Nghiên cứu tổng hợp vật liệu polymer in dấu phân tử MIP bằng phương pháp điện hóa định hướng ứng dụng phát hiện dư lượng chất lượng kháng sinh

Nghiên cứu tổng hợp vật liệu polymer in dấu phân tử MIP bằng phương pháp điện hóa định hướng ứng dụng phát hiện dư lượng chất lượng kháng sinh Nghiên cứu tổng hợp vật liệu polymer in dấu phân tử MIP bằng phương pháp điện hóa định hướng ứng dụng phát hiện dư lượng chất lượng kháng sinh luận văn tốt nghiệp thạc sĩ

MINISTRY OF EDUCATION AND TRAINING HANOI UNIVERSITY OF SCIENCE AND TECHNOLOGY INTERNATIONAL TRAINING INSTITUTE FOR MATERIALS SCIENCE - VU VAN PHU ELECTROCHEMICAL SYNTHESIS OF MOLECULARLY IMPRINTED POLYMER (MIP), TOWARDS THE APPLICATION IN ANTIBIOTIC RESIDUE DETECTION MASTER THESIS OF MATERIALS SCIENCE Hanoi – 2018 MINISTRY OF EDUCATION AND TRAINING HANOI UNIVERSITY OF SCIENCE AND TECHNOLOGY INTERNATIONAL TRAINING INSTITUTE FOR MATERIALS SCIENCE - VU VAN PHU ELECTROCHEMICAL SYNTHESIS OF MOLECULARLY IMPRINTED POLYMER (MIP), TOWARDS THE APPLICATION IN ANTIBIOTIC RESIDUE DETECTION MASTER THESIS OF MATERIALS SCIENCE Batch ITIMS-2016 SUPERVISOR DR PHAM DUC THANH Hanoi – 2018 ACKNOWLEDGMENTS It is a pleasure to thank the many people who made this thesis possible First of all, I would like to express my sincere gratitude to my advisor Dr Pham Duc Thanh of the ITIMS Institute for the continuous support of my M.Sc study and research, for his patience, motivation, and immense knowledge I would also like to express my deepest thanks and sincere appreciation to Assoc Prof Mai Anh Tuan, MEMS/NEMS Laboratory – NACENTECH, for his valuable advice, constructive criticism, and his extensive discussions around my work, and lots of good ideas Especially, for the fantastic internship time he offered me at Tokyo University of Science - Japan, which brought me valuable experience and knowledge My sincere thanks also go to Dr Chu Thi Xuan, ITIMS for her untired help, and generous advice, and MSc Tran Quang Thinh of the MEMS/NEMS Laboratory – NACENTECH, for his support during my experimentation in the laboratory and contributed positively in the analysis and interpretation of data in my study I also thank MSc Nguyen Minh Hieu of the Nano and Energy Center for his devoted support and guidance during the fabrication process of electrochemical sensors in cleanroom, which helped me improve my skills very well I thank my fellow members in BIOMAT Group for the stimulating discussions, have made valuable comment suggestions on this thesis which gave me the inspiration to improve my assignment Last but not the least, I must express my very profound gratitude to members in my family for providing me with unfailing support and continuous encouragement throughout my years of study and through the process of researching this thesis This accomplishment would not have been possible without them Thank you! Hanoi, October 2018 i DECLARATION I hereby declare that matter embodied in this thesis entitled, “Electrochemical synthesis of molecularly imprinted polymer (MIP), towards the application in antibiotic residue detection” is a result of investigations carried out by me under the supervision and guidance of Dr Pham Duc Thanh of the International Training Institute for Materials Science (ITIMS), Hanoi University of Science and Technology I further declare that this thesis, to the best of my knowledge and belief, does not contain any data