Fluorescent competitive assay for melamine using dummy molecularly imprinted polymers as antibody mimics

doi:10.1016/S2095-3119(16)61357-6

Journal of Integrative Agriculture ›› 2016, Vol. 15 ›› Issue (05): 1166-1177.DOI: 10.1016/S2095-3119(16)61357-6

• 论文 • 上一篇

Fluorescent competitive assay for melamine using dummy molecularly imprinted polymers as antibody mimics

DU Xin-wei^{1, 2}, ZHANG Yan-xin³, SHE Yong-xin^{1, 2}, LIU Guang-yang³, ZHAO Feng-nian^{1, 2}, WANG Jing^{1, 2}, WANG Shan-shan^{1, 2}, JIN Fen^{1, 2}, SHAO Hua^{1, 2}, JIN Mao-jun^{1, 2}, ZHENG Lu-fei^{1, 2}

¹ Institute of Quality Standards and Testing Technology for Agro-Products, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R.China
² Key Laboratory of Agro-product Quality and Safety, Beijing 100081, P.R.China
³ School of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin 150001, P.R.China

收稿日期:2015-05-13 出版日期:2016-05-03 发布日期:2016-05-03
通讯作者: WANG Jing, Tel: +86-10-82106568, E-mail: w_jing2001@126.com
作者简介:DU Xin-wei, E-mail: wduxinwei@126.com
基金资助:
This work was supported by the National Natural Science Foundation of China (31260620, 31471654) and the Special Fund for Agro-scientific Research in the Public Interest of China (201203094)

Fluorescent competitive assay for melamine using dummy molecularly imprinted polymers as antibody mimics

¹ Institute of Quality Standards and Testing Technology for Agro-Products, Chinese Academy of Agricultural Sciences, Beijing 100081, P.R.China
² Key Laboratory of Agro-product Quality and Safety, Beijing 100081, P.R.China
³ School of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin 150001, P.R.China

Received:2015-05-13 Online:2016-05-03 Published:2016-05-03
Contact: WANG Jing, Tel: +86-10-82106568, E-mail: w_jing2001@126.com
About author:DU Xin-wei, E-mail: wduxinwei@126.com
Supported by:
This work was supported by the National Natural Science Foundation of China (31260620, 31471654) and the Special Fund for Agro-scientific Research in the Public Interest of China (201203094)

摘要/Abstract

Abstract: A fluorescent competitive assay for melamine was first developed utilizing dummy molecularly imprinted polymers (DMIPs) as artificial antibodies. This method is based on the competition between fluorescent substances and the unlabeled analyte for binding sites in synthesized DMIPs and the decreased binding of fluorescent substances to DMIPs due to increased concentrations of melamine in the solutions. DMIPs for melamine were synthesized under a hot water bath in the presence of the initiator azobisisobutyronitrile (AIBN) using 2,4-diamino-6-methyl-1,3,5-triazine (DAMT) as a dummy template, methacrylic acid (MAA) as a functional monomer, and ethylene glycol dimethacrylate (EGDMA) as a crosslinking agent. The adsorption capacity and selectivity of DMIPs for melamine were evaluated by the isothermal adsorption curve and Scatchard analysis. The evaluation results showed that the synthesized DMIPs had specific recognition sites for melamine and the maximum adsorption amount was 1 066.33 μg g^–1. Later, 5-(4,6-dichlorotriazinyl) amino fluorescein (DTAF) with a triazine ring, which slightly resembles melamine, was selected as the fluorescent substance. The fluorescent competitive assay using DMIPs as the antibody mimics was finally established by selecting and optimizing the reaction solvents, DMIPs amount, DTAF concentration, and incubation time. The optimal detection system showed a linear response within range of 0.05–40 mg L^–1 and the limit of detection (LOD) was 1.23 μg L^–1. It was successfully applied to the detection of melamine in spiked milk samples with satisfactory recoveries (71.9 to 86.3%). According to the comparative analysis, the result of optimized fluorescent competitive assay revealed excellent agreement with the HPLC-MS/MS result for melamine.

Key words: dummy molecularly imprinted polymers , melamine , fluorescent competitive assay , artificial antibody

DU Xin-wei, ZHANG Yan-xin, SHE Yong-xin, LIU Guang-yang, ZHAO Feng-nian, WANG Jing, WANG Shan-shan, JIN Fen, SHAO Hua, JIN Mao-jun, ZHENG Lu-fei. Fluorescent competitive assay for melamine using dummy molecularly imprinted polymers as antibody mimics[J]. Journal of Integrative Agriculture, 2016, 15(05): 1166-1177.

