Synthesis and characterization of tracers and development of a fluorescence polarization immunoassay for amantadine with high sensitivity in chicken.


Journal

Journal of food science
ISSN: 1750-3841
Titre abrégé: J Food Sci
Pays: United States
ID NLM: 0014052

Informations de publication

Date de publication:
Oct 2021
Historique:
revised: 24 07 2021
received: 24 04 2021
accepted: 02 08 2021
pubmed: 23 9 2021
medline: 21 10 2021
entrez: 22 9 2021
Statut: ppublish

Résumé

Fluorescence polarization immunoassay (FPIA) is a homogeneous and rapid analytical method that is suitable for high-throughput screening of large numbers of samples. However, FPIA typically suffers from lower sensitivity than the well-established enzyme-linked immunosorbent assay (ELISA), limiting its wide application as an analytical tool that can be run with trace levels of an analyte. Herein, a highly sensitive FPIA for detecting amantadine (AMD) in chicken is described. To achieve high sensitivity, nine chemical tracers of AMD that employ different fluoresceins, fluorescein derivatives, and haptens were synthesized and paired with four previously produced monoclonal antibodies (mAbs). The effect of the tracer structure on the sensitivity of FPIA was investigated and discussed. We found that the tracers with a linear and shorter bridge between adamantane and fluorescein generally provided higher sensitivity. After optimization, N'-(1-adamantyl) ethylenediamine (AEDA), an AMD structural analogue labeled with fluorescein isothiocyanate (FITC), achieved the lowest IC

Identifiants

pubmed: 34549423
doi: 10.1111/1750-3841.15896
doi:

Substances chimiques

Amantadine BF4C9Z1J53

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

4754-4767

Informations de copyright

© 2021 Institute of Food Technologists®.

