The enantioselective toxicity and oxidative stress of dinotefuran on zebrafish (Danio rerio)

Ran, Lulu; Yang, Yunxia; Zhou, Xia; Jiang, Xiaoxia; Hu, Deyu; Lü, Ping

doi:10.1016/j.ecoenv.2021.112809

Cited by 31 publications

(5 citation statements)

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“…In the highest concentration group, SOD activity was significantly lower than that in the SC group, while CAT activity was significantly higher than that in the SC group. Similar alterations to SOD and CAT activities were observed after dinotefuran or thiamethoxam exposure, which were consistent with our results [ 40 , 66 ]. Previous studies showed that mild oxidative stress can induce the increase in GST activity, which is beneficial to cope with oxidative damage [ 67 , 68 ].…”

Section: Discussionsupporting

confidence: 93%

“…For instance, THCP exposure led to lower growth and delay in the development of the common carp ( Cyprinus carpio ) [ 18 ]. Environmentally relevant concentrations of dinotefuran (a neonicotinoid) were reported to adversely affect the growth of zebrafish [ 40 ]. In addition, acetamiprid (a neonicotinoid) exposure could decrease the hatching, survival and heart rates, and increase malformation rate of zebrafish, which were consistent with our results [ 41 ].…”

Section: Discussionmentioning

confidence: 99%

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Early-Stage High-Concentration Thiacloprid Exposure Induced Persistent Behavioral Alterations in Zebrafish

Xie

2022

IJERPH

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As a major neonicotinoid insecticide, thiacloprid (THCP) is frequently detected in aquatic environments worldwide due to its heavy use, posing potential threats to aquatic organisms. In this study, zebrafish (Danio rerio) embryos were exposed to THCP (1, 10, 100, 1000 and 10,000 μg/L) for 5 days and then recovered in THCP-free water for 20 days to investigate the effects of early-stage THCP exposure on the development, antioxidant defense, and neurotransmitter systems of zebrafish, and explore their recovery mechanism. The results show that THCP exposure induced developmental toxicity and oxidative stress in zebrafish. The hypoactivity, behavioral alterations (decreased avoidance and edge preference behaviors) and neurotoxicity were found throughout the exposure-recovery experiments. THCP exposure altered the expression of γ-aminobutyric acid (GABA)- and serotonin (5-HT)-related genes accompanied by the decrease in GABA and 5-HT contents. However, after recovery, GABA content returned to the control level, but 5-HT did not, indicating that only the serotonergic system was persistently disrupted. Overall, our results suggest that the disruption of the serotonergic system and oxidative stress may aggravate neurotoxicity and that the former was the main reason for the depressive-like behavior. This study could help to unravel the mechanisms of the behavioral alterations induced by early-stage THCP exposure in zebrafish.

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Section: Discussionsupporting

confidence: 93%

Section: Discussionmentioning

confidence: 99%

Early-Stage High-Concentration Thiacloprid Exposure Induced Persistent Behavioral Alterations in Zebrafish

Xie

2022

IJERPH

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“…On the other hand, although there is no evidence that DIN_ free directly causes oxidative stress, it is strongly speculated that the Phase II metabolic reaction of DIN (e.g., DIN_ conjugated ) may be an important factor to induce oxidative stress. Many experimental animal studies revealed that DIN induces oxidative stress. − The mechanism of DIN-induced oxidative stress was also similar to that of IMI, and elevated levels of SOD and CAT, MDA and GSH were observed in fish (Gobiocypris rarus) . Moreover, DIN can induce hepatotoxicity and carcinogenicity via oxidative stress …”

Section: Resultsmentioning

confidence: 92%

Insights into Free and Conjugated Forms of Neonicotinoid Insecticides in Human Serum and Their Association with Oxidative Stress