参考文献

Abbate V, Bassindale A R, Brandstadt K F, Taylor P G. 2011. Biomimetic catalysis at silicon centre using molecularly imprinted polymers. Journal of Catalysis, 284, 68–76.

Ai K L, Liu Y L, Lu L H. 2009. Hydrogen-bonding recognition-induced color change of gold nanoparticles for visual detection of melamine in raw milk and infant formula. Journal of the American Chemical Society, 131, 9496–9497.

Ali M S, Rafiuddin S, Ghori M, Khatri A R. 2008. Simultaneous determination of metformin hydrochloride, cyanoguanidine and melamine in tablets by mixed-mode HILIC. Chromatographia, 67, 517–525.

Anirudhan T S, Alexander S. 2015. Design and fabrication of molecularly imprinted polymer-based potentiometric sensor from the surface modified multiwalled carbon nanotube for the determination of lindane (gamma-hexachlorocyclohexane), an organochlorine pesticide. Biosensors and Bioelectronics, 64, 586–593.

Asadi E, Azodi-Deilami S, Abdouss M, Kordestani D, Rahimi A, Asadi S. 2014. Synthesis, recognition and evaluation of molecularly imprinted polymer nanoparticle using miniemulsion polymerization for controlled release and analysis of risperidone in human plasma samples. Korean Journal of Chemical Engineering, 31, 1028–1035.

Benito-Pena E, Moreno-Bondi M C, Aparicio S, Orellana G, Cederfur J, Kempe M. 2006. Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays. Analytical Chemistry, 78, 2019–2027.

Cao B Y, Yang H, Song J, Chang H F, Li S Q, Deng A P. 2013. Sensitivity and specificity enhanced enzyme-linked immunosorbent assay by rational hapten modification and heterogeneous antibody/coating antigen combinations for the detection of melamine in milk, milk powder and feed samples. Talanta, 116, 173–180.

Chen L X, Xu S F, Li J H. 2011. Recent advances in molecular imprinting technology: Current status, challenges and highlighted applications. Chemical Society Reviews, 40, 2922–2942.

Curcio M, Puoci F, Cirillo G, Iemma F, Spizzirri U G, Picci N. 2010. Selective determination of melamine in aqueous medium by molecularly imprinted solid phase extraction. Journal of Agricultural and Food Chemistry, 58, 11883–11887.

Dai C M, Zhang J, Zhang Y L, Zhou X F, Liu S G. 2013. Application of molecularly imprinted polymers to selective removal of clofibric acid from water. PLOS ONE, 8, e78167.

Garber E A E. 2008. Detection of melamine using commercial enzyme-linked immunosorbent assay technology. Journal of Food Protection, 71, 590–594.

Haupt K, Mayes A G, Mosbach K. 1998. Herbicide assay using an imprinted polymer-based system analogous to competitive fluoroimmunoassays. Analytical Chemistry, 70, 3936–3939.

He L M, Su Y J, Zheng Y Q, Huang X H, Wu L, Liu Y H. 2009. Novel cyromazine imprinted polymer applied to the solid-phase extraction of melamine from feed and milk samples. Journal of Chromatography A, 1216, 6196–6203.

Levi R, McNiven S, Piletsky S A, Cheong S H, Yano K, Karube I. 1997. Optical detection of chloramphenicol using molecularly imprinted polymers. Analytical Chemistry, 69, 2017–2021.

Li Y Q, Li X, Li Y, Dong C K, Jin P F, Qi J Y. 2009. Selective recognition of veterinary drugs residues by artificial antibodies designed using a computational approach. Biomaterials, 30, 3205–3211.

Lin M S. 2009. A review of traditional and novel detection techniques for melamine and its analogues in foods and animal feed. Frontiers of Chemical Engineering in China, 3, 427–435.

Lu C H, Zhou W H, Han B, Yang H H, Chen X, Wang X R. 2007. Surface-imprinted core-shell nanoparticles for sorbent assays. Analytical Chemistry, 79, 5457–5461.

