Analysis of chiral drugs in environmental matrices: Current knowledge and trends in environmental, biodegradation and forensic fields

Ribeiro, Ana R.; Maia, Alexandra S.; Ribeiro, Cláudia; Tiritan, Maria Elizabeth

doi:10.1016/j.trac.2019.115783

Cited by 37 publications

(9 citation statements)

References 67 publications

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“…Separation of enantiomers is undoubtedly a matter of crucial importance in diverse research areas [44], allowing to achieve different goals, such as preparative enantioresolution of chiral drugs and other analytes [177,178], monitoring enantiomeric reactions [167,179], evaluation of enantiomeric purity in quality control [180,181], food analysis [182,183], stereochemistry determination of natural compounds [184,185], pharmacokinetic [25] and environmental studies [186,187], among other applications.…”

Section: Enantioresolution Studies By Chromatographic and Electrophoretic Methods Using Hsa As Chiral Selectormentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

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The interaction between proteins and drugs or other bioactive compounds has been widely explored over the past years. Several methods for analysis of this phenomenon have been developed and improved. Nowadays, increasing attention is paid to innovative methods, such as high performance affinity liquid chromatography (HPALC) and affinity capillary electrophoresis (ACE), taking into account various advantages. Moreover, the development of separation methods for the analysis and resolution of chiral drugs has been an area of ongoing interest in analytical and medicinal chemistry research. In addition to bioaffinity binding studies, both HPALC and ACE al-low one to perform other type of analyses, namely, displacement studies and enantioseparation of racemic or enantiomeric mixtures. Actually, proteins used as chiral selectors in chromatographic and electrophoretic methods have unique enantioselective properties demonstrating suitability for the enantioseparation of a large variety of chiral drugs or other bioactive compounds. This review is mainly focused in chromatographic and electrophoretic methods using human serum albumin (HSA), the most abundant plasma protein, as chiral selector for binding affinity analysis and enantioresolution of drugs. For both analytical purposes, updated examples are presented to highlight recent applications and current trends.

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Section: Enantioresolution Studies By Chromatographic and Electrophoretic Methods Using Hsa As Chiral Selectormentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

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“…Regarding enantioselective methods for PAS analysis, liquid chromatography (LC) and gas chromatography (GC) are among the most used [9,14] for water matrices such as wastewaters and surface waters [7,15,16]. The enantioseparation can be done by a direct method using chiral stationary phases [9,17] or an indirect method through formation of diastereomers by reaction with an enantiomerically pure reagent [7,16].…”

Section: Introductionmentioning

confidence: 99%

Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters

et al. 2021

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Determination of psychoactive substances (PAS) and/or their metabolites in surface waters is crucial for environmental risk assessment, and disclosure of their enantiomeric fractions (EF) allows discrimination between consumption, direct disposal, and synthesis pathways. The aim of this study was to develop and validate an indirect method by gas chromatography coupled to mass spectrometry (GC–MS) based on derivatization using (R)-(−)-α-methoxy-α-(trifluoromethyl) phenylacetyl chloride as chiral derivatization reagent, for enantiomeric quantification of amphetamine (AMP), methamphetamine (MAMP), 3,4-methylenedioxymethamphetamine (MDMA), norketamine, buphedrone (BPD), butylone, 3,4-dimethylmethcathinone (3,4-DMMC), 3-methylmethcathinone, and quantification of 1-benzylpiperazine and 1-(4-metoxyphenyl)-piperazine. The method allowed to evaluate the occurrence, spatial distribution, and the EF of the target chiral PAS in Portuguese surface waters and in effluents from 2 wastewater treatment plants (WWTP). For that, water samples were pre-concentrated by solid phase extraction using OASIS® MCX cartridges, derivatized and further analyzed by GC–MS. Both enantiomers of AMP, (R)-MDMA, (S)-MAMP, and the first eluted enantiomer of BPD (configuration not assigned) were found in surface waters, while effluent samples showed both enantiomers of MDMA, (S)-MAMP, (R)-AMP, and the first eluted enantiomer of BPD and 3,4-DMMC. According to our knowledge, this is the first multiresidue analytical method by CG–MS enrolling cathinones, amphetamines, and piperazines. The presence of illicit synthetic cathinones in Douro River estuary is here reported for the first time, along with other amphetamine derivatives. The potential of the method to monitor consumption of the target PAS was demonstrated.

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“…Enantiomers may differ significantly in their biological response, including toxicity and potency (Guo et al 2017; Ribeiro et al 2017, 2018). Despite the well‐known importance in pharmacology of evaluating both enantiomers of a given drug, the enantiomers are often neglected in ecotoxicological studies, and the racemate is considered a unique molecular entity (Ribeiro et al 2014, 2020).…”

Section: Introductionmentioning

confidence: 99%

Ketamine and Norketamine: Enantioresolution and Enantioselective Aquatic Ecotoxicity Studies

Pérez-Pereira

Ribeiro

Teles

et al. 2021

Enviro Toxic and Chemistry

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Ketamine is a chiral drug used for various clinical purposes but often misused. It is metabolized to norketamine, an active chiral metabolite. Both substances have been detected in environmental matrices, but studies about their enantioselective toxic effects are scarce. In the present study, the enantiomers of ketamine and norketamine were separated by a semipreparative enantioselective liquid chromatography method, and their toxicity was investigated in different aquatic organisms. The enantioseparation was achieved using a homemade semipreparative chiral column. Optimized conditions allowed the recovery of compounds with enantiomeric purity higher than 99%, except for (R)‐ketamine (97%). The absolute configuration of the enantiomers was achieved by experimental electronic circular dichroism (ECD). The ecotoxicity assays were performed with the microcrustacean Daphnia magna and the protozoan Tetrahymena thermophila using Toxkit MicroBioTests. Different concentrations were tested (0.1–10 000 µg/L) to include environmental levels (~0.5–~100 µg/L), for racemates (R,S) and the isolated enantiomers (R or S) of ketamine and norketamine. No toxicity was observed in either organism at environmental levels. However, at greater concentrations, (R,S)‐ketamine presented higher mortality for D. magna compared with its metabolite (R,S)‐norketamine (85 and 20%, respectively), and the (S)‐ketamine enantiomer showed higher toxicity than the (R)‐ketamine enantiomer. In addition, (S)‐ketamine also presented higher growth inhibition than (R)‐ketamine for T. thermophila at the highest concentrations (5000 and 10 000 µg/L). Contrary to D. magna, growth inhibition was observed for both enantiomers of norketamine and in the same magnitude order of the (S)‐ketamine enantiomer. The results showed that the 2 organisms had different susceptibilities to norketamine and that the toxicity of ketamine at high concentrations is enantioselective for both organisms. Environ Toxicol Chem 2022;41:569–579. © 2020 SETAC

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Analysis of chiral drugs in environmental matrices: Current knowledge and trends in environmental, biodegradation and forensic fields

Cited by 37 publications

References 67 publications

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Gas Chromatography Multiresidue Method for Enantiomeric Fraction Determination of Psychoactive Substances in Effluents and River Surface Waters

Ketamine and Norketamine: Enantioresolution and Enantioselective Aquatic Ecotoxicity Studies

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