Stereoselective degradation of chiral drugs during wastewater treatment
Project No: EP/I038608/1 (project details)
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.
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.
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.
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.
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.
Dr Barbara Kasprzyk-Hordern, University of Bath, Department of Chemistry, Bath BA2 &AY, UK, mailto:B.Kasprzyk-Hordern@bath.ac.uk