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Surface-imprinted magnetic particles for highly selective sulfonamides recognition prepared by reversible addition fragmentation chain transfer polymerization

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Abstract

In this work, novel magnetic molecularly imprinted polymers (MMIPs) were prepared by reversible addition fragmentation chain transfer (RAFT) polymerization using sulfamerazine as the template. With the controlled/living property of RAFT polymerization, the resulting MMIPs showed high selectivity for sulfonamides recognition. The MMIPs were characterized by transmission electron microscopy, Fourier transform infrared, vibrating sample magnetometer, X-ray diffraction, X-ray photoelectron spectroscopy, and thermogravimetric analysis. The static and selectivity binding experiments demonstrated the desirable adsorption capacity and high selectivity of the MMIPs. The developed MMIPs were used as the solid-phase extraction sorbents to selectively extract four sulfonamides from aqueous solution. The recoveries of the spiked pond water ranged from 61.2 to 94.1 % with RSD lower than 6.5 %. This work demonstrated a versatile approach for the preparation of well-constructed MMIPs for application in the field of solid-phase extraction.

Surface-imprinted magnetic particles with high magnetism and binding capacity

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References

  1. Marzo A, Dal Bo L (1998) Chromatography as an analytical tool for selected antibiotic classes: a reappraisal addressed to pharmacokinetic applications. J Chromatogr A 812:17–34

    Article  CAS  Google Scholar 

  2. Jiang W, Beloglazova NV, Wang Z, Jiang H, Wen K, de Saeger S, Luo P, Wu Y, Shen J (2015) Development of a multiplex flow-through immunoaffinity chromatography test for the on-site screening of 14 sulfonamide and 13 quinolone residues in milk. Biosens Bioelectron 66:124–128

    Article  CAS  Google Scholar 

  3. Kloth K, Rye-Johnsen M, Didier A, Dietrich R, Martlbauer E, Niessner R, Seidel M (2009) A regenerable immunochip for the rapid determination of 13 different antibiotics in raw milk. Analyst 134:1433–1439

    Article  CAS  Google Scholar 

  4. Shi X, Meng Y, Liu J, Sun A, Li D, Yao C, Lu Y, Chen J (2011) Group-selective molecularly imprinted polymer solid-phase extraction for the simultaneous determination of six sulfonamides in aquaculture products. J Chromatogr B 879:1071–1076

    Article  CAS  Google Scholar 

  5. Wu L, Song Y, Hu M, Xu X, Zhang H, Yu A, Ma Q, Wang Z (2015) Determination of sulfonamides in butter samples by ionic liquid magnetic bar liquid-phase microextraction high-performance liquid chromatography. Anal Bioanal Chem 407:569–580

    Article  CAS  Google Scholar 

  6. Littlefield NA, Sheldon WG, Allen R, Gaylor DW (1990) Chronic toxicity carcinogenicity studies of sulfamethazine in fischer 344/N rats-2-generation exposure. Food Chem Toxicol 28:157–167

    Article  CAS  Google Scholar 

  7. Wang S, Zhang HY, Wang L, Duan ZJ, Kennedy I (2006) Analysis of sulphonamide residues in edible animal products: a review. Food Addit Contam 23:362–384

    Article  CAS  Google Scholar 

  8. Muriano A, Chabottaux V, Diserens JM, Granier B, Sanchez-Baeza F, Marco MP (2015) Rapid immunochemical analysis of the sulfonamide-sugar conjugated fraction of antibiotic contaminated honey samples. Food Chem 178:156–163

    Article  CAS  Google Scholar 

  9. Bedatty Fernandes FC, Silva AS, Rufino JL, Pezza HR, Pezza L (2015) Screening and determination of sulphonamide residues in bovine milk samples using a flow injection system. Food Chem 166:309–315

    Article  Google Scholar 

  10. Spietelun A, Marcinkowski L, de la Guardia M, Namiesnik J (2013) Recent developments and future trends in solid phase microextraction techniques towards green analytical chemistry. J Chromatogr A 1321:1–13

