Abstract
The magnetic hypercrosslinked polystyrene was used for the first time as a sorbent in effervescence-assisted magnetic solid-phase extraction. An effervescent tablet composed of magnetic hypercrosslinked polystyrene, sodium bicarbonate, and citric acid was used for extraction of nitroimidazoles and their metabolites from honey samples prior to their LC-MS/MS determination. In the proposed method, the dispersing of the sorbent occurs without the help of additional energy sources (such as ultrasound and stirring devices) due to the intensive release of carbon dioxide during dissolution of the tablet. The magnetic properties of the sorbent make it possible to separate it without the use of centrifugation or filtration. As a result, the extraction procedure takes only 3 min. The effects of important parameters, including the molar ratio of sodium bicarbonate to citric acid, mass of magnetic hypercrosslinked polystyrene, mass of the tablet, and desorption conditions, were systematically studied. The proposed method was validated using spiked honey samples. Under the optimum experimental conditions, the proposed method provided the limit of detection and limit of quantification of 0.3 and 1 μg kg−1, respectively. Precision values expressed as relative standard deviation were < 16% for the intra-day and inter-day experiments. In general, the developed method is simple, fast, resource-efficient, and has good analytical characteristics.
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Data Availability
The data mentioned in the current study are available from the corresponding author on request.
References
An Y, Meng X, Li S, Wang Q, Liu W, Hao L, Yang X, Wang C, Wang Z, Wu Q (2022) Facile fabrication of tyrosine-functionalized hypercrosslinked polymer for sensitive determination of nitroimidazole antibiotics in honey and chicken muscle. Food Chem 389:133121. https://doi.org/10.1016/j.foodchem.2022.133121
Chisvert A, Cardenas S, Lucena R (2019) Dispersive micro-solid phase extraction. Trends Anal Chem 112:226–233. https://doi.org/10.1016/j.trac.2018.12.005
European Commission (2009) Commission Regulation (EU) No 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin. Off J Eur Communities L15(1):1–72
European Union Reference Laboratories (EURLs) (2020) Guidance on minimum method performance requirements (MMPRs) for specific pharmacologically active substances in specific animal matrices. EURLs for Residues of Veterinary Medicinal Products. https://eurl-residues.eu/wp-content/uploads/2020/12/EURL_MMPR_guidance-paper_final.pdf. Accessed 21 June 2023
Fahimirad B, Rajabi M, Elhampour A (2019) A rapid and simple extraction of anti-depressant drugs by effervescent salt-assisted dispersive magnetic micro solid-phase extraction method using new adsorbent Fe3O4@SiO2@N3. Anal Chim Acta 1047:275–284. https://doi.org/10.1016/j.aca.2018.10.028
Gao M, Zhang X, Ma S, Wang J, Mammah M, Dua L, Wang X (2022) Ionic-liquid-based effervescence-enhanced magnetic solid-phase extraction for organophosphorus pesticide detection in water samples. Anal Methods 14:661. https://doi.org/10.1039/D1AY01698A
Guo X, Xia Z, Wang H, Kang W, Lin L, Cao W, Zhang H, Zhou W (2017) Molecularly imprinted solid phase extraction method for simultaneous determination of seven nitroimidazoles from honey by HPLC-MS/MS. Talanta 166:101–108. https://doi.org/10.1016/j.talanta.2017.01.047
Guo Y, Wang J, Hao L, Wu Q, Wang C, Wang Z (2021) Triazine-triphenylphosphine based porous organic polymer as sorbent for solid phase extraction of nitroimidazoles from honey and water. J Chromatogr A 1649:462238. https://doi.org/10.1016/j.chroma.2021.462238
Hernández-Mesa M, García-Campaña AM, Cruces-Blanco C (2014) Novel solid phase extraction method for the analysis of 5-nitroimidazoles and metabolites in milk samples by capillary electrophoresis. Food Chem 145:161–167. https://doi.org/10.1016/j.foodchem.2013.08.002
