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Environmental Science and Pollution Research

, Volume 25, Issue 16, pp 16121–16134 | Cite as

Simultaneous determination of sulfonamides and fluoroquinolones from environmental water based on magnetic double-template molecularly imprinting technique

  • Yang Xu
  • Jiangnan Li
  • Liyan Jiang
  • Zhengqiang Li
  • Yi Li
  • Lan Ding
Research Article

Abstract

In this work, a fast and selective method based on magnetic extraction is presented for the simultaneous extraction of sulfonamides (SAs) and fluoroquinolones (FQs), followed by liquid chromatography-tandem mass spectrometry detection. In this method, magnetic surface double-template molecularly imprinted polymers (MSdt-MIPs) with superparamagnetic property and high selectivity toward both SAs and FQs were synthesized and directly applied to the simultaneous extraction of SAs and FQs from environmental water as magnetic adsorbents. The extraction and enrichment procedures could be accomplished in one single step by stirring the mixture of MSdt-MIPs and water sample, and the MSdt-MIPs with adsorbed analytes were easily separated from the water sample by a magnet afterwards. The adsorption mechanism of MSdt-MIPs was investigated by employing the adsorption thermodynamic and kinetic studies, and the selectivity of the MSdt-MIPs toward target analytes was evaluated through the selectivity test. For validation of the proposed method, the matrix effect was evaluated and compared to that of the traditional SPE method. Excellent linearity (R > 0.9990) for both SAs and FQs were obtained in the concentration range of 20–2000 ng L−1, and the limits of detection are in the range of 3.0–4.7 ng L−1 for SAs while 4.1–6.1 ng L−1 for FQs. Finally, the proposed method was successfully applied to the simultaneous determination of SAs and FQs in several environmental water samples.

Keywords

Sulfonamides Fluoroquinolones Magnetic surface double-template molecularly imprinted polymer Environmental water Liquid chromatography-tandem mass spectrometry 

Notes

Funding information

This work was supported by the Development Program of the Ministry of Science and Technology of Jilin Province, China (Grant number 20150204070GX).

Supplementary material

11356_2018_1581_MOESM1_ESM.doc (525 kb)
ESM 1 (DOC 525 kb)

