 0.5% of total alkylation, respectively), in addition to the previously identified DNA-adducts. The 3-substituted uracil may have implications for the mutagenicity of SO. 
cytosine; hydrolytic deamination; DNA adducts; styrene oxide 
IRIS
• Chloroprene
     Cited 2009 Draft
     Cited 2010 Final