2-Chloroethyl (methylsulfonyl)methanesulfonate (NSC-338947), a more selective DNA alkylating agent than the chloroethylnitrosoureas.

The novel chloroethylating agent 2-chloroethyl (methylsulfonyl)methanesulfonate (CIEtSoSo) has been shown to act like the chloroethylnitrosoureas (CIEtNu's) in its DNA damaging and cytotoxic effects in human cell lines and has similar activity to the CIEtNu's in the National Cancer Institute antitumor screening tests. Its simpler chemistry, however, suggests that it may alkylate DNA more selectively than do the CIEtNu's. The DNA base adducts produced in calf thymus DNA by CIEtSoSo have been compared to a representative, non-carbamoylating CIEtNu, 1-(2-chloroethyl)-3-(cis-2-OH)cyclohexyl-1-nitrosourea, using high-pressure liquid chromatography. Two major modified base peaks were observed from the nitrosourea treated sample which have been subsequently identified by high-pressure liquid chromatography comparison of synthesized standards and by electron impact gas chromatography/mass spectrometric analysis to be 7-hydroxyethylguanine and 7-chloroethylguanine. In contrast only 7-chloroethylguanine was obtained from the CIEtSoSo treated DNA at equimolar doses. Thus CIEtSoSo was found to be more specific in its reaction with DNA in that it produced less variety of products than the nitrosourea, with no apparent generation of hydroxyethyl products, which are major side reactions of the CIEtNu's.