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Magnetic-assisted biotinylated single-chain variable fragment antibody-based immunoassay for amantadine detection in chicken

  • Sanlei Xie
  • Kai Wen
  • Jie Xie
  • Yongjun Zheng
  • Tao Peng
  • Jianyi Wang
  • Kai Yao
  • Shuangyang Ding
  • Haiyang Jiang
Research Paper
  • 44 Downloads

Abstract

A sensitive competitive immunoassay with simple operation was developed for the detection of the anti-virus drug amantadine (AMD). The single-chain variable fragment (scFv) antibody against AMD was site-specific biotinylated and overexpressed as a secreted body in Escherichia coli AVB101. Horseradish peroxidase-labeled streptavidin-biotinylated scFv antibody (HRP-SA-BIO-scFv) could specifically bind to AMD-functionalized magnetic beads (MBs) and then the immune complexes were separated from the matrix solution by magnet. The concentration of the AMD could be known by the measurement of the signal produced by the horseradish peroxidase. The newly established assay provides a significant improvement in comparison to the conventional ELISA without SA-BIO signal amplification and MBs separation. The limit of detection and assay time was 0.64 vs. 8.4 ng/mL and 50 vs. 150 min, respectively. The recoveries ranged from 77.8 to 112% with the coefficient of variation less than 13%. The immunoassay exhibited an obvious cross-reactivity to rimantadine (84%), 1-(1-adamantyl)ethylamine (72%), and somantadine (63%). These results demonstrated that the developed immunoassay provided a sensitive, rapid, and accurate approach for the detection of AMD in chicken by employing MBs as solid phase and SA-BIO as signal amplification. When applied in natural chicken samples, the newly established method provided results consistent with those from UPLC-MS/MS, suggesting that the proposed method could be used for rapid screening of the target of interest; the new immunoassay could also be extended to other small molecular contaminants and thus represents a universal strategy for food safety analysis.

Graphical abstract

Keywords

Immunoassay Biotinylated scFv Magnetic beads Amantadine Chicken 

Notes

Acknowledgments

This work was supported by grants from the National Natural Science Foundation of China (No. 31472236 and 31672600).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Human and/or animal participation

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

Supplementary material

216_2018_1227_MOESM1_ESM.pdf (2.3 mb)
ESM 1 (PDF 2353 kb)

