Abstract
Pharmaceuticals and pesticides are important analytes of interest in clinical, environmental, and food analyses for ensuring public health. Sample pretreatment steps are often prerequisites for the quantitative analysis of these compounds, which are generally present in low concentrations in samples with complex matrices. In compliance with the current trend towards green analytical chemistry, the replacement of conventional toxic organic solvents with ecofriendly and safe solvents has been pursued in developing sample pretreatment methods. Subsequent to several reports in 2017, deep eutectic solvents (DESs) have been increasingly applied as desirable alternative solvents in numerous types of sample pretreatment methods for the analysis of pharmaceuticals and pesticides. The present review summarizes analytical methods involving DESs as extraction solvents and as the reaction media or functional materials for preparing adsorbents to quantify pharmaceuticals and pesticides in various matrices.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Novel solvent properties of choline chloride/urea mixtures. Chem Commun 7:70–71. https://doi.org/10.1039/b210714g
Bonacci S, Di Gioia ML, Costanzo P, Maiuolo L, Tallarico S, Nardi M (2020) Natural deep eutectic solvent as extraction media for the main phenolic compounds from olive oil processing wastes. Antioxidants (Basel) 9:513. https://doi.org/10.3390/antiox9060513
Chen J, Li Y, Wang X, Liu W (2019) Application of deep eutectic solvents in food analysis: a review. Molecules 24:4594. https://doi.org/10.3390/molecules24244594
Cunha SC, Fernandes JO (2018) Extraction techniques with deep eutectic solvents. Trac-Trend Anal Chem 105:225–239. https://doi.org/10.1016/j.trac.2018.05.001
Deng W, Yu L, Li X, Chen J, Wang X, Deng Z, Xiao Y (2019) Hexafluoroisopropanol-based hydrophobic deep eutectic solvents for dispersive liquid-liquid microextraction of pyrethroids in tea beverages and fruit juices. Food Chem 274:891–899. https://doi.org/10.1016/j.foodchem.2018.09.048
De Los Angeles Fernandez M, Boiteux J, Espino M, Gomez FJ, Silva MF (2018) Natural deep eutectic solvents-mediated extractions: the way forward for sustainable analytical developments. Anal Chim Acta 1038:1–10. https://doi.org/10.1016/j.aca.2018.07.059
Dil EA, Ghaedi M, Asfaram A (2019) Application of hydrophobic deep eutectic solvent as the carrier for ferrofluid: a novel strategy for pre-concentration and determination of mefenamic acid in human urine samples by high performance liquid chromatography under experimental design optimization. Talanta 202:526–530. https://doi.org/10.1016/j.talanta.2019.05.027
Emami S, Shayanfar A (2020) Deep eutectic solvents for pharmaceutical formulation and drug delivery applications. Pharm Dev Technol 25:779–796. https://doi.org/10.1080/10837450.2020.1735414
Farajzadeh MA, Abbaspour M, Kazemian R (2019) Synthesis of a green high density deep eutectic solvent and its application in microextraction of seven widely used pesticides from honey. J Chromatogr A 1603:51–60. https://doi.org/10.1016/j.chroma.2019.06.051
Farajzadeh MA, Sattari Dabbagh M, Yadeghari A (2017) Deep eutectic solvent based gas-assisted dispersive liquid-phase microextraction combined with gas chromatography and flame ionization detection for the determination of some pesticide residues in fruit and vegetable samples. J Sep Sci 40:2253–2260. https://doi.org/10.1002/jssc.201700052
Farajzadeh MA, Shahedi Hojghan A, Afshar Mogaddam MR (2018) Development of a new temperature-controlled liquid phase microextraction using deep eutectic solvent for extraction and preconcentration of diazinon, metalaxyl, bromopropylate, oxadiazon, and fenazaquin pesticides from fruit juice and vegetable samples followed by gas chromatography-flame ionization detection. J Food Compos Anal 66:90–97. https://doi.org/10.1016/j.jfca.2017.12.007