References

  1. Attallah OA, Alghobashy MA, Nebsen M, Salem MY (2017) Adsorptive removal of fluoroquinolones from water by pectin-functionalized magnetic nanoparticles: process optimization using a spectrofluorimetric assay. RSC Adv 5:133–145Google Scholar
  2. Bossi A, Piletsky SA, Piletska EV, Righetti PG, Turner APF (2001) Surface-grafted molecularly imprinted polymers for protein recognition. Anal Chem 73:5281–5286CrossRefGoogle Scholar
  3. Chen LG, Li B (2013) Magnetic molecularly imprinted polymer extraction of chloramphenicol from honey. Food Chem 141:23–28CrossRefGoogle Scholar
  4. Chen LG, Liu J, Zeng QL, Wang H, Yu AM, Zhang HQ, Ding L (2009) Preparation of magnetic molecularly imprinted polymer for the separation of tetracycline antibiotics from egg and tissue samples. J Chromatogr A 1216:3710–3719CrossRefGoogle Scholar
  5. Chen H, Zhang Y, Gao B, Xu Y, Zhao Q, Hou J, Yan J, Li G, Wang H, Ding L, Ding J, Zhao C (2013) Fast determination of sulfonamides and their acetylated metabolites from environmental water based on magnetic molecularly imprinted polymers. Environ Sci Pollut Res 20:8567–8578CrossRefGoogle Scholar
  6. de Oliveira LH, Trindade MAG (2016) Baseline-corrected second-order derivative electroanalysis combined with ultrasound-assisted liquid-liquid microextraction: simultaneous quantification of fluoroquinolones at low levels. Anal Chem 88:6554–6562CrossRefGoogle Scholar
  7. de Oliveira HL, Anacleto SD, da Silva ATM, Pereira AC, Borges WD, Figueiredo EC, Borges KB (2016) Molecularly imprinted pipette-tip solid phase extraction for selective determination of fluoroquinolones in human urine using HPLC-DAD. J Chromatogr B 1033–1034:27–39CrossRefGoogle Scholar
  8. Díaz-Álvarez M, Barahona F, Turiel E, Martín-Esteban A (2014) Supported liquid membrane-protected molecularly imprinted beads for micro-solid phase extraction of sulfonamides in environmental waters. J Chromatogr A 1357:158–164CrossRefGoogle Scholar
  9. Díaz-Cruz MS, García-Galán MJ, Barceló D (2008) Highly sensitive simultaneous determination of sulfonamide antibiotics and one metabolite in environmental waters by liquid chromatography–quadrupole linear ion trap–mass spectrometry. J Chromatogr A 1193:50–59CrossRefGoogle Scholar
  10. Dubreil-Chéneau E, Pirotais Y, Verdon E, Hurtaud-Pessel D (2014) Confirmation of 13 sulfonamides in honey by liquid chromatography–tandem mass spectrometry for monitoring plans: validation according to European Union Decision 2002/657/EC. J Chromatogr A 1339:128–136CrossRefGoogle Scholar
  11. Galarini R, Diana F, Moretti S, Puppini B, Saluti G, Persic L (2014) Development and validation of a new qualitative ELISA screening for multiresidue detection of sulfonamides in food and feed. Food Control 35:300–310CrossRefGoogle Scholar
  12. Guillén I, Gabaldón JA, Núñez-Delicado E, Puchades R, Maquieira A, Morais S (2011) Detection of sulphathiazole in honey samples using a lateral flow immunoassay. Food Chem 129:624–629CrossRefGoogle Scholar
  13. Hoff RB, Pizzolato TM, Peralba MDCR, Díaz-Cruz MS, Barceló D (2015) Determination of sulfonamide antibiotics and metabolites in liver, muscle and kidney samples by pressurized liquid extraction or ultrasound-assisted extraction followed by liquid chromatography–quadrupole linear ion trap-tandem mass spectrometry (HPLC–QqLIT-MS/MS). Talanta 134:768–778CrossRefGoogle Scholar
  14. Jansomboon W, Boontanon SK, Boontanon N, Polprasert C, Da CT (2016) Monitoring and determination of sulfonamide antibiotics (sulfamethoxydiazine, sulfamethazine, sulfamethoxazole and sulfadiazine) in imported Pangasius catfish products in Thailand using liquid chromatography coupled with tandem mass spectrometry. Food Chem 212:635–640CrossRefGoogle Scholar
  15. Kaur R, Hasan A, Iqbal N, Alam S, Saini MK, Raza SK (2014) Synthesis and surface engineering of magnetic nanoparticles for environmental cleanup and pesticide residue analysis: a review. J Sep Sci 37:1805–1825CrossRefGoogle Scholar
  16. Konak Üİ, Certel M, Şık B, Tongur T (2017) Development of an analysis method for determination of sulfonamides and their five acetylated metabolites in baby foods by ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry (Orbitrap-MS). J Chromatogr B 1057:81–91CrossRefGoogle Scholar
  17. Li C, Wang Z, Cao X, Beier RC, Zhang S, Ding S, Li X, Shen J (2008) Development of an immunoaffinity column method using broad-specificity monoclonal antibodies for simultaneous extraction and cleanup of quinolone and sulfonamide antibiotics in animal muscle tissues. J Chromatogr A 1209:1–9CrossRefGoogle Scholar
  18. Liu C, Liao Y, Huang X (2016) Preparation of a boronic acid functionalized magnetic adsorbent for sensitive analysis of fluoroquinolones in environmental water samples. Anal Methods 8:4744–4754CrossRefGoogle Scholar
  19. Mei M, Huang X (2016) Determination of fluoroquinolones in environmental water and milk samples treated with stir cake sorptive extraction based on a boron-rich monolith. J Sep Sci 39:1908–1918CrossRefGoogle Scholar
