Assessment of toxicity and environmental behavior of chiral ethiprole and its metabolites using zebrafish model

Gao, Jing; Wang, Fang; Cui, Jingna; Zhang, Qiang; Wang, Peng; Liu, Donghui; Zhou, Zhiqiang

doi:10.1016/j.jhazmat.2021.125492

Cited by 23 publications

(14 citation statements)

References 30 publications

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“…It was found that the metabolic profile of the sulfoxide moiety is parallel; for example, the phenylpyrazole pesticides containing sulfoxide were readily converted to their corresponding sulfone metabolites in the organism and environment. 40,41 It has also been reported that cytochrome P450 (CYP3A4) is responsible for metabolizing phenylpyrazole pesticides into their sulfone metabolites. 42 Similarly, our results found that pyraquinil-sulfone was the most abundant metabolite, suggesting that the oxidative metabolism induced by cytochrome P450s might be the principal pathway to eliminate pyraquinil in the larvae.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Study on Absorption, Distribution, Metabolism, and Excretion Properties of Novel Insecticidal GABA Receptor Antagonist, Pyraquinil, in Diamondback Moth Combining MALDI Mass Spectrometry Imaging and High-Resolution Mass Spectrometry

Wan

Jiang

Tang

et al. 2022

J. Agric. Food Chem.

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A thorough understanding of absorption, distribution, metabolism, and excretion (ADME) of insecticide candidates is essential in insecticide development and structural optimization. Here, ADME of pyraquinil, a novel insecticidal GABA receptor antagonist, in Plutella xylostella larvae during the accumulation phase and depuration phase was investigated separately using a combination of UHPLC-Q-Orbitrap, HPLC-MS/MS, and MALDI-MSI. Five new metabolites of pyraquinil were identified, and a metabolic pathway was proposed. The oxidative metabolite (pyraquinil-sulfone) was identified as the main metabolite and confirmed by its standard. Quantitative results showed that pyraquinil was taken up by the larvae rapidly and then undergone a cytochrome P450s-mediated oxidative transformation into pyraquinil-sulfone. Both fecal excretion and oxidative metabolism were demonstrated to be predominant ways to eliminate pyraquinil in P. xylostella larvae during accumulation, while oxidative metabolism followed by fecal excretion was probably the major pathway during depuration. MALDI-MSI revealed that pyraquinil was homogeneously distributed in the larvae, while pyraquinil-sulfone presented a continuous enrichment in the midgut during accumulation. Conversely, pyraquinil-sulfone located in hemolymph can be preferentially eliminated during depuration, suggesting its tissue tropism. It improves the understanding of the fate of pyraquinil in P. xylostella and provides useful information for insecticidal mechanism elucidation and structural optimization of pyraquinil.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Study on Absorption, Distribution, Metabolism, and Excretion Properties of Novel Insecticidal GABA Receptor Antagonist, Pyraquinil, in Diamondback Moth Combining MALDI Mass Spectrometry Imaging and High-Resolution Mass Spectrometry

Wan

Jiang

Tang

et al. 2022

J. Agric. Food Chem.

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“…Recently, a study was performed to evaluate zebrafish embryotoxicity and effects on antioxidant enzymes (catalase, CAT and superoxide dismutase, SOD, activities) and oxidative stress (lipid peroxidation) of its main metabolites, i.e. ethiprole sulfone, ethiprole sulphide, ethiprole amide, ethiprole sulfone amide and desethylsulfinyl ethiprole (Gao et al 2021 ). Results showed that only ethiprole sulfone and sulphide had effects on antioxidant defences and embryonic development.…”

Section: Risks Of Pharmaceutical and Pesticide Transformation Productsmentioning

confidence: 99%

“…Ethiprole sulphide had an LC50 value of 111 μg/L, induced antioxidant enzymes and increased developmental anomalies at 10 μg/L or higher. Rac-ethiprole amide and ethiprole sulfone amide had LC50 values higher than 5000 μg/L, whilst the LC50 value for desethylsulfinyl ethiprole was 1728 μg/L (Gao et al 2021 ).…”

Section: Risks Of Pharmaceutical and Pesticide Transformation Productsmentioning

confidence: 99%

Occurrence of Pharmaceutical and Pesticide Transformation Products in Freshwater: Update on Environmental Levels, Toxicological Information and Future Challenges

Rodrigues

Oliva-Teles

Guimarães

et al. 2022

Reviews Env.Contamination (formerly:Residue Reviews)

