Multi-residue enantiomeric analysis of pharmaceuticals and their active metabolites in the Guadalquivir River basin (South Spain) by chiral liquid chromatography coupled with tandem mass spectrometry

Rebeca López-Serna, Barbara Kasprzyk-Hordern, Mira Petrović, Damià Barceló

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

This paper describes the development and application of a multi-residue chiral LC-MS/MS method for simultaneous enantiomeric profiling of 18 chiral pharmaceuticals and their active metabolites, (belonging to several therapeutic classes including analgesics, psychiatric drugs, antibiotics, cardiovascular drugs and β-agonists) in surface water and wastewater. To the authors’ knowledge this is the first time an enantiomeric method including such a high number of pharmaceuticals and their metabolites has been reported. Some of the pharmaceuticals have never been studied before in environmental matrices. Among them are: timolol, betaxolol, carazolol and clenbuterol.
A monitoring programme of the Guadalquivir River basin (South Spain), including 24 sampling sites and 5 WWTPs along the basin, revealed that enantiomeric composition of studied pharmaceuticals is dependent on compound and sampling site. Several compounds such as ibuprofen, atenolol, sotalol and metoprolol were frequently found as racemic mixtures. On the other hand, fluoxetine, propranolol and albuterol were found to be enriched with one enantiomer. Such an outcome might be of significant environmental relevance as two enantiomers of the same chiral compound might reveal different ecotoxicity. For example propranolol was enriched with S(-)-enantiomer, which is known to be more toxic to Primephales promelas than R(+)-propranolol. Fluoxetine was found to be enriched with S(+)-enantiomer, which is more toxic to Pimephales promelas than R(-)-fluoxetine.
Original languageEnglish
Pages (from-to)5859-5873
Number of pages15
JournalAnalytical and Bioanalytical Chemistry
Volume405
Issue number18
Early online date12 Apr 2013
DOIs
Publication statusPublished - 1 Jul 2013

Fingerprint

Enantiomers
Liquid chromatography
Metabolites
Tandem Mass Spectrometry
Rivers
Liquid Chromatography
Catchments
Spain
Mass spectrometry
Fluoxetine
Propranolol
Poisons
Pharmaceutical Preparations
Betaxolol
Clenbuterol
Sampling
Sotalol
Cardiovascular Agents
Timolol
Metoprolol

Cite this

@article{01d1057a8a6b46df8e3b17bd852cf099,
title = "Multi-residue enantiomeric analysis of pharmaceuticals and their active metabolites in the Guadalquivir River basin (South Spain) by chiral liquid chromatography coupled with tandem mass spectrometry",
abstract = "This paper describes the development and application of a multi-residue chiral LC-MS/MS method for simultaneous enantiomeric profiling of 18 chiral pharmaceuticals and their active metabolites, (belonging to several therapeutic classes including analgesics, psychiatric drugs, antibiotics, cardiovascular drugs and β-agonists) in surface water and wastewater. To the authors’ knowledge this is the first time an enantiomeric method including such a high number of pharmaceuticals and their metabolites has been reported. Some of the pharmaceuticals have never been studied before in environmental matrices. Among them are: timolol, betaxolol, carazolol and clenbuterol. A monitoring programme of the Guadalquivir River basin (South Spain), including 24 sampling sites and 5 WWTPs along the basin, revealed that enantiomeric composition of studied pharmaceuticals is dependent on compound and sampling site. Several compounds such as ibuprofen, atenolol, sotalol and metoprolol were frequently found as racemic mixtures. On the other hand, fluoxetine, propranolol and albuterol were found to be enriched with one enantiomer. Such an outcome might be of significant environmental relevance as two enantiomers of the same chiral compound might reveal different ecotoxicity. For example propranolol was enriched with S(-)-enantiomer, which is known to be more toxic to Primephales promelas than R(+)-propranolol. Fluoxetine was found to be enriched with S(+)-enantiomer, which is more toxic to Pimephales promelas than R(-)-fluoxetine.",
author = "Rebeca L{\'o}pez-Serna and Barbara Kasprzyk-Hordern and Mira Petrović and Dami{\`a} Barcel{\'o}",
year = "2013",
month = "7",
day = "1",
doi = "10.1007/s00216-013-6900-7",
language = "English",
volume = "405",
pages = "5859--5873",
journal = "Analytical and Bioanalytical Chemistry",
issn = "1618-2642",
publisher = "Springer Verlag",
number = "18",

