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PubMed1976

Mechanism of the mutagenic action of hydroxylamine. X. Certain specificities in the mutagenesis of N-hydroxy and N-methoxy analogs of cytosine and adenine derivatives.

In contrast with N4-methoxycytidine, N6-methoxyadenosine and the corresponding 2'-deoxynucleosides, N4-hydroxycytidine readily penetrates cells of Escherichia coli. Apparently this explains the non-mutagenicity of the N-methoxy compounds when added to an E. coli suspension, and the potent mutagenic effects of the N4-hydroxy analogs under the same conditions. 1-Deazaadenosine and N9- and N1-hydroxyalkyl-substituted adenines and cytosines, inhibitors of adenosine and cytidinedeaminases, are also incapable of crossing the E. coli cell wall.

Adenine↗
PubMed1985

Mutagenicity of N-hydroxylamines and N-hydroxycarbamates towards strains of Escherichia coli and Salmonella typhimurium.

The mutagenic activity of several arylamines, alkyl- and arylcarbamates and their corresponding N-hydroxylated derivatives towards Escherichia coli WP2uvrA was investigated using the fluctuation test without a metabolic activation system. None of the parent amines or carbamates were mutagenic while several arylhydroxylamines and N-hydroxycarbamates were direct-acting base-pair substitution mutagens. With the exception of n-hexyl-N-hydroxycarbamate, the mutagenic activity of the N-hydroxycarbamates increased with increase in the length of alkyl substituent. Some arylamines and arylhydroxylamines were further examined, again without a metabolic activation system, using a plate test in conjunction with bacterial strains which detect either base-pair or frameshift mutagens. The arylhydroxylamines were found to cause both base-pair and frameshift mutations but were more active as frameshift mutagens. Possible reasons for the observed mutagenic activity are considered.

Carbamates↗