Enantioselective degradation of the organophosphorus insecticide isocarbophos in Cupriavidus nantongensis X1T: Characteristics, enantioselective regulation, degradation pathways, and toxicity assessment

Fang, Liancheng; Xu, Luyuan; Zhang, Nan; Shi, Qiongying; Shi, Taozhong; Ma, Xiaoli; Wu, Xiangwei; Li, Qing X.; Hua, Rimao

doi:10.1016/j.jhazmat.2021.126024

Cited by 18 publications

(7 citation statements)

References 41 publications

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“…It was previously reported that the X1 T strain is well known to have a great ability to degrade eight kinds of organophosphorus insecticides [ 40 , 41 , 46 ]. Organophosphate pesticides (OPs) can be degraded by various enzymes expressed in micro-organisms and mammals, including OP acid anhydrolase (OPAA) from rabbit tissue samples, OP-degrading hydrolases (OPHs) such as phosphotriesterase (PTE) and organophosphorus degradation enzyme (OPD), methyl parathion hydrolase (MPH) and glycerophosphodiesterase (GpdQ) from soil-dwelling microorganisms [ 47 ].…”

Section: Discussionmentioning

confidence: 99%

Efficient Knocking Out of the Organophosphorus Insecticides Degradation Gene opdB in Cupriavidus nantongensis X1T via CRISPR/Cas9 with Red System

Zhang

Geng

et al. 2023

IJMS

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Cupriavidus nantongensis X1T is a type strain of the genus Cupriavidus, that can degrade eight kinds of organophosphorus insecticides (OPs). Conventional genetic manipulations in Cupriavidus species are time-consuming, difficult, and hard to control. The clustered regularly interspaced short palindromic repeat (CRISPR)/associated protein 9 (Cas9) system has emerged as a powerful tool for genome editing applied in prokaryotes and eukaryotes due to its simplicity, efficiency, and accuracy. Here, we combined CRISPR/Cas9 with the Red system to perform seamless genetic manipulation in the X1T strain. Two plasmids, pACasN and pDCRH were constructed. The pACasN plasmid contained Cas9 nuclease and Red recombinase, and the pDCRH plasmid contained the dual single-guide RNA (sgRNA) of organophosphorus hydrolase (OpdB) in the X1T strain. For gene editing, two plasmids were transferred to the X1T strain and a mutant strain in which genetic recombination had taken place, resulting in the targeted deletion of opdB. The incidence of homologous recombination was over 30%. Biodegradation experiments suggested that the opdB gene was responsible for the catabolism of organophosphorus insecticides. This study was the first to use the CRISPR/Cas9 system for gene targeting in the genus Cupriavidus, and it furthered our understanding of the process of degradation of organophosphorus insecticides in the X1T strain.

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Section: Discussionmentioning

confidence: 99%

Efficient Knocking Out of the Organophosphorus Insecticides Degradation Gene opdB in Cupriavidus nantongensis X1T via CRISPR/Cas9 with Red System

Zhang

Geng

et al. 2023

IJMS

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“…The use of pesticides has also been gradually increasing in recent years. In 2018, approximately 300,000 tonnes of pesticides were applied in China [13]. Organophosphorus pesticides (OPs) account for one-third of all other agrochemicals used [14].…”

Section: Introductionmentioning

confidence: 99%

“…Organophosphorus pesticides (OPs) account for one-third of all other agrochemicals used [14]. In addition, more than 99.9% of pesticides end up in the environment, causing serious environmental pollution and severe risks of human exposure [13,15]. Numerous research have shown that the high use of OPs prejudicial to health [16,17].…”

Section: Introductionmentioning

confidence: 99%

The association of isocarbophos and isofenphos with different types of glucose metabolism: the role of inflammatory indicators Running Title: Isocarbophos, isofenphos, inflammatory indicators, and glucose metabolism

Geng

Wei

Wang

et al. 2023

Preprint

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Aims Our investigation focused on the associations between isocarbophos and isofenphos with impaired fasting glucose (IFG) and type 2 diabetes mellitus (T2DM), as well as how much of these associations might be accounted for by markers of inflammation. Methods There were 2701 participants in a case-control study. Plasma isocarbophos and isofenphos concentrations were measured using gas chromatography and triple quadrupole tandem mass spectrometry. Generalized linear models were used to calculate the relationships between plasma isofenphos and isocarbophos levels with inflammatory factor levels and T2DM. Inflammatory indicators were used as mediators to estimate the mediating effects on the above associations. Results Isocarbophos and isofenphos were positively related with T2DM after adjusting for other factors. The odds ratio (OR) (95% confidence interval (CI)) for T2DM was 4.1% (OR (95% CI): 1.041 (1.015, 1.068)) and the odds ratio (95% CI) for IFG was 6.6% (OR (95% CI): 1.066 (1.009, 1.127)) per unit rise in ln-isocarbophos. The incidence of T2DM increased by 6.4% for every 1 unit more of ln-isofenphos (OR (95% CI): 1.064 (1.041, 1.087)). Additionally, a 100% rise in ln-isocarbophos was linked to 3.3% higher ln-HOMA2IR and a 0.029 mmol/L higher glycosylated hemoglobin A1c (HbA1c) (95% CI: 0.007, 0.051). While a 100% rise in ln-isofenphos was linked to increases in ln-HOMA2 (95% CI: 1.6%, 5.2%) and ln-HOMA2IR (95% CI: 3.6%, 8.1%) of 5.8% and 3.4%, respectively. Furthermore, white blood cell (WBC) and neutrophilic (NE) were found to be mediators in the relationship between isocarbophos and T2DM, and the corresponding proportions were 17.12% and 17.67%, respectively. Conclusion Isofenphos and isocarbophos are associated with IFG and T2DM in the rural Chinese population, and the inflammatory indicators (WBC and NE) have a significant role in this relationship.

