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Identification of mutagenic transformation products generated during oxidation of 3-methyl-4-nitrophenol solutions by orbitrap tandem mass spectrometry and quantitative structure activity relationship analyses

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Title: Identification of mutagenic transformation products generated during oxidation of 3-methyl-4-nitrophenol solutions by orbitrap tandem mass spectrometry and quantitative structure activity relationship analyses
Authors: Matsushita, Taku Browse this author →KAKEN DB
Honda, Shiho Browse this author
Kuriyama, Taisuke Browse this author
Fujita, Yuki Browse this author
Kondo, Takashi Browse this author
Matsui, Yoshihiko Browse this author →KAKEN DB
Shirasaki, Nobutaka Browse this author
Takanashi, Hirokazu Browse this author
Kameya, Takashi Browse this author
Keywords: Advanced oxidation process
Ames assay
Chlorination
Fenitrothion
Ozonation
Toxicity
Issue Date: 1-Feb-2018
Publisher: Elsevier
Journal Title: Water research
Volume: 129
Start Page: 347
End Page: 356
Publisher DOI: 10.1016/j.watres.2017.11.033
Abstract: We used Ames assays to investigate the effects of ozonation (designated O-3), ozonation followed by chlorination (O-3/Cl), an advanced oxidation process (AOP, UV/H2O2), and AOP followed by chlorination (AOP/Cl) on the mutagenicity of solutions of 3-methy1-4-nitrophenol (3M4NP), a major environmental degradation product of the organopliosphorus insecticide fenitrothion. Whereas O-3 did not induce mutagenicity, O-3/Cl, AOP, and AOP/Cl converted 3M4NP into mutagenic transformation products (TPs). Using liquid chromatography mass spectrometry, we detected a total of 138 peaks in the solutions subjected to O-3/Cl, AOP, and AOP/Cl. To elucidate the TPs responsible for the observed mutagenicity, we performed simple regression analyses of the relationship between the area of each peak and the observed mutagenicity of samples withdrawn periodically during each oxidation process. The area of each of 10 peaks was found to be positively correlated (r(2) >= 0.8) with the observed mutagenicity, suggesting that the TPs corresponding to these peaks contributed to the mutagenicity. After taking into account the consistency of mutagenicity induction by the oxidation processes and analyzing the peaks by tandem mass spectrometry, we identified 3 TPs, corresponding to 6 peaks, as candidate mutagens. These TPs were assessed by means of 4 quantitative structure activity relationship (QSAR) models, and all 3 were predicted to be mutagenic by at least one model. This result was consistent with our assumption that these TPs were mutagens. Ames assays of an authentic sample of one of the 3 TPs revealed that it did not contribute to the mutagenicity. This left 3-methoxy-4-nitrophenol and 2-[(E)-[(2,5-dihydroxyphenyl) methylidene]amino]-5-dihydroxybenzaldehyde on the list of mutagens suspected of contributing to the mutagenicity induced by AOP. No TPs were identified as candidate mutagens responsible for the mutagenicity induced by O-3/Cl and AOP/Cl.
Rights: © 2018. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
http://creativecommons.org/licenses/by-nc-nd/4.0/
Type: article (author version)
URI: http://hdl.handle.net/2115/76643
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 松下 拓

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