}

TY - JOUR

T1 - Multi-residue enantiomeric analysis of pharmaceuticals and their active metabolites in the Guadalquivir River basin (South Spain) by chiral liquid chromatography coupled with tandem mass spectrometry

AU - López-Serna, Rebeca

AU - Kasprzyk-Hordern, Barbara

AU - Petrović, Mira

AU - Barceló, Damià

PY - 2013/7/1

Y1 - 2013/7/1

N2 - This paper describes the development and application of a multi-residue chiral LC-MS/MS method for simultaneous enantiomeric profiling of 18 chiral pharmaceuticals and their active metabolites, (belonging to several therapeutic classes including analgesics, psychiatric drugs, antibiotics, cardiovascular drugs and β-agonists) in surface water and wastewater. To the authors’ knowledge this is the first time an enantiomeric method including such a high number of pharmaceuticals and their metabolites has been reported. Some of the pharmaceuticals have never been studied before in environmental matrices. Among them are: timolol, betaxolol, carazolol and clenbuterol. A monitoring programme of the Guadalquivir River basin (South Spain), including 24 sampling sites and 5 WWTPs along the basin, revealed that enantiomeric composition of studied pharmaceuticals is dependent on compound and sampling site. Several compounds such as ibuprofen, atenolol, sotalol and metoprolol were frequently found as racemic mixtures. On the other hand, fluoxetine, propranolol and albuterol were found to be enriched with one enantiomer. Such an outcome might be of significant environmental relevance as two enantiomers of the same chiral compound might reveal different ecotoxicity. For example propranolol was enriched with S(-)-enantiomer, which is known to be more toxic to Primephales promelas than R(+)-propranolol. Fluoxetine was found to be enriched with S(+)-enantiomer, which is more toxic to Pimephales promelas than R(-)-fluoxetine.

AB - This paper describes the development and application of a multi-residue chiral LC-MS/MS method for simultaneous enantiomeric profiling of 18 chiral pharmaceuticals and their active metabolites, (belonging to several therapeutic classes including analgesics, psychiatric drugs, antibiotics, cardiovascular drugs and β-agonists) in surface water and wastewater. To the authors’ knowledge this is the first time an enantiomeric method including such a high number of pharmaceuticals and their metabolites has been reported. Some of the pharmaceuticals have never been studied before in environmental matrices. Among them are: timolol, betaxolol, carazolol and clenbuterol. A monitoring programme of the Guadalquivir River basin (South Spain), including 24 sampling sites and 5 WWTPs along the basin, revealed that enantiomeric composition of studied pharmaceuticals is dependent on compound and sampling site. Several compounds such as ibuprofen, atenolol, sotalol and metoprolol were frequently found as racemic mixtures. On the other hand, fluoxetine, propranolol and albuterol were found to be enriched with one enantiomer. Such an outcome might be of significant environmental relevance as two enantiomers of the same chiral compound might reveal different ecotoxicity. For example propranolol was enriched with S(-)-enantiomer, which is known to be more toxic to Primephales promelas than R(+)-propranolol. Fluoxetine was found to be enriched with S(+)-enantiomer, which is more toxic to Pimephales promelas than R(-)-fluoxetine.

UR - http://www.scopus.com/inward/record.url?scp=84875966005&partnerID=8YFLogxK

UR - http://dx.doi.org/10.1007/s00216-013-6900-7

U2 - 10.1007/s00216-013-6900-7

DO - 10.1007/s00216-013-6900-7

M3 - Article

VL - 405

SP - 5859

EP - 5873

JO - Analytical and Bioanalytical Chemistry

JF - Analytical and Bioanalytical Chemistry

SN - 1618-2642

IS - 18

ER -