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Stereoselective
degradation of chiral drugs during wastewater treatment |
Funder: Engineering and Physical Research
Council Project No: EP/I038608/1
(project details) |
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Pharmacologically
active compounds (PACs) constitute a vast and diverse group of chemicals.
Despite low ppt concentrations of these compounds in environmental matrices,
PACs pose considerable environmental concern as many of them are active at
very low concentrations. Additionally, PACs are present in the environment as
multi-residue mixtures, and therefore synergistic effects of PACs should also
be considered. Due to the non-volatile nature of the majority of PACs, and
their continuous introduction into the environment, their environmental
impact cannot be underestimated. PACs have also been detected in drinking
water, which poses a direct risk to humans and raises the issue of
contaminated water sources and especially water reuse. Water
is a limited resource in an expanding global economy and population. In the
future its accessibility will be significantly impacted by changing climate.
Reclaiming water for non-potable (irrigation, urban, industrial) or potable
purposes is therefore considered to be an important element of sustainable
water resource management. There are, however, certain risks associated with
water reuse including microbiological and chemical risks (e.g. the presence
of PACs in reclaimed water). They have to be verified before water reuse is
to be implemented on a wider scale. Several groups of PACs such as
beta-blockers, antibiotics or analgesics have been studied before in the
environment but surprisingly their chiral character, despite its great
importance in the pharmaceutical industry, has been overlooked by
environmental researchers. More
than half of the drugs currently in use are chiral compounds and many of
those are distributed as racemates consisting of an equimolar mixture of two
enantiomers. Enantiomers of the same drug have the same chemical formula and
physicochemical properties but they differ in interactions with chiral
environments such as enzymes. Therefore in biological systems they have to be
recognised as two different substances that elicit different responses: one
enantiomer of the same drug may produce the desired therapeutic activity,
while the other may be inactive or even toxic. The ratio of active/inactive
enantiomer of the chiral drug can change significantly after its
administration, metabolism in and excretion from the body. It can be
subsequently altered during wastewater treatment and when the drug is already
present in the environment. This is because degradation of enantiomers can be
stereo-specific and can in some cases lead to an increase in the drug's
toxicity. As a result chiral PACs might reveal different environmental
persistence, fate and toxicity. Currently, the environmental fate and
toxicity of chiral drugs are assessed without taking into consideration their
enantiomeric form. This might lead to a significant under or overestimation
of toxicity of chiral drugs and to inaccurate environmental risk assessment. As a
consequence there is an urgent need to identify chiral drugs, which are
resistant to currently used wastewater treatment technologies, are
characterised by stereoselective degradation during wastewater treatment and
can as a result be released into the environment or remain in reclaimed water
in the form of non-racemic mixtures. This project will tackle this issue as
it aims to test the hypothesis that degradation of chiral drugs during
wastewater treatment and in receiving waters is stereoselective and will be
undertaken at the laboratory scale with the usage of microcosm protocol and
in a full scale wastewater treatment plant. |
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Objective 1: To
investigate the hypothesis that stereoselective biodegradation of chiral
drugs during biological sewage treatment takes place. Objective 2: To
investigate the hypothesis that stereoselective biodegradation of chiral
drugs can also take place in receiving waters. Objective 3: To
verify stereoselectivity of degradation of chiral drugs in a full scale WWTP
utilising activated sludge treatment. |
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Publications: Evans, S. E., Davies, P., Lubben, A.
and Kasprzyk-Hordern, B., 2015. Forthcoming. Determination of chiral
pharmaceuticals and illicit drugs in wastewater and sludge using microwave
assisted extraction, solid-phase extraction and chiral liquid chromatography
coupled with tandem mass spectrometry. Analytica Chimica Acta, 882, pp.