et al. 2023

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Following exposure, neonicotinoid insecticides (NEOs) can be metabolized by both Phase I and Phase II reactions catalyzed by human cytochrome P450 enzymes. However, toxicities of parent NEOs and their metabolites are still unclear, and little is known about biotransformation rates and pathways of NEOs in humans. In this study, 98 serum samples collected in China were analyzed for free, conjugated and total forms of six parent NEOs (i.e., acetamiprid (ACE), imidacloprid (IMI), clothianidin (CLO), thiacloprid (THD), thiamethoxam (THM), and dinotefuran (DIN)) and four metabolites (i.e., N-desmethyl-acetamiprid (N-dm-ACE), 1-methyl-3-(tetrahydro-3-furylmethyl) (DIN-U), 5-hydroxy-imidacloprid (5-OH-IMI), olefin-imidacloprid (Of-IMI)). NEOs and their metabolites were detected in all serum samples, and the total median concentrations of free, conjugated, and total forms of 10 NEOs were 2.04, 2.01, and 5.12 ng/mL, respectively. Conjugated forms of NEOs accounted for only half (53%) of the total forms of NEOs. Based on the profiles of Phase I and Phase II metabolites of NEOs in serum, it was found that age is a determinant in Phase I metabolism of DIN and Phase II metabolism of IMI. The Phase II metabolites of NEOs are associated with oxidative DNA damage, and the conjugated forms of IMI, DIN, and 5-OH-IMI in serum were significantly positively correlated with oxidative stress. Overall, the amount of NEOs present in conjugated forms in human serum was determined to document the existence of a considerable proportion of free forms of these insecticides.

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“…17 Some enantiomers may have not only low or no activity but also toxic effects on nontarget organisms and increase environmental pollution. 18 Moreover, some enantiomers of chiral pesticides that are prone to configuration transformation cannot exist stably and inde- pendently. 19 Hence, the activity behaviors and stability of the enantiomers of chiral pesticides are essential for the development of environment-friendly green pesticides and the rational use of pesticides.…”

Section: Introductionmentioning

confidence: 99%

“…Despite the similarity in structural and physicochemical characteristics, different enantiomers can exhibit vastly different biological and toxicity properties and metabolic, migration, and transformation behaviors under different chiral conditions. − The enantiomeric activities of some chiral pesticides remarkably differ, and a mere 7% of chiral pesticides are vended as pure enantiomers . Some enantiomers may have not only low or no activity but also toxic effects on nontarget organisms and increase environmental pollution . Moreover, some enantiomers of chiral pesticides that are prone to configuration transformation cannot exist stably and independently .…”

Section: Introductionmentioning

confidence: 99%

Absolute Configuration, Enantioselective Bioactivity, and Mechanism Study of the Novel Chiral Fungicide Benzovindiflupyr

Chen

Xiang

Yuan

et al. 2023

J. Agric. Food Chem.

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Benzovindiflupyr has gained increasing attention as a new chiral succinate dehydrogenase inhibitor fungicide; however, its determination, bioactivity, and mechanism at the enantiomeric level are very limited. In the present study, optical rotation determination and X-ray single-crystal diffraction results identified that the absolute configurations were (+)-(1R,4S)-benzovindiflupyr and (−)-(1S,4R)-benzovindiflupyr. A quantitative determination method for enantiomers was established using high-performance liquid chromatography tandem mass spectrometry (HPLC–MS/MS) for pesticide detection. The stereoselective bioactivity assay indicated that (−)-(1S,4R)-benzovindiflupyr exhibited greater potency than (+)-(1R,4S)-benzovindiflupyr against seven phytopathogenic fungi. Molecular docking analysis showed that (−)-(1S,4R)-benzovindiflupyr possessed a stronger binding affinity to succinate dehydrogenase than (+)-(1R,4S)-benzovindiflupyr. The binding modes between enantiomers and the mutant with H272(B) predicted that the phytopathogenic fungi with H272(B) of succinate dehydrogenase mutation would not be resistant to benzovindiflupyr enantiomers. This study provides a basis for residue evaluation, risk assessment, and the safe application of benzovindiflupyr at the enantiomer level.

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The enantioselective toxicity and oxidative stress of dinotefuran on zebrafish (Danio rerio)

Cited by 31 publications

References 50 publications

Early-Stage High-Concentration Thiacloprid Exposure Induced Persistent Behavioral Alterations in Zebrafish

Early-Stage High-Concentration Thiacloprid Exposure Induced Persistent Behavioral Alterations in Zebrafish

Insights into Free and Conjugated Forms of Neonicotinoid Insecticides in Human Serum and Their Association with Oxidative Stress

Absolute Configuration, Enantioselective Bioactivity, and Mechanism Study of the Novel Chiral Fungicide Benzovindiflupyr

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