Environmental Chemistry Letters

, Volume 11, Issue 1, pp 83–90 | Cite as

Enantioselective HPLC analysis and biodegradation of atenolol, metoprolol and fluoxetine

  • Ana Rita Ribeiro
  • Carlos Magalhães Afonso
  • Paula M. L. Castro
  • Maria Elizabeth TiritanEmail author
Original Paper


The accurate quantification of enantiomers is crucial for assessing the biodegradation of chiral pharmaceuticals in the environment. Methods to quantify enantiomers in environmental matrices are scarce. Here, we used an enantioselective method, high-performance liquid chromatography with fluorescence detection (HPLC-FD), to analyze two beta-blockers, metoprolol and atenolol, and the antidepressant fluoxetine in an activated sludge consortium from a wastewater treatment plant. The vancomycin-based chiral stationary phase was used under polar ionic mode to achieve the enantioseparation of target chiral pharmaceuticals in a single chromatographic run. The method was successfully validated over a concentration range of 20–800 ng/mL for each enantiomer of both beta-blockers and of 50–800 ng/mL for fluoxetine enantiomers. The limits of detection were between 5 and 20 ng/mL and the limits of quantification were between 20 and 50 ng/mL, for all enantiomers. The intra- and inter-batch precision was lower than 5.66 and 8.37 %, respectively. Accuracy values were between 103.03 and 117.92 %, and recovery rates were in the range of 88.48–116.62 %. Furthermore, the enantioselective biodegradation of atenolol, metoprolol and fluoxetine was followed during 15 days. The (S)-enantiomeric form of metoprolol was degraded at higher extents, whereas the degradation of atenolol and fluoxetine did not show enantioselectivity under the applied conditions.


Pharmaceuticals Chiral ecotoxicity Enantioselective biodegradation HPLC-FD Polar ionic mode Chirobiotic V 



The work has been supported by Fundacão para a Ciência e Tecnologia—FCT (PhD grant attributed to Ana Rita Ribeiro, SFRH/BD/64999/2009, from QREN-POPH, European Social Fund and MCTES). Authors also wish to acknowledge the support from CESPU (09-GCQF-CICS-09) and FCT: FLUOROPHARMA, PTDC/EBB-EBI/111699/2009 and PEst-OE/EQB/LA0016/2011. The authors thank Virginia Gonçalves for her collaboration and to Parada wastewater treatment plant for activated sludge supplying.


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Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Ana Rita Ribeiro
    • 1
    • 2
    • 3
  • Carlos Magalhães Afonso
    • 3
  • Paula M. L. Castro
    • 2
  • Maria Elizabeth Tiritan
    • 1
    • 3
    Email author
  1. 1.Centro de Investigação em Ciências da Saúde do Instituto Superior de Ciências da Saúde-Norte (CICS-ISCS-N)Gandra PRDPortugal
  2. 2.Centro de Biotecnologia e Química Fina (CBQF), Escola Superior de BiotecnologiaCentro Regional do Porto da Universidade Católica PortuguesaPortoPortugal
  3. 3.Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP)PortoPortugal

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