Structure-activity relationships within a series of 2,4-diaminoalkoxybenzene compounds

Shahin, Majdi M.; Rouers, D.; Bugaut, Anthony; Kalopissis, G.

doi:10.1016/0165-1218(80)90153-6

Cited by 41 publications

(7 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among the alkoxy compounds (Tables I-III), 2,4-diaminoanisole was the most mutagenic compound in all three strains, followed by 2,4-diaminoethoxybenzene and 2,4-diaminopropoxybenzene, in that order (Table VII). This observation confirms our earlier findings concerning structure-activity relationships within this series of compounds [Shahin et al, 1980b[Shahin et al, , 1983a and extends them to the new tester strain TA97. In all three strains with both amounts of S9 (4% and 10% S9 in S9 mix), m-phenylenediamine exhibited greater mutagenic activity than did 2,4-diaminotoluene (Tables IV, V).…”

Section: Solventssupporting

confidence: 91%

Comparisons of mutation induction by six monocyclic aromatic amines in salmonella typhimurium tester strains TA97, TA1537, and TA1538

Shahin¹,

Chopy²,

Lequesne³

1985

Environ. mutagen

Self Cite

View full text Add to dashboard Cite

The mutagenicity of six monocyclic aromatic amines (2,4-diaminoanisole, 2,4-diaminoethoxybenzene, 2,4-diaminopropoxybenzene, m-phenylenediamine, 2,4-diaminotoluene, and nitro-p-phenylenediamine) was investigated in Salmonella typhimurium strains TA97, TA1537, and TA1538 in the presence of two different amounts of Aroclor 1254-induced S9 preparations. Strain TA1538 was found to be the most responsive of the three strains with this group of compounds. Regarding the other strains, TA1537 responded to three of the compounds better than strain TA97, if one calculates responsiveness as the fold-increase in numbers of revertants per plate. However, if one calculates the number of revertants per nanomole or compares the number of induced revertants per plate, TA97 was more responsive than TA1537 for all six compounds. Comparisons of mutagenesis from tests involving strain TA97 are complicated by the large variations in spontaneous mutation frequencies in this strain. The amount of S9 per plate is another important variable in tests of monocyclic aromatic amines; in general, more revertants are detected when the S9 mix contains 10% S9 than when it contains 4% S9. Nevertheless, in all our tests of 2,4-diaminoanisole, 2,4-diaminoethoxybenzene, and 2,4-diaminopropoxybenzene, the same relationship between chemical structure and mutagenic activity was observed. In all three strains, the mutagenic responses become less when the alkoxy substituent on the molecule becomes larger.

show abstract

Section: Solventssupporting

confidence: 91%

Comparisons of mutation induction by six monocyclic aromatic amines in salmonella typhimurium tester strains TA97, TA1537, and TA1538

Shahin¹,

Chopy²,

Lequesne³

1985

Environ. mutagen

Self Cite

View full text Add to dashboard Cite

show abstract

“…In those studies, it was shown that mutagenicity was reduced and eventually removed as the length of the alkyl chain was increased (cf. Figure 23) (27)(28). Similar studies were conducted with para-phenylenediamines, with the same outcome.…”

Section: Genotoxicitysupporting

confidence: 53%

Aromatic amines: use in azo dye chemistry

Freeman¹

2013

Front Biosci

View full text Add to dashboard Cite

show abstract

“…The properties of these strains, as described by Ames et al (62) and by Maron and Ames (63), were confirmed in our laboratories. Strain TA1538 was chosen for the detailed studies because of its known sensitivity in tests with other monocyclic aromatic amines (64)(65)(66).…”

Section: Bacterial Strainsmentioning

confidence: 99%

Studies on the mutagenicity of aniline in association with norharman in the Salmonella/mammalian microscome assay

Shahin¹

1989

Intern J of Cosmetic Sci

Self Cite

View full text Add to dashboard Cite

Synopsis The mutagenicity of aniline was investigated in association with norharman using Aroclor 1254-induced and uninduced liver S9 fractions. The non-mutagenicity of aniline in the Salmonella/mammalian microsome test was also re-examined under various experimental conditions. Aniline caused no increase in the number of revertants per plate in Salmonella typhimurium strains TA1535, TA100, TA1537, TA1538 and TA98 at concentrations of up to 5000 mug/plate. S9 preparations from rat liver, hamster liver, rat spleen, or hamster spleen were all ineffective in activating aniline to a mutagen in tests using various concentrations of S9 in S9 mix. In contrast to the results with aniline alone, mixtures of aniline and norharman were mutagenic in strain TA1538 in the presence of S9 fractions from liver of rats pretreated with Aroclor 1254. The observed mutagenicity decreased as a function of the concentration of S9 in S9 mix. In the presence of uninduced liver S9 preparations, the mutagenicity of the mixture of the two compounds was slight (three-fold).

show abstract

Structure-activity relationships within a series of 2,4-diaminoalkoxybenzene compounds

Cited by 41 publications

References 3 publications

Comparisons of mutation induction by six monocyclic aromatic amines in salmonella typhimurium tester strains TA97, TA1537, and TA1538

Comparisons of mutation induction by six monocyclic aromatic amines in salmonella typhimurium tester strains TA97, TA1537, and TA1538

Aromatic amines: use in azo dye chemistry

Studies on the mutagenicity of aniline in association with norharman in the Salmonella/mammalian microscome assay

Contact Info

Product

Resources

About