Farajzadeh MA, Abbaspour M, Kazemian R, Afshar Mogaddam MR (2020) Preparation of a new three-component deep eutectic solvent and its use as an extraction solvent in dispersive liquid-liquid microextraction of pesticides in green tea and herbal distillates. J Sci Food Agric 100:1904–1912. https://doi.org/10.1002/jsfa.10200
Huang J, Guo X, Xu T, Fan L, Zhou X, Wu S (2019) Ionic deep eutectic solvents for the extraction and separation of natural products. J Chromatogr A 1598:1–19. https://doi.org/10.1016/j.chroma.2019.03.046
Ji Y, Meng Z, Zhao J, Zhao H, Zhao L (2020) Eco-friendly ultrasonic assisted liquid-liquid microextraction method based on hydrophobic deep eutectic solvent for the determination of sulfonamides in fruit juices. J Chromatogr A 1609:460520. https://doi.org/10.1016/j.chroma.2019.460520
Jouyban A, Farajzadeh MA, Afshar Mogaddam MR (2019) Dispersive liquid-liquid microextraction based on solidification of deep eutectic solvent droplets for analysis of pesticides in farmer urine and plasma by gas chromatography-mass spectrometry. J Chromatogr B 1124:114–121. https://doi.org/10.1016/j.jchromb.2019.06.004
Jouyban A, Farajzadeh MA, Afshar Mogaddam MR (2020) In matrix formation of deep eutectic solvent used in liquid phase extraction coupled with solidification of organic droplets dispersive liquid-liquid microextraction; application in determination of some pesticides in milk samples. Talanta 206:120169. https://doi.org/10.1016/j.talanta.2019.120169
Lamei N, Ezoddin M, Abdi K (2017) Air assisted emulsification liquid-liquid microextraction based on deep eutectic solvent for preconcentration of methadone in water and biological samples. Talanta 165:176–181. https://doi.org/10.1016/j.talanta.2016.11.036
Lee J, Jung D, Park K (2019) Hydrophobic deep eutectic solvents for the extraction of organic and inorganic analytes from aqueous environments. Trac-Trend Anal Chem 118:853–868. https://doi.org/10.1016/j.trac.2019.07.008
Li X, Row KH (2016) Development of deep eutectic solvents applied in extraction and separation. J Sep Sci 39:3505–3520. https://doi.org/10.1002/jssc.201600633
Li Z, Jia J, Wang M, Zhang H, Yan H, Qiao F (2017) Bifunctionalized ordered mesoporous organosilica synthesized in deep eutectic solvent for extraction of triazine herbicides from watermelon. J Chromatogr A 1529:50–56. https://doi.org/10.1016/j.chroma.2017.10.074
Li X, Wang M, Zhao J, Guo H, Gao X, Xiong Z, Zhao L (2019) Ultrasound-assisted emulsification liquid phase microextraction method based on deep eutectic solvent as extraction solvent for determination of five pesticides in traditional Chinese medicine. J Pharmaceut Biomed 166:213–221. https://doi.org/10.1016/j.jpba.2019.01.018
Li K, Jin Y, Jung D, Park K, Kim H, Lee J (2020) In situ formation of thymol-based hydrophobic deep eutectic solvents: application to antibiotics analysis in surface water based on liquid-liquid microextraction followed by liquid chromatography. J Chromatogr A 1614:460730. https://doi.org/10.1016/j.chroma.2019.460730
Liang S, Yan H, Cao J, Han Y, Shen S, Bai L (2017) Molecularly imprinted phloroglucinol-formaldehyde-melamine resin prepared in a deep eutectic solvent for selective recognition of clorprenaline and bambuterol in urine. Anal Chim Acta 951:68–77. https://doi.org/10.1016/j.aca.2016.11.009
Liu L, Tang W, Tang B, Han D, Row KH, Zhu T (2017) Pipette-tip solid-phase extraction based on deep eutectic solvent modified graphene for the determination of sulfamerazine in river water. J Sep Sci 40:1887–1895. https://doi.org/10.1002/jssc.201601436
