Abstract
In this work, hippuric acid (log P = 0.5), anthranilic acid (log P = 1.3), ketoprofen (log P = 3.6), and naproxen (log P = 3.0) were simultaneously extracted by a green microfluidic device based on the principles of liquid-phase microextraction (LPME). Different deep eutectic solvents (DESs) were investigated as supported liquid membrane (SLM), and a mixture of camphor and menthol as eutectic solvents in the molar ratio 1:1 was found to be highly efficient for the simultaneous extraction of non-polar and polar acidic drugs. LPME was conducted for 6 min per sample. Urine sample was delivered to the system at 1 μL min−1, and target analytes were extracted exhaustively (75–100% recovery) across the DES SLM, and into pure aqueous phosphate buffer pH 11.0 delivered as acceptor at 1 μL min−1. The acceptor was analyzed with liquid chromatography-UV detection. Interestingly, the DES enabled extraction of both the polar and non-polar model analytes at the same time; all chemicals were green and non-hazardous, and the chemical waste was less than 1 mg per sample.
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References
Petersen NJ, Jensen H, Hansen SH, Foss ST, Snakenborg D, Pedersen-Bjergaard S. On-chip electro membrane extraction. Microfluid Nanofluid. 2010;9:881–8.
Sikanen T, Pedersen-Bjergaard S, Jensen H, Kostiainen R, Rasmussen KE, Kotiaho T. Implementation of droplet-membrane-droplet liquid-phase microextraction under stagnant conditions for lab-on-a-chip applications. Anal Chim Acta. 2010;658:133–40.
Asl YA, Yamini Y, Seidi S. Development of a microfluidic-chip system for liquid–phase microextraction based on two immiscible organic solvents for the extraction and preconcentration of some hormonal drugs. Talanta. 2016;160:592–9.
Petersen NJ, Foss ST, Jensen H, Hansen SH, Skonberg C, Snakenborg D, et al. On-chip electro membrane extraction with online ultraviolet and mass spectrometric detection. Anal Chem. 2011;83:44–51.
Petersen NJ, Pedersen JS, Poulsen NN, Jensen H, Skonberg C, Hansen SH, et al. On-chip electromembrane extraction for monitoring drug metabolism in real time by electrospray ionization mass spectrometry. Analyst. 2012;137:3321–7.
Wang X, Saridara C, Mitra S. Microfluidic supported liquid membrane extraction. Anal Chim Acta. 2005;543:92–8.
Ramos Payán M. Liquid - phase microextraction and electromembrane extraction in millifluidic devices: a tutorial. Anal Chim Acta. 2019;1080:12–21.
Seidi S, Yamini Y, Rezazadeh M, Esrafili A. Low-voltage electrically-enhanced microextraction as a novel technique for simultaneous extraction of acidic and basic drugs from biological fluids. J Chromatogr A. 2012;1243:6–13.
Huang C, Seip KF, Gjelstad A, Shen X, Pedersen-Bjergaard S. Combination of electromembrane extraction and liquid-phase microextraction in a single step: simultaneous group separation of acidic and basic drugs. Anal Chem. 2015;87:6951–7.
Karami M, Yamini Y. On-disc electromembrane extraction-dispersive liquid-liquid microextraction: a fast and effective method for extraction and determination of ionic target analytes from complex biofluids by GC/MS. Anal Chim Acta. 2020;1105:95–104.
Vakh C, Likanov G, Bulatov A. Stir flat sheet membrane liquid phase microextraction for the selective chemiluminescence determination of ofloxacin and fleroxacin in human urine. Microchem J. 2021;163:105913.
Maghsoudi M, Nojavan S, Alexovič M, Tabani H. Two-phase agarose gel-electromembrane extraction: effect of organic solvent as an acceptor phase in electroendosmosis flow phenomenon. J Pharm Biomed Anal. 2021;195:113862.
Rahimi A, Nojavan S, Maghsoudi M. Analysis of basic drugs in biological samples using dynamic single-interface hollow fiber liquid-phase microextraction combined with fast electromembrane extraction. Microchem J. 2020;157:105001.
Mahdavi P, Nojavan S, Asadi S. Sugaring-out assisted electromembrane extraction of basic drugs from biological fluids: improving the efficiency and stability of extraction system. J Chromatogr A. 2019;1608:460411.
Sobhi HR, Ghambarian M, Behbahani M, Esrafili A. Application of modified hollow fiber liquid phase microextraction in conjunction with chromatography-electron capture detection for quantification of acrylamide in waste water samples at ultra-trace levels. J Chromatogr A. 2017;1487:30–5.
Ramos Payán M, López MÁ, Fernández-Torres R, Callejón Mochón M, Gómez Ariza JL. Application of hollow fiber-based liquid-phase microextraction (HF-LPME) for the determination of acidic pharmaceuticals in wastewaters. Talanta. 2010;82:854–8.
Drouin N, Rudaz S, Schappler J. New supported liquid membrane for electromembrane extraction of polar basic endogenous metabolites. J Pharm Biomed Anal. 2018;159:53–9.
