Characterization of reaction products between styrene oxide and deoxynucleosides and DNA.

ABSTRACT

Styrene oxide was reacted with deoxynucleosides and DNA in aqueous buffer at pH 7.4. The products were purified by HPLC, characterized by UV spectroscopy and by chemical ionization mass spectrometry. The main products identified were 7-alkyl-, N2-alkyl- and O6-alkyldeoxyguanosine, 1-alkyl-, and N6-alkyldeoxyadenosine, N4-alkyl-, 3-alkyl- and O2-alkyldeoxycytidine and 3-alkylthymidine. The relative yields of alkylated deoxynucleosides were dG greater than dC greater than dA greater than T. In the reactions of styrene oxide with DNA the dominant product isolated was 7-alkylguanine but N2-alkylguanine was also detected.