References

  1. 1.
    Ziegler T, Hemphill ML, Ziegler ML, Perez-Oronoz G, Klimov AI, Hampson A, et al. Low incidence of rimantadine resistance in field isolates of influenza A viruses. J Infect Dis. 1999;180:935–9.  https://doi.org/10.1086/314994.CrossRefGoogle Scholar
  2. 2.
    Belshe RB, Smith MH, Hall CB, Betts R, Hay AJ. Genetic-basis of resistance to Rimantadine emerging during treatment of influenza-virus infection. J Virol. 1988;62:1508–12.Google Scholar
  3. 3.
    Gasparini R, Amicizia D, Lai PL, Bragazzi NL, Panatto D. Compounds with anti-influenza activity: present and future of strategies for the optimal treatment and management of influenza. Part I: influenza life-cycle and currently available drugs. J Prev Med Hyg. 2014;55:69–85.Google Scholar
  4. 4.
    Tsuruoka Y, Nakajima T, Kanda M, Hayashi H, Matsushima Y, Yoshikawa S, et al. Simultaneous determination of amantadine, rimantadine, and memantine in processed products, chicken tissues, and eggs by liquid chromatography with tandem mass spectrometry. J Chromatogr B. 2017;1044:142–8.  https://doi.org/10.1016/j.jchromb.2017.01.014.CrossRefGoogle Scholar
  5. 5.
    Liu Z, Yang F, Yao M, Lin Y, Su Z. Simultaneous determination of antiviral drugs in chicken tissues by ultra high performance liquid chromatography with tandem mass spectrometry. J Sep Sci. 2015;38:1784–93.  https://doi.org/10.1002/jssc.201401461.CrossRefGoogle Scholar
  6. 6.
    Higashi Y, Fujii Y. Liquid chromatographic determination of 1-adamantanamine and 2-adamantanamine in human plasma after pre-column derivatization with o-phthalaldehyde and 1-thio-beta-D-glucose. J Chromatogr B. 2004;799:349–54.  https://doi.org/10.1016/j.jchromb.2003.10.062.CrossRefGoogle Scholar
  7. 7.
    Stumph MJ, Noall MW, Knight V. Gas-chromatographic determination of amantadine in human-urine. Clin Chem. 1980;26:295–6.Google Scholar
  8. 8.
    Peng D, Wei W, Pan Y, Wang Y, Chen D, Liu Z, et al. Preparation of a monoclonal antibody against amantadine and rimantadine and development of an indirect competitive enzyme-linked immunosorbent assay for detecting the same in chicken muscle and liver. J Pharmaceut Biomed. 2017;133:56–63.  https://doi.org/10.1016/j.jpba.2016.11.009.CrossRefGoogle Scholar
  9. 9.
    Xu L, Peng S, Liu L, Song S, Kuang H, Xu C. Development of sensitive and fast immunoassays for amantadine detection. Food Agric Immunol. 2016;27:678–88.  https://doi.org/10.1080/09540105.2016.1148667.CrossRefGoogle Scholar
  10. 10.
    Wu S, Zhu F, Hu L, Xi J, Xu G, Liu D, et al. Development of a competitive immunochromatographic assay for the sensitive detection of amantadine in chicken muscle. Food Chem. 2017;232:770–6.  https://doi.org/10.1016/j.foodchem.2017.04.058.CrossRefGoogle Scholar
  11. 11.
    Liu A, Xiong Q, Shen L, Li W, Zeng Z, Li C, et al. A sandwich-type ELISA for the detection of Listeria monocytogenes using the well-oriented single chain Fv antibody fragment. Food Control. 2017;79:156–61.  https://doi.org/10.1016/j.foodcont.2017.03.042.CrossRefGoogle Scholar
  12. 12.
    Xu Z, Dong J, Wang H, Li Z, Beier RC, Jiang Y, et al. Production and characterization of a single-chain variable fragment linked alkaline phosphatase fusion protein for detection of O,O-diethyl organophosphorus pesticides in a one-step enzyme-linked immunosorbent assay. J Agric Food Chem. 2012;60:5076–83.  https://doi.org/10.1021/jf300570q.CrossRefGoogle Scholar
  13. 13.
    Wang J, Majkova Z, Bever CR, Yang J, Gee SJ, Li J, et al. One-step immunoassay for Tetrabromobisphenol A using a camelid single domain antibody-alkaline phosphatase fusion protein. Anal Chem. 2015;87:4741–8.  https://doi.org/10.1021/ac504735p.CrossRefGoogle Scholar
  14. 14.
    Yu C, Zhou H, Zhang W, Yang H, Tang J. Site-specific, covalent immobilization of BirA by microbial transglutaminase: a reusable biocatalyst for in vitro biotinylation. Anal Biochem. 2016;511:10–2.  https://doi.org/10.1016/j.ab.2016.07.026.CrossRefGoogle Scholar
  15. 15.
    Tang J, Tang Y, Yang H. Development of an efficient signal amplification strategy for label-free enzyme immunoassay using two site-specific biotinylated recombinant proteins. Anal Chim Acta. 2015;859:66–71.  https://doi.org/10.1016/j.aca.2014.12.020.CrossRefGoogle Scholar
  16. 16.
    Yang H, Bao R, Yu C, Lv Y, Zhang W, Tang J. Fc-specific biotinylation of antibody using an engineered photoactivatable Z-biotin and its biosensing application. Anal Chim Acta. 2017;949:76–82.  https://doi.org/10.1016/j.aca.2016.10.039.CrossRefGoogle Scholar
  17. 17.
    Fairhead M, Howarth M. Site-specific biotinylation of purified proteins using BirA. Methods Mol Biol (Clifton NJ). 2015;1266:171–84.  https://doi.org/10.1007/978-1-4939-2272-7_12.CrossRefGoogle Scholar
  18. 18.
    Cull MG, Schatz PJ. Biotinylation of proteins in vivo and in vitro using small peptide tags. Applic Chimer Gene Hybrid Prot, PT A. 2000;326:430–40.  https://doi.org/10.1016/S0076-6879(00)26068-0.Google Scholar
  19. 19.