Hernández-Mesa M, Carbonell-Rozas L, Cruces-Blanco C, García-Campaña AM (2017) A high-throughput UHPLC method for the analysis of 5-nitroimidazole residues in milk based on salting-out assisted liquid–liquid extraction. J Chromatogr B 1068–1069:125–130. https://doi.org/10.1016/j.jchromb.2017.10.016
Hong Z, Dong Y, Wang R, Chen Y, Wang G (2022) Exploration of an imine-based covalent organic framework for the solid phase extraction of nitroimidazoles in milk and meat samples. J Chromatogr A 1678:463357. https://doi.org/10.1016/j.chroma.2022.463357
Huang X, Lin J, Yuan D (2011) Simple and sensitive determination of nitroimidazole residues in honey using stir bar sorptive extraction with mixed mode monolith followed by liquid chromatography. J Sep Sci 34:2138–2144. https://doi.org/10.1002/jssc.201000880
Jing X, Cheng X, Zhao W, Wang H, Wang X (2020) Magnetic effervescence tablet-assisted switchable hydrophilicity solvent-based liquid phase microextraction of triazine herbicides in water samples. J Mol Liq 306:112934. https://doi.org/10.1016/j.molliq.2020.112934
Kanda M, Sasamoto T, Takeba K, Hayashi H, Kusano T, Matsushima Y, Nakajima T, Kanai S, Takano I (2012) Rapid determination of nitroimidazole residues in honey by liquid chromatography/tandem mass spectrometry. J AOAC Int 95:923–931. https://doi.org/10.5740/jaoacint.11-362
Lasarte-Aragonés G, Lucena R, Cárdenas S (2020) Effervescence-assisted microextraction—one decade of developments. Molecules 25:6053. https://doi.org/10.3390/molecules25246053
Li S, Zhou X, Wang Q, Liu W, Hao L, Wang C, Wang Z, Wu Q (2022) Facile synthesis of hypercrosslinked polymer as high-efficiency adsorbent for the enrichment of nitroimidazoles from water, honey and chicken meat. J Chromatogr A 1682:463527. https://doi.org/10.1016/j.chroma.2022.463527
Liu T, AgyeKum E, Ma S, Ye H, Li J, Gao M, Ni M, Zhang X, Wang X (2021) Novel nanohybrids for effervescence enhanced magnetic solid-phase microextraction of wide-polarity organic pollutants in roasted meat samples. J Sep Sci 44:4313–4326. https://doi.org/10.1002/jssc.202100482
Liu Z, Wang J, Guo Y, Liu J, Wang J, Wang C, Wu Q, Wang Z (2022) Amino-functionalized hypercrosslinked polymer as sorbent for effective extraction of nitroimidazoles from water, drink and honey samples. J Chromatogr A 1676:463206. https://doi.org/10.1016/j.chroma.2022.463206
Mahugo-Santana C, Sosa-Ferrera Z, Torres-Padrón ME, Santana-Rodríguez JJ (2010) Analytical methodologies for the determination of nitroimidazole residues in biological and environmental liquid samples: a review. Anal Chim Acta 665:113–122. https://doi.org/10.1016/j.aca.2010.03.022
Melekhin AO, Tolmacheva VV, Shubina EG, Dmitrienko SG, Apyari VV, Grudev AI (2021) Determination of nitrofuran metabolites in honey using a new derivatization reagent, magnetic solid-phase extraction and LC–MS/MS. Talanta 230:122310. https://doi.org/10.1016/j.talanta.2021.122310
Mitrowska K, Antczak M (2017) Transfer of nitroimidazoles from contaminated beeswax to honey. Food Addit Contam A 34:573–581. https://doi.org/10.1080/19440049.2016.1260166
Rajendran S, Loh SH, Ariffin MM, Khalik WMAWM (2021) CO2-effervescence in liquid phase microextraction for the determination of micropollutants in environmental water: a review. J Anal Chem 76:1371–1383. https://doi.org/10.1134/S1061934821120091
Tolmacheva VV, Apyari VV, Ibragimova BN, Kochuk EV, Dmitrienko SG, Zolotov YA (2015) Polymeric magnetic adsorbent based on Fe3O4 nanoparticles and hypercrosslinked polystyrene for the preconcentration of tetracycline antibiotics. J Anal Chem 70:1313–1321. https://doi.org/10.1134/S1061934815110155
Tolmacheva VV, Apyari VV, Furletov AA, Dmitrienko SG, Zolotov YA (2016) Facile synthesis of magnetic hypercrosslinked polystyrene and its application in the magnetic solid-phase extraction of sulfonamides from water and milk samples before their HPLC determination. Talanta 152:203–210. https://doi.org/10.1016/j.talanta.2016.02.010
