Chuanlai Xu · Hua Kuang · Liguang Xu Food Immunoassay Food Immunoassay Chuanlai Xu Hua Kuang Liguang Xu (cid:129) (cid:129) Food Immunoassay 123 ChuanlaiXu Hua Kuang Schoolof FoodScience andTechnology Schoolof FoodScience andTechnology JiangnanUniversity JiangnanUniversity Wuxi,China Wuxi,China Liguang Xu Schoolof FoodScience andTechnology JiangnanUniversity Wuxi,China ISBN978-981-13-9033-3 ISBN978-981-13-9034-0 (eBook) https://doi.org/10.1007/978-981-13-9034-0 Projectno.:2017-2-148 ©SpringerNatureSingaporePteLtd.2019 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpart of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission orinformationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar methodologynowknownorhereafterdeveloped. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfrom therelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, expressed or implied, with respect to the material contained hereinorforanyerrorsoromissionsthatmayhavebeenmade.Thepublisherremainsneutralwithregard tojurisdictionalclaimsinpublishedmapsandinstitutionalaffiliations. ThisSpringerimprintispublishedbytheregisteredcompanySpringerNatureSingaporePteLtd. The registered company address is: 152 Beach Road, #21-01/04 Gateway East, Singapore 189721, Singapore Acknowledgements Thanks for the list of contributors below who have contributed to this book. Chuanlai Xu School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Hua Kuang School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Liguang Xu School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Yanni Chen CollegeofFoodScienceandEngineering,CentralSouthUniversityofForestryand Technology. E-mail: [email protected] Dezhao Kong School of Grain Science and Technology, Jiangsu University of Science and Technology. E-mail: [email protected] Changrui Xing Nanjing University of Finance and Economics. E-mail: [email protected] Xiujin Chen CollegeofFoodandBioengineering,HenanUniversityofScienceandTechnology. E-mail: [email protected] v vi Acknowledgements Zhongxing Wang State Key Lab of Food Science and Technology, Jiangnan University. E-mail: [email protected]. Naifeng Xu Institute of Food Engineering, College of Life Science, Shanghai Normal University. E-mail: [email protected] Zhuokun Li College of Food Science, Fujian Agriculture and Forestry University. E-mail: [email protected] Lingling Guo School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Wenbin Wang Collegeofmarinelifeandfisheries,HuaihaiInstituteofTechnology,Lianyungang, Jiangsu, P.R. China. E-mail: [email protected] Yue Li School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Liqiang Liu School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Wei Ma School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Xiaoling Wu School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Shanshan Song School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Jianping Zhu School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Haiying Liu School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Acknowledgements vii Maozhong Sun School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Changlong Hao School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Si Li School of Food Science and Technology, Jiangnan University. E-mail: [email protected] Contents 1 Introduction of Immunoassays . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.1 Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.2 ELISA . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.2.1 Principle of ELISA. . . . . . . . . . . . . . . . . . . . . . . . . . . 2 1.2.2 Classification of ELISA . . . . . . . . . . . . . . . . . . . . . . . 2 1.2.3 Preparation of mAb . . . . . . . . . . . . . . . . . . . . . . . . . . 3 1.2.4 Establishment of Indirect and Competitive ELISA . . . . 7 1.3 Development of Strip Test. . . . . . . . . . . . . . . . . . . . . . . . . . . . 11 1.3.1 Principle of Strip Test. . . . . . . . . . . . . . . . . . . . . . . . . 11 1.3.2 Steps for Strip Test . . . . . . . . . . . . . . . . . . . . . . . . . . 12 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 14 2 Mycotoxin Immunoassay in Food . . . . . . . . . . . . . . . . . . . . . . . . . . 15 2.1 Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 2.1.1 Aflatoxins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 2.1.2 Ochratoxin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 18 2.1.3 Fumonisins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19 2.1.4 Trichothecenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 20 2.1.5 Zearalenone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 2.1.6 Sterigmatocystin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24 2.1.7 Citrinin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26 2.1.8 Alternaria Toxins . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27 2.1.9 Patulin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27 2.1.10 Other Mycotoxin . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29 2.2 Design and Synthesis of Antigen. . . . . . . . . . . . . . . . . . . . . . . 31 2.2.1 Aflatoxins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 31 2.2.2 Ochratoxin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32 2.2.3 Fumonisins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 2.2.4 Trichothecenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 2.2.5 Zearalenone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 ix x Contents 2.2.6 Sterigmatocystin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36 2.2.7 Citrinin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37 2.2.8 Alternaria Toxins . