Skip to main content
SpringerLink
Log in

Fast determination of sulfonamides and their acetylated metabolites from environmental water based on magnetic molecularly imprinted polymers

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

Group-selective magnetic molecularly imprinted polymers (MMIPs) that can extract four widely used sulfonamide antibiotics and their acetylated metabolites from environmental water were synthesized in this study. The MMIPs with saturation magnetization value of 16.7 emu g-1 could be separated from the environmental water samples easily by the application of an adscititious magnetic field, reducing the time consumption of pretreatment. The extraction conditions were evaluated, and optimal extraction conditions were as follows: extraction time, 25 min; amount of polymers, 90 mg; washing solvent, 30 % methanol aqueous solution; and elution solvent, methanol–acetic acid (95:5, v/v). The target analytes were detected by liquid chromatography–tandem mass spectrometry, and the detection limits of the method are in the range of 0.38–1.32 ng L-1. The relative standard deviations of intra- and inter-day are in the range of 1.3–6.8 % and 1.7–9.1 %, respectively. The proposed method is suitable for the analysis of environmental water samples.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  • Ariffin MM, Miller EI, Cormack PAG, Anderson RA (2007) Molecularly imprinted solid-phase extraction of diazepam and its metabolites from hair samples. Anal Chem 79:256–262

    Article  CAS  Google Scholar 

  • Batt AL, Snow DD, Aga DS (2006) Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA. Chemosphere 64:1963–1971

    Article  CAS  Google Scholar 

  • Batt AL, Aga DS (2005) Simultaneous analysis of multiple classes of antibiotics by ion trap LC/MS/MS for assessing surface water and groundwater contamination. Anal Chem 77:2940–2947

    Article  CAS  Google Scholar 

  • Carballa M, Omil F, Lema JM, Llompart M, García-Jares C, Rodríguez I, Gómez M, Ternes T (2004) Behavior of pharmaceuticals, cosmetics and hormones in a sewage treatment plant. Water Res 38:2918–2926

    Article  CAS  Google Scholar 

  • Chen LG, Zhang XP, Sun L, Xu Y, Zeng QL, Wang H, Xu HY, Yu AM, Zhang HQ, 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 

  • D’Orazio G, Rocchi S, Fanali S (2012) Nano-liquid chromatography coupled with mass spectrometry: separation of sulfonamides employing non-porous core-shell particles. J Chromatogr A 1255:277–285

    Article  Google Scholar 

  • 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 1193:50–59

    Article  Google Scholar 

  • Díaz-Cruz MS, López de Alda MJ, Barceló D (2006) Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction–liquid chromatography–tandem mass spectrometry. J Chromatogr A 1130:72–82

    Article  Google Scholar 

  • García-Galán MJ, Garrido T, Fraile J, Ginebreda A, Díaz-Cruz MS, Barceló D (2011) Application of fully automated online solid phase extraction–liquid chromatography-electrospray–tandem mass spectrometry for the determination of sulfonamides and their acetylated metabolites in groundwater. Anal Bioanal Chem 399:795–806

    Article  Google Scholar 

  • García-Galán MJ, Díaz-Cruz MS, Barceló D (2008) Identification and determination of metabolites and degradation products of sulfonamide antibiotics. Trends Anal Chem 27:1008–1022

    Article  Google Scholar 

  • Hosoya K, Shirasu Y, Kimata K, Tanaka N (1998) Molecularly imprinted chiral stationary phase prepared with racemic template. Anal Chem 70:943–945

    Article  CAS  Google Scholar 

  • Kan XW, Geng ZR, Zhao Y, Wang ZL, Zhu JJ (2009) Magnetic molecularly imprinted polymer for aspirin recognition and controlled release. Nanotechnology 20:165601–165607

    Article  Google Scholar 

  • Koeber R, Fleischer C, Lanza F, Boos KS, Sellergren B, Barceló D (2001) Evaluation of a multidimensional solid-phase extraction platform for highly selective on-line cleanup and high-throughput LC-MS analysis of triazines in river water samples using molecularly imprinted polymers. Anal Chem 73:2437–2444

    Article  CAS  Google Scholar 

  • Kong X, Gao RX, He XW, Chen LX, Zhang YK (2012) Synthesis and characterization of the core-shell magnetic molecularly imprinted polymers (Fe3O4@MIPs) adsorbents for effective extraction and deterrmination of sulfonamides in the poultry feed. J Chromatogr A 1245:8–16

    Article  CAS  Google Scholar 

  • Le-Minh N, Stuetz RM, Khan SJ (2011) Determination of six sulfonamide antibiotics, two metabolites and trimethoprim in wastewater by isotope dilution liquid chromatography/tandem mass spectrometry. Talanta 89:407–416

    Article  Google Scholar 

  • Li X, Husson SM (2006) Two-dimensional molecular imprinting approach to produce optical biosensor recognition elements. Langmuir 22:9658–9663

    Article  CAS  Google Scholar 

  • Lin CY, Huang SD (2008) Application of liquid–liquid–liquid microextraction and high-performance liquid-chromatography for the determination of sulfonamides in water. Anal Chim Acta 612:37–43

    Article  CAS  Google Scholar 

  • Lindsey ME, Meyer M, Thurman EM (2001) Analysis of trace levels of sulfonamide and tetracycline antimicrobials in groundwater and surface water using solid-phase extraction and liquid chromatography/mass spectrometry. Anal Chem 73:4640–4646

    Article  CAS  Google Scholar 

  • Lopes RP, de Freitas Passos ÉE, de Alkimim Filho JF, Vargas EA, Augusti DV, Augusti R (2012) Development and validation of a method for the determination of sulfonamides in animal feed by modified QuEChERS and LC-MS/MS analysis. Food Control 28:192–198

