Publication: Enantioselective determination of ibuprofen residues
by chiral liquid chromatography: a systematic study
of enantiomeric transformation in surface water
and sediments
Loading...
Official URL
Full text at PDC
Publication Date
2016
Advisors (or tutors)
Editors
Journal Title
Journal ISSN
Volume Title
Publisher
CSIRO Publising
Abstract
The enantioselective composition of ibuprofen in sediments in contact with surface water was evaluated over 168 h in the presence and absence of light. Multivariate techniques applied for the evaluation of enantiomeric fraction (EF) and recoveries of enantiomers in water and sediments show differences in the EF and composition of each enantiomer. In sediments, differences in the EF are a result of the presence or absence of light, whereas in water it is attributable to degradation of the two enantiomers with time. To achieve enantioselective separation of ibuprofen in surface water and sediments, a clean-up and preconcentration procedure using solid phase extraction combined with a direct chiral liquid chromatography–ultraviolet method was developed. Quantitation limits of the proposed method were between 0.12 and 0.15 mg g �1 for each enantiomer in sediments, and between 2.4 and 3.0 mg L �1 in surface water. Intra- and inter-day precisions were between 5.1 and 8.9 %. Multivariate techniques can be useful to identify enantiomeric modifications and to select the variables that should be used for modelling such transformations.
Description
UCM subjects
Unesco subjects
Keywords
Citation
[1] M. A. Sousa, C. Gonc¸alves, E. Cunha, J. Hajsˇlova´, M. F. Alpendurada,
Cleanup strategies and advantages in the determination of several
therapeutic classes of pharmaceuticals in wastewater samples by SPELC-
MS/MS. Anal. Bioanal. Chem. 2011, 399, 807. doi:10.1007/
S00216-010-4297-0
[2] R. Lo´pez-Serna, B. Kasprzyk-Hordern, M. Petrovic´, D. Barcelo´,
Multi-residue enantiomeric analysis of pharmaceuticals and their
active metabolites in the Guadalquivir River basin (South Spain) by
chiral chromatography coupled with tandem mass spectrometry. Anal.
Bioanal. Chem. 2013, 405, 5859. doi:10.1007/S00216-013-6900-7
[3] P. Paı´ga, L. H. M. L. M. Santos, C. G. Amorim, A. N. Arau´jo,
M. C. B. S. M. Montenegro, A. Pena, C. Delerue-Matos, Pilot monitoring
study of ibuprofen in surface waters of north of Portugal. Environ
Sci. Pollut. Res. 2013, 20, 2410. doi:10.1007/S11356-012-1128-1
[4] H. Chen, X. Li, S. Zhu, Ocurrence and distribution of selected
pharmaceuticals and personal care products in aquatic environments:
a comparative study of regions in China with different urbanization
levels. Environ. Sci. Pollut. Res. 2012, 19, 2381. doi:10.1007/S11356-
012-0750-2
[5] C. Caballo, M. D. Sicilia, Enantioselective determination of representative
profens in wastewater by a single step sample treatment and
chiral liquid chromatography-tandem mass spectrometry. Talanta
2015, 134, 325. doi:10.1016/J.TALANTA.2014.11.016
[6] P. Vazquez-Roig, V. Andreu, C. Blasco, Y. Pico´ , Risk assessment on
the presence of pharmaceuticals in sediments, soil and water of the
Pego-Oliva Marshlands (Valencia, eastern Spain). Sci. Total Environ.
2012, 440, 24. doi:10.1016/J.SCITOTENV.2012.08.036
[7] I. Ali, S. Prashant, Y. A. Hassan, S. Bhavtosh, Chiral analysis of
ibuprofen residues in water and sediments. Anal. Lett. 2009, 42, 1747.
doi:10.1080/00032710903060768
[8] A. R. Ribeiro, P. M. L. Castro, M. E. Tiritan, Chiral pharmaceuticals in
the environment. Environ. Chem. Lett. 2012, 10, 239. doi:10.1007/
S10311-011-0352-0
[9] S. Ortiz de Garcı´a, G. Pinto Pinto, P. Garcı´a Encina, R. Irusta Mata,
Consumption and occurrence of pharmaceutical and personal care
products in the aquatic environment in Spain. Sci. Total Environ.
2013, 444, 451. doi:10.1016/J.SCITOTENV.2012.11.057
[10] K. M. Nowak, C. Girardi, A. Miltner, M. Gehre, A. Scha¨ffer,
M. Ka¨stner, Contribution of microorganism to non-extractable residue
formation during biodegradation of ibuprofen in soil. Sci. Total
Environ. 2013, 445–446, 377. doi:10.1016/J.SCITOTENV.2012.
