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Chiral perspective evaluations: Enantioselective hydrolysis of 6PPD and 6PPD-quinone in water and enantioselective toxicity to Gobiocypris rarus and Oncorhynchus mykiss

文献类型： 外文期刊

作者： Di, Shanshan 1 ; Liu, Zhenzhen 1 ; Zhao, Huiyu 1 ; Li, Ying 1 ; Qi, Peipei 1 ; Wang, Zhiwei 1 ; Xu, Hao 1 ; Jin, Yuanxiang 3 ; Wang, Xinquan 1 ;

作者机构： 1.Zhejiang Acad Agr Sci, Inst Agroprod Safety & Nutr, State Key Lab Managing Biot & Chem Threats Qual &, key Lab Detect Pesticide Residues & Control Zhejia, Hangzhou 310021, Peoples R China

2.Agr Minist, Key Lab Pesticide Residue Detect, Hangzhou 310021, Peoples R China

3.Zhejiang Univ Technol, Coll Biotechnol & Bioengn, Hangzhou 310032, Peoples R China

4.Chaowang Rd 18, Hangzhou 310014, Zhejiang, Peoples R China

5.Desheng Middle Rd 298, Hangzhou 310021, Zhejiang, Peoples R China

关键词： Enantioselective evaluations; Absolute configuration; Enantioseparation; Enantioselective hydrolysis; Enantioselective toxicity

期刊名称：ENVIRONMENT INTERNATIONAL （ 影响因子：13.352； 五年影响因子：13.238 ）

ISSN： 0160-4120

年卷期： 2022 年 166 卷

页码：

收录情况： SCI

摘要： As a ubiquitous tire antidegradant, N-(1, 3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) is persistently released into the environment. It is highly toxic to aquatic organisms, and its transformation product 6PPD-quinone (6PPD-Q), is "very highly toxic" to Oncorhynchus kisutch at a median lethal concentration (LC50) of < 0.1 ng/mL. Notably, 6PPD and 6PPD-Q are chiral compounds. Here, enantioselective evaluations, including hydrolysis and acute toxicity were conducted after preparing the enantiomer, confirming the enantiomer absolute configuration and establishing enantioseparation methods. In the 6PPD hydrolysis experiments, the products 6PPD-Q, phenol, 4-[(1, 3-dimethylbutyl)amino]-(4-DBAP) and 4-hydroxydiphenylamine (4-HDPA) were detected. In different water solutions, the hydrolysis of 4-DBAP and 4-HDPA was very fast (0.87-107 h), while the 6PPD-Q hydrolysis half-lives (12.8-16.3 d) were significantly longer than 6PPD (4.83-64.1 h). At the enantiomeric level, no enantioselective hydrolysis and conversion occurred. R-6PPD generated R-6PPD-Q, and S-6PPD generated S-6PPD-Q, and the formation rate of S-6PPD-Q was 1.77 times faster than R-6PPD-Q. In terms of the enantioselective toxicity, the 6PPD enantiomer was highly toxic to China-specific Gobiocypris rarus (LC50, 162-201 ng/mL), and it had no enantioselective difference. 6PPD-Q was "very highly toxic" (LC50, 1.66-4.31 ng/mL) to Oncorhynchus mykiss, which is of commercial importance, and the toxicities of rac-6PPD-Q and S-6PPD-Q were 1.9 and 2.6 times higher than R-6PPD-Q. Furthermore, the formation concentrations of S-6PPD-Q and R-6PPD-Q in 6PPD water solutions were higher than the LC50 values of O. kisutch and O. mykiss, and the toxicity of 6PPD-Q was highly species-specific, which should raise concern. These results provide important information for environmental risk assessments of 6PPD and 6PPD-Q, especially from the perspective of enantiomers.

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