Mutagenic activity of dichloroethylamino derivatives of nitronaphtofuran and some nitrobenzofurans in the Salmonella/microsome assay - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Accéder directement au contenu
Article Dans Une Revue Mutation Research/Mutation Research Genomics Année : 1992

Mutagenic activity of dichloroethylamino derivatives of nitronaphtofuran and some nitrobenzofurans in the Salmonella/microsome assay

Résumé

The mutagenic activity of five dichloroethylamino 2-nitrobenzofuran derivatives and one dichloroethylamino 2-nitronaphthofuran derivative was analysed in the Salmonella/microsome assay. We investigated the influence of the position of the dichloroethylamino and/or the methoxy groups on the mutagenic activity of these nitro arenofurans in S. typhimurium strain TA100 and its variant TA100NR, deficient in nitroreductase. Without metabolic activation 7-[bis(2-chloroethyl)amino]-2-nitronaphtho[2,1-b]furan (1), 4-[bis(2-chloroethyl) amino]-7-methoxy-2-nitrobenzofuran (2), 7-[bis(2-chloroethyl)amino]-4-methoxy-2-nitrobenzofuran (5) and 6-[bis(2-chloroethyl)amino]-2-nitrobenzofuran (6) are mutagenic in TA100, while 4-[bis(2-chloroethyl)amino]-5-methoxy-2-nitrobenzofuran (4) is weakly mutagenic and 5-[bis(2-chloroethyl)amino]-2-nitrobenzofuran (3) toxic. In the NR deficient strain compounds 1, 3 and 6 are strong mutagens and 4 is weakly positive. The two isomers 2 and 5 are negative in that strain. The naphthofuran derivative 1 is highly mutagenic in the absence of S9 mix in both strains considered, but less than R7000 (7). A decrease in the electronic polarity of compound 1 versus compound 7 according to the hypothesis developed by Royer et al. is a possible explanation. After exogenous metabolic activation by S9 mix all the compounds tested are highly mutagenic in both Salmonella strains. The position of the dichloroethylamino group and/or the presence of a methoxyl on the alpha-nitroarenofuran derivatives seem to modify the activity of bacterial as well as exogenous nitroreductases or other activating enzymes.

Dates et versions

hal-02716067 , version 1 (01-06-2020)

Identifiants

Citer

P. Castelain, B. Hendrickx, Anne Tromelin, P. Demerseman, W. Moens. Mutagenic activity of dichloroethylamino derivatives of nitronaphtofuran and some nitrobenzofurans in the Salmonella/microsome assay. Mutation Research/Mutation Research Genomics, 1992, 280 (1), pp.9-15. ⟨10.1016/0165-1218(92)90013-p⟩. ⟨hal-02716067⟩
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