previously published by another person or submitted for the award of any degree or diploma at any other university or institute except where due reference is made in the text Author Vu Van Phu ii TABLE OF CONTENTS ACKNOWLEDGMENTS i DECLARATION ii LIST OF ABBREVIATIONS vi LIST OF TABLES viii LIST OF FIGURES ix INTRODUCTION .1 CHAPTER 1: THEORY & FUNDAMENTALS 1.1 Molecularly imprinted polymers 1.1.1 Types of imprinting mechanism 1.1.2 Removal of the imprinted template 1.1.3 Applications of MIPs 1.2 Polyaniline 1.2.1 Properties of PANi 12 1.2.1.1 Chemical properties 12 1.2.1.2 Optical properties .12 1.2.1.3 Thermal stability 12 1.2.1.4 Conductivity properties of PANi .12 1.2.2 Synthesis of PANi 14 1.3 Antibiotics: Chloramphenicol 16 1.4 Methods of electrochemical analysis 17 1.4.1 Cyclic voltammetry (CV) 17 1.4.2 Chronoamperometry (CA) .18 iii 1.4.3 Differential pulse voltammetry (DPV) .19 1.4.4 Fourier transform infrared spectroscopy (FT-IR) 19 CHAPTER 2: FABRICATION OF MIP-BASED ELECTROCHEMICAL SENSOR 21 2.1 Fabrication of electrochemical sensor 21 2.1.1 Photo-mask design 21 2.1.2 Fabrication processes of electrochemical sensors 22 2.1.3 Electrode surface pretreatment 27 2.2 Synthesis of CAP-imprinted PANi NWs 27 2.2.1 Chemical and instrumentation 27 2.2.2 Experimental schema .29 2.2.3 Electrochemical synthesis of PANi NWs .30 2.2.3.1 Synthesis of PANi NWs by CV method 30 2.2.3.2 Synthesis of PANi NWs by CA method 30 2.2.4 Synthesis of CAP-imprinted PANi NWs 30 2.2.5 Removal of CAP from CAP-imprinted PANi NWs 31 2.3 Detection of CAP by using MIP-based electrochemical sensor .31 CHAPTER 3: RESULTS AND DISCUSSIONS 32 3.1 Au electrode-based electrochemical sensor 32 3.2 Synthesis of PANI NWs 33 3.2.1 Synthesis of PANi NWs using CV technique 33 3.2.1.1 Effect of scanning potential ranges on CV-based polymerization 33 3.2.1.2 CV behavior of polymerization of aniline 35 iv 3.2.1.3 The effect of number of sweeps on the morphology of PANi 37 3.2.2 Synthesis of PANi NWs using CA technique 41 3.2.2.1 CA behavior of the polymerization of aniline 41 3.2.2.2 Effect of CA scanning time on the morphology of PANi 42 3.2.3 Choice of CA or CV for fabrication CAP-imprinted PANi NWs 45 3.3 MIP-based electrochemical sensor 47 3.3.1 CA behavior of synthesis of CAP-imprinted PANi NWs 47 3.3.2 The morphology of CAP-imprinted PANi .48 3.3.3 FT-IR spectrum of CAP-imprinted PANi 50 3.3.4 Removal of CAP from CAP-imprinted PANi 54 3.3.5 Electrochemical characteristics of the MIP-based sensor 56 3.3.5.1 CV behavior of the MIP-based sensor .57 3.3.5.2 DPV behavior of the MIP-based sensor 59 3.4 Detection of CAP-based on MIP sensor 61 CONCLUSIONS .64 REFERENCES 66 v LIST OF ABBREVIATIONS ANi Aniline CA Chronoamperometry CAP Chloramphenicol CE Counter electrode CPs Conductive polymers CV Cyclic voltammetry DPV Differential pulse voltammetry EB Emeraldine base ES Emeraldine salt FT-IR Fourier transform infrared microscopes GC-MS Gas chromatography-mass spectrometry HA Arbitrary acid HPLC High performance liquid chromatography LB Leucoemeraldine base LC-MS Liquid chromatography-mass spectrometry MIPs Molecularly imprinted polymers MRPL Minimum required performance limit NWs Nanowires PANi Polyaniline PANi NWs Polyaniline nanowires PB Pernigraniline base PR Photoresist vi PVD Physical vapor deposition RE Reference electrode SEM Scanning electron microscope TMAH Tetramethylammonium hydroxide