Tolmacheva VV, Savinova VY, Goncharov NO, Dmitrienko SG, Apyari VV, Chernavsky PA, Pankina GV (2022) Sorption of amphenicols on magnetic hypercrosslinked polystyrene. Rus J Phys Chem A 96:1268–1272. https://doi.org/10.1134/S0036024422060267
Wang Q, Wang C, Wu Q, Wang Z (2019) Preparation of a magnetic nanoporous polymer for the fast and efficient extraction of 5-nitroimidazoles in milk. J Agric Food Chem 67:11527–11535. https://doi.org/10.1021/acs.jafc.9b03127
Wang Q, Liu W, Hao L, Wang C, Wu Q, Wang Z (2020) Fabrication of magnetic porous organic framework for effective enrichment and assay of nitroimidazoles in chicken meat. Food Chem 332:127427. https://doi.org/10.1016/j.foodchem.2020.127427
Wang Y, Yuan H, Wan Y, Zhang L (2022) Three-dimensional acanthosphere-like hierarchical Co@graphitic carbon for dispersive magnetic solid-phase extraction of nitroimidazole. J Chromatogr A 1675:463163. https://doi.org/10.1016/j.chroma.2022.463163
Xu M, Guo L, Wang Y, Wang Q, Hao L, Wang C, Wu Q, Wang Z (2021) Heterocyclic frameworks as efficient sorbents for solid phase extraction-high performance liquid chromatography analysis of nitroimidazoles in chicken meat. Microchem J 165:106096. https://doi.org/10.1016/j.microc.2021.106096
Xu M, Wang J, Zhang L, Wang Q, Liu W, An Y, Hao L, Wang C, Wang Z, Wu Q (2022) Construction of hydrophilic hypercrosslinked polymer based on natural kaempferol for highly effective extraction of 5-nitroimidazoles in environmental water, honey and fish samples. J Hazard Mater 429:128288. https://doi.org/10.1016/j.jhazmat.2022.128288
Yang X, Mi Y, Liu F, Li J, Gao H, Zhang S, Zhou W, Lu R (2020) Preparation of magnetic attapulgite/polypyrrole nanocomposites for magnetic effervescence-assisted dispersive solid-phase extraction of pyrethroids from honey samples. J Sep Sci 43:2419–2428. https://doi.org/10.1002/jssc.202000049
Yang J, Chen L, Wang Q, Mei X, Yang X, Huo F (2022) Determination of nitroimidazole antibiotics based on dispersive solid-phase extraction combined with capillary electrophoresis. Electrophoresis 44:1–12. https://doi.org/10.1002/elps.202200114
Zhao W, Jing X, Tian Y, Feng C (2020) Magnetic Fe3O4@porous activated carbon effervescent tablet-assisted deep eutectic solvent-based dispersive liquid–liquid microextraction of phenolic endocrine disrupting chemicals in environmental water. Microchem J 159:105416. https://doi.org/10.1016/j.microc.2020.105416
Zhou P, Chen K, Gao M, Qu J, Zhang Z, Dahlgren RA, Li Y, Liu W, Huang H, Wang X (2018) Magnetic effervescent tablets containing ionic liquids as a non-conventional extraction and dispersive agent for determination of pyrethroids in milk. Food Chem 268:468–475. https://doi.org/10.1016/j.foodchem.2018.06.099
Acknowledgements
This work was carried out within the state contract number АААА-А21-121011990021-7 and according to the Development Program of the Interdisciplinary Scientific and Educational School of Lomonosov Moscow State University “The future of the planet and global environmental change.”
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N.O.G.: data collection, data analysis and interpretation, writing— original manuscript preparation and finalization. V.V.T.: supervision, conceptualization, methodology, data interpretation, writing—reviewing and editing. A.O.M.: data collection, data interpretation, writing—reviewing. V.V.A.: conceptualization, methodology, writing—reviewing and editing. S.G.D.: supervision, conceptualization, methodology, writing—reviewing and editing.
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Goncharov, N.O., Tolmacheva, V.V., Melekhin, A.O. et al. Effervescence-Assisted Magnetic Solid-Phase Extraction of Nitroimidazoles and Their Metabolites Using Magnetic Hypercrosslinked Polystyrene. Food Anal. Methods 17, 382–392 (2024). https://doi.org/10.1007/s12161-024-02570-4
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DOI: https://doi.org/10.1007/s12161-024-02570-4