    Article  CAS  Google Scholar 

  • Luo XB, Zhan YC, Huang YN, Yang LX, Tu XM, Luo SL (2011) Removal of water-soluble acid dyes from water environment using a novel magnetic molecularly imprinted polymer. J Hazard Mater 187:274–282

    Article  CAS  Google Scholar 

  • Wang X, Wang LY, He XW, Zhang YK, Chen LX (2009) A molecularly imprinted polymer-coated nanocomposite of magnetic nanoparticles for estrone recognition. Talanta 78:327–332

    Article  CAS  Google Scholar 

  • McClure EL, Wong CS (2007) Solid phase microextraction of macrolide, trimethoprim, and sulfonamide antibiotics in wastewaters. J Chromatogr A 1169:53–62

    Article  CAS  Google Scholar 

  • Msagati TAM, Nindi MM (2004) Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography–electrospray mass spectrometry detection. Talanta 64:87–100

    Article  CAS  Google Scholar 

  • Murray A, Örmeci B (2012) Application of molecularly imprinted and non-imprinted polymers for removal of emerging contaminants in water and wastewater treatment: a review. Environ Sci Pollut Res 19:3820–3830

    Article  CAS  Google Scholar 

  • Pailler JY, Krein A, Pfister L, Hoffmann L, Guignard C (2009) Solid phase extraction coupled to liquid chromatography–tandem mass spectrometry analysis of sulfonamides, tetracyclines, analgesics and hormones in surface water and wastewater in Luxembourg. Sci Total Environ 407:4736–4743

    Article  CAS  Google Scholar 

  • Pfeifer T, Tuerk J, Fuchs R (2005) Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments. J Am Soc Mass Spectrom 16:1687–1694

    Article  CAS  Google Scholar 

  • Raich-Montiu J, Folch J, Compañó R, Granados M, Prat MD (2007) Analysis of trace levels of sulfonamides in surface water and soil samples by liquid chromatography-fluorescence. J Chromatogr A 1172:186–193

    Article  CAS  Google Scholar 

  • Shi XZ, Meng Y, Liu JH, Sun AL, Li DX, Yao CX, 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 

  • Soto-Chinchilla JJ, García-Campaña AM, Gámiz-Gracia L (2007) Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS. Electrophoresis 28:4164–4172

    Article  CAS  Google Scholar 

  • Soto-Chinchilla JJ, García-Campaña AM, Gámiz-Gracia L, Cruces-Blanco C (2006) Application of capillary zone electrophoresis with large-volume sample stacking to the sensitive determination of sulfonamides in meat and ground water. Electrophoresis 27:4060–4068

    Article  CAS  Google Scholar 

  • Stoob K, Singer HP, Goetz CW, Ruff M, Mueller SR (2005) Fully automated online solid phase extraction coupled directly to liquid chromatography–tandem mass spectrometry: Quantification of sulfonamide antibiotics, neutral and acidic pesticides at low concentrations in surface waters. J Chromatogr A 1097:138–147

    Article  CAS  Google Scholar 

  • Strikovsky A, Hradil J, Wulff G (2003) Catalytically active, molecularly imprinted polymers in bead form. React Funct Polym 54:49–61

    Article  CAS  Google Scholar 

  • Sun L, Chen LG, Sun X, Du XB, Yue YS, He DQ, Xu HY, Zeng QL, Wang H, Ding L (2009) Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection. Chemosphere 77:1306–1312

    Article  CAS  Google Scholar 

  • Urraca JL, Moreno-Bondi MC, Hall AJ, Sellergren B (2007) Direct extraction of penicillin G and derivatives from aqueous samples using a stoichiometrically imprinted polymer. Anal Chem 79:695–701

    Article  CAS  Google Scholar 

  • Xia XL, Lai EPC, Örmeci B (2012) Duo-molecularly imprinted polymer-coated magnetic particles for class-selective removal of endocrine-disrupting compounds from aqueous environment. Environ Sci Pollut Res. doi:10.1007/s11356-012-1262-9

    Google Scholar 

Download references

Acknowledgments

The authors would like to thank the National Natural Science Fund of China (Grant No. 51078108), the Program for New Century Excellent Talents in University (Grant No. NCET-11-0795), and the Development Program of the Ministry of Science and Technology of Jilin Province (Grant No. 20120327) for their support in this study.

Author information

Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130012, China

    Haiyan Chen, Yiqun Zhang, Yang Xu, Qi Zhao, Juan Hou, Jin Yan, Guijie Li, Hui Wang & Lan Ding

  2. Joint State Key Laboratory on Integrated Optoelectronics, Jilin University, Changchun, 130012, China

    Bo Gao & Chun Zhao

  3. College of Resources and Environmental Sciences, Jilin Agricultural University, Changchun, 130018, China

    Bo Gao

  4. State Key Laboratory of Urban Water Resource and Environment, Harbin Institute of Technology, Harbin, 150090, China

    Jie Ding

Authors
  1. Haiyan Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yiqun Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bo Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yang Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qi Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Juan Hou
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jin Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Guijie Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Hui Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Lan Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Jie Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Chun Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chun Zhao.

Additional information

Responsible editor: Philippe Garrigues

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chen, H., Zhang, Y., Gao, B. et al. Fast determination of sulfonamides and their acetylated metabolites from environmental water based on magnetic molecularly imprinted polymers. Environ Sci Pollut Res 20, 8567–8578 (2013). https://doi.org/10.1007/s11356-013-1795-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-013-1795-6

Keywords

Search

Navigation