UV Ultra violet WE Working electrode vii LIST OF TABLES Table 3.1 Data of the average diameter and length of PANi NWs by using CV .40 Table 3.2 Data of the average diameter and length of PANi NWs by using CA .45 Table 3.3 The CV parameters obtained from Figure 3.23 58 viii  The relationship between the peak currents and the CAP concentrations: The performance of the MIP-based electrochemical sensor was evaluated by determining CAP solution with a range of various concentration from 10-8 to 10-3 M The peak currents obtained from the DPVs corresponding to the concentration samples of CAP are expressed in the plot as shown in Figure 3.26 As seen in Figure 3.26, the peak current of the MIP-based sensor decreases when the concentration of CAP is diluted from 10-3 M to 10-8 M In this range of concentrations, the MIP-based sensor shows the linear relationship between Ipeak and log[CCAP] with the regression equation of Ipeak = 3.207 × log[CCAP] + 28.62 (R2 = 0.983) Figure 3.26 The calibration curve of the Ipeak with the CAP concentration The results also show that the minimum concentration of CAP, which was detected by the MIP-based electrochemical sensor, is experimentally determined at 10-8 M This concentration is converted to the ppb unit as equal to ppb 63 CONCLUSIONS This thesis reported the study of the MIP-based electrochemical sensor for the detection of chloramphenicol The main results were obtained as the following: Electrochemical sensors integrating three gold thin-film electrodes on the silicon wafer were fabricated by the cleanroom process The process produced 150 utilizable sensors, which show a success rate of 85% of 178 designed sensors on the mask The polymerization of aniline was investigated on the fabricated sensor by using cyclic voltammetry (CV) and chronoamperometry (CA) Both electrochemical techniques allow the deposition of polyaniline nanowires (PANi NWs) on the WE electrode CA was considered as a more advantageous technique for the PANi NWs synthesis, including short polymerization time and good surface morphology, in comparison with CV Using CA technique, the co-precipitation of chloramphenicol during the electro-polymerization of aniline was performed, which produced PANi NWs imprinting chloramphenicol molecules (MIP) The presence of chloramphenicol as the template molecule in MIP was demonstrated by FT-IR The results also shown that hydrogen bonding is the main interaction between chloramphenicol and PANi chains CA technique was also used for the removal of the template molecule to generate the cavities on the polymer matrix, which enables the specific recognition of chloramphenicol The removal of the template was demonstrated by electrochemical characterizations using CV and differential pulse voltammetry (DPV) The performance of the MIP-based electrochemical sensor was evaluated by determining CAP solution with concentrations vary from 10-8 to 10-3 M In this range of concentrations, the MIP-based sensor shows the linear relationship between Ipeak and log[CCAP] with the regression equation of Ipeak = 3.207 × log[CCAP] + 28.62 (R2 = 64 0.983) The minimum concentration of CAP was experimentally determined at 10-8 M that converted to the ppb unit as equal to ppb 65 REFERENCES Ali, I., H Y Aboul-Enein, V K Gupta, P Singh, and U Negi (2009), “Analyses of Chloramphenicol in Biological Samples by HPLC,” Anal Lett., vol 42, no 10, pp 