Synthesis and characterization of 06-(2-chloroethyl)guanine: A putative intermediate in the cytotoxic reaction of chloroethylnitrosoureas with DNA

Add time:07/20/2019    Source:sciencedirect.com

The chloroethylnitrosoureas are useful antitumor agents which evidently exert a significant part of their cytotoxic action through the formation of a unique 1-(3-deoxycytidyl),2-(1-deoxyguanosinyl)ethane cross-link in DNA. It has been suggested that this cross-link is formed from 06-(2-chloro-ethyl)guanine, an initial product of DNA alkylation by the chloroethylnitrosoureas; however, 06-(2-chloroethyl)guanine has never been described. We have synthesized this derivative from the reaction of thionyl chloride with O6-(2-hydroxyethyl)guanine, and have found that it decomposes to 1-(2-hydroxyethyl)guanine through an intermediate, presumably 1,06-ethanoguanine. Its half life at 37° and pH 7.4 is 17.8 min.

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