Reactions of ethyleneimine with guanosine and deoxyguanosine

Ethyleneimine was reacted with guanosine in aqueous medium and the products were purified by Sephadex G-10 and high-performance liquid chromatography (HPLC). Two products were identified by UV-spectroscopy: imidazole-ring opened 7-alkylguanosine and 1-alkylguanosine, accounting for 80% and 14% of all adduct radioactivity, respectively. When the incubation with ethyleneimine and guanosine or deoxyguanosine was carried out at pH 6.0 for 1 h intact 7-alkylation products were detected. The half-life of imidazole ring opening of 7-alkylguanosine was 11, 5 and 2.8 min at pH-values 7.0, 7.7 and 8.0, respectively, as measured fluorometrically at 25 degrees C. The respective half-life of alkylated deoxyguanosine was 21 min at pH 7.7. The half-life of depurination of alkylated deoxyguanosine was 42 min at pH 6.0 and 25 degrees C.