Enantioselective determination of representative profens in wastewater by a single-step sample treatment and chiral liquid chromatography–tandem mass spectrometry

Caballo, Carmen; Sicilia, María Dolores; Rubio, Soledad

doi:10.1016/j.talanta.2014.11.016

Cited by 59 publications

(27 citation statements)

References 33 publications

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“…Although ibuprofen is marketed as a racemic mixture, only the active S‐(+)‐enantiomer was detected in influent wastewater samples (0.35 ± 0.09 μg l −1 ). It has been reported that R‐(−)‐ibuprofen undergoes chiral inversion during metabolism causing excess of the S‐(+)‐enantiomer in urine . This effect was reflected in this study in the higher concentrations of this enantiomer in influent wastewater.…”

Section: Resultssupporting

confidence: 50%

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Simultaneous enantiomeric analysis of pharmacologically active compounds in environmental samples by chiral LC–MS/MS with a macrocyclic antibiotic stationary phase

Camacho‐Muñoz

Kasprzyk-Hordern

2017

J. Mass Spectrom.

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This paper presents a multi-residue method for direct enantioselective separation of chiral pharmacologically active compounds in environmental matrices. The method is based on chiral liquid chromatography and tandem mass spectrometry detection. Simultaneous chiral discrimination was achieved with a macrocyclic glycopeptide-based column with antibiotic teicoplanin as a chiral selector working under reverse phase mode. For the first time, enantioresolution was reported for metabolites of ibuprofen: carboxyibuprofen and 2-hydroxyibuprofen with this chiral stationary phase. Moreover, enantiomers of chloramphenicol, ibuprofen, ifosfamide, indoprofen, ketoprofen, naproxen and praziquantel were also resolved. The overall performance of the method was satisfactory in terms of linearity, precision, accuracy and limits of detection. The method was successfully applied for monitoring of pharmacologically active compounds at enantiomeric level in influent and effluent wastewater and in river water. In addition, the chiral recognition and analytical performance of the teicoplanin-based column was critically compared with that of the α -acid glycoprotein chiral stationary phase. Copyright © 2017 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 50%

“…S‐(+)‐naproxen was detected at a mean concentration of 0.37 ± 0.05 μg l −1 in influent wastewater. Although the R‐enantiomer was not detected in this study, chiral inversion has been reportedly previously . The average concentration of S‐(+)‐O‐desmethylnaproxen reached 0.23 ± 0.05 μg l −1 .…”

Section: Resultssupporting

confidence: 42%

Simultaneous enantiomeric analysis of pharmacologically active compounds in environmental samples by chiral LC–MS/MS with a macrocyclic antibiotic stationary phase

Camacho‐Muñoz

Kasprzyk-Hordern

2017

J. Mass Spectrom.

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“…Nevertheless, only a few therapeutic classes of chiral PACs Enantioselectivity has also been demonstrated in several ecotoxicological studies, regarding the survival and sublethal effects of highly ecologically relevant end points, such as growth, reproduction, and feeding rate [47,48]. Nevertheless, only a few therapeutic classes of chiral PACs have been reported in environmental matrices, concerning the quantification of their enantiomers [43][44][45][49][50][51][52][53][54][55]. Additionally, the biodegradation in biotic mediums, as occurs in secondary treatment of WWTPs, adds complexity to this issue since it is also expected to be enantioselective [8,56,57].…”

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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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“…Solvent extraction coupled to ultrasonic baths [9] was already reported and only a few works reported the use of liquid-liquid extraction (LLE) [11,62] and dispersive liquid-liquid microextraction (DLLME) [63,64]. One recent work described the use of supramolecular solvent (SUPRAS) microextraction [65] and another one microwave assisted extraction for sludge [66]. Since 2009, SPE has been generally used as sample preparation procedure in enantioselective environmental analysis [13,57,61,62,64,.…”

Section: Basic Concepts Of Chiralitymentioning

confidence: 99%

“…GC-MS/MS was employed in the first works reporting enantioselective environmental analysis by indirect methods using enantiomerically-pure derivatizing reagents [9,60], or by direct methods using CSPs [61,85]. Despite indirect [70,83] and direct methods [67,80,89] remaining in some studies, LC-MS/MS has been the analytical technique of election for illicit drugs and pharmaceutical while GC-MS and GC-ECD have been the most used for pesticides [13,54,55,57,62,[64][65][66][67][68][69][71][72][73][74][75][76][77][80][81][82]84,87,88,[90][91][92]95,[100][101][102][103][104][105]. Although much less used, LC-DAD, LC-UV and LC-FD detection have been used in some of the studies [11,26,27,…”

Section: Basic Concepts Of Chiralitymentioning

confidence: 99%

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

Ribeiro

Maia

et al. 2017

Symmetry

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Abstract:In recent decades, the presence of micropollutants in the environment has been extensively studied due to their high frequency of occurrence, persistence and possible adverse effects to exposed organisms. Concerning chiral micropollutants in the environment, enantiomers are frequently ignored and enantiomeric composition often neglected. However, enantioselective toxicity is well recognized, highlighting the need to include enantioselectivity in environmental risk assessment. Additionally, the information about enantiomeric fraction (EF) is crucial since it gives insights about: (i) environmental fate (i.e., occurrence, distribution, removal processes and (bio)degradation); (ii) illicit discharges; (iii) consumption pattern (e.g., illicit drugs, pharmaceuticals used as recreational drugs, illicit use of pesticides); and (iv) enantioselective toxicological effects. Thus, the purpose of this paper is to provide a comprehensive review about the enantioselective occurrence of chiral bioactive compounds in aquatic environmental matrices. These include pharmaceuticals, illicit drugs, pesticides, polychlorinated biphenyls (PCBs) and polycyclic musks (PCMs). Most frequently analytical methods used for separation of enantiomers were liquid chromatography and gas chromatography methodologies using both indirect (enantiomerically pure derivatizing reagents) and direct methods (chiral stationary phases). The occurrence of these chiral micropollutants in the environment is reviewed and future challenges are outlined.

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Enantioselective determination of representative profens in wastewater by a single-step sample treatment and chiral liquid chromatography–tandem mass spectrometry

Cited by 59 publications

References 33 publications

Simultaneous enantiomeric analysis of pharmacologically active compounds in environmental samples by chiral LC–MS/MS with a macrocyclic antibiotic stationary phase

Simultaneous enantiomeric analysis of pharmacologically active compounds in environmental samples by chiral LC–MS/MS with a macrocyclic antibiotic stationary phase

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

Occurrence of Chiral Bioactive Compounds in the Aquatic Environment: A Review

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