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“…Di et al 40,41 exhibited that the developmental toxicity or acute toxicity of (S)-isocarbophos to three model nontarget species (i.e., Danio rerio, Gobiocypris rarus, and Oryzias latipes) or four nontarget organisms (i.e., Apis mellifera L., Bombyx mori, Trichogramma nubilale, and E. fetida) was 2.9−101 times or up to 232 times greater than that of (R)-isocarbophos upon 24, 48, 72, or 96 h of exposure, respectively, and the enantioselective bioaccumulation of (Rac)-isocarbophos in earthworms was detected with an enantioenrichment of (R)-isocarbophos. Fang et al 42 uncovered that the rate constant of (R)-isocarbophos degradation was 42-fold higher than that of (S)-isocarbophos in an isolated bacterial strain Cupriavidus nantongensis X1 T , and the acute and chronic biotoxicity of (R)-isocarbophos to nontarget species such as D. rerio and Pseudokirchneriella subcapitata was larger than that of (S)-isocarbophos. These available pieces of evidence strongly suggest that the environmental safety of chiral isocarbophos needs to be assessed by using the individual enantiomers.…”

Section: ■ Introductionmentioning

confidence: 99%

“…fetida) was 2.9–101 times or up to 232 times greater than that of ( R )-isocarbophos upon 24, 48, 72, or 96 h of exposure, respectively, and the enantioselective bioaccumulation of ( Rac )-isocarbophos in earthworms was detected with an enantioenrichment of ( R )-isocarbophos. Fang et al uncovered that the rate constant of ( R )-isocarbophos degradation was 42-fold higher than that of ( S )-isocarbophos in an isolated bacterial strain Cupriavidus nantongensis X1 T , and the acute and chronic biotoxicity of ( R )-isocarbophos to nontarget species such as D. rerio and Pseudokirchneriella subcapitata was larger than that of ( S )-isocarbophos.…”

Section: Introductionmentioning

confidence: 99%

Dissecting the Enantioselective Neurotoxicity of Isocarbophos: Chiral Insight from Cellular, Molecular, and Computational Investigations

Wang

Peng

et al. 2023

Chem. Res. Toxicol.

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Chiral organophosphorus pollutants are found abundantly in the environment, but the neurotoxicity risks of these asymmetric chemicals to human health have not been fully assessed. Using cellular, molecular, and computational toxicology methods, this story is to explore the static and dynamic toxic actions and its stereoselective differences of chiral isocarbophos toward SH-SY5Y nerve cells mediated by acetylcholinesterase (AChE) and further dissect the microscopic basis of enantioselective neurotoxicity. Cell-based assays indicate that chiral isocarbophos exhibits strong enantioselectivity in the inhibition of the survival rates of SH-SY5Y cells and the intracellular AChE activity, and the cytotoxicity of (S)-isocarbophos is significantly greater than that of (R)-isocarbophos. The inhibitory effects of isocarbophos enantiomers on the intracellular AChE activity are dose-dependent, and the half-maximal inhibitory concentrations (IC50) of (R)-/(S)-isocarbophos are 6.179/1.753 μM, respectively. Molecular experiments explain the results of cellular assays, namely, the stereoselective toxic actions of isocarbophos enantiomers on SH-SY5Y cells are stemmed from the differences in bioaffinities between isocarbophos enantiomers and neuronal AChE. In the meantime, the modes of neurotoxic actions display that the key amino acid residues formed strong noncovalent interactions are obviously different, which are related closely to the molecular structural rigidity of chiral isocarbophos and the conformational dynamics and flexibility of the substrate binding domain in neuronal AChE. Still, we observed that the stable “sandwich-type π–π stacking” fashioned between isocarbophos enantiomers and aromatic Trp-86 and Tyr-337 residues is crucial, which notably reduces the van der Waals’ contribution (ΔG vdW) in the AChE–(S)-isocarbophos complexes and induces the disparities in free energies during the enantioselective neurotoxic conjugations and thus elucidating that (S)-isocarbophos mediated by synaptic AChE has a strong toxic effect on SH-SY5Y neuronal cells. Clearly, this effort can provide experimental insights for evaluating the neurotoxicity risks of human exposure to chiral organophosphates from macroscopic to microscopic levels.

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Enantioselective degradation of the organophosphorus insecticide isocarbophos in Cupriavidus nantongensis X1T: Characteristics, enantioselective regulation, degradation pathways, and toxicity assessment

Cited by 18 publications

References 41 publications

Efficient Knocking Out of the Organophosphorus Insecticides Degradation Gene opdB in Cupriavidus nantongensis X1T via CRISPR/Cas9 with Red System

Efficient Knocking Out of the Organophosphorus Insecticides Degradation Gene opdB in Cupriavidus nantongensis X1T via CRISPR/Cas9 with Red System

The association of isocarbophos and isofenphos with different types of glucose metabolism: the role of inflammatory indicators Running Title: Isocarbophos, isofenphos, inflammatory indicators, and glucose metabolism

Dissecting the Enantioselective Neurotoxicity of Isocarbophos: Chiral Insight from Cellular, Molecular, and Computational Investigations

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