Biological and chemical properties of alkanediazotates as active species of N-nitroso compounds.

The mutagenicity and chemical reactivity of (E)- and (Z)-potassium alkanediazotates, as precursors of corresponding alkanediazohydroxides, were investigated. In three microbial strains, Salmonella typhimurium TA1535 and Escherichia coli WP2 and WP2hcr-, the effect of changing the alkyl group on mutagenic potency was similar for (E)- and (Z)-diazotates, N-alkyl-N-nitrosoureas and alpha-hydroxynitrosamines. The capacity to alkylate nicotinamide, measured in an aqueous phosphate buffer, decreased with increasing alkyl chain length. Specific mutagenicity in S. typhimurium TA1535 was linearly related to alkylating activity. These results confirm that alkanediazohydroxides are the active alkylating species of N-nitroso compounds, and that their mutagenicity is determined by their alkylating activity.