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Mechanism of action of 2 halo ethylnitroso ureas on dna nature of the chemical reactions with dna


, : Mechanism of action of 2 halo ethylnitroso ureas on dna nature of the chemical reactions with dna. Biochemical Pharmacology 28(14): 2123-2128

The antitumor agent 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) covalently cross-links DNA under physiological conditions. Methyl substitution at either carbon atom of the 2-chloroethyl molecule portion prevents cross-linking. Haloalkyl nitrosoureas including 3-chloropropyl, 4-chlorobutyl and 5-chloropentyl, although they readily alkylate DNA, exhibit no ability to cross-link DNA. 3-(2-Chloroethyl)-1-methylcytosine hydrochloride and N4-(2-chloroethyl)-1-methylcytosine hydrochloride, similar to intermediates suggested in the cross-linking process, alkylate PM2-CCC-DNA readily. These 2 cytosine derivatives also cyclize readily to give 3,N4-ethano-1-methylcytosine closely similar to a species isolated from treatment of poly.cntdot.C with BCNU. A number of processes including the extent of DNA alkylation, measured with [14C]CCNU labeled in the ethylene portion of the molecule, as well as concomitant DNA single strand scission, and intramolecular alkylation and/or hydrolysis of the chloroethyl cytidine intermediate were investigated for effects on the interstrand cross-linking process.

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