Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples
A highly sensitive and reliable method for the enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples has been developed. These three pharma�ceuticals are chiral molecules and the variable presence of their individual (R)- and (S)-enantiomers i...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2011
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| Subjects: | |
| Online Access: | http://eprints.uthm.edu.my/7987/1/59J5716_2c99e89a5fcdc11672b9428e7b95b0c8.pdf |
| _version_ | 1796869671086981120 |
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| author | Hashim, Nor H. Stuart J. Khan, Stuart J. Khan |
| author_facet | Hashim, Nor H. Stuart J. Khan, Stuart J. Khan |
| author_sort | Hashim, Nor H. |
| collection | UTHM |
| description | A highly sensitive and reliable method for the enantioselective analysis of ibuprofen, ketoprofen and
naproxen in wastewater and environmental water samples has been developed. These three pharma�ceuticals are chiral molecules and the variable presence of their individual (R)- and (S)-enantiomers is of
increasing interestfor environmental analysis. An indirect method for enantioseparation was achieved by
the derivatization of the (R)- and (S)-enantiomers to amide diastereomers using (R)-1-phenylethylamine
((R)-1-PEA). After initial solid phase extraction from aqueous samples, derivatization was undertaken at
room temperature in less than 5 min. Optimum recovery and clean-up of the amide diastereomers from
the derivatization solution was achieved by a second solid phase extraction step. Separation and detec�tion ofthe individual diastereomers was undertaken by gas chromatography–tandem mass spectrometry
(GC–MS/MS). Excellent analyte separation and peak shapes were achieved for the derivatized (R)- and
(S)-enantiomers for all three pharmaceuticals with peak resolution, Rs is in the range of 2.87–4.02 for
all diastereomer pairs. Furthermore, the calibration curves developed for the (S)-enantiomers revealed
excellent linearity (r2 ≥ 0.99) for all three compounds. Method detection limits were shown to be within
the range of 0.2–3.3 ng L−1 for individual enantiomers in ultrapure water, drinking water, surface water
and a synthetic wastewater. Finally, the method was shown to perform well on a real tertiary treated
wastewater sample, revealing measurable concentrations of both (R)- and (S)-enantiomers of ibupro�fen, naproxen and ketoprofen. Isotope dilution using racemic D3-ibuprofen, racemic D3-ketoprofen and
racemic D3-naproxen was shown to be an essential aspect of this method for accurate quantification
and enantiomeric fraction (EF) determination. This approach produced excellent reproducibility for EF
determination of triplicate tertiary treated wastewater samples. |
| first_indexed | 2024-03-05T21:58:20Z |
| format | Article |
| id | uthm.eprints-7987 |
| institution | Universiti Tun Hussein Onn Malaysia |
| language | English |
| last_indexed | 2024-03-05T21:58:20Z |
| publishDate | 2011 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | uthm.eprints-79872022-11-08T01:37:23Z http://eprints.uthm.edu.my/7987/ Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples Hashim, Nor H. Stuart J. Khan, Stuart J. Khan T Technology (General) A highly sensitive and reliable method for the enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples has been developed. These three pharma�ceuticals are chiral molecules and the variable presence of their individual (R)- and (S)-enantiomers is of increasing interestfor environmental analysis. An indirect method for enantioseparation was achieved by the derivatization of the (R)- and (S)-enantiomers to amide diastereomers using (R)-1-phenylethylamine ((R)-1-PEA). After initial solid phase extraction from aqueous samples, derivatization was undertaken at room temperature in less than 5 min. Optimum recovery and clean-up of the amide diastereomers from the derivatization solution was achieved by a second solid phase extraction step. Separation and detec�tion ofthe individual diastereomers was undertaken by gas chromatography–tandem mass spectrometry (GC–MS/MS). Excellent analyte separation and peak shapes were achieved for the derivatized (R)- and (S)-enantiomers for all three pharmaceuticals with peak resolution, Rs is in the range of 2.87–4.02 for all diastereomer pairs. Furthermore, the calibration curves developed for the (S)-enantiomers revealed excellent linearity (r2 ≥ 0.99) for all three compounds. Method detection limits were shown to be within the range of 0.2–3.3 ng L−1 for individual enantiomers in ultrapure water, drinking water, surface water and a synthetic wastewater. Finally, the method was shown to perform well on a real tertiary treated wastewater sample, revealing measurable concentrations of both (R)- and (S)-enantiomers of ibupro�fen, naproxen and ketoprofen. Isotope dilution using racemic D3-ibuprofen, racemic D3-ketoprofen and racemic D3-naproxen was shown to be an essential aspect of this method for accurate quantification and enantiomeric fraction (EF) determination. This approach produced excellent reproducibility for EF determination of triplicate tertiary treated wastewater samples. Elsevier 2011 Article PeerReviewed text en http://eprints.uthm.edu.my/7987/1/59J5716_2c99e89a5fcdc11672b9428e7b95b0c8.pdf Hashim, Nor H. and Stuart J. Khan, Stuart J. Khan (2011) Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples. Journal of Chromatography A, A (1218). pp. 4746-4754. https://doi.org/10.1016/j.chroma.2011.05.046 |
| spellingShingle | T Technology (General) Hashim, Nor H. Stuart J. Khan, Stuart J. Khan Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples |
| title | Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples |
| title_full | Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples |
| title_fullStr | Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples |
| title_full_unstemmed | Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples |
| title_short | Enantioselective analysis of ibuprofen, ketoprofen and naproxen in wastewater and environmental water samples |
| title_sort | enantioselective analysis of ibuprofen ketoprofen and naproxen in wastewater and environmental water samples |
| topic | T Technology (General) |
| url | http://eprints.uthm.edu.my/7987/1/59J5716_2c99e89a5fcdc11672b9428e7b95b0c8.pdf |
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