Références

Arndt, T., Guessregena, B., Hohla, A., & Reis, J. (2005). Determination of serum amantadine by liquid chromatography-tandem mass spectrometry. Clinica Chimica Acta, 359, 125-131. https://doi.org/10.1016/j.cccn.2005.03.040
Kolosova A. Y., Park J. H., Eremin S. A., Kang S. J., & Chung D. H. (2003). Fluorescence polarization immunoassay based on a monoclonal antibody for the detection of the organophosphorus pesticide parathion-methyl. Journal of Agricultural and Food Chemistry, 51, 1107-1114. https://doi.org/10.1111/j.1365-2621.2004.00856.x
Krasnova A. I., Eremin S. A., Natangelo M., Tavazzi S., & Benfenati E. (2001). A polarization fluorescence immunoassay for the herbicide propanil. Analytical Letters, 34, 2285-2301. https://doi.org/10.1081/AL-100107295
Chayrov, R., Parisis, N. A., Chatziathanasiadou, M. V., Vrontaki, E., Moschovou, K., Melagraki, G., Sbirkova-Dimitrova, H., Shivachev, B., Schmidtke, M., Mitrev, Y., Sticha, M., Mavromoustakos, T., Tzakos, A. G., & Stankova, I. (2020). Synthetic analogues of aminoadamantane as influenza viral inhibitors-in vitro, in silico and QSAR studies. Molecules (Basel, Switzerland), 25(17), 3989. https://doi.org/10.3390/molecules25173989
Chen, J., Shanin I. A., Lv, S., Wang, Q., Mao, C., & Xu, Z. (2016). Heterologous strategy enhancing the sensitivity of the fluorescence polarization immunoassay of clinafloxacin in goat milk. Journal of the Science of Food and Agriculture, 96, 1341-1346. https://doi.org/10.1002/jsfa.7228
Dong, B., Li, H., Ghulam Mujtaba, M., Yu, X., Yu, W., Wen, K., Ke, Y., Shen, J., & Wang, Z. (2019a). Fluorescence immunoassay based on the inner-filter effect of carbon dots for highly sensitive amantadine detection in foodstuffs. Food Chemistry, 294, 347-354. https://doi.org/10.1016/j.foodchem.2019.05.082
Ding, Y., Chen, H., Yang, Q., Feng, L., Hua, X., & Wang, M. (2019). A fluorescence polarization immunoassay for detection of thiacloprid in environmental and agricultural samples. RSC Advances, 63, 36825-36830. https://doi.org/10.1039/C9RA04776J
Dong, B., Zhao, S., Li, H., Wen, K., Ke, Y., Shen, J., Zhang, S., Shi, W., & Wang, Z. (2019b). Design, synthesis and characterization of tracers and development of a fluorescence polarization immunoassay for the rapid detection of ractopamine in pork. Food Chemistry, 271, 9-17. https://doi.org/10.1016/j.foodchem.2018.07.147
Du, Q., Liu, P., & Mezey, P. G. (2005). Theoretical derivation of heuristic molecular lipophilicity potential: A quantum chemical description for molecular solvation. Journal of Chemical Information and Modeling, 45, 347-353. https://doi.org/10.1021/ci049707l
Fodey, T. L., Greer, N. M., & Crooks, S. R. (2009). Antibody production: Low dose immunogen vs. low incorporation hapten using salmeterol as a model. Analytica Chimica Acta, 637, 328-32. https://doi.org/10.1016/j.aca.2008.09.025
He G., Qiao J., Dong C., He C., Zhao L., & Tian Y. (2008). Amantadine-resistance among H5N1 avian influenza viruses isolated in northern China. Antiviral Research, 77, 72-76. https://doi.org/10.1016/j.antiviral.2007.08.007
Hu, Y., Musharrafieh, R., Ma, C., Zhang, J., Smee, D. F., De Grado, W. F., & Wang, J. (2017). An M2-V27A channel blocker demonstrates potent in vitro and in vivo antiviral activities against amantadine-sensitive and -resistant influenza A viruses. Antiviral Research, 140, 45-54. https://doi.org/10.1016/j.antiviral.2017.01.006
Chun H. S., Choi E. H., Chang H. J., Choi S. W., & Eremin S. A. (2009). A fluorescence polarization immunoassay for the detection of zearalenone in corn. Analytica Chimica Acta, 639, 83-89. https://doi.org/10.1016/j.aca.2009.02.048
Gorris H. H., Bade S., & Frey A. (2011). Pushing antibody-based labeling systems to higher sensitivity by linker-assisted affinity enhancement. Bioconjugate Chemistry, 22, 1619-1624. https://doi.org/10.1021/bc2001787
Lu, T., & Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry, 33, 580-592. https://doi.org/10.1002/jcc.22885
Liang, X., Sheng, Y., Yu W., Zhao, S., Shan, H., Zhang, Q., & Wang, Z. (2018). Comparison of chicken IgY and mammalian IgG in three immunoassays for detection of sulfamethazine in milk. Food Analytical Methods, 11, 2352-2463. https://doi.org/10.1007/s12161-018-1316-9
Mi, T., Liang, X., Ding, L., Zhang, S., Eremin S. A., Beier R. C., Shen, J., & Wang, Z. (2014). Development and optimization of a fluorescence polarization immunoassay for orbifloxacin in milk. Analytical Methods, 3849-3857. https://doi.org/10.1039/C3AY42034E
Mi, T., Wang, Z., Eremin S. A., Shen, J., & Zhang, S. (2013). Simultaneous determination of multiple (fluoro)quinolone antibiotics in food samples by a one-step fluorescence polarization immunoassay. Journal of Agricultural and Food Chemistry, 61, 9347-9355. https://doi.org/10.1021/jf403972r
Spilovska, K., Zemek, F., Korabecny, J., Nepovimova, E., Soukup, O., Windisch, M., & Kuca, K. (2016). Adamantane-A lead structure for drugs in clinical practice. Current Medicinal Chemistry, 23, 3245-3266. https://www.ingentaconnect.com/contentone/ben/cmc/2016/00000023/00000029/art00003
Wu, S., Zhu, F., Hu, L., Xi, J., Xu, G., Liu, D., Guo, Q., Luo, K., & Lai, W. (2017). Development of a competitive immunochromatographic assay for the sensitive detection of amantadine in chicken muscle. Food Chemistry, 232, 770. https://doi.org/10.1016/j.foodchem.2017.04.058
Wu, Y. L., Chen, R. X., Xue, Y., Yang, T., Zhao, J., & Zhu, Y. (2014). Simultaneous determination of amantadine, rimantadine and memantine in chicken muscle using multi-walled carbon nanotubes as a reversed-dispersive solid phase extraction sorbent. Journal of Chromatography B Analytical Technologies in the Biomedical and Life Sciences, 965, 197-205. https://doi.org/10.1016/j.jchromb.2014.06.038.
