Degradation of fluoroquinolone antibiotics and identification of metabolites/transformation products by liquid chromatography–tandem mass spectrometry

Maia, Alexandra S.; Ribeiro, Ana R.; Amorim, Catarina L.; Barreiro, Juliana Cristina; Cass, Quézia B.; Castro, Paula M. L.; Tiritan, Maria Elizabeth

doi:10.1016/j.chroma.2014.01.069

Cited by 105 publications

(45 citation statements)

References 68 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%

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%

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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“…Concerning antibiotics, there are many reports regarding biodegradation [100,101], but very few citations about enantioselectivity in degradation studies. In our recent work, concerning biodegradation of racemic-ofloxacin and (S)-ofloxacin (levofloxacin) by an activated sludge consortium, enantioselective degradation was observed with the (S)-enantiomer from the racemic mixture being degraded at higher extents and the degradation of the enantiopure (S)-ofloxacin leading to enrichment of the R-form [77].…”

Section: Biodegradation Studies Of Chiral Drugsmentioning

confidence: 99%

Chiral Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction

et al. 2017

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Abstract:The importance of stereochemistry for medicinal chemistry and pharmacology is well recognized and the dissimilar behavior of enantiomers is fully documented. Regarding the environment, the significance is equivalent since enantiomers of chiral organic pollutants can also differ in biodegradation processes and fate, as well as in ecotoxicity. This review comprises designed biodegradation studies of several chiral drugs and pesticides followed by enantioselective analytical methodologies to accurately measure the enantiomeric fraction (EF). The enantioselective monitoring of microcosms and laboratory-scale experiments with different environmental matrices is herein reported. Thus, this review focuses on the importance of evaluating the EF variation during biodegradation studies of chiral pharmaceuticals, drugs of abuse, and agrochemicals and has implications for the understanding of the environmental fate of chiral pollutants.

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“…FP1, and Rhodococcus sp. S2 transformed norfloxacin and liberated 60.5 % of the fluorine supplied during four successive feedings in the form of fluoride (Maia et al 2014). L. portucalensis F11 alone completely removed up to 2 μM of norfloxacin from the medium, but achieved a defluorination of only about 38 % (Amorim et al 2014b).…”

Section: Quinolonesmentioning

confidence: 97%

“…FP1, and Rhodococcus sp. S2 in the presence of acetate as a cosubstrate (Amorim et al 2014b;Maia et al 2014). A mixed culture of these three strains released fluoride during successive feedings of ciprofloxacin at a steady, but lower rate compared to the elimination of the substrate itself.…”

Section: Quinolonesmentioning

confidence: 98%

“…A mixed culture of these three strains released fluoride during successive feedings of ciprofloxacin at a steady, but lower rate compared to the elimination of the substrate itself. Of the fluorine supplied, 62 % was transformed to fluoride at the end of the test period (Maia et al 2014). As a pure strain, L. portucalensis F11 was able to transform 0.8 μM of ciprofloxacin completely, but without defluorination to be seen.…”

Section: Quinolonesmentioning

confidence: 99%

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The biodegradation vs. biotransformation of fluorosubstituted aromatics

Kiel

Engesser

2015

Appl Microbiol Biotechnol

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Fluoroaromatics are widely and--in recent years--increasingly used as agrochemicals, starting materials for chemical syntheses and especially pharmaceuticals. This originates from the special properties the carbon-fluorine bond is imposing on organic molecules. Hence, fluoro-substituted compounds more and more are considered to be important potential environmental contaminants. On the other hand, the microbial potentials for their transformation and mineralization have received less attention in comparison to other haloaromatics. Due to the high electronegativity of the fluorine atom, its small size, and the extraordinary strength of the C-F bond, enzymes and mechanisms known to facilitate the degradation of chloro- or bromoarenes are not necessarily equally active with fluoroaromatics. Here, we review the literature on the microbial degradation of ring and side-chain fluorinated aromatic compounds under aerobic and anaerobic conditions, with particular emphasis being placed on the mechanisms of defluorination reactions.

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Degradation of fluoroquinolone antibiotics and identification of metabolites/transformation products by liquid chromatography–tandem mass spectrometry

Cited by 105 publications

References 68 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 Analysis of Pesticides and Drugs of Environmental Concern: Biodegradation and Enantiomeric Fraction

The biodegradation vs. biotransformation of fluorosubstituted aromatics

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