    Article  CAS  Google Scholar 

  11. Purra M, Cinca R, Legaz J, Nunez O (2014) Solid-phase extraction and field-amplified sample injection-capillary zone electrophoresis for the analysis of benzophenone UV filters in environmental water samples. Anal Bioanal Chem 406:6189–6202

    Article  CAS  Google Scholar 

  12. Wang Z, Han Q, Xia J, Xia L, Ding M, Tang J (2013) Graphene-based solid-phase extraction disk for fast separation and preconcentration of trace polycyclic aromatic hydrocarbons from environmental water samples. J Sep Sci 36:1834–1842

    Article  CAS  Google Scholar 

  13. Tan J, Jiang ZT, Li R, Yan XP (2012) Molecularly-imprinted monoliths for sample treatment and separation. Trends Anal Chem 39:207–217

    Article  CAS  Google Scholar 

  14. Hu Y, Pan J, Zhang K, Lian H, Li G (2013) Novel applications of molecularly-imprinted polymers in sample preparation. Trends Anal Chem 43:37–52

    Article  CAS  Google Scholar 

  15. Chen FF, Wang R, Shi YP (2012) Molecularly imprinted polymer for the specific solid-phase extraction of kirenol from Siegesbeckia pubescens herbal extract. Talanta 89:505–512

    Article  CAS  Google Scholar 

  16. Li Q, Yang K, Liang Y, Jiang B, Liu J, Zhang L, Liang Z, Zhang Y (2014) Surface protein imprinted core-shell particles for high selective lysozyme recognition prepared by reversible addition-fragmentation chain rransfer strategy. ACS Appl Mater Interfaces 6:21954–21960

    Article  CAS  Google Scholar 

  17. Zhao C, Ji Y, Shao Y, Jiang X, Zhang H (2009) Novel molecularly imprinted polymer prepared by nanoattapulgite as matrix for selective solid-phase extraction of diethylstilbestrol. J Chromatogr A 1216:7546–7552

    Article  CAS  Google Scholar 

  18. Chen FF, Xie XY, Shi YP (2013) Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine. J Chromatogr A 1300:112–118

    Article  CAS  Google Scholar 

  19. Xie X, Wei F, Chen L, Wang S (2015) Preparation of molecularly imprinted polymers based on magnetic nanoparticles for the selective extraction of protocatechuic acid from plant extracts. J Sep Sci 38:1046–1052

    Article  CAS  Google Scholar 

  20. Wang X, Fang Q, Liu S, Chen L (2012) Preparation of a magnetic molecularly imprinted polymer with pseudo template for rapid simultaneous determination of cyromazine and melamine in bio-matrix samples. Anal Bioanal Chem 404:1555–1564

    Article  CAS  Google Scholar 

  21. Zhang Y, Liu R, Hu Y, Li G (2009) Microwave heating in preparation of magnetic molecularly imprinted polymer beads for trace triazines analysis in complicated samples. Anal Chem 81:967–976

    Article  CAS  Google Scholar 

  22. Chen L, Xu S, Li J (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942

    Article  CAS  Google Scholar 

  23. Hu X, Pan J, Hu Y, Li G (2011) Preparation of molecularly imprinted polymer coatings with the multiple bulk copolymerization method for solid-phase microextraction. J Appl Polym Sci 120:1266–1277

    Article  CAS  Google Scholar 

  24. Bompart M, Haupt K (2009) Molecularly imprinted polymers and controlled/living radical polymerization. Aust J Chem 62:751–761

    Article  CAS  Google Scholar 

  25. Hu X, Fan Y, Zhang Y, Dai G, Cai Q, Cao Y, Guo C (2012) Molecularly imprinted polymer coated solid-phase microextraction fiber prepared by surface reversible addition-fragmentation chain transfer polymerization for monitoring of Sudan dyes in chilli tomato sauce and chilli pepper samples. Anal Chim Acta 731:40–48