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38 2.2.9 Patulin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39 2.2.10 Other Mycotoxin . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39 2.3 ELISA . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 2.3.1 Aflatoxins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42 2.3.2 Ochratoxin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43 2.3.3 Fumonisins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44 2.3.4 Trichothecenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44 2.3.5 Zearalenone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46 2.3.6 Sterigmatocystin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46 2.3.7 Citrinin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47 2.3.8 Alternaria Toxins . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47 2.3.9 Patulin. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 48 2.4 Colloidal Gold Immunochromatographic Strips. . . . . . . . . . . . . 48 2.5 Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50 3 Heavy Metal Immunoassay in Food . . . . . . . . . . . . . . . . . . . . . . . . 53 3.1 Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53 3.2 Design and Synthesis of Antigen. . . . . . . . . . . . . . . . . . . . . . . 58 3.2.1 Lead . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58 3.2.2 Cadmium. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59 3.2.3 Mercury. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60 3.2.4 Chromium . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61 3.2.5 Copper . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 62 3.3 Enzyme-Linked Immunosorbent Assay. . . . . . . . . . . . . . . . . . . 62 3.4 Colloidal Gold Lateral Flow Assay . . . . . . . . . . . . . . . . . . . . . 64 3.5 Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 65 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66 4 Pesticide Immunoassay in Food . . . . . . . . . . . . . . . . . . . . . . . . . . . 69 4.1 Pesticide Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69 4.1.1 Pyrethroid Insecticides . . . . . . . . . . . . . . . . . . . . . . . . 69 4.1.2 Organic Phosphorus Insecticide. . . . . . . . . . . . . . . . . . 72 4.1.3 Neonicotinoid Insecticides . . . . . . . . . . . . . . . . . . . . . 74 4.1.4 Triazole Fungicides . . . . . . . . . . . . . . . . . . . . . . . . . . 74 4.1.5 Strobilurin Fungicides. . . . . . . . . . . . . . . . . . . . . . . . . 77 4.1.6 Anilinopyrimidine Fungicides . . . . . . . . . . . . . . . . . . . 80 4.1.7 Amide Fungicides . . . . . . . . . . . . . . . . . . . . . . . . . . . 80 4.1.8 Herbicide Pesticides . . . . . . . . . . . . . . . . . . . . . . . . . . 83 4.1.9 Other Pesticides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89 Contents xi 4.2 Design and Synthesis of Antigen (Hapten) . . . . . . . . . . . . . . . . 94 4.2.1 Design and Synthesis of Pyrethroid Antigens. . . . . . . . 95 4.2.2 Design and Synthesis of Organophosphorus Insecticides Antigen . . . . . . . . . . . . . . . . . . . . . . . . . . 97 4.2.3 Design and Synthesis of Neonicotinoid Insecticides Antigen . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 101 4.2.4 Design and Synthesis of Triazole Fungicides Antigen . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 102 4.2.5 Design and Synthesis of Strobilurin Fungicides Antigen . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 4.2.6 Design and Synthesis of Anilinopyrimidine Fungicides Haptens . . . . . . . . . . . . . . . . . . . . . . . . . . 108 4.2.7 Design and Synthesis of Trifloxystrobin Antigen Amide Fungicides . . . . . . . . . . . . . . . . . . . . . 115 4.2.8 Design and Synthesis of Bensulfuron-Methyl Herbicide Antigen . . . . . . . . . . . . . . . . . . . . . . . . . . . 120 4.2.9 Other Pesticides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 121 4.3 Enzyme-Linked Immunosorbent Assay. . . . . . . . . . . . . . . . . . . 127 4.3.1 ELISA for Pyrethroids Analysis . . . . . . . . . . . . . . . . . 127 4.3.2 ELISA of Organophosphorus Pesticides. . . . . . . . . . . . 129 4.3.3 ELISA of Neonicotinoid Insecticides. . . . . . . . . . . . . . 131 4.3.4 ELISA of Triazole Fungicides. . . . . . . . . . . . . . . . . . . 133 4.3.5 ELISA of Strobilurin Fungicides. . . . . . . . . . . . . . . . . 134 4.3.6 ELISA of Anilinopyrimidine Fungicides . . . . . . . . . . . 138 4.3.7 ELISA of Amide Fungicides. . . . . . . . . . . . . . . . . . . . 140 4.3.8 ELISA of Herbicide Pesticides . . . . . . . . . . . . . . . . . . 142 4.3.9 ELISA of Other Pesticides . . . . . . . . . . . . . . . . . . . . . 143 4.4 Strip Test . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 147 4.5 Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150 5 b-Agonist and Hormone Immunoassays in Food. . . . . . . . . . . . . . . 155 5.1 Overview . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 155 5.2 Design and Synthesis of Antigen. . . . . . . . . . . . . . . . . . . . . . . 158 5.2.1 b-Agonists. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 158 5.2.2 Artificial Hormone . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 5.3 Enzyme-Linked Immunosorbent Assay. . . . . . . . . . . . . . . . . . . 169 5.3.1 Sample Pretreatment. . . . . . . . . . . . . . . . . . . . . . . . . . 169 5.3.2 Enzyme-Linked Immunosorbent Assay (ELISA) . . . . . 170 5.4 Colloidal Gold Immunochromatographic Strips. . . . . . . . . . . . . 171 5.5 Perspectives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173