Bioaccumulation, metabolism and toxicological effects of chiral insecticide malathion and its metabolites in zebrafish (Danio rerio)

Cui, Jingna; Wei, Yimu; Jiang, Jiangong; Xiao, Shouchun; Liu, Xueke; Zhou, Zhiqiang; Liu, Donghui; Wang, Peng

doi:10.1016/j.chemosphere.2023.137898

Cited by 16 publications

(8 citation statements)

References 45 publications

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“…Esterases can transform malathion to less toxic metabolites such as malathion/malaoxon monocarboxylic acid (DMA), malathion/malaoxon dicarboxylic acid (DCA), dimethylthiophosphate (DMTP), and dimethyldithiophosphate (DMDTP). 13 Indeed, several malathion derived metabolites, such as DMA, were found when malathion was incubated with LbEST-inte4 (data not showed). These results are in agreement with the action of LbEST-inte4 on malathion and are likely to play a role in its detoxification, enhancing the insect cell tolerance to malathion.…”

Section: Discussionmentioning

confidence: 95%

“…Further support for the involvement of LbEST-inte4 in malathion detoxification comes from in vitro enzymatic tests where the malathion content was reduced by incubation with recombinant LbEST-inte4 protein extract. Esterases can transform malathion to less toxic metabolites such as malathion/malaoxon monocarboxylic acid (DMA), malathion/malaoxon dicarboxylic acid (DCA), dimethylthiophosphate (DMTP), and dimethyldithiophosphate (DMDTP) . Indeed, several malathion derived metabolites, such as DMA, were found when malathion was incubated with LbEST-inte4 (data not showed).…”

Section: Discussionmentioning

confidence: 99%

“…Malathion, a broad-spectrum organophosphorus insecticide, is extensively used to control agricultural pest, as well as sanitary pests, such as mosquitoes, flies and animal parasites. − In stored products, malathion can be applied via surface treatments or directly mixed with grains, and it can be rapidly absorbed by insect chewing . The convenience and long-term usage of malathion have led to a serious insecticide resistance/tolerance problem, and residues of malathion have also been found to penetrate into the grains .…”

Section: Introductionmentioning

confidence: 99%

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Overexpression of an Integument Esterase Gene LbEST-inte4 Infers the Malathion Detoxification in Liposcelis bostrychophila (Psocoptera: Liposcelididae)

Jing,

Jiang,

Tang

et al. 2024

J. Agric. Food Chem.

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

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Section: Discussionmentioning

confidence: 95%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Overexpression of an Integument Esterase Gene LbEST-inte4 Infers the Malathion Detoxification in Liposcelis bostrychophila (Psocoptera: Liposcelididae)

Jing,

Jiang,

Tang

et al. 2024

J. Agric. Food Chem.

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“…29,30 For example, Cui et al showed that MLX is highly toxic to zebrafish and that S-MLX is first enriched in zebrafish. 26 Therefore, the identification and development of single enantiomers with efficient and environmentally friendly properties to replace the racemates of chiral pesticides is an effective strategy to reduce the use of pesticides and their environmental risks. 31 However, the actual production of pesticides with only one single enantiomer is very difficult or expensive to do.…”

Section: Introductionmentioning

confidence: 99%

“…22,23 Most of OPs have chirality and are sold as racemates, but generally only one of the enantiomeric structures is highly toxic. 24 Among them, malaoxon (MLX) is a common chiral OP, and compared with other chiral OPs, MLX is much more toxic than malathion [25][26][27] and has better selectivity than paraoxon. 22 In addition, it was found that R-MLX is a more potent inhibitor compared to S-MLX.…”

Section: Introductionmentioning

confidence: 99%

Unraveling complexation and enantioseparation of a new chiral‐at‐uranium complex to chiral pesticides R/S‐malaoxons

Guo,

Ouyang,

Wang

et al. 2024

Applied Organom Chemis

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Unraveling uranium complexes has become a popular study topic in recent years to address the problem of spent fuel treatment. An important and promising investigation is the enantiomer separation of chiral organophosphorus pesticides (OPs) via uranyl‐containing receptors. Among them, malaoxon (MLX), as a chiral OP with high toxicity and good selectivity, is controversial because of the different toxicity differences caused by the R and S configurations to target and non‐target organisms. Therefore, it is crucial to explore effective methods for separating its enantiomers. In this work, a novel 2‐(9‐[1H‐pyrazole‐1‐carbonyl]‐1,10‐phenanthrolin‐2‐yl)‐1H‐inden‐1‐one (HPIDO) ligand, which combines with uranyl to form the chiral‐at‐uranium complex (Uranyl‐HPIDO receptor), was designed for the enantioseparation of R/S‐malaoxons (R/S‐MLXs). Based on density functional theory (DFT), we explored the potential coordination modes between the Uranyl‐HPIDO receptor and R/S‐MLXs at various sites. The analyses of bonding properties, orbital interactions, and weak interactions of intramolecular groups of the complexes, along with the study of thermodynamic properties, revealed that the Uranyl‐HPIDO receptor preferred to bind to the phosphoryl oxygen (O5) of R/S‐MLXs to form stable complexes. Good enantioseparations of the two enantiomers were achieved in various solvents (water, n‐Butanol, n‐Octanol, dichloromethane, propanoic acid, toluene, and cyclohexane); the separation factors (SFR/S) ranged 21–853, and the enantioselectivity coefficients (ESCR/S) were more than 95%. The findings could theoretically offer useful information and guidance for the separation of R/S‐MLXs, in addition to providing fresh concepts for the creation of novel uranyl receptors.

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Theoretical exploring the complexation and enantioseparation of novel chiral-at-uranium complexes with R/S-O,O-dimethyl-S-[1,2-bis(ethoxycarbonyl)ethyl]thiophosphates

Wang,

Guo,

et al. 2024

J Radioanal Nucl Chem

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Bioaccumulation, metabolism and toxicological effects of chiral insecticide malathion and its metabolites in zebrafish (Danio rerio)

Cited by 16 publications

References 45 publications

Overexpression of an Integument Esterase Gene LbEST-inte4 Infers the Malathion Detoxification in Liposcelis bostrychophila (Psocoptera: Liposcelididae)

Overexpression of an Integument Esterase Gene LbEST-inte4 Infers the Malathion Detoxification in Liposcelis bostrychophila (Psocoptera: Liposcelididae)

Unraveling complexation and enantioseparation of a new chiral‐at‐uranium complex to chiral pesticides R/S‐malaoxons

Theoretical exploring the complexation and enantioseparation of novel chiral-at-uranium complexes with R/S-O,O-dimethyl-S-[1,2-bis(ethoxycarbonyl)ethyl]thiophosphates

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