Enantioselective Toxicity of Ibuprofen to Earthworms: Unraveling the Effect and Mechanism on Enhanced Toxicity of S-Ibuprofen Over R-Ibuprofen DOI

Wenqi Jiang,

Zeyu Zhao, Qi Zhao

et al.

Environmental Science & Technology, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 21, 2024

With the global implementation of wastewater reuse, accurately assessing soil ecological risk chiral pollutants from necessitates a comprehensive understanding their enantioselective toxicity to animals. Ibuprofen (IBU) is most prevalent pharmaceutical in municipal wastewater. However, its toward animals and underlying mechanism remain largely unknown. In this study, IBU enantiomers, S-IBU R-IBU, earthworms was evaluated at environmentally relevant concentrations (10 100 μg/L), simulating reuse for irrigation. The results demonstrated that adversely affects growth, reproduction, regeneration, defense systems, metabolic processes earthworms, with exhibiting stronger toxic effects than R-IBU. bioavailability assessment revealed more readily absorbed by converted enantiomer within This consistent molecular docking showing had affinities functional proteins associated xenobiotic transport transformation. findings study highlight poses higher R-IBU organisms under scenarios chirality chemical deserves attention when implementing reuse. addition, our underscores differences bioactivity may account pollutants.

Language: Английский

Enantioselective analysis of pesticides in food, biological, and environmental samples by chromatographic techniques and capillary electrophoresis DOI Creative Commons
Lucía Abad‐Gil, Marı́a Luisa Marina

Journal of Chromatography Open, Journal Year: 2023, Volume and Issue: 4, P. 100099 - 100099

Published: July 26, 2023

The use of pesticides such as herbicides, insecticides, and fungicides, has increased due to the high demand for food production. A significant percentage are chiral, their desired activity can reside in one stereoisomers being other(s) inactive or having a lesser activity. In these cases, it would be desirable using pure have avoiding presence higher amounts than those required obtain intended effect. However, chiral usually commercialized racemic mixtures causing potential harmful effects environment nontarget organisms if stereoisomer that exhibits main used. Different metabolism degradation, dissipation, toxicological also observed depending on stereoisomer. Therefore, efficient, selective, sensitive analytical methods enabling enantioselective determination residue analysis food, biological environmental samples. These methodologies powerful tools control production agrochemical formulations evaluate ecotoxicity at enantiomeric level. Various separation techniques liquid chromatography, gas supercritical fluid capillary electrophoresis been employed this purpose. Current trends applied including pyrethroids, samples provided review covering period from 2019 2023.

Language: Английский

Citations

14
Overexpression of an Integument Esterase Gene LbEST-inte4 Infers the Malathion Detoxification in Liposcelis bostrychophila (Psocoptera: Liposcelididae) DOI
Tian‐Xing Jing,

Shi‐Die Jiang,

Xin-Ping Tang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(19), P. 11221 - 11229

Published: May 4, 2024

Liposcelis bostrychophila, commonly known as booklouse, is an important stored-product pest worldwide. Studies have demonstrated that booklices developed resistance to several insecticides. In this study, integument esterase gene, LbEST-inte4, with upregulated expression, was characterized in L. bostrychophila. Knockdown of LbEST-inte4 resulted a substantial increase the booklice susceptibility malathion. Overexpression Drosophila melanogaster significantly enhanced its malathion tolerance. Molecular modeling and docking analysis suggested potential interactions between When overexpressed Sf9 cells, notable elevation activity tolerance observed. HPLC indicated enzyme could effectively degrade Taken together, appears contribute bostrychophila by facilitating depletion This study elucidates molecular mechanism underlying detoxification provides foundations for development effective prevention control measures against psocids.

Language: Английский

Citations

5
Development of Sustainable Insecticide Candidates for Protecting Pollinators: Insight into the Bioactivities, Selective Mechanism of Action and QSAR of Natural Coumarin Derivatives against Aphids DOI
Hong Zhou,

Yufan Jian,

Qingyi Shao

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(47), P. 18359 - 18374

Published: Nov. 15, 2023

Plants employ abundant toxic secondary metabolites to withstand insect attack, while pollinators can tolerate some natural defensive compounds. Coumarins, as promising green alternatives chemical insecticides, possess wide application prospects in the crop protection field. Herein, bioactivities of 30 coumarin derivatives against Aphis gossypii were assessed and revealed that 6-methylcoumarin exhibited potent aphicidal activity aphids but displayed no toxicity honeybees. Additionally, using biochemical, bioinformatic, molecular assays, we confirmed action mode was by inhibiting acetylcholinesterase (AChE). Meanwhile, functional assays difference site, which located Lys585 aphid AChE (equivalent Val548 honeybee AChE), principal reason for being safe pollinators. This site further validated mutagenesis data, uncovered how unique selective over or mammalian AChE. Furthermore, a 2D-QSAR model established, revealing central structural feature H3m, offers guidance future design more work provides sustainable strategy take advantage analogues pest management protecting nontarget

Language: Английский

Citations

11
Enantioselection behaviors and risk assessments of chiral pesticide ethiprole and its chiral metabolite ethiprole amide in five kinds of vegetables DOI
Wenjun Qu, Xinquan Wang, Huiyu Zhao

et al.