    Maeda Y, Yoshino T, Matsunaga T. In vivo biotinylation of bacterial magnetic particles by a truncated form of Escherichia coli biotin ligase and biotin acceptor peptide. Appl Environ Microbiol. 2010;76:5785–90.  https://doi.org/10.1128/AEM.00916-10.CrossRefGoogle Scholar
  20. 20.
    Dong J, Li Z, Lei H, Sun Y, Ducancel F, Xu Z, et al. Development of a single-chain variable fragment-alkaline phosphatase fusion protein and a sensitive direct competitive chemiluminescent enzyme immunoassay for detection of ractopamine in pork. Anal Chim Acta. 2012;736:85–91.  https://doi.org/10.1016/j.aca.2012.05.033.CrossRefGoogle Scholar
  21. 21.
    Wang Z, Wen K, Zhang X, Li X, Wang Z, Shen J, et al. New Hapten synthesis, antibody production, and indirect competitive enzyme-linked immunosorbent assay for amantadine in chicken muscle. Food Anal Method. 2017, 2017–07-23;  https://doi.org/10.1007/s12161-017-1000-5.
  22. 22.
    Froger A, Hall JE. Transformation of plasmid DNA into E. coli using the heat shock method. J Vis Exp : JoVE. 2007:253. doi: 10.3791/253. PubMed ID:18997900.Google Scholar
  23. 23.
    Jiang W, Wang W, Pan B, Zhang Q, Zhang W, Lv L. Facile fabrication of magnetic chitosan beads of fast kinetics and high capacity for copper removal. ACS Appl Mater Interfaces. 2014;6:3421–6.  https://doi.org/10.1021/am405562c.CrossRefGoogle Scholar
  24. 24.
    Xiao C, Liu X, Mao S, Zhang L, Lu J. Sub-micron-sized polyethyleneimine-modified polystyrene/Fe3O4/chitosan magnetic composites for the efficient and recyclable adsorption of Cu(II) ions. Appl Surf Sci. 2017;394:378–85.  https://doi.org/10.1016/j.apsusc.2016.10.116.CrossRefGoogle Scholar
  25. 25.
    Yan H, Liu X, Cui F, Yun H, Li J, Ding S, et al. Determination of amantadine and rimantadine in chicken muscle by QuEChERS pretreatment method and UHPLC coupled with LTQ Orbitrap mass spectrometry. J Chromatogr B. 2013;938:8–13.  https://doi.org/10.1016/j.jchromb.2013.08.020.CrossRefGoogle Scholar
  26. 26.
    Xie J, Jiang H, Shen J, Peng T, Wang J, Yao K, et al. Design of multifunctional nanostructure for ultrafast extraction and purification of aflatoxins in foodstuffs. Anal Chem. 2017;89:10556–64.  https://doi.org/10.1021/acs.analchem.7b02777.CrossRefGoogle Scholar
  27. 27.
    Zhang X, Song M, Yu X, Wang Z, Ke Y, Jiang H, et al. Development of a new broad-specific monoclonal antibody with uniform affinity for aflatoxins and magnetic beads-based enzymatic immunoassay. Food Control. 2017;79:309–16.  https://doi.org/10.1016/j.foodcont.2017.02.049.CrossRefGoogle Scholar
  28. 28.
    Chen D, Miao H, Zhao Y, Wu Y. Dispersive micro solid phase extraction of amantadine, rimantadine and memantine in chicken muscle with magnetic cation exchange polymer. J Chromatogr B. 2017;1051:92–6.  https://doi.org/10.1016/j.jchromb.2017.03.005.CrossRefGoogle Scholar
  29. 29.
    Wu H, Wang J, Yang H, Li G, Zeng Y, Xia W, et al. Development and application of an in-cell cleanup pressurized liquid extraction with ultra-high-performance liquid chromatography-tandem mass spectrometry to detect prohibited antiviral agents sensitively in livestock and poultry feces. J Chromatogr A. 2017;1488:10–6.  https://doi.org/10.1016/j.chroma.2017.01.070.CrossRefGoogle Scholar
  30. 30.
    Turnipseed SB, Storey JM, Andersen WC, Filigenzi MS, Heise AS, Lohne JJ, et al. Determination and confirmation of the antiviral drug amantadine and its analogues in chicken jerky pet treats. J Agric Food Chem. 2015;63:6968–78.  https://doi.org/10.1021/acs.jafc.5b02416.CrossRefGoogle Scholar
  31. 31.
    Zhao F, Shen Q, Wang H, Han X, Yang Z. Development of a rapid magnetic bead-based immunoassay for sensitive detection of zearalenone. Food Control. 2017;79:227–33.  https://doi.org/10.1016/j.foodcont.2017.03.051.CrossRefGoogle Scholar
  32. 32.
    Xie J, Sun Y, Zheng Y, Wang C, Sun S, Li J, et al. Preparation and application of immunoaffinity column coupled with dcELISA detection for aflatoxins in eight grain foods. Food Control. 2017;73:445–51.  https://doi.org/10.1016/j.foodcont.2016.08.035.CrossRefGoogle Scholar

Copyright information

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

Authors and Affiliations

  • Sanlei Xie
    • 1
    • 2
  • Kai Wen
    • 1
    • 2
  • Jie Xie
    • 1
    • 2
  • Yongjun Zheng
    • 3
  • Tao Peng
    • 1
    • 2
  • Jianyi Wang
    • 1
    • 2
  • Kai Yao
    • 1
    • 2
  • Shuangyang Ding
    • 1
    • 2
  • Haiyang Jiang
    • 1
    • 2
  1. 1.Beijing Advanced Innovation Center for Food Nutrition and Human Health, College of Veterinary MedicineChina Agricultural UniversityBeijingPeople’s Republic of China
  2. 2.Beijing Key Laboratory of Detection Technology for Animal-Derived Food SafetyBeijing Laboratory for Food Quality and SafetyBeijingPeople’s Republic of China
  3. 3.Department of Mechanical and Electrical Engineering, College of EngineeringChina Agricultural UniversityBeijingChina

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