Mc-Niven S, Kato M, Levi R, Yano K, Karube I. 1998. Chloramphenicol sensor based on an in situ imprinted polymer. Analytica Chimica Acta, 365, 69–74.

Nicholls C, Karim K, Piletsky S A, Saini S, Setford S. 2006. Displacement imprinted polymer receptor analysis (DIPRA) for chlorophenolic contaminants in drinking water and packaging materials. Biosensors Bioelectronics, 21, 1171–1177.

Pavlovic D M, Niksic K, Livazovic S, Brnardic I, Anzlovar A. 2015. Preparation and application of sulfaguanidine-imprinted polymer on solid-phase extraction of pharmaceuticals from water. Talanta, 131, 99–107.

Piletsky S A, Piletskaya E V, Bossi A, Karim K, Lowe P, Turner A P F. 2001. Substitution of antibodies and receptors with molecularly imprinted polymers in enzyme-linked and fluorescent assays. Biosensors Bioelectronics, 16, 701–707.

Piletsky S A, Piletskaya E V, Elskaya A V, Levi R, Yano K, Karube I. 1997. Optical detection system for triazine based on molecularly-imprinted polymers. Analytical Letters, 30, 445–455.

Rostamizadeh K, Vahedpour M, Bozorgi S. 2012. Synthesis, characterization and evaluation of computationally designed nanoparticles of molecular imprinted polymers as drug delivery systems. International Journal of Pharmaceutics, 424, 67–75.

Sainz-Gonzalo F J, Fernandez-Sanchez J F, Fernandez-Gutierrez A. 2011. The development of a screening molecularly imprinted polymer optosensor for detecting xylenes in water samples. Microchemical Journal, 99, 278–282.

Sancho J V, Ibanez M, Grimait-Brea S, Pozo O J, Hernandez F. 2005. Residue determination of cyromazine and its metabolite melamine in chard samples by ion-pair liquid chromatography coupled to electrospray tandem mass spectrometry. Analytica Chimica Acta, 530, 237- 243.

Suarez-Rodriguez J L, Diaz-Garcia M E. 2001. Fluorescent competitive flow-through assay for chloramphenicol using molecularly imprinted polymers. Biosensors Bioelectronics, 16, 955–961.

Su X M, Li X Y, Li J J, Liu M, Lei F H, Tan X C, Li P F, Luo W Q. 2015. Synthesis and characterization of core-shell magnetic molecularly imprinted polymers for solid-phase extraction and determination of Rhodamine B in food. Food Chemistry, 171, 292–297.

Tittlemier S A. 2010. Methods for the analysis of melamine and related compounds in foods: A review. Food Additives and Contaminants, 27, 129–145.

Urraca J L, Moreno-Bondi M C, Orellana G, Hall A J, Sellergren B. 2007. Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays. Analytical Chemistry, 79, 4915–4923.

Vlatakis G, Andersson L I, Müller R, Mosbach K. 1993. Drug assay using antibody mimics made by molecular imprinting. Nature, 361, 645–647.

Wang M, She Y X, Du X W, Huang Y T, Shi X M, Jin M J. 2013. Determination of melamine using magnetic molecular imprinted polymers and high performance liquid chromatography. Analytical Letters, 46, 120–130.

Wang X H, Fang Q X, Liu S P, Chen L. 2012. Preparation of a magnetic molecularly imprinted polymer with pseudo template for rapid simultaneous determination of cyromazine and melamine in bio-matrix samples. Analytical and Bioanalytical Chemistry, 404, 1555–1564.

Xu X M, Ren Y P, Zhu Y, Cai Z X, Han J L, Huang B F. 2009. Direct determination of melamine in dairy products by gas chromatography/mass spectrometry with coupled column separation. Analytica Chimica Acta, 650, 39–43.

Ye L, Mosbach K. 2008. Molecular imprinting: Synthetic materials as substitutes for biological antibodies and receptors. Chemistry of Materials, 20, 859–868.

Zhang J J, Wu M, Chen D, Song Z. 2011. Ultrasensitive determination of melamine in milk products and biological fluids by luminol-hydrogen peroxide chemiluminescence. Journal of Food Composition and Analysis, 24, 1038–1042.

Fluorescent competitive assay for melamine using dummy molecularly imprinted polymers as antibody mimics

Fluorescent competitive assay for melamine using dummy molecularly imprinted polymers as antibody mimics

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics