1. Beijing Advanced Innovation Center for Food Nutrition and Human Health/College of Veterinary Medicine, China Agricultural University, Beijing 100193, China 2. Beijing Key Laboratory of Detection Technology for Animal-Derived Food Safety, Beijing 100193, China 3. Department for Safety Supervision of Animal Products, China Animal Health and Epidemiology Center, Qingdao 266032, China 4. Department of Genetic Toxicology, Shenzhen Center for Disease Control and Prevention, Shenzhen 518020, China 5. Beijing Laboratory for Food Quality and Safety/National Reference Laboratory for Veterinary Drug Residues, Beijing 100193, China
Three immunizing haptens of bisphenol A (BPA), including two new haptens, were used to produce highly sensitive and specific polyclonal antibodies. The spacer arms of haptens for coupling to the protein carrier were located at different positions in BPA, and different length spacer arms were tested. Highly sensitive polyclonal antibodies were obtained and characterized using indirect competitive enzyme-linked immunosorbent assay (icELISA). Under optimized conditions, the half maximal inhibitory concentration (IC50) value of the best polyclonal antibody was 2.1 mg·L−1, based on coating heterogeneous antigens, and this optimal polyclonal antibody was highly sensitive toward BPA and displayed negligible cross-reactivity with bisphenol B and bisphenol E. A sensitive icELISA method utilizing the polyclonal antibody was developed for the determination of BPA in milk. In spiked samples (5, 10 and 20 mg·L−1), the recovery ranged from 80% to 102% with a coefficient of variation (CV) value below 15.8%. The limit of detection of icELISA was 1.95 mg·L−1. These results indicate that the icELISA method is suitable for the detection of BPA in milk.
. [J]. Frontiers of Agricultural Science and Engineering, 2017, 4(3): 366-372.
Xiya ZHANG, Xiaoyun DONG, Sijun ZHAO, Yuebin KE, Kai WEN, Suxia ZHANG, Zhanhui WANG, Jianzhong SHEN. Synthesis of haptens and production of antibodies to bisphenol A. Front. Agr. Sci. Eng. , 2017, 4(3): 366-372.
Kim A, Li C R, Jin C F, Lee K W, Lee S H, Shon K J, Park N G, Kim D K, Kang S W, Shim Y B, Park J S. A sensitive and reliable quantification method for bisphenol A based on modified competitive ELISA method. Chemosphere, 2007, 68(7): 1204–1209 https://doi.org/10.1016/j.chemosphere.2007.01.079
2
Choi K C, Jeung E B. The biomarker and endocrine disruptors in mammals. Journal of Reproduction and Development, 2003, 49(5): 337–345 https://doi.org/10.1262/jrd.49.337
3
Iso T, Watanabe T, Iwamoto T, Shimamoto A, Furuichi Y. DNA damage caused by bisphenol A and estradiol through estrogenic activity. Biological & Pharmaceutical Bulletin, 2006, 29(2): 206–210 https://doi.org/10.1248/bpb.29.206
4
Diel P, Schulz T, Smolnikar K, Strunck E, Vollmer G, Michna H. Ability of xeno- and phytoestrogens to modulate expression of estrogen-sensitive genes in rat uterus: estrogenicity profiles and uterotropic activity. Journal of Steroid Biochemistry, 2000, 73(1–2): 1–10 https://doi.org/10.1016/S0960-0760(00)00051-0
5
Steinmetz R, Mitchner N A, Grant A, Allen D L, Bigsby R M, Ben-Jonathan N. The xenoestrogen bisphenol A induces growth, differentiation, and c-fos gene expression in the female reproductive tract. Endocrinology, 1998, 139(6): 2741–2747 https://doi.org/10.1210/en.139.6.2741
6
Markey C M, Rubin B S, Soto A M, Sonnenschein C. Endocrine disruptors: from Wingspread to environmental developmental biology. Journal of Steroid Biochemistry, 2002, 83(1–5): 235–244 https://doi.org/10.1016/S0960-0760(02)00272-8
7
Rudel R A, Brody J G, Spengler J C, Vallarino J, Geno P W, Sun G, Yau A. Identification of selected hormonally active agents and animal mammary carcinogens in commercial and residential air and dust samples. Journal of the Air & Waste Management Association, 2001, 51(4): 499–513 https://doi.org/10.1080/10473289.2001.10464292
8
Behnisch P A, Fujii K, Shiozaki K, Kawakami I, Sakai S. Estrogenic and dioxin-like potency in each step of a controlled landfill leachate treatment plant in Japan. Chemosphere, 2001, 43(4–7): 977–984 https://doi.org/10.1016/S0045-6535(00)00458-6
Meesters R J W, Schroder H F. Simultaneous determination of 4-nonylphenol and bisphenol A in sewage sludge. Analytical Chemistry, 2002, 74(14): 3566–3574 https://doi.org/10.1021/ac011258q
11
Inoue K, Kato K, Yoshimura Y, Makino T, Nakazawa H. Determination of bisphenol A in human serum by high-performance liquid chromatography with multi-electrode electrochemical detection. Journal of Chromatography. B, Biomedical Sciences and Applications, 2000, 749(1): 17–23 https://doi.org/10.1016/S0378-4347(00)00351-0
12
De Meulenaer B, Baert K, Lanckriet H, Van Hoed V, Huyghebaert A. Development of an enzyme-linked immunosorbent assay for bisphenol A using chicken immunoglobulins. Journal of Agricultural and Food Chemistry, 2002, 50(19): 5273–5282 https://doi.org/10.1021/jf0202739
13
Lu Y, Peterson J R, Gooding J J, Lee N A. Development of sensitive direct and indirect enzyme-linked immunosorbent assays (ELISAs) for monitoring bisphenol A in canned foods and beverages. Analytical and Bioanalytical Chemistry, 2012, 403(6): 1607–1618 https://doi.org/10.1007/s00216-012-5969-8
14
Maiolini E, Ferri E, Pitasi A L, Montoya A, Di Giovanni M, Errani E, Girotti S. Bisphenol A determination in baby bottles by chemiluminescence enzyme-linked immunosorbent assay, lateral flow immunoassay and liquid chromatography tandem mass spectrometry. Analyst (London), 2014, 139(1): 318–324 https://doi.org/10.1039/C3AN00552F
15
Moreno M J, D’Arienzo P, Manclus J J, Montoya A. Development of monoclonal antibody-based immunoassays for the analysis of bisphenol A in canned vegetables. Journal of Environmental Science and Health. Part. B, Pesticides, Food Contaminants, and Agricultural Wastes, 2011, 46(6): 509–517
16
Ohkuma H, Abe K, Ito M, Kokado A, Kambegawa A, Maeda M. Development of a highly sensitive enzyme-linked immunosorbent assay for bisphenol A in serum. Analyst, 2002, 127(1): 93–97 https://doi.org/10.1039/b103515k
17
Wu X L, Wang L B, Ma W, Zhu Y Y, Xu L G, Kuang H, Xu C L. A simple, sensitive, rapid and specific detection method for bisphenol A based on fluorescence polarization immunoassay. Immunological Investigations, 2012, 41(1): 38–50 https://doi.org/10.3109/08820139.2011.579671
18
Zhao M P, Li Y Z, Guo Z Q, Zhang X X, Chang W B. A new competitive enzyme-linked immunosorbent assay (ELISA) for determination of estrogenic bisphenols. Talanta, 2002, 57(6): 1205–1210
Nishi K, Takai M, Morimune K, Ohkawa H. Molecular and immunochemical characteristics of monoclonal and recombinant antibodies specific to bisphenol A. Bioscience, Biotechnology, and Biochemistry, 2003, 67(6): 1358–1367 https://doi.org/10.1271/bbb.67.1358
21
O’Keeffe M, Crabbe P, Salden M, Wichers J, Van Peteghem C, Kohen F, Pieraccini G, Moneti G. Preliminary evaluation of a lateral flow immunoassay device for screening urine samples for the presence of sulphamethazine. Journal of Immunological Methods, 2003, 278(1–2): 117–126 https://doi.org/10.1016/S0022-1759(03)00207-2
22
Jiang W X, Luo P J, Wang X, Chen X, Zhao Y F, Shi W, Wu X P, Wu Y N, Shen J Z. Development of an enzyme-linked immunosorbent assay for the detection of nitrofurantoin metabolite, 1-amino-hydantoin, in animal tissues. Food Control, 2012, 23(1): 20–25 https://doi.org/10.1016/j.foodcont.2011.05.014
23
Wang J J, Liu B H, Hsu Y T, Yu F Y. Sensitive competitive direct enzyme-linked immunosorbent assay and gold nanoparticle immunochromatographic strip for detecting aflatoxin M1 in milk. Food Control, 2011, 22(6): 964–969 https://doi.org/10.1016/j.foodcont.2010.12.003
24
Zhang X, Wen K, Wang Z, Jiang H, Beier R C, Shen J. An ultra-sensitive monoclonal antibody-based fluorescent microsphere immunochromatographic test strip assay for detecting aflatoxin M1 in milk. Food Control, 2016, 60(2): 588–595 https://doi.org/10.1016/j.foodcont.2015.08.040
25
Goodrow M H, Hammock B D, Goodrow M H, Hammock B D. Hapten design for compound-selective antibodies: ELISAs for environmentally deleterious small molecules. Analytica Chimica Acta, 1998, 376(1): 83–91 https://doi.org/10.1016/S0003-2670(98)00433-4
26
Goodrow M H, Sanborn J R, Stoutamire D W, Gee S J, Hammock B D. Strategies for immunoassay hapten design. ACS Symposium Series, 1995, 586: 119–139
27
Lei H T, Shen Y D, Song L J, Yang J Y, Chevallier O P, Haughey S A, Wang H, Sun Y M, Elliott C T. Hapten synthesis and antibody production for the development of a melamine immunoassay. Analytica Chimica Acta, 2010, 665(1): 84–90 https://doi.org/10.1016/j.aca.2010.03.007
28
Kim Y J, Cho Y A, Lee H S, Lee Y T, Gee S J, Hammock B D. Synthesis of haptens for immunoassay of organophosphorus pesticides and effect of heterology in hapten spacer arm length on immunoassay sensitivity. Analytica Chimica Acta, 2003, 475(1–2): 85–96 https://doi.org/10.1016/S0003-2670(02)01037-1
29
Kaddar N, Bendridi N, Harthé C, de Ravel M R, Bienvenu A L, Cuilleron C Y, Mappus E, Pugeat M, Déchaud H. Development of a radioimmunoassay for the measurement of Bisphenol A in biological samples. Analytica Chimica Acta, 2009, 645(1–2): 1–4 https://doi.org/10.1016/j.aca.2009.04.036
30
Yang F, Xu L, Zhu L, Zhang Y, Meng W, Liu R. Competitive immunoassay for analysis of bisphenol A in children’s sera using a specific antibody. Environmental Science and Pollution Research International, 2016, 23(11): 10714–10721 https://doi.org/10.1007/s11356-016-6231-2
31
Huang P, Zhao S, Eremin S A, Zheng S, Lai D, Chen Y, Guo B. Fluorescence polarization immunoassay method for bisphenol A residue in environmental water samples based on monoclonal antibody and 4′-(aminomethyl) fluorescein. Analytical Methods, 2015, 7(10): 4246–4251 https://doi.org/10.1039/C5AY00818B