    Article  CAS  Google Scholar 

  26. Zhou T, Jorgensen L, Mattebjerg MA, Chronakis IS, Ye L (2014) Molecularly imprinted polymer beads for nicotine recognition prepared by RAFT precipitation polymerization: a step forward towards multi-functionalities. RSC Adv 4:30292–30299

    Article  CAS  Google Scholar 

  27. Moraes J, Ohno K, Maschmeyer T, Perrier S (2013) Synthesis of silica-polymer core-shell nanoparticles by reversible addition-fragmentation chain transfer polymerization. Chem Commun 49:9077–9088

    Article  CAS  Google Scholar 

  28. Ganachaud F, Monteiro MJ, Gilbert RG, Dourges MA, Thang SH, Rizzardo E (2000) Molecular weight characterization of poly(N-isopropylacrylamide) prepared by living free-radical polymerization. Macromolecules 33:6738–6745

    Article  CAS  Google Scholar 

  29. He Y, Huang Y, Jin Y, Liu X, Liu G, Zhao R (2014) Well-defined nanostructured surface-imprinted polymers for highly selective magnetic separation of fluoroquinolones in human urine. Acs Appl Mater Interfaces 6:9634–9642

    Article  CAS  Google Scholar 

  30. Xie X, Pan X, Han S, Wang S (2015) Development and characterization of magnetic molecularly imprinted polymers for the selective enrichment of endocrine disrupting chemicals in water and milk samples. Anal Bioanal Chem 407:1735–1744

    Article  CAS  Google Scholar 

  31. Li Y, Li X, Chu J, Dong C, Qi J, Yuan Y (2010) Synthesis of core-shell magnetic molecular imprinted polymer by the surface RAFT polymerization for the fast and selective removal of endocrine disrupting chemicals from aqueous solutions. Environ Pollut 158:2317–2323

    Article  CAS  Google Scholar 

  32. Guo L, Jiang X, Yang C, Zhang H (2008) Analysis of sulfamerazine in pond water and several fishes by high-performance liquid chromatography using molecularly imprinted solid-phase extraction. Anal Bioanal Chem 391:2291–2298

    Article  CAS  Google Scholar 

  33. Chen L, Zhang X, Sun L, Xu Y, Zeng Q, Wang H, Xu H, Yu A, Zhang H, Ding L (2009) Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer. J Agric Food Chem 57:10073–10080

    Article  CAS  Google Scholar 

  34. Zhang HF, Shi YP (2012) Magnetic retrieval of chitosan: extraction of bioactive constituents from green tea beverage samples. Analyst 137:910–916

    Article  CAS  Google Scholar 

  35. Lu F, Li H, Sun M, Fan L, Qiu H, Li X, Luo C (2012) Flow injection chemiluminescence sensor based on core-shell magnetic molecularly imprinted nanoparticles for determination of sulfadiazine. Anal Chim Acta 718:84–91

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by National Natural Science Foundation of China (81503033 and 81227802), China Postdoctoral Science Foundation (2014M550501), Shaanxi Province Postdoctoral Science Foundation, and the Fundamental Research Funds for the Central Universities (xjj2014066).

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Authors and Affiliations

  1. School of Pharmacy, Health Science Center, Xi’an Jiaotong University, 710061, Xi’an, China

    Xiaoyu Xie, Xia Liu, Xiaoyan Pan, Liang Chen & Sicen Wang

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  1. Xiaoyu Xie
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  2. Xia Liu
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  3. Xiaoyan Pan
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  4. Liang Chen
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  5. Sicen Wang
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Correspondence to Sicen Wang.

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Xie, X., Liu, X., Pan, X. et al. Surface-imprinted magnetic particles for highly selective sulfonamides recognition prepared by reversible addition fragmentation chain transfer polymerization. Anal Bioanal Chem 408, 963–970 (2016). https://doi.org/10.1007/s00216-015-9190-4

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  • DOI: https://doi.org/10.1007/s00216-015-9190-4

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