Dual enantioselective LC–MS/MS method to analyse chiral drugs in surface water: Monitoring in Douro River estuary

Coelho, Maria Miguel; Ribeiro, Ana R.; Sousa, J.; Ribeiro, Cláudia; Fernandes, Carla; Silva, Adrián M.T.; Tiritan, Maria Elizabeth

doi:10.1016/j.jpba.2019.03.032

Cited by 39 publications

(22 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The method was successfully applied to track daily fluctuations in surface waters obtained from different locations on Douro River estuary over a period of 1 week. VFX was determined on the Chirobiotic V column (150 × 2.1 mm, 5 μm) and was found in high concentrations, but its main metabolite ODVFX was found at concentrations three times higher (Coelho et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Enantioselective analysis of venlafaxine and its active metabolites: A review on the separation methodologies

Hancu

Lupu

Milan

et al. 2020

Biomedical Chromatography

View full text Add to dashboard Cite

Venlafaxine (VFX) is a serotonin and norepinephrine reuptake inhibitor chiral drug used in therapy as an antidepressant in the form of a racemate consisting of R-and S-VFX. The two enantiomers of VFX exhibit different pharmacological activities: R-VFX inhibits both norepinephrine and serotonin synaptic reuptake, whereas S-VFX inhibits only the serotonin one. R-and S-VFX are metabolized in the liver to the respective Rand SO -desmethylvenlafaxine (ODVFX), R-and S-N-desmethylvenlafaxine (NDVFX), and R-and S-N,O-didesmethylvenlafaxine (NODVFX). The pharmacological profile of ODVFX is close to that of VFX, whereas the other two chiral metabolites (NDVFX and NODVFX) have lower affinity for the receptor sites. The pharmacokinetics of the VFX enantiomers appear stereoselective, including the metabolism process. In the past 20 years, several studies describing the enantioselective analysis of R-and S-VFX in pharmaceutical formulations and its chiral metabolites in biological matrices were published. These methods encompass liquid chromatography coupled with UV detection, mass spectrometry, or tandem mass spectrometry, and capillary electrophoresis. This paper reviews the published methods used for the determination of the individual enantiomers of VFX and its chiral metabolites in different matrices.

show abstract

Section: Introductionmentioning

confidence: 99%

Enantioselective analysis of venlafaxine and its active metabolites: A review on the separation methodologies

Hancu

Lupu

Milan

et al. 2020

Biomedical Chromatography

View full text Add to dashboard Cite

show abstract

“…The SPE procedure was adapted from that described by Coelho et al [15]. Briefly, for method optimization and validation, 1 L of pre-filtered and acidified spring water was spiked with 250 µL of mixture of the standards of the target compounds at different ranges of concentrations (Tables S2 and S3) and the IS at 500 ng mL −1 .…”

Section: Solid-phase Extraction (Spe) Proceduresmentioning

confidence: 99%

“…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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…Here, three functional groups around the stereogenic centre of one of the enantiomers undergo molecular interactions with the chiral stationary phase (Berthod 2006). A variety of chiral stationary phases have been utilized for enantioseparation of NSAIDs including derivatized polysaccharides (Camacho-Muñoz et al 2016;Li et al 2020;Ma et al 2019;Wang et al 2018;Yuan et al 2018), glycopeptides (Camacho-Muñoz and Kasprzyk-Hordern 2017), glycoproteins (Camacho-Muñoz and Kasprzyk-Hordern 2015) and Pirkletype columns (Caballo et al 2015a;Coelho et al 2019).…”

Section: Liquid Chromatography-mass Spectrometrymentioning

confidence: 99%

“…It was initially used for the separation of naproxen enantiomers (Welch 1994) and separates analytes with an aromatic system with a hydrogen-bond acceptor group near the stereogenic centre (Fernandes et al 2013). Coelho et al (2019) successfully developed a separation method for flurbiprofen, ibuprofen, ketoprofen and naproxen using a 1-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthrene stationary phase. The optimum mobile phase of 60:40 (v/v) methanol/0.1% acetic acid required a chromatographic run time of 90 min (Table 2).…”

Section: Chiral Selector: Pirkle-type Phasesmentioning

confidence: 99%

Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review

Petrie

Camacho‐Muñoz

2020

Environ Chem Lett

View full text Add to dashboard Cite

Non-steroidal anti-inflammatory drugs (NSAIDs) are found in the aquatic environment globally. Such drugs including naproxen, ibuprofen and ketoprofen are chiral molecules. Enantiomers of those drugs have identical physicochemical properties but can behave and interact differently in chiral environments due to differences in their three-dimensional shape. This results in enantiospecific differences in environmental fate and toxicity, which is often overlooked. Therefore, we review the analytical methods, occurrence and fate, and toxicity of chiral non-steroidal anti-inflammatory drugs at the enantiomeric level. The advancement of enantioselective chromatography methods, particularly the use of polysaccharide-based stationary phases, has enabled trace determination of enantiomers in complex environmental matrices. Macrocosm and microcosm studies of engineered and natural environments revealed that such drugs can undergo both enantioselective degradation and chiral inversion. Enantioselectivity has been reported during wastewater treatment, in surface waters and in agricultural soils. The use of microcosms spiked with individual enantiomers over racemates is essential to evaluate these degradation and inversion fate processes. The chiral inversion process whereby one enantiomer converts into its antipode can be significant if the more toxic enantiomers are formed. Existing enantiospecific effect studies report less than an order of magnitude difference in enantiomer toxicity. However, toxicity data for enantiomers are limited and further research is needed to better appreciate the environmental risk at the enantiomeric level.

show abstract

Dual enantioselective LC–MS/MS method to analyse chiral drugs in surface water: Monitoring in Douro River estuary

Cited by 39 publications

References 28 publications

Enantioselective analysis of venlafaxine and its active metabolites: A review on the separation methodologies

Enantioselective analysis of venlafaxine and its active metabolites: A review on the separation methodologies

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

Analysis, fate and toxicity of chiral non-steroidal anti-inflammatory drugs in wastewaters and the environment: a review

Contact Info

Product

Resources

About