Ramos Payán M, López MÁ, Fernández Torres R, González JAO, Callejón Mochón M. Hollow fiber-based liquid phase microextraction (HF-LPME) as a new approach for the HPLC determination of fluoroquinolones in biological and environmental matrices. J Pharm Biomed Anal. 2011;55:332–41.
Tabani H, Fakhari AR, Shahsavani A. Simultaneous determination of acidic and basic drugs using dual hollow fibre electromembrane extraction combined with CE. Electrophoresis. 2013;34:269–76.
Li B, Petersen NJ, Ramos Payán M, Hansen SH, Pedersen-Bjergaard S. Design and implementation of an automated liquid-phase microextraction-chip system coupled on-line with high performance liquid chromatography. Talanta. 2014;120:224–9.
Ramos Payán M, Maspoch S, Llobera A. A simple and fast double-flow microfluidic device based liquid-phase microextraction (DF-μLPME) for the determination of parabens in water samples. Talanta. 2017;165:496–501.
Santigosa-Murillo E, Muñoz-Berbel X, Maspoch S, Muñoz M, Ramos Payán M. Impedance model for voltage optimization of parabens extraction in an electromembrane millifluidic device. J Chromatogr A. 1625;2020:461270.
Santigosa-Murillo E, Maspoch S, Ramos Payán M. Liquid phase microextraction integrated into a microchip device for the extraction of fluoroquinolones from urine samples. Microchem J. 2019;145:280–6.
Ramos Payán M, Maspoch S, Llobera A. An effective microfluidic based liquid-phase microextraction device (μLPME) for extraction of non-steroidal anti-inflammatory drugs from biological and environmental samples. Anal Chim Acta. 2016;946:56–63.
Ramos Payán M, Santigosa-Murillo E, Coello J, López MÁ. A comprehensive study of a new versatile microchip device based liquid phase microextraction for stopped-flow and double-flow conditions. J Chromatogr A. 2018;1556:29–36.
Ramos Payán M, Jensen H, Petersen NJ, Hansen SH, Pedersen-Bjergaard S. Liquid-phase microextraction in a microfluidic-chip – high enrichment and sample clean-up from small sample volumes based on three-phase extraction. Anal Chim Acta. 2012;735:46–53.
Kamankesh M, Mollahosseini A, Mohammadi A, Seidi S. Haas in grilled meat: determination using an advanced lab-on-a-chip flat electromembrane extraction coupled with on-line HPLC. Food Chem. 2020;311:125876.
Asl YA, Yamini Y, Seidi S. A novel approach to the consecutive extraction of drugs with different properties via on chip electromembrane extraction. Analyst. 2016;141:311–8.
Baharfar M, Yamini Y, Seidi S, Arain MB. Approach for downscaling of electromembrane extraction as a lab on-a-chip device followed by sensitive red-green-blue detection. Anal Chem. 2018;90:8478–86.
Karami M, Yamini Y, Abdossalami Asl Y, Rezazadeh M. On-chip pulsed electromembrane extraction as a new concept for analysis of biological fluids in a small device. J Chromatogr A. 2017;1527:1–9.
Asl YA, Yamini Y, Seidi S, Rezazadeh M. Simultaneous extraction of acidic and basic drugs via on-chip electromembrane extraction. Anal Chim Acta. 2016;937:61–8.
Ramos Payán M, Santigosa-Murillo E, Fernández Torres R, López MÁ. A new microchip design. A versatile combination of electromembrane extraction and liquid-phase microextraction in a single chip device. Anal Chem. 2018;90:10417–24.
Zarghampour F, Yamini Y, Baharfar M, Faraji M. Simultaneous extraction of acidic and basic drugs via on-chip electromembrane extraction using a single-compartment microfluidic device. Analyst. 2019;144:1159–66.
Román C, Martín Valero MJ, Fernández Torres R, López MÁ. Use of polymer inclusion membranes (PIMs) as support for electromembrane extraction of non-steroidal anti-inflammatory drugs and highly polar acidic drugs. Talanta. 2018;179:601–7.
Hansen FA, Santigosa-Murillo E, Ramos Payán M, Muñoz M, Leere Øiestad E, Pedersen-Bjergaard S. Electromembrane extraction using deep eutectic solvents as the liquid membrane. Anal Chim Acta. 2021;1143:109–16.
Acknowledgements
This work was supported by the Agencia de Gestió d’Ajusts Universitaris i the Recerca (2017-SGR-329). Elia Santigosa thanks Universitat Autònoma de Barcelona (UAB) for the PIF fellowship.
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Santigosa, E., Pedersen-Bjergaard, S., Muñoz, M. et al. Green microfluidic liquid-phase microextraction of polar and non-polar acids from urine. Anal Bioanal Chem 413, 3717–3723 (2021). https://doi.org/10.1007/s00216-021-03320-9
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DOI: https://doi.org/10.1007/s00216-021-03320-9