Enantioselective quantification of fluoxetine and norfluoxetine by HPLC in wastewater effluents

Ribeiro, Ana R.; Maia, Alexandra S.; Moreira, Irina S.; Afonso, Carlos; Castro, Paula M. L.; Tiritan, Maria Elizabeth

doi:10.1016/j.chemosphere.2013.09.118

Cited by 50 publications

(45 citation statements)

References 48 publications

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“…The method was validated according to previous works [2,36,[43][44][45][46] considering the following parameters: selectivity, linearity and range, limits of detection and quantification, accuracy, recovery and precision.…”

Section: Methods Validation Parametersmentioning

confidence: 99%

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Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry

Ribeiro

Santos

Maia

et al. 2014

Journal of Chromatography A

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a b s t r a c tThe interest for environmental fate assessment of chiral pharmaceuticals is increasing and enantioselective analytical methods are mandatory. This study presents an enantioselective analytical method for the quantification of seven pairs of enantiomers of pharmaceuticals and a pair of a metabolite. The selected chiral pharmaceuticals belong to three different therapeutic classes, namely selective serotonin reuptake inhibitors (venlafaxine, fluoxetine and its metabolite norfluoxetine), beta-blockers (alprenolol, bisoprolol, metoprolol, propranolol) and a beta 2 -adrenergic agonist (salbutamol). The analytical method was based on solid phase extraction followed by liquid chromatography tandem mass spectrometry with a triple quadrupole analyser. Briefly, Oasis® MCX cartridges were used to preconcentrate 250 mL of water samples and the reconstituted extracts were analysed with a Chirobiotic TM V under reversed mode. The effluent of a laboratory-scale aerobic granular sludge sequencing batch reactor (AGS-SBR) was used to validate the method. Linearity (r 2 > 0.99), selectivity and sensitivity were achieved in the range of 20-400 ng L −1 for all enantiomers, except for norfluoxetine enantiomers which range covered 30-400 ng L −1 . The method detection limits were between 0.65 and 11.5 ng L −1 and the method quantification limits were between 1.98 and 19.7 ng L −1 . The identity of all enantiomers was confirmed using two MS/MS transitions and its ion ratios, according to European Commission Decision 2002/657/EC. This method was successfully applied to evaluate effluents of wastewater treatment plants (WWTP) in Portugal. Venlafaxine and fluoxetine were quantified as non-racemic mixtures (enantiomeric fraction / 0.5). The enantioselective validated method was able to monitor chiral pharmaceuticals in WWTP effluents and has potential to assess the enantioselective biodegradation in bioreactors. Further application in environmental matrices as surface and estuarine waters can be exploited.

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Section: Methods Validation Parametersmentioning

confidence: 99%

“…The optimized SPE procedure was carried out accordingly to work published elsewhere [2,36]. Several sample volumes of a 220 ng L −1 spiked AGS-SBR sample were tested (25, 50, 100, 250, 500, 1000 mL) to determine the adequate volume to achieve the highest recovery.…”

Section: Solid Phase Extractionmentioning

confidence: 99%

Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry

Ribeiro

Santos

Maia

et al. 2014

Journal of Chromatography A

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“…29,47 Na biodegradação, ecotoxicidade e destino ambiental, o reconhecimento de enantiosseletividade é essencial para fornecer uma avaliação de risco mais realista de compostos quirais. [48][49][50][51][52][53][54] 56 constatando-se que a maioria desses estudos é realizada somente com misturas racémicas. Um estudo recente realizado por Connors et al 57 demonstrou que, em modelos animais, o metabolismo enantiosseletivo dos FQ não pode ser diretamente extrapolado a partir dos dados disponíveis para o organismo humano.…”

Section: Fármacos Quiraisunclassified

“…Pelo contrário, a degradação do ATE e FLX foi não-enantiosseletiva. Num outro estudo, 53 a degradação dos enantiômeros da FLX em efluentes de águas residuais foi quase total após 21 dias, não se tendo verificado mais remoção, nem degradação enantiosseletiva durante o processo de degradação. Também a biodegradação da FLX racémica e dos seus enantiômeros separados pela estirpe bacteriana Labrys portucalensis F11 foi estudada, 52 tendo-se observado a degradação completa dos dois enantiômeros separados, com degradação preferencial da (R)-FLX em 24 dias e degradação da (S)-FLX em 32 dias, sem formação observada do metabolito NFLX nem ocorrência de enantiomerização.…”

Section: Seletores Quirais Para Cromatografiaunclassified

“…62,66,86 Não obstante, os dois métodos têm sido utilizados até ao momento. 71 28,[50][51][52][53][54]68,69,72,77,83,90 Uma FEQ baseada em poli-prolina foi descrita num estudo de biodegradação com varfarina, sob o modo de eluição normal. 48 Três outros estudos com modo normal de eluição foram publicados em 2012, dois deles sobre pesquisa de beta-bloqueadores em águas superficiais 90,91 e um trabalho sobre a biodegradação enantiosseletiva da varfarina em solos.…”

Section: Tendências Analíticas Para Amostras Quirais No Ambiente E Emunclassified

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Chiral Pharmaceuticals in Diverse Environmental Matrices: Occurrence, Removal and Toxicity

Ribeiro¹,

Afonso²,

Castro³

et al. 2016

Química Nova

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Chiral Pharmaceuticals

Tiritan

Ribeiro

Fernandes

et al. 2016

Kirk-Othmer Encyclopedia of Chemical Technology

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The implication of chirality in pharmaceuticals is briefly reviewed, presenting the basic concepts and the chiral recognition phenomenon in biological systems. The importance to recognize enantiomers of chiral pharmaceuticals, both in pharmacology and environmental fields, is emphasized and many examples were selected to demonstrate the significance of chirality in both areas. Methodologies to obtain single enantiomers and to control the enantiomeric fraction associated with enantioseparation of chiral pharmaceuticals are also discussed. Several enantioselective methods using liquid chromatography (LC) with chiral stationary phases (CSPs) in biomedical and environmental fields are presented. The most used CSPs, their advantages and drawbacks, are swiftly revised.

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Enantioselective quantification of fluoxetine and norfluoxetine by HPLC in wastewater effluents

Cited by 50 publications

References 48 publications

Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry

Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry

Chiral Pharmaceuticals in Diverse Environmental Matrices: Occurrence, Removal and Toxicity

Chiral Pharmaceuticals

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