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Synthesis and Characterization of Selected 4,4'-Diaminoalkoxyazobenzenes
Citation:
Freeman, H. S., L. D. CLAXTON, AND E. Jeong. Synthesis and Characterization of Selected 4,4'-Diaminoalkoxyazobenzenes. DYES AND PIGMENTS. Elsevier Science Ltd, New York, NY, 87(2):100-108, (2010).
Impact/Purpose:
This study was done to determine if non-mutagenic (and potentially non-carcinogenic) dyes could be developed so that they could replace presently used toxic dyes.
Description:
The role of the -N(CH2CH20H)2 group in producing a mutagenic response from 4-«3-(2h) Uroxyethoxy)4-amino)phenylazo)-N,N-bis(2-hydroxyethyl)-aniline has been investigated. To accomplish this goal, a group ofsubstituted 4,4'-diaminoazobenzene dyes was synthesized, and their structures were characterized using IH NMR, TOF-LC-ESI mass spectrometry, and combustion analysis. Mutagenicity was determined using the standard Ames test in Salmonella strains TA98, TAIOO, and TAI538 with and without S9 enzyme activation. The results ofthis study provide evidencethat themutagenicity oftheparentdyearisesfrom themetaboliccleavage ofN-h)Uroxyethyl groups to give the corresponding -NHCH2CH20H and -NH2 substituted monoazo dyes as directacting mutagens. All 5 ofthe dyes studied were mutagenic at various levels with and without S9 enzyme activation in TA1538. In addition, the results show that removing one N-hydroxyethyl group and capping both -OH groups in the parent dye did not affect mutagenicity, whereas removing both Nhydroxyethyl groups produced a strorig direct-acting mutagen in all thtee bacterial strains. Increasing the length ofthe N-alkyl chain from two to three carbon atoms eliminated mutagenicity in TA98 without S9 activation.