Mutagenic activity of dichloroethylamino derivatives of nitronaphthofuran and some nitrobenzofurans in the Salmonella/microsome assay
| Autor: | W. Moens, Pierre Demerseman, Ph. Castelain, B. Hendrickx, A. Tromelin |
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| Přispěvatelé: | Military Institute of Hygiene and Epidemiology (WIHE), Vrije Universiteit Brussel (VUB), Institut Curie [Paris] |
| Předmět: |
Salmonella typhimurium
040301 veterinary sciences Stereochemistry (salmonella microsome [SDV.CAN]Life Sciences [q-bio]/Cancer [CHIM.THER]Chemical Sciences/Medicinal Chemistry Toxicology Ames test 0403 veterinary science 03 medical and health sciences Nitroreductase Biotransformation 2-nitrobenzofurans Genetics typhimurium analogs Structure–activity relationship Animals induction 030304 developmental biology Benzofurans chemistry.chemical_classification 0303 health sciences 2-nitronaphthofurans biology Mutagenicity Tests [CHIM.ORGA]Chemical Sciences/Organic chemistry 04 agricultural and veterinary sciences structure activity relationship furan r-7000 biology.organism_classification Enterobacteriaceae mutagenicity assay) rats Enzyme chemistry Nitro Microsome Microsomes Liver dichloroethylamino 2-nitrobenzofuran derivatives Mutagens |
| Zdroj: | Scopus-Elsevier Mutation Research/Mutation Research Genomics Mutation Research/Mutation Research Genomics, Elsevier, 1992, 280 (1), pp.9-15. ⟨10.1016/0165-1218(92)90013-p⟩ |
| ISSN: | 1383-5726 |
| DOI: | 10.1016/0165-1218(92)90013-p⟩ |
| Popis: | Mut. Res. ISI Document Delivery No.: JC401 Times Cited: 4 Castelain, P; Hendrickx, B; Tromelin, A; Demerseman, P; Moens, W Elsevier science bv Amsterdam Cited Reference Count: 26; International audience; 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. |
| Databáze: | OpenAIRE |
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