Identification of a New Mutagenic Polychlorinated Biphenyl Derivative in the Waka River, Wakayama, Japan, Showing Activation of an Aryl Hydrocarbon Receptor-Dependent Transcription
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- 作者：Takeji Takamura-Enya ; Tetsushi Watanabe ; Atsuko Tada ; Teruhisa Hirayama ; Haruo Nukaya ; Takashi Sugimura ; and Keiji Wakabayashi
- 刊名：Chemical Research in Toxicology
- 出版年：2002
- 出版时间：March 2002
- 年：2002
- 卷：15
- 期：3
- 页码：419 - 425
- 全文大小：87K
- 年卷期：v.15,no.3(March 2002)
- ISSN：1520-5010
文摘
Water samples from the Waka River, which runs through an area housing many chemicalindustry facilities in Wakayama, Japan, have been found to show significant mutagenicity,especially without a mammalian metabolic activation system (S9 mix) in the Salmonellatyphimurium YG1024 strain. Mutagens in the river water were adsorbed to 3 kg of blue cotton,extracted with methanol/ammonia, and separated by several low- and high-pressure liquidchromatography steps with reversed-phase columns. One mutagen (0.6 mg), accounting for50% of the total mutagenicity of the adsorbed materials, was isolated. On the basis of themass, high-resolution mass, 1H NMR and 13C NMR spectra, the chemical was determined tohave a polychlorinated biphenyl skeleton with nitro and amino substitution groups. Well-designed chemical synthesis of the putative mutagen revealed it to be 4-amino-3,3'-dichloro-5,4'-dinitrobiphenyl. This novel compound exerted strong mutagenicity without the S9 mix,inducing 66 000 and 140 000 revertants/nmol in S. typhimurium TA98 and YG1024, respectively. Moreover, this polychlorinated biphenyl derivative was proven to activate the humanaryl hydrocarbon receptor-mediated transcription in a lac Z reporter gene assay with anefficiency almost the same as that of 
-naphthoflavone, well-known to be a synthetic arylhydrocarbon receptor agonist. It is possible that the mutagen is formed unintentionally viapostemission modification of drainage water containing parent chemicals, such as 3,3'-dichlorobenzidine or 3,3'-dichloro-4,4'-dinitrobiphenyl, which are known to be raw materialsin the manufacture of polymers and dye intermediates in chemical plants.
-naphthoflavone, well-known to be a synthetic arylhydrocarbon receptor agonist. It is possible that the mutagen is formed unintentionally viapostemission modification of drainage water containing parent chemicals, such as 3,3'-dichlorobenzidine or 3,3'-dichloro-4,4'-dinitrobiphenyl, which are known to be raw materialsin the manufacture of polymers and dye intermediates in chemical plants.