112-126. Petrie, B., Camacho-Munoz, M.,
Castrignano, E., Evans, S. and Kasprzyk-Hordern, B., 2015. Chiral Liquid
Chromatography Coupled with Tandem Mass Spectrometry for Environmental
Analysis of Pharmacologically Active Compounds. LCGC Europe, 2 (28), p. 151. Camacho-Muñoz,
D., Petrie, B., Castrignano, E. and Kasprzyk-Hordern, B., 2015. Enantiomeric
Profiling of Chiral Pharmacologically Active Compounds in the Environment
with the usage of chiral Liquid Chromatography Coupled with Tandem Mass
Spectrometry. Current Analytical Chemistry, 12. Vazquez-Roig, P., Kasprzyk-Hordern, B., Blasco, C. and Picó, Y.,
2014.Stereoisomeric profiling of drugs of abuse and pharmaceuticals in wastewaters
of Valencia (Spain). Science of the Total Environment, 494-495, pp. 49-57. Evans, S. and Kasprzyk-Hordern, B.,
2014. Applications of chiral chromatography coupled with mass spectrometry in
the analysis of chiral pharmaceuticals in the environment. Trends in
Environmental Analytical Chemistry, 1 (1), 1. Emke, E., Evans, S., Kasprzyk-Hordern,
B. and de Voogt, P., 2014. Enantiomer profiling of high loads of amphetamine
and MDMA in communal sewage : A Dutch perspective. Science of the Total
Environment, 487, pp. 666-672. López-Serna, R., Kasprzyk-Hordern, B.,
Petrović, M. and Barceló, D., 2013. 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. Analytical and Bioanalytical Chemistry, 405 (18), pp.
5859-5873. Bagnall, J.P., Evans, S.E., Wort, M.T., Lubben, A.T. and Kasprzyk-Hordern,
B., 2012. Using chiral liquid chromatography quadrupole time-of-flight mass
spectrometry for the analysis of pharmaceuticals and illicit drugs in surface
and wastewater at the enantiomeric level. Journal of Chromatography A, 1249,
pp. 115-129. Presentations: Kasprzyk-Hordern,
B., 2015. Stereochemistry of Pharmacologically Active Compounds:A New
Paradigm in Environmental Analysis and Risk Assessment. In: ‘Emerging
contaminants in waters and soils, practical considerations: -Sampling,
analysis and consequences’, Royal Society of Chemistry Water Science Forum,
2015-03-04 - 2015-03-04, Sheffield. Kasprzyk-Hordern,
B., 2015. Urban water profiling for community-wide public health assessment.
In: IX Polish Conference on Analytical Chemistry, 2015-07-06 - 2015-07-09,
Poznan. Kasprzyk-Hordern,
B., Castrignano, E., Rydevik, A., Lopardo, L., Rice, J. and Yang, Z., 2015.
Wastewater-based epidemiology and future perspectives:testing urban water for
community-wide public health assessment. In: 15th EuCheMS International
Conference on Chemistry and the Environment, 2015-09-20 - 2015-09-25,
Leipzig. Kasprzyk-Hordern,
B., ‘Divining human health through urban wastewater profiling’, Bath Science
Café, Bath, 2014-09-08 Kasprzyk-Hordern,
B., ‘Testing urban water for community-wide public health assessment’, CCAF
Symposium ‘The alchemy of what we swallow’, 2014-09-09, Bath Kasprzyk-Hordern,
B., ‘Chiral chromatography coupled with tandem mass spectrometry for
enantiomeric profiling of chiral pharmacologically active compounds’, 9th
Aegean Analytical Chemistry Days, Chios, Greece, 2014 Kasprzyk-Hordern,
B., 2014. Urban water cycle: environmental and health perspectives, STEM CPD
Day, 2014-06-18, Bath. Kasprzyk-Hordern,
B., 2014. Water and you: green, grey and blue’, Pint-of-Science Festival,
2014 -05-19, Bath. Evans, S. and Kasprzyk-Hordern,
B., 2014. Chiral pharmaceuticals and illicit drugs stereoselective
degradation in activated sludge: Methodology and results of quantification in
microcosm study. In: SETAC Europe 24th Annual Meeting, 2014-05-11 -
2014-05-15, Basel. Kasprzyk-Hordern,
