Toxic effects of indoxacarb enantiomers on the embryonic development and induction of apoptosis in zebrafish larvae (<i><scp>D</scp>anio rerio</i>)

Fan, Yongmei; Feng, Qing; Lai, Kehua; Huang, Weikang; Zhang, Chenghui; Li, Qing X.

doi:10.1002/tox.22207

Cited by 26 publications

(9 citation statements)

References 25 publications

(32 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the literature, the insecticidal activity of indoxacarb is mainly attributed to (+)‐ S ‐indoxacarb (McCann et al 2001). However, it was reported that (−)‐ R‐ indoxacarb was 1.3 times more toxic to zebrafish embryos at 96 h postfertilization than was (+)‐ S‐ indoxacarb (Fan et al 2017). It was found that (−)‐ R‐ indoxacarb was more toxic to male zebrafish liver and female zebrafish brain than (+)‐ S‐ indoxacarb (Wang et al 2020).…”

Section: Discussionmentioning

confidence: 99%

Enantioselective Bioaccumulation of the Chiral Insecticide Indoxacarb in Zebrafish (Danio rerio)

Liang

Qiu

2021

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

Indoxacarb is a typical chiral insecticide widely used in agricultural pest control. In the present study, zebrafish was used as a model animal to explore the enantioselective bioaccumulation behavior of indoxacarb to nontarget species in aquatic environments. Zebrafish were exposed to 0.025 and 0.1 mg/L rac-indoxacarb solution for 12 d under the semistatic method, and the bioconcentration factor (BCF) and enantiomeric fraction of zebrafish were investigated. The results showed that the (−)-R-indoxacarb preferentially accumulated in zebrafish. The BCF values at 0.025 mg/L exposure levels were 1079.8 and 83.4 L/kg for (−)-R-indoxacarb and (+)-S-indoxacarb after 12 d, respectively. The BCF values at 0.1 mg/L exposure levels were 1752.1 and 137.0 L/kg for (−)-R-indoxacarb and (+)-S-indoxacarb after 10 d, respectively. The half-life values of (−)-Rindoxacarb and (+)-S-indoxacarb were 3.47 and 2.05 d for 0.025 mg/L concentration exposure and 4.95 and 2.66 d for 0.1 mg/L concentration exposure, respectively. The enantiomeric fraction values were in the range of 0.48 to 0.55 and 0.89 to 1.00 for water and zebrafish samples, respectively. Studies on the enantioselective bioaccumulation behavior of indoxacarb will provide data for assessing the environmental fate and potential toxic effects of indoxacarb on aquatic organisms.

show abstract

Section: Discussionmentioning

confidence: 99%

Enantioselective Bioaccumulation of the Chiral Insecticide Indoxacarb in Zebrafish (Danio rerio)

Liang

Qiu

2021

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

show abstract

“…Furthermore, although the potential adverse effects of chiral substances have been recognized, their enantioselective effects on nontarget organisms are still poorly understood. This type of study is of great importance for an accurate risk assessment (Fan et al 2017; Song et al 2017, 2018). For instance, a recent report showed the enantioselective toxicity, distribution, and bioaccumulation of venlafaxine and O ‐desmethylvenlafaxine in loach Misgurnus anguillicaudatus co‐exposed to microplastics (Qu et al 2019).…”

Section: Resultsmentioning

confidence: 99%

Ketamine and Norketamine: Enantioresolution and Enantioselective Aquatic Ecotoxicity Studies

Pérez-Pereira

Ribeiro

Teles

et al. 2021

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

Ketamine is a chiral drug used for various clinical purposes but often misused. It is metabolized to norketamine, an active chiral metabolite. Both substances have been detected in environmental matrices, but studies about their enantioselective toxic effects are scarce. In the present study, the enantiomers of ketamine and norketamine were separated by a semipreparative enantioselective liquid chromatography method, and their toxicity was investigated in different aquatic organisms. The enantioseparation was achieved using a homemade semipreparative chiral column. Optimized conditions allowed the recovery of compounds with enantiomeric purity higher than 99%, except for (R)‐ketamine (97%). The absolute configuration of the enantiomers was achieved by experimental electronic circular dichroism (ECD). The ecotoxicity assays were performed with the microcrustacean Daphnia magna and the protozoan Tetrahymena thermophila using Toxkit MicroBioTests. Different concentrations were tested (0.1–10 000 µg/L) to include environmental levels (~0.5–~100 µg/L), for racemates (R,S) and the isolated enantiomers (R or S) of ketamine and norketamine. No toxicity was observed in either organism at environmental levels. However, at greater concentrations, (R,S)‐ketamine presented higher mortality for D. magna compared with its metabolite (R,S)‐norketamine (85 and 20%, respectively), and the (S)‐ketamine enantiomer showed higher toxicity than the (R)‐ketamine enantiomer. In addition, (S)‐ketamine also presented higher growth inhibition than (R)‐ketamine for T. thermophila at the highest concentrations (5000 and 10 000 µg/L). Contrary to D. magna, growth inhibition was observed for both enantiomers of norketamine and in the same magnitude order of the (S)‐ketamine enantiomer. The results showed that the 2 organisms had different susceptibilities to norketamine and that the toxicity of ketamine at high concentrations is enantioselective for both organisms. Environ Toxicol Chem 2022;41:569–579. © 2020 SETAC

show abstract

“…The fish embryo acute toxicity test (FET) with zebrafish embryos, which is a general model in ecotoxicology and toxicology had been established in our labs [ 15 , 16 ]. The mortality in the positive control was 40% greater than 30% and survival in the negative control was 100%.…”

Section: Resultsmentioning

confidence: 99%

“…20 embryos were distributed in each of different concentrations of the compounds to be analyzed, a positive control (3,4-dichloroaniline), a negative control (water) and a solvent control (10% Hank’s solution). All of the treatments were cared at 26 °C ± 1 °C, light/dark cycle of 14/10 h. The entire experiment was carried out for 96 h. All of the data were analyzed by SPSS 19.0 (IBM Corporation, New York, NY, USA), LC 50 was corrected taking into account control mortality with Abbott’s formula [ 15 ].…”

Section: Methodsmentioning

confidence: 99%

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

et al. 2018

Self Cite

View full text Add to dashboard Cite

In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 µg mL−1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 µg mL−1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

show abstract

Toxic effects of indoxacarb enantiomers on the embryonic development and induction of apoptosis in zebrafish larvae (Danio rerio)

Cited by 26 publications

References 25 publications

Enantioselective Bioaccumulation of the Chiral Insecticide Indoxacarb in Zebrafish (Danio rerio)

Enantioselective Bioaccumulation of the Chiral Insecticide Indoxacarb in Zebrafish (Danio rerio)

Ketamine and Norketamine: Enantioresolution and Enantioselective Aquatic Ecotoxicity Studies

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

Contact Info

Product

Resources

About