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3-PBA
Analytical Methods · 2017 ·Vol. 9 ·期 30 ·4439-4446 · IF 1.9

Chiral pyrethroid insecticide fenpropathrin and its metabolite: enantiomeric separation and pharmacokinetic degradation in soils by reverse-phase high-performance liquid chromatography

Ping Zhang,Qian Yu,Yuhan He,Wentao Zhu,Zhiqiang Zhou,Lin He

The enantiomeric separation of fenpropathrin enantiomers on Lux Cellulose-1, Lux Cellulose-3 and Chiralpak IC chiral columns as well as enantioselective degradation of fenpropathrin in soil were investigated by reverse-phase high-performance liquid chromatography (RP-HPLC). The effects of the chiral stationary phase, mobile phase component, mobile phase ratio, temperature and thermodynamic parameters on resolution were carefully evaluated. Fenpropathrin enantiomers achieve a baseline separation (Rs = 2.30) on the Lux Cellulose-3 column with a mobile phase of methanol/water at a ratio of 85/15. Partial separations were achieved on Lux Cellulose-1 and Chiralpak IC columns with maximum Rs = 1.01 and Rs = 0.64, respectively. Enantioselective degradation of fenpropathrin enantiomers in soil was investigated based on the proposed separation method. The half-life (t1/2) of S-fenpropathrin and R-fenpropathrin was 17.8 days and 12.6 days, respectively, indicating that the degradation of fenpropathrin in soil was enantioselective, with R-fenpropathrin preferentially degraded. Furthermore, the formation and degradation of 3-PBA, the main metabolite of fenpropathrin, were also investigated in three soils. Soil microorganisms were confirmed as the main factor that is responsible for enantioselective degradation of fenpropathrin enantiomers in soil. Such results provide a new approach for fenpropathrin enantiomer separation and contribute to a comprehensive risk assessment of fenpropathrin at the enantiomer level.

研究领域: 环境科学 · 农药化学 · 微生物学
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ENVIRONMENTAL SCIENCE & TECHNOLOGY · 2017 · IF 6.198

Relationships of Pyrethroid Exposure with Gonadotropin Levels and Pubertal Development in Chinese Boys

Xiaoqing Ye,Wuye Pan,Shilin Zhao,Yuehao Zhao,Yimin Zhu,Jing Liu,Weiping Liu

Although an acceleration of male pubertal development has been observed, precisely which endocrine-disrupting chemicals (EDCs) might contribute to the advancing onset of puberty in boys remains unclear. Here, pyrethroids, a class of widely used insecticides that have been considered as EDCs, are proposed as new environmental risk factors. In this study, 463 boys at the age of 9–16 years old were recruited in Hangzhou, Zhejiang, China. The common metabolites of pyrethroids, 3-phenoxybenzoic acid (3-PBA), and 4-fluoro-3-phenoxybenzoic acid (4-F-3-PBA), as well as gonadotropins, including luteinizing hormone (LH) and follicle-stimulating hormone (FSH), were analyzed in urine samples. Pubertal development was assessed based on Tanner stages and testicular volume (TV). A positive association between 3-PBA and gonadotropins was found (p < 0.001), in which a 10% increase in 3-PBA was associated with a 2.4% and 2.9% increase in LH and FSH, respectively. Higher urinary levels of 3-PBA in boys were associated with 275% and 280% increase in the risk of being genitalia stage 3 (G3) and G4, respectively (p < 0.05). There was a significant (132%) induction in odd of being TV 12–19 mL with increasing 3-PBA concentration compared to being in TV < 4 mL (p < 0.05). For the first time to our knowledge, this work reports on an association of increased pyrethroid exposure with elevated gonadotropins levels and earlier pubertal development in boys.

研究领域: 环境科学 · 内分泌学 · 公共卫生
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APPLIED MICROBIOLOGY AND BIOTECHNOLOGY · 2020 ·Vol. 104 ·期 17 ·7345-7354 · IF 3.53

Construction and characterization of a class-specific single-chain variable fragment against pyrethroid metabolites

Liu Yuan,Liu Dan,Shen Chen,Dong Sa,Hu Xiaodan,Lin Manman,Zhang Xiao,Xu Chongxin,Zhong Jianfeng,Xie Yajing,Zhang Cunzheng,Wang Donglan,Liu Xianjin

Abstract Pyrethroids are insecticides that are widely used in rural and urban areas worldwide. After entering the environment, pyrethroids are rapidly metabolized or degraded by various biological or abiotic methods. In this study, a single-chain variable fragment (scFv) which could simultaneously detect three pyrethroid metabolites was constructed based on a hybridoma raised against 3-phenoxybenzoic acid (3-PBA). By molecular docking, it showed that there were hydrogen bonds, hydrophobic interactions, CH-π interaction, and cation-π interaction between 3-PBA and its scFv. All the contact residues contributing to hydrogen bonds are located in VH-CDR2 or its neighboring region, and two of them were mutants of the closest germline sequence. Based on competitive ELISA, the half maximal inhibitory concentration (IC 50 ) of the scFv for 3-PBA, 3-phenoxybenzaldehyde (PBAld), and 3-phenoxybenzyl alcohol (PBAlc) were calculated to be 0.55, 0.59, and 0.63 μgmL −1 , respectively. The scFv also showed 23.91%, 13.41%, 1.15%, 1.00%, and 0.56% cross-reactivity with phenothrin, deltamethrin, fenvalerate, beta-cypermethrin, and fenpropathrin. The broad specificity of the scFv may be due to its hapten design. The scFv could be employed in class-specific immunoassays for pyrethroid metabolites with phenoxybenzyl (PB) group. It is also potentially used for characterizing degradation of pyrethroids or detecting PBAlc (PBAld) alone, and the detection results should be confirmed by other selective methods. Key points • A scFv which can simultaneously detect 3-PBA, PBAlc, and PBAld was constructed. • Antibody informatics and binding mode of the scFv were obtained. • The reason for its broad specificity was discussed. • It could be used to monitor single or multi-pyrethroid metabolites with PB group.

研究领域: 环境科学 · 免疫学
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Analytical Methods · 2021 ·Vol. 13 ·期 14 ·1757-1765 · IF 2.896

Development of nanobody-based flow-through dot ELISA and lateral-flow immunoassay for rapid detection of 3-phenoxybenzoic acid

Can Zhang,Xiaoxiao Wu,Dongyang Li,Jinnuo Hu,Debin Wan,Zhen Zhang,Bruce D. Hammock

As a major metabolite of pyrethroid pesticides, 3-phenoxybenzoic acid (3-PBA) can be an indicator of health risk and human exposure assessment. Based on nanobodies (Nbs), we have developed a rapid flow-through dot enzyme linked immunosorbent assay (dot ELISA) and gold nanoparticle (GNP) lateral-flow immunoassay for detecting 3-PBA. The limit of detection (LOD) values for detecting 3-PBA by flow-through dot ELISA and GNP lateral-flow immunoassay were 0.01 ng mL−1 and 0.1 ng mL−1, respectively. The samples (urine and lake water) with and without 3-PBA were detected by both nanobody-based flow-through dot ELISA and GNP lateral-flow immunoassay, as well as liquid chromatography-mass spectrometry (LC-MS) for validation. There was good consistency between the results of the immunoassays. This demonstrated that the two developed nanobody-based immunoassays are suitable for rapid detection of 3-PBA.

研究领域: 环境科学 · 分析化学 · 免疫学 · 纳米技术
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