Skip to main content
Log in

Study on a Biomimetic Enzyme-Linked Immunosorbent Assay for Rapid Detection of Flumequine in Animal Foods

  • Published:
Food Analytical Methods Aims and scope Submit manuscript

Abstract

Flumequine (FLU) is widely used as an antibiotic in the treatment and control of animal diseases, which may result in the presence of residues harmful to humans in food products of animal origin. A novel and fast biomimetic enzyme-linked immunosorbent assay (BELISA) was developed for the determination of FLU based on a molecularly imprinted polymer (MIP) as a selective affinity agent. With an optimized molar ratio of FLU to methacrylic acid (MAA) of 1:2 determined by molecular dynamic simulations, the MIP was directly synthesized on the surface of a 96-well plate (as solid support) with FLU as the template molecule, MAA as the functional monomer, ethylene glycol dimethacrylate (EGDMA) as the cross-linker, and azodiisobutyronitrile (AIBN) as the initiator. Under the optimized conditions, the BELISA method was established with a sensitivity (IC50) of 0.141 μg/mL and a detection limit (IC15) of 1.09 × 10−3 μg/mL. The developed method was applied to determine FLU concentrations in spiked beef and shrimp samples, with satisfactory recovery values ranging from 80.7 to 92.2% with relative standard deviations (n = 3) between 3.3% and 7.0%. This method can be used for the rapid determination of FLU in animal foods and has promising applications in food safety monitoring.

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

Access this article

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

Instant access to the full article PDF.

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

Similar content being viewed by others

References

  • Abraham MJ, Murtola T, Schulz R, Páll S, Smith JC, Hess B, Lindahl E (2015) GROMACS: high performance molecular simulations through multi-level parallelism from laptops to supercomputers. Softwarex C:19-25.

    Article  Google Scholar 

  • Ali SY, Nourolhoda R (2015) Application of molecularly-imprinted polymers in solid-phase microextraction techniques. TrAC Trends Anal Chem 73:81–90

    Article  Google Scholar 

  • Barrón D, Jiménez-Lozano E, Bailac S, Barbosa J (2003) Simultaneous determination of flumequine and oxolinic acid in chicken tissues by solid phase extraction and capillary electrophoresis. Anal Chim Acta 1:21–27

    Article  Google Scholar 

  • CFIA (2018) Canadian Food Inspection Agency aquaculture therapeutant residue monitoring list, http://www.inspection.gc.ca/food/requirements-and-guidance/preventive-controls-food-businesses/fish/aquaculture-therapeutant-residue-monitoring-list/eng/1515417397242/1515417466758

  • Coillie EV, Block JD, Reybroeck W (2004) Development of an indirect competitive ELISA for flumequine residues in raw milk using chicken egg yolk antibodies. J Agric Food Chem 52:4975–4978

    Article  Google Scholar 

  • EU (2010) Commission Regulation (EU) 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(20 January 2010):1–76

    Google Scholar 

  • Ferraresi C, Lucatello L, Meucci V, Intorre L, Grilli G, Piccirillo A, Russo E, Villa R, Montesissa C, Cagnardi P (2013) Pharmacokinetic/pharmacodynamic evaluation of the efficacy of flumequine in treating colibacillosis in turkeys. Poult Sci 12:3158–3165

    Article  Google Scholar 

  • Huet A-C, Charlier C, Tittlemier SA, Singh G, Benrejeb S, Delahaut P (2006) Simultaneous determination of (fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA). J Agric Food Chem 54:2822–2827

    Article  CAS  Google Scholar 

  • Ktari N, Fourati N, Zerrouki C, Ruan M, Seydou M, Barbaut F, Nal F, Yaakoubi N, Chehimi MM, Kalfat R (2015) Design of a polypyrrole MIP-SAW sensor for selective detection of flumequine in aqueous media. Correlation between experimental results and DFT calculations. RSC Adv 108:88666–88674

    Article  Google Scholar 

  • Li L, Lin Z, Peng A, Zhong H, Chen X, Huang Z (2016) Biomimetic ELISA detection of malachite green based on magnetic molecularly imprinted polymers. J Chromatogr B 1035:25–30

    Article  CAS  Google Scholar 

  • Liu XM, Feng SY, Zhou P, Chen YQ, Zhang H, Chen W (2013) Simultaneous determination of danofloxacin and flumequine in milk based on fluorescence spectroscopy and chemometrics tools. Food Anal Methods 6:1739–1749

    Article  Google Scholar 

  • Liu QR, Jiang MD, Ju ZL, Qiao XG, Xu ZX (2018) Development of direct competitive biomimetic immunosorbent assay based on quantum dot label for determination of trichlorfon residues in vegetables. Food Chem 250:134–139

    Article  CAS  Google Scholar 

  • Martinez L, Andrade R, Birgin EG, Martinez JM (2009) PACKMOL: A package for building initial configurations for molecular dynamics simulations. J Comput Chem 13:2157–2164

    Article  Google Scholar 

  • MOA (2002) Ministry of Agriculture of the People’s Republic of China announcement No. 235. Maximum residue limit of veterinary drugs in animal foods

