Stereoselective determination of benalaxyl in plasma by chiral high‐performance liquid chromatography with diode array detector and application to pharmacokinetic study in rabbits

Qiu, Jing; Wang, Qiuxia; Zhu, Wentao; Jia, Guifang; Wang, Xinquan; Zhou, Zhiqiang

doi:10.1002/chir.20341

Cited by 23 publications

(12 citation statements)

References 15 publications

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“…EF of (−)‐R‐BX is defined by eq. 1.EF =Peak areas of the where (−) and (+) are the first and second enantiomers determined by the result of polarimeter in previous works 11. The EF for racemate is 0.50, whereas preferential degradation of the (+) or (−) yields EF <0.50 and >0.50, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…BX has a chiral carbon and consists of two enantiomers. The activity of BX is mainly attributed to the (−)‐R‐enantiomer 11. A number of methods have been reported for the determination of BX residues in various samples, such as enzyme‐linked immunosorbent assay in water and wine12, 13 and gas chromatography in vegetables and fruits 14.…”

Section: Introductionmentioning

confidence: 99%

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Stereoselective metabolism of benalaxyl in liver microsomes from rat and rabbit

et al. 2011

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Benalaxyl (BX), methyl-N-phenylacetyl-N-2,6-xylyl alaninate, is a potent acylanilide fungicide and consist of a pair of enantiomers. The stereoselective metabolism of BX was investigated in rat and rabbit microsomes in vitro. The degradation kinetics and the enantiomer fraction (EF) were determined using normal high-performance liquid chromatography with diode array detection and a cellulose-tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase (CDMPC-CSP). The t(1/2) of (-)-R-BX and (+)-S-BX in rat liver microsomes were 22.35 and 10.66 min of rac-BX and 5.42 and 4.03 of BX enantiomers. However, the t(1/2) of (-)-R-BX and (+)-S-BX in rabbit liver microsomes were 11.75 and 15.26 min of rac-BX and 5.66 and 9.63 of BX enantiomers. The consequence was consistent with the stereoselective toxicokinetics of BX in vitro. There was no chiral inversion from the (-)-R-BX to (+)-S-BX or inversion from (+)-S-BX to (-)-R-BX in both rabbit and rat microsomes. These results suggested metabolism of BX enantiomers was stereoselective in rat and rabbit liver microsomes.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Stereoselective metabolism of benalaxyl in liver microsomes from rat and rabbit

et al. 2011

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“…As abundantly documented (Zhu et al 2007b;Qiu et al 2007), two enantiomers of a chiral pesticide often display differences in pharmacokinetic processes. In general, the passive processes in absorption, distribution, and excretion do not differentiate between enantiomers of a chiral drug.…”

Section: Discussionmentioning

confidence: 99%

Species differences for stereoselective metabolism of ethofumesate and its enantiomersin vitro

et al. 2009

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1. The stereoselective metabolism of ethofumesate (ETO) and its enantiomers in rabbit and rat liver microsomes have been studied by chiral high-performance liquid chromatography (HPLC) method. Two metabolites were detected in both liver microsomes in the presence of beta-nicotinamide adenine dinucleotide phosphate (NADPH). 2. The T(1/2) of (+)-ETO and (-)-ETO in rabbit liver microsomes were 12.2 and 4.7 min of rac-ETO and 25.9 and 6.7 of ETO enantiomers. However, the T(1/2) of (+)-ETO and (-)-ETO in rat liver microsomes were 5.3 and 5.9 min of rac-ETO and 7.8 and 10.6 of ETO enantiomers. The stereoselective selectivity is similar to the in vivo study. 3. After incubation of ETO enantiomers, stereoselectivity was present in the formation of ETO-OH enantiomer in rabbit liver microsomes, but stereoselectivity was not evident in rat liver microsomes. 4. There was no chiral inversion from the (+)-ETO to (-)-ETO or inversion from (-)-ETO to (+)-ETO in both rabbit and rat liver microsomes.

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“…The first eluted enantiomer was R-(2)-form and the second was S-(1)-form determined by the previous research work. 8 …”

Section: High-performance Liquid Chromatographic Analysismentioning

confidence: 97%

Stereoselective degradation of benalaxyl in tomato, tobacco, sugar beet, capsicum, and soil

Wang

Liu

et al. 2007

Chirality

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The stereoselective degradation of the racemic benalaxyl in vegetables such as tomato, tobacco, sugar beet, capsicum, and the soil has been investigated. The two enantiomers of benalaxyl in the matrix were extracted by organic solvent and determined by validated chiral high-performance liquid chromatography with a cellulose-tris-(3, 5-dimethylphenylcarbamate)-based chiral column. Rac-benalaxyl was fortified into the soil and foliar applied to vegetables. The assay method was linear over a range of concentrations (0.5-50 microg ml(-1)) and the mean recoveries in all the samples were more than 70% for the two enantiomers. The limit of detection for both enantiomers was 0.05 microg g(-1). The results in soil showed that R-(-)-enantiomer dissipated faster than S-(+)-enantiomer and the stereoselectivity might be caused by microorganisms. In tomato, tobacco, sugar, beet, and capsicum plants, there was significantly stereoselective metabolism. The preferential absorption and degradation of S-(+)-enantiomer resulted an enrichment of the R-(-)-enantiomer residue in all the vegetables.

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Stereoselective determination of benalaxyl in plasma by chiral high‐performance liquid chromatography with diode array detector and application to pharmacokinetic study in rabbits

Cited by 23 publications

References 15 publications

Stereoselective metabolism of benalaxyl in liver microsomes from rat and rabbit

Stereoselective metabolism of benalaxyl in liver microsomes from rat and rabbit

Species differences for stereoselective metabolism of ethofumesate and its enantiomersin vitro

Stereoselective degradation of benalaxyl in tomato, tobacco, sugar beet, capsicum, and soil

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