1368–1381 An, M Y., J Gao, X F Zhao, and J X Wang (2016), “A new subfamily of penaeidin with an additional serine-rich region from kuruma shrimp (Marsupenaeus japonicus) contributes to antimicrobial and phagocytic activities,” Dev Comp Immunol., vol 59, pp 186–198 Andersson, L I (2000), “Molecular imprinting for drug bioanalysis: A review on the application of imprinted polymers to solid-phase extraction and binding assay,” J Chromatogr B Biomed Sci Appl., vol 739, no 1, pp 163–173 Antony, M J and M Jayakannan (2011), “Polyaniline nanoscaffolds for colorimetric sensing of biomolecules via electron transfer process,” Langmuir, vol 27, no 10, pp 6268–6278 Arshady, R and K Mosbach (1981), “Synthesis of Substrate-selective Polymers by Host-Guest Polymerizatioa,” vol 692, pp 687–692 Batlokwa, B S., J Mokgadi, T Nyokong, and N Torto (2011), “Optimal template removal from molecularly imprinted polymers by pressurized hot water extraction,” Chromatographia, vol 73, no 5–6, pp 589–593 Bhadra, S., D Khastgir, N K Singha, and J H Lee (2009), “Progress in preparation, processing and applications of polyaniline,” Prog Polym Sci., vol 34, no 8, pp 783–810 Blanco-López, M C., S Gutiérrez-Fernández, M J Lobo-Castón, A J Miranda-Ordieres, and P Tón-Blanco (2004), “Electrochemical sensing with electrodes modified with molecularly imprinted polymer films,” Anal Bioanal Chem., vol 378, no 8, pp 1922–1928 Blasco, C., Y Picó, and C M Torres (2007), “Progress in analysis of residual 66 antibacterials in food,” TrAC - Trends Anal Chem., vol 26, no 9, pp 895– 913 10 Bossi, A., D Lakshmi, A Bossi, M J Whitcombe, I Chianella, S A Fowler, S Subrahmanyam, E V Piletska, and S A Piletsky (2009), “Electrochemical Sensor for Catechol and Dopamine Based on a Catalytic Molecularly Imprinted Polymer-Conducting Electrochemical Sensor for Catechol and Dopamine Based on a Catalytic Molecularly Imprinted Polymer-Conducting Polymer Hybrid Recognition El,” Anal Chem., vol 81, no May 2009, pp 3576–3584 11 Cháfer-Pericás, C., Á Maquieira, R Puchades, J Miralles, and A Moreno (2011), “Multiresidue determination of antibiotics in feed and fish samples for food safety evaluation Comparison of immunoassay vs LC-MS-MS,” Food Control, vol 22, no 6, pp 993–999 12 Chen, L and B Li (2013), “Magnetic molecularly imprinted polymer extraction of chloramphenicol from honey,” Food Chem., vol 141, no 1, pp 23–28 13 Chen, S A and G W Hwang (1997), “Structures and properties of the watersoluble self-acid-doped conducting polymer blends: Sulfonic acid ringsubstituted polyaniline/poly(vinyl alcohol) and poly(aniline-co-N- propanesulfonic acid aniline)/poly(vinyl alcohol),” Polymer (Guildf)., vol 38, no 13, pp 3333–3346 14 Chen, X., Z Zhang, X Yang, Y Liu, J Li, M Peng, and S Yao (2012), “Novel molecularly imprinted polymers based on multiwalled carbon nanotubes with bifunctional monomers for solid-phase extraction of rhein from the root of kiwi fruit,” J Sep Sci., vol 35, no 18, pp 2414–2421 15 Cheong, W J., S H Yang, and F Ali (2013), “Molecular imprinted polymers for separation science: A review of reviews,” J Sep Sci., vol 36, no 3, pp 609–628 67 16 Chiral, O F., C As, and S Receptor (1982), “OF CHIRAL CAVITIES AS SPECIFIC RECEPTOR SITES Günter Wuiff,” Construction, vol 54, no 1, pp 2093–2102 17 Chuanlai, X., P Cifang, H Kai, J Zhengyu, and W Wukang (2005), “Quantitative analysis of chloramphenicol residues in