B., 2014. Testing wastewater in public health epidemiology: Pharmaceuticals,
illicit drugs and the phenomenon of chirality. In: The SfAM Meeting
"Control of water-borne disease: A century of the activated sludge
sewage treatment process", 2014-04-01 - 2014-04-02, Manchester. Kasprzyk-Hordern,
B., 2013. Wastewater profiling at a community level: a new paradigm in
epidemiological studies of public health, University of Bristol, School of
Social and Community Medicine, 2013-0-01, Bristol Evans, S.,
Bagnall, J. and Kasprzyk-Hordern, B., 2013. Chiral illicit drugs and
pharmaceuticals – stereoselective degradation, and its implications for
analysis, toxicology and regulatory frameworks. In: Joint Annual Meeting of
the Ecotoxicology Research and Innovation Centre Plymouth University, and the
Society of Environmental Toxicology and Chemistry UK Branch, 2013-09-09 -
2013-09-10, Plymouth. Kasprzyk-Hordern,
B., 2013. Illicit drugs in wastewater: chirality and other under-investigated
phenomena. In: 14th EuCheMS International Conference on Chemistry and the
Environment, Satellite Event 'Illicit drugs in wastewater', 2013-06-25,
Barcelona. Evans, S. and
Kasprzyk-Hordern, B., 2013. Study of stereoselective degradation of
pharmaceuticals and illicit drugs in wastewater and receiving water bodies.
In: 14th EuCheMS International Conference on Chemistry and the Environment,
2013-06-25 - 2013-06-28, Barcelona. Kasprzyk-Hordern,
B., Bagnall, J., Baker, D. and Evans, S., 2013. Enantiomerism of medicinal
products – a new paradigm in environmental risk assessment. In: Book of
abstracts, 23rd Annual Meeting of the Society of Environmental Toxicology and
Chemistry (SETAC Europe), 2013-05-12 - 2013-05-16, Glasgow. Kasprzyk-Hordern,
B., 2013. Wastewater analysis — an emerging science: key issues and their
application: General overview of analytical methods and chiral analysis. In:
Testing the waters: first international multidisciplinary conference on
detecting illicit drugs in wastewater, 2013-05-06 - 2013-05-08, Lisbon. Kasprzyk-Hordern,
B., 2013. Enantioselective analysis of chiral pharmacologically active
compounds in urban water. In: The RSC Analytical Division Separation Science
Group and the RSC Environmental Chemistry Group Meeting, 'Recent Advances in
the Analysis of Complex Environmental Matrices', 2013-02-28, London. Kasprzyk-Hordern,
B., 2012. Enantiomeric profiling of chiral drugs in the environment with the
usage of Chiral-LCMS/MS. In: 8th Annual LC/MS/MS Workshop on Environmental
Applications and Food Safety, 2012-07-01 - 2012-07-03, Barcelona. Kasprzyk-Hordern,
B. and Baker, D. R., 2012. PACs during wastewater treatment and in receiving
waters – emerging issues. In: 6th SETAC World Congress/SETAC Europe 22nd
Annual Meeting, 2012-05-19 - 2012-05-23, Berlin. B. Kasprzyk-Hordern,
‘The significance of chirality of illicit drugs for the estimation of drugs
of abuse using the sewage epidemiology approach’ EMCDDA Workshop ‘The
determination of illicit drug consumption in populations through wastewater
biomarker analysis’, Lisbon, Portugal, 2012. Evans, S., Davies, P., Lubben, A. and
Kasprzyk-Hordern, B., 2012. Enantiomeric profiling of chiral drugs from
environmental solid matrices with the use of microwave assisted extraction
and chiral LC-MSMS. In: 8th Annual LC/MS/MS Workshop on Environmental
Applications and Food Safety, 2012-07-01 - 2012-07-03, Barcelona. |
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Dr Barbara Kasprzyk-Hordern, University
of Bath, Department of Chemistry, Bath BA2 &AY, UK, mailto:B.Kasprzyk-Hordern@bath.ac.uk