  • OuYang XK, Luo YY, Wen ZS, Wu WJ, Cao GZ, Zhu XY, Yang LY, Wang YG, Dong JY (2014) Simultaneous determination of flumequine and oxolinic acid residues in aquatic products using pressurized capillary electrochromatography. Food Anal Methods 7:1770–1775

    Article  Google Scholar 

  • Peng J, Liu L, Xu L, Song S, Kuang H, Cui G, Xu C (2017) Gold nanoparticle-based paper sensor for ultrasensitive and multiple detection of 32 (fluoro)quinolones by one monoclonal antibody. Nano Res 1:108–120

    Article  Google Scholar 

  • Shi C, Liu X, Song L, Qiao X, Xu Z (2015) Biomimetic enzyme-linked immunosorbent assay_using_a_hydrophilic_molecularly imprinted membrane for recognition and fast determination of trichlorfon and acephate residues in vegetables. Food Anal Methods 8:2496–2503

    Article  Google Scholar 

  • Sousa da Silva AW, Vranken WF (2012) ACPYPE – Ante chamber PYthon parser interface. BMC Res Notes 1:367–367

    Article  Google Scholar 

  • SNT1751.3-2011 (2011) Standards for entry-exit inspection and quarantine of the People’s Republic of China.

  • Steven MP, Kathleen RES, Steven MM (2000) Pharmacokinetics, tissue distribution, and metabolism of flumequine in channel catfish (Ictalurus punctatus). Aquaculture 187:1–14

    Article  Google Scholar 

  • Sun Q, Xu L, Ma Y, Qiao X, Xu Z (2014) Study on a biomimetic enzyme-linked immunosorbent assay method for rapid determination of trace acrylamide in French fries and cracker samples. J Sci Food Agric 94:102–108

    Article  CAS  Google Scholar 

  • Tang Y, Fang G, Wang S, Sun J (2013) Rapid determination of metolcarb residues in foods using a biomimetic enzyme-linked immunosorbent assay employing a novel molecularly imprinted polymer film as artificial antibody. J AOAC Int 96(2):453–458

    Article  CAS  Google Scholar 

  • Wang JM, Wang W, Kollman PA, Case DA (2006) Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model 2:247–260

    Article  Google Scholar 

  • Wang Y, Shen YD, Xu ZL, Lei HT, Wang H, Sun YM (2010) Production and identification of monoclonal antibody against flumequine and development of indirect competitive enzyme-linked immunosorbent assay. Chin J Anal Chem 38(3):313–317

    Article  CAS  Google Scholar 

  • Wang J, Sang YX, Liu WH, Liang N, Wang XH (2017) The development of biomimetic enzyme-linked immunosorbent assay based on molecular imprinting technique for the detection of enrofloxacin in animal food. Anal Methods 47:6682–6688

    Article  Google Scholar 

  • Willem H, Husniye G, Geert C, Michel WFN (2007) Biosensor immunoassay for flumequine in broiler serum and muscle. Anal Chim Acta 586:312–318

    Article  Google Scholar 

  • Xu ZX, Gao HJ, Zhang LM, Chen XQ, Qiao XG (2011) The biomimetic immunoassay based on molecularly imprinted polymer: a comprehensive review of recent progress and future prospects. J Food Sci 2:69–75

    Article  Google Scholar 

  • Ye L, Haupt K (2004) Molecularly imprinted polymers as antibody and receptor mimics for assays, sensors and drug discovery. Anal Bioanal Chem 8:1887–1897

    Article  Google Scholar 

  • Zhang B, Du D, Meng M, Eremin SA, Rybakov VB, He X, Yin Y (2014) A magnetic particle-based competitive enzyme immunoassay for rapid determination of ciprofloxacin: a potential method for the general detection of fluoroquinolones. Anal Lett 7:1134–1146

    Article  Google Scholar 

  • Zhu Y, Li L, Wang Z, Chen Y, Zhao Z, Zhu L, Wu X, Wan Y, He F, Shen J (2008) Development of an immunochromatography strip for the rapid detection of 12 fluoroquinolones in chicken muscle and liver. J Agric Food Chem 14:5469–5474

    Article  Google Scholar 

Download references

Funding

The study is financially supported by the National Key R & D Program of China, the Ministry of Science and Technology of the People’s Republic of China (No. 2016YFD0401101).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xianghong Wang.

Ethics declarations

Conflict of Interest

Weihua Liu declares that she has no conflict of interest. Jing Wang declares that she has no conflict of interest. Wenlong Yu declares that he has no conflict of interest. Xianghong Wang declares that she has no conflict of interest.

Ethical Approval

This article does not contain any studies with human or animal subjects performed by the any of the authors.

Informed Consent

Not applicable.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, W., Wang, J., Yu, W. et al. Study on a Biomimetic Enzyme-Linked Immunosorbent Assay for Rapid Detection of Flumequine in Animal Foods. Food Anal. Methods 13, 403–411 (2020). https://doi.org/10.1007/s12161-019-01660-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12161-019-01660-y

Keywords

Navigation