  20. Mor F, Sahindokuyucu Kocasari F, Ozdemir G, Oz B (2012) Determination of sulphonamide residues in cattle meats by the Charm-II system and validation with high performance liquid chromatography with fluorescence detection. Food Chem 134:1645–1649CrossRefGoogle Scholar
  21. Nong C, Niu Z, Li P, Wang C, Li W, Wen Y (2017) Dual-cloud point extraction coupled to high performance liquid chromatography for simultaneous determination of trace sulfonamide antimicrobials in urine and water samples. J Chromatogr B 1051:9–16CrossRefGoogle Scholar
  22. Ou D, Chen B, Bai R, Song P, Lin H (2015) Contamination of sulfonamide antibiotics and sulfamethazine-resistant bacteria in the downstream and estuarine areas of Jiulong River in Southeast China. Environ Sci Pollution Res 22:12104–12113CrossRefGoogle Scholar
  23. Peixoto PS, Tóth IV, Segundo MA, Lima JLFC (2016) Fluoroquinolones and sulfonamides: features of their determination in water. A review. Int J Environ An Chem 96:185–202CrossRefGoogle Scholar
  24. Poliwoda A, KrzyżAk M, Wieczorek PP (2010) Supported liquid membrane extraction with single hollow fiber for the analysis of fluoroquinolones from environmental surface water samples. J Chromatogr A 1217:3590–3597CrossRefGoogle Scholar
  25. Santos B, Lista A, Simonet BM, Ríos A, Valcárcel M (2005) Screening and analytical confirmation of sulfonamide residues in milk by capillary electrophoresis-mass spectrometry. Electrophoresis 26:1567–1575CrossRefGoogle Scholar
  26. Segura PA, Gagnon C, Sauvé S (2009) Application of turbulent flow chromatography load columns for the on-line analysis of anti-infectives in wastewaters. Chromatographia 70:239–245CrossRefGoogle Scholar
  27. Speltini A, Sturini M, Maraschi F, Mandelli E, Vadivel D, Dondi D, Profumo A (2016) Preparation of silica-supported carbon by Kraft lignin pyrolysis, and its use in solid-phase extraction of fluoroquinolones from environmental waters. Microchim Acta 183:2241–2249CrossRefGoogle Scholar
  28. Spielmeyer A, Ahlborn J, Hamscher G (2014) Simultaneous determination of 14 sulfonamides and tetracyclines in biogas plants by liquid-liquid-extraction and liquid chromatography tandem mass spectrometry. Anal Bioanal Chem 406:2513–2524CrossRefGoogle Scholar
  29. Tetzner NF, Maniero MG, Rodrigues-Silva C, Rath S (2016) On-line solid phase extraction-ultra high performance liquid chromatography-tandem mass spectrometry as a powerful technique for the determination of sulfonamide residues in soils. J Chromatogr A 1452:89–97CrossRefGoogle Scholar
  30. 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 152:203–210CrossRefGoogle Scholar
  31. Wang N, Su M, Liang S, Sun H (2015) Sensitive residue analysis of quinolones and sulfonamides in aquatic product by capillary zone electrophoresis using large-volume sample stacking with polarity switching combined with accelerated solvent extraction. Food Anal Method 9:1020–1028CrossRefGoogle Scholar
  32. Wang H, Ding J, Ding L, Ren N (2016) Analysis of sulfonamides in soil, sediment, and sludge based on dynamic microwave-assisted micellar extraction. Environ Sci Pollut Res 23:12954–12965CrossRefGoogle Scholar
  33. Wu J, Zhao H, Chen R, Chuong PH, Hui X, He H (2016) Adsorptive removal of trace sulfonamide antibiotics by water-dispersible magnetic reduced graphene oxide-ferrite hybrids from wastewater. J Chromatogr B 1029–1030:106–112CrossRefGoogle Scholar
  34. Xu Y, Ding J, Chen H, Zhao Q, Hou J, Yan J, Wang H, Ding L, Ren N (2013) Fast determination of sulfonamides from egg samples using magnetic multiwalled carbon nanotubes as adsorbents followed by liquid chromatography-tandem mass spectrometry. Food Chem 140:83–90CrossRefGoogle Scholar
  35. Xu Y, Zhao Q, Jiang L, Li Z, Chen Y, Ding L (2017) Selective determination of sulfonamides from environmental water based on magnetic surface molecularly imprinting technology. Environ Sci Pollut Res 24:9174–9186CrossRefGoogle Scholar
  36. Zhao YG, Zhou LX, Pan SD, Zhan PP, Chen XH, Jin MC (2014) Fast determination of 22 sulfonamides from chicken breast muscle using core–shell nanoring amino-functionalized superparamagnetic molecularly imprinted polymer followed by liquid chromatography-tandem mass spectrometry. J Chromatogr A 1345:17–28CrossRefGoogle Scholar
  37. Zhao YG, Zhang Y, Zhan PP, Chen XH, Pan SD, Jin MC (2016) Fast determination of 24 steroid hormones in river water using magnetic dispersive solid phase extraction followed by liquid chromatography–tandem mass spectrometry. Environ Sci Pollut Res 23:1529–1539CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.College of Life SciencesJilin UniversityChangchunChina
  2. 2.College of ChemistryJilin UniversityChangchunChina
  3. 3.State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of ChemistryJilin UniversityChangchunChina

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