shrimp muscle tissues by chemiluminescent enzyme immunoassay,” Czech J Food Sci., vol 23, no 6, pp 251–256 18 Chullasat, K., P Kanatharana, W Limbut, A Numnuam, and P Thavarungkul (2011), “Ultra trace analysis of small molecule by label-free impedimetric immunosensor using multilayer modified electrode,” Biosens Bioelectron., vol 26, no 11, pp 4571–4578 19 Cui, H., Q Li, Y Qian, R Tang, H An, and J Zhai (2011), “Defluoridation of water via electrically controlled anion exchange by polyaniline modified electrode reactor,” Water Res., vol 45, no 17, pp 5736–5744 20 Database, S U., “Characteristic infrared absorption bands of functional groups,” p 840 21 Degradation, P and K Ridge (1994), “Degradation behavior of polyanUines with different modes of doping,” vol 43, pp 141–147 22 Dickert, F L.; Forth, P.; Lieberzeit, P.; Tortschanoff, M (1998), “Molecular imprinting in chemical sensing - detction of aromtaic and halogenated hydrocarbons as well as polar solvent vapors,” Fresenius J Anal Chem., vol 360, no 759–762, pp 759–760 23 Ding, L., X Wang, and R V Gregory (1999), “Thermal properties of chemically synthesized polyaniline (EB) powder,” Synth Met., vol 104, no 2, pp 73–78 24 Ebarvia, B S., I E Ubando, and F B Sevilla (2015), “Biomimetic piezoelectric quartz crystal sensor with chloramphenicol-imprinted polymer 68 sensing layer,” Talanta, vol 144, pp 1260–1265 25 EC (2003), “Commission Decision (2003/181/EC) of 13 March 2003,” Off J Eur Union, vol L71, no 4, pp 17–18 26 Fuchs, Y., O Soppera, A G Mayes, and K Haupt (2013), “Holographic molecularly imprinted polymers for label-free chemical sensing,” Adv Mater., vol 25, no 4, pp 566–570 27 Gao, F., S Feng, Z Chen, E C Y Li-Chan, E Grant, and X Lu (2014), “Detection and Quantification of Chloramphenicol in Milk and Honey Using Molecularly Imprinted Polymers: Canadian Penny-Based SERS NanoBiosensor,” J Food Sci., vol 79, no 12, pp N2542–N2549 28 Geniès, E M., M Lapkowski, and J F Penneau (1988), “Cyclic voltammetry of polyaniline: interpretation of the middle peak,” J Electroanal Chem., vol 249, no 1–2, pp 97–107 29 Ghanbari, K., M F Mousavi, and M Shamsipur (2006), “Preparation of polyaniline nanofibers and their use as a cathode of aqueous rechargeable batteries,” Electrochim Acta, vol 52, no 4, pp 1514–1522 30 Han, W., Y Pan, Y Wang, D Chen, Z Liu, Q Zhou, L Feng, D Peng, and Z Yuan (2016), “Development of a monoclonal antibody-based indirect competitive enzyme-linked immunosorbent assay for nitroimidazoles in edible animal tissues and feeds,” J Pharm Biomed Anal., vol 120, pp 84–91 31 Hedborg, E., F Winquist, I Lundström, L I Andersson, and K Mosbach (1993), “Some studies of molecularly-imprinted polymer membranes in combination with field-effect devices,” Sensors Actuators A Phys., vol 37– 38, no C, pp 796–799 32 Hummert, C (1995), “Determination of chloramphenicol in animal tissue using high- performance liquid chromatography with a column-switching system and ultraviolet detection,” vol 668, pp 53–58 69 33 Jakusch, M., M Janotta, B Mizaikoff, K Mosbach, and K Haupt (1999), “Molecularly imprinted polymers and infrared evanescent wave spectroscopy A chemical sensors approach,” Anal Chem., vol 71, no 20, pp 4786–4791 34 Javanbakht, M., S E Fard, A Mohammadi, M Abdouss, M R Ganjali, P Norouzi, and L Safaraliee (2008), “Molecularly imprinted polymer based potentiometric sensor for the determination of