Liquid chromatography determination of the anti-androgen vinclozolin and its metabolites in rat serum

Sierra-Santoyo, Adolfo; Barton, Hugh A.; Hughes, Michael F.

doi:10.1016/j.jchromb.2004.06.002

Cited by 13 publications

(7 citation statements)

References 19 publications

(35 reference statements)

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“…It has been proposed that vinclozolin may not be stable in aqueous solutions 27. It has also been shown that vinclozolin may be degraded to the metabolites, 2‐[[(3,5‐dichlorophenyl)carbamoyl]oxy]‐2‐methyl‐3‐butenoic acid and 3,5‐dichloro‐2‐hydroxy‐2‐methylbut‐3‐enanilide, at physiological conditions in rat plasma 12. It is possible that both iprodione and vinclozolin and their metabolites are degraded in urine during storage.…”

Section: Resultsmentioning

confidence: 99%

“…The use of 3,5‐DCA as a biomarker has been suggested for several of the dicarboximide fungicides such as vinclozolin, iprodione and procymidone. Several liquid chromatography (LC) methods with ultraviolet (UV) or electrochemical (EC) detection have been reported for determination of DCA in human urine,10, 11 or in biological samples from mouse, rat and rabbit 12, 13. Although these methods may be applicable for high occupational exposures, they are insufficient for assessment of low‐level exposures in the general population.…”

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confidence: 99%

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Analysis of 3,5‐dichloroaniline as a biomarker of vinclozolin and iprodione in human urine using liquid chromatography/triple quadrupole mass spectrometry

Lindh

Littorin

Amilon

et al. 2007

Rapid Comm Mass Spectrometry

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The fungicides vinclozolin and iprodione are widely used in agriculture. These pesticides are dicarboximide fungicides containing the common moiety 3,5-dichloroaniline (3,5-DCA). It has been suggested that low-level exposures to such compounds may be associated with adverse health effects such as endocrine disruption.In this study a method using liquid chromatography triple quadrupole mass spectrometry (LC-MS/MS) was developed for the analysis of 3,5-DCA as a biomarker of exposure to these fungicides in human urine. The urine samples were treated by basic hydrolysis to degrade the fungicides, their metabolites and conjugates to 3,5-DCA. The 3,5-DCA was then extracted using toluene and derivatized using pentafluoropropionic anhydride (PFPA). Analysis of the derivative was carried out using selected reaction monitoring (SRM) in the negative ion mode. Quantification of the derivative was performed using [ 13 C 6 ] labeled 3,4-DCA as an internal standard with good precision and linearity in the range 0.1-200 ng/mL urine. The limit of detection was determined to 0.1 ng/mL. The metabolites in urine were found stable at storage in -20°C. To validate 3,5-DCA as a biomarker the method was applied in a human experimental exposure to iprodione and vinclozolin. Two healthy volunteers received 200 μg single oral doses of each pesticide followed by urine sampling during 72-120h post exposure.Between 78-107 % of the dose was recovered as 3,5-DCA in the urine after exposure.The dicarboximide fungicides vinclozolin, iprodione and procymidone are commonly used for the control of diseases on fruits, vegetables, ornamental plants and turf grasses. Human exposure to these fungicides can occur from occupational use but the general public may also be exposed via ingestion of contaminated produce.Vinclozolin has been classified as an endocrine disrupting chemical and it has been suggested that low-level exposures may be associated with adverse health effects. Vinclozolin is an androgen receptor antagonist with effects shown in adult, pubertal and neonatal rodents. [1][2][3][4] In addition, epigenetic transgenerational effects have been observed in rats. 5 The US EPA suggests that vinclozolin-induced malformations of the male reproductive tract are highly plausible to occur in humans. 6 However, only one report on human effects has been published and in that no antiandrogenic or reproductive effects were found after occupational exposure to vinclozolin. 7 Iprodione is chemically similar in structure to vinclozolin but there are few reports on its toxicity. In a study on rats by Gray et al.,8 no maternal or fetal endocrine toxicity was observed. The two fungicides contain the common moiety 3,5-dichloroaniline (3,5-DCA), which also has been found as a metabolite after exposure, this isomer has been shown to be nephrotoxic. 9 A prerequisite for epidemiological studies, and for determination of exposure-response relationships, is an accurate measurement of exposure. There is a lack of human exposure and effect data for fungicides overall, i...