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Pharmaceuticals and pesticides are recognized micropollutants in freshwater systems. Their ever-increasing frequency of detection, levels found and little information available about their effects on non-target organisms, make them emerging contaminants. However, parental compounds are not the only substances of concern. Their metabolites and degradation products, hereby referred to as transformation products, are increasingly detected in freshwater samples and wastewater effluents. In the past years, a wealth of publications provided concentration levels detected in freshwater and some toxicological data, which required critical systematization. This review identified concentrations for 190 transformation products (92 from pesticides and 98 from pharmaceuticals) in water bodies and wastewater effluents. A concentration heatmap was produced to easily spot the substances found at higher levels and plan future research. The very limited available toxicological data link exposure to transformation products to adverse outcomes in humans (genotoxicity and alteration in detoxification processes) and aquatic species (mostly related to apical endpoints). Overall, environmental levels of these transformation products may pose a severe threat to aquatic organisms and need to be further investigated in sound experimental designs, testing for the effects of the single substances as well as of their mixtures. Such toxicological information is highly needed to improve both water treatment technologies and monitoring programmes. Supplementary Information The online version contains supplementary material available at 10.1007/s44169-022-00014-w.

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“…There is enantioselective metabolism in algae suspension, zebrafish and Chlorella pyrenoidosa. The metabolic rate of S-ethiprole is faster than that of R-ethiprole; R-ethiprole accumulates preferentially in zebrafish and algae [19][20][21][22]. According to the above literatures, it is shown that while killing pests, R-ethiprole causes more damage to the environment and other organisms than Sethiprole.…”

Section: Introductionmentioning

confidence: 99%

Probing into complexation and separation of chiral‐at‐uranium complex to chiral sulphur enantiomers R/S‐ethiproles

Xiao

et al. 2023

Applied Organom Chemis

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Chiral pesticides R/S-ethiproles(R/S-EPLs) have different biotoxicity. Due to the difficulty in the separation of chiral sulphur enantiomers, it is of great significance to study the selective recognition and separation of chiral sulphur enantiomers R/S-ethiproles. Based on DFT method, we theoretically designed a novel asymmetrical ligand of 4-amino-6-(9-[5-hydroxy-1H-indol-6-yl]-4,7-dimethoxy-1,10-phenanthrolin-2-yl)-1H-indol-5-ol (AHPIL). Then we further constructed the chiral-at-uranium complex, namely, Uranyl-AHPIL, to recognize and separate the enantiomers R/S-EPLs. Various analyses, including electrostatic potential (ESP), molecular geometric structures, Mayer bond order (MBO), electron density difference diagram (EDDM), independent gradient model based on Hirschfield partition (IGMH), quantum theory of atoms in molecules (QTAIM), molecular orbitals, the extended transition state-natural orbitals for chemical valence (ETS-NOCV), hard-soft acid-base (HSAB), relaxed force constants (RFCs) and binding free energy, furthermore unravelled the selective complexation and chiral separation ability of Uranyl-AHPIL receptor to R/S-EPLs guests. The results all indicated that the novel ligand could coordinate with uranyl to form a stable chiral-at-uranium complex, which more inclined selectively to bind with R/S-EPLs through thiyl oxygen O 22 , and its complexation ability to S-EPL was much greater than to R-EPL. In solvents water, acetone, dichloromethane, benzene, cyclohexane and in gas phase, the separation factors of Uranyl-AHPIL towards R/S-EPL were in range of 189-633, and the enantioselectivity coefficients were all above 99%. These results provide a theoretical guidance for the complexation and separation of chiral pesticides and at the same time offer a new reference for the design of actinide complexes.

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Assessment of toxicity and environmental behavior of chiral ethiprole and its metabolites using zebrafish model

Cited by 23 publications

References 30 publications

Study on Absorption, Distribution, Metabolism, and Excretion Properties of Novel Insecticidal GABA Receptor Antagonist, Pyraquinil, in Diamondback Moth Combining MALDI Mass Spectrometry Imaging and High-Resolution Mass Spectrometry

Study on Absorption, Distribution, Metabolism, and Excretion Properties of Novel Insecticidal GABA Receptor Antagonist, Pyraquinil, in Diamondback Moth Combining MALDI Mass Spectrometry Imaging and High-Resolution Mass Spectrometry

Occurrence of Pharmaceutical and Pesticide Transformation Products in Freshwater: Update on Environmental Levels, Toxicological Information and Future Challenges

Probing into complexation and separation of chiral‐at‐uranium complex to chiral sulphur enantiomers R/S‐ethiproles

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