Food Chemistry, Journal Year: 2025, Volume and Issue: 473, P. 143017 - 143017

Published: Jan. 23, 2025

Language: Английский

Citations

0
Enantioselective Assessment of Etoxazole Enantiomers in Earthworms (Eisenia fetida): Bioaccumulation, Degradation, Transcriptome, and Oxidative Stress DOI
Ping Zhang,

Lulu Ran,

Furong Yang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This study systemically investigated the enantioselective bioaccumulation and degradation of etoxazole (ETZ) in earthworms along with transcriptome oxidative stress responses to ETZ enantiomer exposure. Based on M-shaped trends for enantiomers,

Language: Английский

Citations

0
Chemo- and enantioselective analysis of high hydrophilic organophosphate pesticides by liquid chromatography under different elution modes DOI Creative Commons

Leandro Oka-Duarte,

Quézia B. Cass, Anderson Rodrigo Moraes de Oliveira

et al.

Journal of Chromatography Open, Journal Year: 2024, Volume and Issue: 5, P. 100142 - 100142

Published: May 1, 2024

Acephate and malathion are prevalent chiral organophosphate insecticides, giving rise to more toxic metabolites such as methamidophos malaoxon, respectively. Enantioselective separation of pesticides is crucial due the differing pharmacological, environmental, toxicological profiles enantiomers. This study systematically evaluates an enantio- chemoselective performance eight polysaccharide-based columns (Chiralcel OB-H, Chiralcel OD-H, OJ-R, Chiralpak AD-H, AS-H, IG-3, IK-3, Lux-Amylose-2) ten mobile phases across multimodal elution (normal-phase, polar organic, reversed-phase conditions). Within 80 combinations per analyte, screening highlights specific enantioselectivity trends concerning hydrophilic hydrophobic compounds when utilizing amylose- or cellulose-based polymers under different conditions. Notably, a set including AD-H demonstrated superior coverage, achieving at least 62% success rate for enantioseparation. For resolution between pairs acephate/methamidophos malathion/malaoxon, where no further optimizations were undertaken, chemoselectivity was 10% 30%,

Language: Английский

Citations

2
Chirality in Insecticide Design and Efficacy DOI
Karla Irazú Ventura-Hernández, Enrique Delgado-Alvarado, Tushar Janardan Pawar

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(38), P. 20722 - 20737

Published: Sept. 10, 2024

Chirality plays a crucial role in the design and efficacy of insecticides, significantly influencing their biological activity, selectivity, environmental impact. Recent advancements chiral insecticides have focused on enhancing effectiveness, reducing toxicity to nontarget organisms, improving sustainability. This review provides comprehensive overview current state knowledge including neonicotinoids, isoxazolines, sulfiliminyls. We discuss stereochemistry, synthetic development, mode action, fate these compounds. The highlights importance chirality optimizing insecticidal properties underscores need for continued research into novel compounds advanced synthesis technologies. By understanding chirality, we can develop more effective environmentally friendly sustainable pest management.

Language: Английский

Citations

1
Enantioselective Toxicity of Ibuprofen to Earthworms: Unraveling the Effect and Mechanism on Enhanced Toxicity of S-Ibuprofen Over R-Ibuprofen DOI

Wenqi Jiang,

Zeyu Zhao, Qi Zhao

et al.

Environmental Science & Technology, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 21, 2024

With the global implementation of wastewater reuse, accurately assessing soil ecological risk chiral pollutants from necessitates a comprehensive understanding their enantioselective toxicity to animals. Ibuprofen (IBU) is most prevalent pharmaceutical in municipal wastewater. However, its toward animals and underlying mechanism remain largely unknown. In this study, IBU enantiomers, S-IBU R-IBU, earthworms was evaluated at environmentally relevant concentrations (10 100 μg/L), simulating reuse for irrigation. The results demonstrated that adversely affects growth, reproduction, regeneration, defense systems, metabolic processes earthworms, with exhibiting stronger toxic effects than R-IBU. bioavailability assessment revealed more readily absorbed by converted enantiomer within This consistent molecular docking showing had affinities functional proteins associated xenobiotic transport transformation. findings study highlight poses higher R-IBU organisms under scenarios chirality chemical deserves attention when implementing reuse. addition, our underscores differences bioactivity may account pollutants.

Language: Английский

Citations

1