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Analysis of 3,5‐dichloroaniline as a biomarker of vinclozolin and iprodione in human urine using liquid chromatography/triple quadrupole mass spectrometry

Lindh

Littorin

Amilon

et al. 2007

Rapid Comm Mass Spectrometry

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“…detection have been reported for determination of DCA in human urine 8 , or in biological samples from mouse, rat and rabbit 9,10 . Although these methods may be applicable for high occupational exposures, they are insufficient for assessment of low-level exposures in the general population.…”

Section: Research Articlementioning

confidence: 99%

Electrochemical Reduction Bahaviour of Vinclozolin Fungicide at Platinum Electrode

Sreedhar¹,

Sivaprasad²,

Naik³

et al. 2013

Chem Sci Trans

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The electrochemical behavior of vinclozolin [3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3 oxazolidine-2,4-dion] in dimethylsulfoxide was performed by cyclic voltammetry (CV) and linear sweep voltammetry (LSV). The main decomposition pathway included in the cleavage of chlorine atoms at platinum electrode. The general reduction mechanism of this compound has been suggested based on the results obtained. The peak potential and peak current were found to be depending on pH of the buffer solution. The measuring system response was linear over the vinclozolin concentration range from 1.0×10-3 to 5.0×10-7 mol L-1 and the detection limit (LOD) achieved was 1.1×10-8 mol L-1 (2.5 µg L-1) at pH 4.0. Vinclozolin was determined in spiked serum sample.

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“…A number of investigations on the residual analysis of vinclozolin in foods and soils have been conducted by gas chromatography (GC), HPLC, and mass spectrometry. [9][10][11][12][13][14][15] Solid-phase microextraction (SPME) coupled to GC analysis was evaluated for extracting trace amounts of vinclozolin in soil samples. 10 Its dissipation during storage of grape juice was analyzed by liquid-liquid extraction (LLE), gas chromatographic separation, and mass spectrometric detection.…”

Section: Introductionmentioning

confidence: 99%

“…A number of investigations on the residual analysis of vinclozolin in foods and soils have been conducted by gas chromatography (GC), HPLC, and mass spectrometry . Solid‐phase microextraction (SPME) coupled to GC analysis was evaluated for extracting trace amounts of vinclozolin in soil samples .…”

Section: Introductionmentioning

confidence: 99%

Chiral Separation and Enantioselective Degradation of Vinclozolin in Soils

et al. 2014

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Vinclozolin is a chiral fungicide with potential environmental problems. The chiral separation of the enantiomers and enantioselective degradation in soil were investigated in this work. The enantiomers were separated by high-performance liquid chromatography (HPLC) on Chiralpak IA, IB, and AZ-H chiral columns under normal phase and the influence of the mobile phase composition on the separation was also studied. Complete resolutions were obtained on all three chiral columns under optimized conditions with the same elution order of (+)/(-). The residual analysis of the enantiomers in soil was conducted using accelerate solvent extraction followed by HPLC determination. The recoveries of the enantiomers ranged from 85.7-105.7% with relative standard deviation (SD) of 0.12-3.83%, and the limit of detection (LOD) of the method was 0.013 µg/g. The results showed that the degradations of vinclozolin enantiomers in the soils followed first-order kinetics. Preferential degradation of the (-)-enantiomer was observed only in one soil with the largest |ES| value of 0.047, and no obvious enantioselective degradation was observed in other soils. It was found that the persistence of vinclozolin in soil was related to pH values based on the half-lives. The two enantiomers disappeared about 8 times faster in basic soils than that in neutral or acidic soils.

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Liquid chromatography determination of the anti-androgen vinclozolin and its metabolites in rat serum

Cited by 13 publications

References 19 publications

Analysis of 3,5‐dichloroaniline as a biomarker of vinclozolin and iprodione in human urine using liquid chromatography/triple quadrupole mass spectrometry

Analysis of 3,5‐dichloroaniline as a biomarker of vinclozolin and iprodione in human urine using liquid chromatography/triple quadrupole mass spectrometry

Electrochemical Reduction Bahaviour of Vinclozolin Fungicide at Platinum Electrode

Chiral Separation and Enantioselective Degradation of Vinclozolin in Soils

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