Liu X, Liu C, Qian H, Qu Y, Zhang S, Lu R, Gao H, Zhou W (2019) Ultrasound-assisted dispersive liquid-liquid microextraction based on a hydrophobic deep eutectic solvent for the preconcentration of pyrethroid insecticides prior to determination by high-performance liquid chromatography. Microchem J 146:614–621. https://doi.org/10.1016/j.microc.2019.01.048
Martins MA, Pinho SP, Coutinho JA (2019) Insights into the nature of eutectic and deep eutectic mixtures. J Solut Chem 48:962–982. https://doi.org/10.1007/s10953-018-0793-1
Moghadam AG, Rajabi M, Asghari A (2018) Efficient and relatively safe emulsification microextraction using a deep eutectic solvent for influential enrichment of trace main anti-depressant drugs from complicated samples. J Chromatogr B 1072:50–59. https://doi.org/10.1016/j.jchromb.2017.09.042
Mohebbi A, Yaripour S, Farajzadeh MA, Afshar Mogaddam MR (2018) Combination of dispersive solid phase extraction and deep eutectic solvent-based air-assisted liquid-liquid microextraction followed by gas chromatography-mass spectrometry as an efficient analytical method for the quantification of some tricyclic antidepressant drugs in biological fluids. J Chromatogr A 1571:84–93. https://doi.org/10.1016/j.chroma.2018.08.022
Mohebbi A, Farajzadeh MA, Nemati M, Sarhangi N, Afshar Mogaddam MR (2019) Development of green sodium sulfate-induced solidification of floating organic droplets-dispersive liquid phase microextraction method: application to extraction of four antidepressants. Biomed Chromatogr 33:e4642. https://doi.org/10.1002/bmc.4642
Nemati M, Farajzadeh MA, Mohebbi A, Khodadadeian F, Afshar Mogaddam MR (2020) Development of a stir bar sorptive extraction method coupled to solidification of floating droplets dispersive liquid-liquid microextraction based on deep eutectic solvents for the extraction of acidic pesticides from tomato samples. J Sep Sci 43:1119–1127. https://doi.org/10.1002/jssc.201901000
Nugbienyo L, Shishov A, Garmonov S, Moskvin L, Andruch V, Bulatov A (2017) Flow method based on liquid-liquid extraction using deep eutectic solvent for the spectrofluorimetric determination of procainamide in human saliva. Talanta 168:307–312. https://doi.org/10.1016/j.talanta.2017.03.057
Oomen WW, Begines P, Mustafa NR, Wilson EG, Verpoorte R, Choi YH (2020) Natural deep eutectic solvent extraction of flavonoids of scutellaria baicalensis as a replacement for conventional organic solvents. Molecules 25:617. https://doi.org/10.3390/molecules25030617
Pedro SN, Freire MG, Freire CS, Silvestre AG (2019) Deep eutectic solvents comprising active pharmaceutical ingredients in the development of drug delivery systems. Expert Opin Drug Del 16:497–506. https://doi.org/10.1080/17425247.2019.1604680
Pena-Pereira F, Kloskowski A, Namiesnik J (2015) Perspectives on the replacement of harmful organic solvents in analytical methodologies: a framework toward the implementation of a generation of eco-friendly alternatives. Green Chem 17:3687–3705. https://doi.org/10.1039/c5gc00611b
Rajabi M, Ghassab N, Hemmati M, Asghari A (2018) Emulsification microextraction of amphetamine and methamphetamine in complex matrices using an up-to-date generation of eco-friendly and relatively hydrophobic deep eutectic solvent. J Chromatogr A 1576:1–9. https://doi.org/10.1016/j.chroma.2018.07.040
Sahin S (2019) Tailor-designed deep eutectic liquids as a sustainable extraction media: an alternative to ionic liquids. J Pharmaceut Biomed 174:324–329. https://doi.org/10.1016/j.jpba.2019.05.059
