Enantiomeric Resolution and Biotoxicity of Methamidophos

Lin, Kunde; Zhou, Shanshan; Xu, Chao; Liu, Weiping

doi:10.1021/jf061547l

Cited by 79 publications

(91 citation statements)

References 20 publications

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“…[5][6][7][8][12][13][14]32,33 In this investigation, satisfactory resolution of salithion enantiomers was achieved on all of the three CSPs of derivative cellulose and amylase we selected, among which the Chiralpak AD column offered the highest a of more than 1.20 suggesting a baseline resolution. 34 Moreover, the chiral recognition ability of Chiralpak AD also seems better than that of Chiralcel OB and Chiralpak OT(1), the two columns that have been used to separate salithion enantiomers previously.…”

Section: Results and Discussion Enantiomer Separation And Identificationmentioning

confidence: 89%

“…Recently, increasing studies have demonstrated that enantioselectivity also exists in the in vivo acute aquatic toxicity of chiral OPs. [5][6][7]9,10,[12][13][14] Salithion ((RS)-2-methoxy-4H-1,3,2 k 5 benzodioxaphosphorin 2-sulfide), an organophosphorus pesticide, which was first synthesized in 1963, is used for control of a broad spectrum of insect pests in orchards or vegetables. 15,16 In recent years, because of its high efficacy, low cost, and capacity to control pyrethrin-resistant pests, 17 salithion has been considered as an effective alternative of the highly toxic OPs in China.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, high-performance liquid chromatography (HPLC) with chiral stationary phase (CSP) column has been employed to prepare small scale of individual enantiomers from racemic chiral OPs. [5][6][7][8][9][10][11][12][13][14] Two chiral HPLC columns, Chiralcel OB [Cellulose tribenzoate] 21 and Chiralpak OT (1)[poly(triphenylmethylmethacrylate)] 24 have been used for enantiomeric separation of salithion. However, we consider that both of them may not be suitable for preparing salithion enantiomers because the majority of labs worldwide may not possess these high analyte-specific columns.…”

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confidence: 99%

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Separation and toxicity of salithion enantiomers

Zhou¹,

Lin²,

Li³

et al. 2009

Chirality

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Enantioseletive toxicities of chiral pesticides have become an environmental concern recently. In this study, we evaluated the enantiomeric separation of salithion on a suite of commercial chiral columns and assessed the toxicity of enantiomers toward butyrylcholinesterase and Daphnia magna. Satisfactory separations of salithion enantiomers could be achieved on all tested columns, that is, Chiralcel OD, Chiralcel OJ, and Chiralpak AD column. However, the Chiralpak AD column offered the best separation and was chosen to prepare micro-scale of pure salithion enantiomers for subsequent bioassays. The first and second enantiomers eluted on the Chiralpak AD column were further confirmed to be (-)-S-salithion and (+)-R-salithion, respectively. The half inhibition concentrations to butyrylcholinesterase of racemate, (+)-R-salithion, and (-)-S-salithion were 33.09, 2.92, and 15.60 mg/l, respectively, showing (+)-R-enantiomer being about 5.0 times more potent than its (-)-S-form. However, the median lethal concentrations (96 h) of racemate, (+)-R-salithion, and (-)-S-salithion toward D. magna were 3.54, 1.10, and 0.36 microg/l, respectively, suggesting that (-)-S-salithion was about 3.0 times more toxic than (+)-R-form. Racemic salithion was less toxic than either of the enantiomers in both bioassays, suggesting that antagonistic interactions might occur between the enantiomers during the toxication action. This work reveals that the toxicity of salithion toward butyrylcholinesterase and D. magna is enantioselective, and this factor should be taken into consideration in the environmental risk assessment of salithion.

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Section: Results and Discussion Enantiomer Separation And Identificationmentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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Separation and toxicity of salithion enantiomers

Zhou¹,

Lin²,

Li³

et al. 2009

Chirality

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“…9,10 Studies showed that there was obvious enantioselectivity in their acute toxicity 11 and, also, inhibition of AChE activity. 12,13 The basis for the difference between stereoisomers lies in the three-dimensional nature of organic drug molecules and their target receptors, which are most often proteins. This provides a basis for the spatial recognition of stereoisomeric forms of chiral molecules and critical binding sites for drug-protein interactions.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective interaction with acetylcholinesterase of an organophosphate insecticide fenamiphos

Wang

Zhang

et al. 2009

Chirality

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Enantioselectivity in the environmental behavior and ecotoxicity of chiral pesticide is widely observed. However, the investigation of the enantioselective mechanisms remains limited. In this study, we used fenamiphos (FAP), an organophosphorus insecticide, to study enantioselectivity in toxicity to arthropods and the inhibition potential towards acetylcholinesterase (AChE) in the rat pheochromocytoma 12 (PC 12) cell line. Furthermore, we carried out molecular docking to help explain the mechanisms of enantioselective toxicity of FAP. The two enantiomers of FAP were successfully separated and identified as R-(+)-FAP and S-(-)-FAP. Toxicological assays revealed that R-(+)-FAP was 2.4-fold more toxic than S-(-)-FAP to Daphnia magna and approximately threefold more to PC12 cells. Based on molecular docking results, dynamic simulation shows that strong hydrophobic interactions and a key hydrogen bond can only exist between R-(+)-FAP and AChE, which helps explain the preference of R-(+) binding to AChE over that of the S-(-)-enantiomer, and supports our biological results. Our present study considers the impact of stereochemistry on ecotoxicological effects and, ultimately, on development of environmentally safe, insecticidally efficient pesticides.

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“…[56][57][58] Recently, enantiomeric separation and quantification of various chiral pesticides by highperformance liquid chromatography and capillary electrophoresis have been reported by various researchers. [59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75] The general advantages of ICP-MS detection for chiral pesticide determinations in complex environmental samples have been reported. 76) Scientists determined the S and R isomers of metolachlor (3) in water by enantioselective enzyme immunoassay.…”

Section: Chiral Separationsmentioning

confidence: 99%

Chiral pesticides

Sekhon

2009

Journal of Pesticide Science

108

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The enantiomers of chiral pesticides are often metabolized at different rates. In agriculture, the preferred chiral form of a pesticide is more effective at lower application rates or more specific toward a targeted pest. Other advantages of chiral pure pesticides include greater environmental safety, reduced cost, greater specificity and extended patent life. Recent progress in optical resolution, asymmetric synthesis and biocatalysis of chiral pesticides has been described. Techniques to separate enantiomers with chiral HPLC and GC columns, electrophoresis and mass spectrometry have been reported. Chiral chase is actively pursuing asymmetric hydrogenation for the manufacture of a pure single-enantiomer pesticide. Enantioselectivity occurs in pesticidal activities toward target organisms as well as non-targeted organisms. There is a need to characterize both enantiomers of chiral pesticides in order to have an accurate understanding of their distribution and fate in the environment. Enantiomeric analysis can be useful in this aim and this is an important consideration in the risk assessment of pesticides. Use of only the target-active enantiomer of pesticides should be encouraged as it will reduce the pollutant load, provided it has no adverse impact on non-target organisms.

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Enantiomeric Resolution and Biotoxicity of Methamidophos

Cited by 79 publications

References 20 publications

Separation and toxicity of salithion enantiomers

Separation and toxicity of salithion enantiomers

Enantioselective interaction with acetylcholinesterase of an organophosphate insecticide fenamiphos

Chiral pesticides

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