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Chemical synthesis and detection of the cross-link 1- -2-


, : Chemical synthesis and detection of the cross-link 1- -2-. Chemical Research in Toxicology 6(4): 434-438

We have synthesized 1-(N-3-(2'-deoxycytidyl))-2-(N-1-(2'-deoxyguanosinyl))ethane and confirmed its structure by ultraviolet and high-resolution mass spectrometry. Treatment of calf thymus DNA with (3H) (2-chloroethyl)1-1-nitrosourea resulted in the formation of at least 13 DNA alkylation products that were separated by HPLC. 1-(N-3-(2'-Deoxycytidyl)-2-(N-1-(2'-deoxyguanosinyl))ethane was a minor product, accounting for 3.4% of the total DNA alkylation. The DNA cross-link 1,2-di-N-7-guanylethane was formed to a similar extent (3.2%). Other minor alkylation products were O-6-(2-hydroxyethyl)deoxyguanosine (1.5%) and N-1-(2-hydroxyethyl)deoxyguanosine (3.8%). The principal alkylation products formed by 1-(2-chloroethyl)-1-nitrosourea (CNU) treatment of DNA were N-7-(2-hydroxyethyl)guanine (36.4%), N-7-(2-chloroethylguanine (14.6%), and phosphotriesters (26.1%). The development of analytical procedures to measure DNA alkylation products after treatment with CNU will allow us to investigate factors influencing their formation and repair.

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