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Synthesis of 2-phenylbenzotriazole-type mutagens, PBTA-5 and PBTA-6, and their detection in river water from Japan
- Source :
- Mutation research. 498(1-2)
- Publication Year :
- 2001
-
Abstract
- We previously determined the chemical structures of four 2-phenylbenzotriazole mutagens (PBTA-1, -2, -3 and -4) in blue rayon-adsorbed material from the Nishitakase River in Kyoto prefecture and the Nikko River in Aichi prefecture in Japan. On the basis of a synthesis study, these four PBTA derivatives were deduced to have originated from corresponding dinitrophenylazo dyes by reduction and chlorination. 2-[(2-Bromo-4,6-dinitrophenyl)azo]-5-[bis(2-acetoxyethyl) amino]-4-methoxyacetanilide (Color Index Name, Disperse Blue 79:1; CAS Registry Number, 75497-74-4) is a very common dinitrophenylazo dye used in textile dyeing factories. In the present study, we synthesized 2-[4-[bis(2-acetoxyethyl)amino]-2-(acetylamino)-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-5) from Disperse Blue 79:1 by reduction with sodium hydrosulfite and subsequent chlorination with sodium hypochlorite. On hydrolysis of PBTA-5 with alkali, 2-[2-(acetylamino)-4-[bis(2-hydroxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-6) was obtained. Both PBTA-5 and -6 were potent mutagens, inducing 723,000 revertants and 485,000 revertants per microgram of Salmonella typhimurium YG1024, respectively, in the presence of S9 mix. To clarify whether PBTA-5 and -6 exist in the environment, water samples were collected from five rivers flowing through regions where textile dyeing industries are developed. PBTA-6 was detected at levels of 3-134 ng/g blue rayon in all water samples that were examined. On the other hand, the amount of PBTA-5 in the samples was less than the detection limit.
- Subjects :
- Indoles
Textile dyeing
Health, Toxicology and Mutagenesis
Sodium
Mineralogy
chemistry.chemical_element
Fresh Water
River water
Hydrolysis
chemistry.chemical_compound
Japan
Genetics
Organometallic Compounds
2-phenylbenzotriazole
Cellulose
Coloring Agents
Chromatography, High Pressure Liquid
Detection limit
Mutagenicity Tests
Triazoles
Alkali metal
chemistry
Sodium hypochlorite
Adsorption
Nuclear chemistry
Mutagens
Subjects
Details
- ISSN :
- 00275107
- Volume :
- 498
- Issue :
- 1-2
- Database :
- OpenAIRE
- Journal :
- Mutation research
- Accession number :
- edsair.doi.dedup.....da11df8cfe82f6373cf068e52b8aa825