Wang, Z., Wen, K., Zhang, X., Li, X., Shen, J., & Ding, S. (2018). New hapten synthesis, antibody production, and indirect competitive enzyme-linked immunosorbent assay for amantadine in chicken muscle. Food Analytical Methods, 11, 302-308. https://doi.org/10.1007/s12161-017-1000-5
Wang, Z., Zhang, S., Ding, S., Eremin S. A., & Shen, J. (2008). Simultaneous determination of sulphamerazine, sulphamethazine and sulphadiazine in honey and chicken muscle by a new monoclonal antibody-based fluorescence polarization immunoassay. Food Additives and Contaminants, 25, 574-582. https://doi.org/10.1080/02652030701713913
Wang, Z., Li, Y., Liang, X., Zhang, S., Shi, W., & Shen, J. (2013). Forcing immunoassay for sulfonamides to higher sensitivity and broader detection spectrum by site heterologous hapten inducing affinity improvement. Analytical Methods, 5, 6990-7000. https://doi.org/10.1039/C3AY40864G
Wang, Z., Zhang, H., Ni, H., Zhang, S., & Shen, J. (2014a). Development of a highly sensitive and specific immunoassay for enrofloxacin based on heterologous coating haptens. Analytica Chimica Acta, 820, 152-158. https://doi.org/10.1016/j.aca.2014.02.043
Wang, Z., Shen, J., Duan, H., Yu, Q., & Zhang, S. (2014b). New haptens synthesis, antibody production and comparative molecular field analysis for tetracyclines. RSC Advances, 4, 53788-53794. https://doi.org/10.1039/C4RA08364D
Wang, X., Wu, X., Lu, Z., & Tao, X. (2020). Comparative study of time-resolved fluorescent nanobeads, quantum dot nanobeads and quantum dots as labels in fluorescence immunochromatography for detection of aflatoxin B1 in grains. Biomolecules, 10(4), 575. https://doi.org/10.3390/biom10040575
Xu, L., Peng, S., Liu, L., Song, S., & Kuang, H. (2016). Development of sensitive and fast immunoassays for amantadine detection. Food and Agricultural Immunology, 27(5), 678-688. https://doi.org/10.1080/09540105.2016.1148667
Xie, S., Wen, K., Xie, J., Zheng, Y., & Peng, T. (2018). Magnetic-assisted biotinylated single-chain variable fragment antibody-based immunoassay for amantadine detection in chicken. Analytical and Bioanalytical Chemistry, 410, 6197-6205.
Yan, H., Liu, X., Cui, F., Yun, H., Li, J., Ding, S., Yang, D., & Zhang, Z. (2013). Determination of amantadine and rimantadine in chicken muscle by QuEChERS pretreatment method and UHPLC coupled with LTQ Orbitrap mass spectrometry. Journal of Chromatography B, 938, 8-13. https://doi.org/10.1016/j.jchromb.2013.08.020
Tsuruoka Y., Nakajima T., Kanda M., Hayashi H., Matsushima Y., Yoshikawa S., Nagata, M., Koike, H., Nagano, C., Sekimura, K., Hashimoto, T., Takano, I., & Shindo, T. (2017). Simultaneous determination of amantadine, rimantadine, and memantine in processed products, chicken tissues, and eggs by liquid chromatography with tandem mass spectrometry. Journal of Chromatography B, 1044-1045, 142-148. https://doi.org/10.1016/j.jchromb.2017.01.014
Caplan Y. H., Levine B., & Goldberger B. (1987). Fluorescence polarization immunoassay evaluated for screening for amphetamine and methamphetamine in urine. Clinical Chemistry, 33, 1200-1202. https://doi.org/10.1093/clinchem/33.7.1200
Chen, D., Miao, H., Zhao, Y., & Wu, Y. (2017). Dispersive micro solid phase extraction of amantadine, rimantadine and memantine in chicken muscle with magnetic cation exchange polymer. Journal of Chromatography B Analytical, 1051, 92-96. https://10.1016/j.jchromb.2017.03.005
Zhang, X., Eremin S. A., Wen, K., Yu, X., Li, C., Ke, Y., Jiang, H., Shen, J., & Wang, Z. (2017). Fluorescence polarization immunoassay based on a new monoclonal antibody for the detection of the zearalenone class of mycotoxins in maize. Journal of Agricultural and Food Chemistry, 65, 2240-2247. https://doi.org/10.1021/acs.jafc.6b05614
Zhang, H., Yang S., De Ruyck K., Beloglazova N., Eremin S. A., Zhang, S., Shen J., & Wang, Z. (2019). Fluorescence polarization assay for chemical contaminants in food and environmental analysis. Trend in Analytical Chemistry, 114, 293-313. https://doi.org/10.1016/j.trac.2019.03.013
Zhang, S., Wang, Z., Nesterenko I. S., Eremin S. A., & Shen J. Z. (2007). Fluorescence polarization immunoassay based on a monoclonal antibody for the detection of sulphamethazine in chicken muscle. International Journal of Food Science and Technology, 42, 36-44. https://doi.org/10.1111/j.1365-2621.2006.01202.x

Auteurs

Liuchuan Guo (L)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Meixuan Liu (M)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Qiang Li (Q)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Baolei Dong (B)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Hongfang Li (H)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Ghulam Mujtaba Mari (GM)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Rui Liu (R)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Wenbo Yu (W)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Xuezhi Yu (X)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Zhanhui Wang (Z)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Suxia Zhang (S)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Jianzhong Shen (J)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

Kai Wen (K)

College of Veterinary Medicine, China Agricultural University, Beijing Key Laboratory of Detection Technology for Animal-Derived Food, Beijing Laboratory for Food Quality and Safety, Beijing, People's Republic of China.

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