Shishov A, Chroma R, Vakh C, Kuchar J, Simon A, Andruch V, Bulatov A (2019) In situ decomposition of deep eutectic solvent as a novel approach in liquid-liquid microextraction. Anal Chim Acta 1065:49–55. https://doi.org/10.1016/j.aca.2019.03.038
Tang W, Dai Y, Row KH (2018) Evaluation of fatty acid/alcohol-based hydrophobic deep eutectic solvents as media for extracting antibiotics from environmental water. Anal Bioanal Chem 410:7325–7336. https://doi.org/10.1007/s00216-018-1346-6
Taylor D, Senac T (2014) Human pharmaceutical products in the environment—the “problem” in perspective. Chemosphere 115:95–99. https://doi.org/10.1016/j.chemosphere.2014.01.011
Tobiszewski M, Mechlinska A, Namiesnik J (2010) Green analytical chemistry-theory and practice. Chem Soc Rev 39:2869–2878. https://doi.org/10.1039/b926439f
Torbati M, Farajzadeh MA, Afshar Mogaddam MR, Torbati M (2019) Deep eutectic solvent based homogeneous liquid-liquid extraction coupled with in-syringe dispersive liquid-liquid microextraction performed in narrow tube; application in extraction and preconcentration of some herbicides from tea. J Sep Sci 42:1768–1776. https://doi.org/10.1002/jssc.201801016
Wang DD, Zhao Y, Ou yang MN, Guo HM, Yang ZH (2019) Magnetic polydopamine modified with deep eutectic solvent for the magnetic solid-phase extraction of sulfonylurea herbicides in water samples. J Chromatogr A 1601:53–59. https://doi.org/10.1016/j.chroma.2019.05.011
Wang M, Fang S, Liang X (2018a) Natural deep eutectic solvents as eco-friendly and sustainable dilution medium for the determination of residual organic solvents in pharmaceuticals with static headspace-gas chromatography. J Pharmaceut Biomed 158:262–268. https://doi.org/10.1016/j.jpba.2018a.06.002
Wang R, Li W, Chen Z (2018b) Solid phase microextraction with poly(deep eutectic solvent) monolithic column online coupled to HPLC for determination of non-steroidal anti-inflammatory drugs. Anal Chim Acta 1018:111–118. https://doi.org/10.1016/j.aca.2018b.02.024
Yousefi SM, Shemirani F, Ghorbanian SA (2017) Deep eutectic solvent magnetic bucky gels in developing dispersive solid phase extraction: application for ultra trace analysis of organochlorine pesticides by GC-micro ECD using a large-volume injection technique. Talanta 168:73–81. https://doi.org/10.1016/j.talanta.2017.03.020
Zainal-Abidin MH, Hayyan M, Ngoh GC, Wong WF, Looi CY (2019) Emerging frontiers of deep eutectic solvents in drug discovery and drug delivery systems. J Control Release 316:168–195. https://doi.org/10.1016/j.jconrel.2019.09.019
Zhang Q, Vigier KDO, Royer S, Jerome F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108–7146. https://doi.org/10.1039/c2cs35178a
Zhao J, Meng Z, Zhao Z, Zhao L (2020a) Ultrasound-assisted deep eutectic solvent as green and efficient media combined with functionalized magnetic multi-walled carbon nanotubes as solid-phase extraction to determine pesticide residues in food products. Food Chem 310:125863. https://doi.org/10.1016/j.foodchem.2019.125863
Zhao RT, Pei D, Yu PL, Wei JT, Wang NL, Di DL, Liu YW (2020b) Aqueous two-phase systems based on deep eutectic solvents and their application in green separation processes. J Sep Sci 43:348–359. https://doi.org/10.1002/jssc.201900991
Acknowledgements
The authors are grateful for the financial support by two research Grants, NRF-2018K1A3A1A39088119 and NRF-2020R1A2C1014006.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Lee, J., Kim, H., Kang, S. et al. Applications of deep eutectic solvents to quantitative analyses of pharmaceuticals and pesticides in various matrices: a brief review. Arch. Pharm. Res. 43, 900–919 (2020). https://doi.org/10.1007/s12272-020-01266-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-020-01266-7