12.011
[11] C. Girardi, K. M. Nowak, O. Carranza-Diaz, B. Lewkow, A. Miltner,
M. Gehre, A. Scha¨ffer, M. Ka¨stner, Microbial degradation of the
pharmaceutical ibuprofen and the herbicide 2,4-D in water and soil –
use and limits of data obtained from aqueous systems for predicting
their fate in soil. Sci. Total Environ. 2013, 444, 32. doi:10.1016/
J.SCITOTENV.2012.11.051
[12] V. Matamoros, M. Hijosa, J. M. Bayona, Assessment of the pharmaceutical
active compounds removal in wastewater treatment systems
at enantiomeric level. Ibuprofen and naproxen. Chemosphere 2009,
75, 200. doi:10.1016/J.CHEMOSPHERE.2008.12.008
[13] M. Stuart, D. Lapworth, E. Crane, A. Hart, Review of risk from
potential emergeing contaminants in UK groundwater. Sci. Total
Environ. 2012, 416, 1. doi:10.1016/J.SCITOTENV.2011.11.072
[14] N. H. Hashim, S. J. Khan, Enantioselective analysis of ibuprofen,
ketoprofen and naproxen in wastewater and environmental water
samples. J. Chromatogr. A 2011, 1218, 4746. doi:10.1016/J.CHRO
MA.2011.05.046
[15] Study on the environmental risks of medicinal products. Final report
2013 (Executive Agency for Health and Consumers). Available at
http://ec.europa.eu/health/files/environment/study_environment.pdf
[Verified 10 November 2015].
[16] C. Caballo, M. D. Sicilia, S. Rubio, Enantioselective analysis of nonsteroidal
anti-inflammatory drugs in freshwater fish based on microextraction
with a supramolecular liquid and chiral liquid chromatography-
tandem mass spectrometry. Anal. Bioanal. Chem. 2015, 407,
4721. doi:10.1007/S00216-015-8675-5
[17] L. E. Jacobs, R. L. Fimmen, Y. Chin, H. E. Mash, L. K. Weavers,
Fulvic acid mediated photolysis of ibuprofen in water. Water Res.
2011, 45, 4449. doi:10.1016/J.WATRES.2011.05.041
[18] H. Hu¨hnerfuss, M. Raza Shah, Enantioselective chromatography – a
powerful tool for the discrimination of biotic and abiotic transformation
processes of chiral environmental pollutants. J. Chromatogr. A
2009, 1216, 481. doi:10.1016/J.CHROMA.2008.09.043
[19] K. B. Borges, A. R. Moraes de Oliveira, T. Barth, V. A. Polizel Jabor,
M. Tallarico Pupo, P. Sueli Bonato, LC-MS-MS determination of
ibuprofen, 2-hydroxyibuprofen enantiomers and carboxyibuprofen
stereoisomers for application in biotransformation studies employing
endophytic fungi. Anal. Bioanal. Chem. 2011, 399, 915. doi:10.1007/
S00216-010-4329-9
[20] B. Vermeulen, J. P. Remon, Validation of a high-performance liquid
chromatographic method for the determination of ibuprofen enantiomers
in plasma of broiler chickens. J. Chromatogr. B Biomed. Sci.
Appl. 2000, 749, 243. doi:10.1016/S0378-4347(00)00428-X
[21] M. Rambla-Alegre, J. Esteve-Romero, S. Carda-Broch, Is it really
necessary to validate an analytical method or not? That is the question.
J. Chromatogr. A 2012, 1232, 101. doi:10.1016/J.CHROMA.2011.
10.050
[22] Harmonised tripartite guideline: validation of analytical procedures:
text and methodology, Q2 (R1) 2005 (ICH: Geneva). Available at
http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/
Guidelines/Quality/Q2_R1/Step4/Q2_R1__Guideline.pdf [Verified
10 November 2015].
[23] V. Guill�en-Casla, J. Magro-Moral, N. Rosales-Conrado, L. V. P�erez-
Arribas, M. E. Leo´n-Gonza´lez, L. M. Polo-Dı´ez, Direct chiral liquid
chromatography determination of aryloxyphenoxypropionic herbicides
in soil: deconvolution tools for peak processing. Anal. Bioanal.
Chem. 2011, 399, 915.