hydroxyzine in tablets and biological fluids,” Anal Chim Acta, vol 612, no 1, pp 65–74 35 Jayalakshmi, K., M Paramasivam, M Sasikala, and T V Tamilam (2017), “Review on antibiotic residues in animal products and its impact on environments and human health,” vol 5, no 3, pp 1446–1451 36 Jiang, D., P Zhu, H Jiang, J Ji, X Sun, W Gu, and G Zhang (2015), “Fluorescent magnetic bead-based mast cell biosensor for electrochemical detection of allergens in foodstuffs,” Biosens Bioelectron., vol 70, pp 482– 490 37 K J Shea (1994), “Molecular Imprinting of Synthetic Network Polymers: The de Novo Synthesis of Macromolecular Binding and Catalytic Sites,” Trends Polym Sci., vol 2, pp 166–173 38 Kang, E T., K G Neoh, and K L Tan (1998), “Polyaniline: A polymer with many interesting intrinsic redox states,” Prog Polym Sci., vol 23, no 2, pp 277–324 39 Karsten Haupt and Klaus Mosbach (2000), “Molecularly Imprinted Polymers and Their Use in Biomimetic Sensors,” Chem Rev., vol 2000, no 100, p 2495 − 2504 40 Karthikeyan, S (2013), “Spectroscopic study of characterisation of commercial drug and its mixture,” Proc Indian Natl Sci Acad., vol 79, no 3, pp 357–363 41 Kirsch, N., J Hedin-Dahlström, H Henschel, M J Whitcombe, S Wikman, 70 and I A Nicholls (2009), “Molecularly imprinted polymer catalysis of a DielsAlder reaction,” J Mol Catal B Enzym., vol 58, no 1–4, pp 110–117 42 Kraljić Roković, M., K Kvastek, V Horvat-Radošević, and L Duić (2007), “Poly(ortho-ethoxyaniline) in corrosion protection of stainless steel,” Corros Sci., vol 49, no 6, pp 2567–2580 43 Lai, H C., T H Ng, M Ando, C Te Lee, I T Chen, J C Chuang, R Mavichak, S H Chang, M De Yeh, Y A Chiang, H Takeyama, H o Hamaguchi, C F Lo, T Aoki, and H C Wang (2015), “Pathogenesis of acute hepatopancreatic necrosis disease (AHPND) in shrimp,” Fish Shellfish Immunol., vol 47, no 2, pp 1006–1014 44 Le, T.-H., Y Kim, and H Yoon (2017), “Electrical and Electrochemical Properties of Conducting Polymers,” Polymers (Basel)., vol 9, no 4, p 150 45 Letheby, H (1862), “XXIX.—On the production of a blue substance by the electrolysis of sulphate of aniline,” J Chem Soc., vol 15, pp 161–163 46 Li, S., Y Ge, S A Piletsky, and A P F Turner (2011), “A zipper-like on/offswitchable molecularly imprinted polymer,” Adv Funct Mater., vol 21, no 17, pp 3344–3349 47 Li, S., Y Ge, and A P F Turner (2011), “A catalytic and positively thermosensitive molecularly imprinted polymer,” Adv Funct Mater., vol 21, no 6, pp 1194–1200 48 Li, S., A Tiwari, Y Ge, and D Fei (2010), “A pH-responsive, low crosslinked, molecularly imprinted insulin delivery system,” Adv Mater Lett., vol 1, no 1, pp 4–10 49 Liang, R N., D A Song, R M Zhang, and W Qin (2010), “Potentiometrie sensing of neutral species based on a uniform-sized molecularly imprinted polymer as a receptor,” Angew Chemie - Int Ed., vol 49, no 14, pp 2556– 2559 71 50 Lorenzo, R A., A M Carro, C Alvarez-Lorenzo, and A Concheiro (2011), “To remove or not to remove? The challenge of extracting the template to make the cavities available in molecularly imprinted polymers (MIPs),” Int J Mol Sci., vol 12, no 7, pp 4327–4347 51 Luliński, P and D MacIejewska (2012), “Effective separation of dopamine from bananas on 2-(3,4-dimethoxyphenyl) ethylamine imprinted polymer,” J Sep Sci., vol 35, no 8, pp 1050–1057 52 Mamma, K., K Siraj, and N Meka (2013), “Synthesis and effect of secondary dopant on the conductivity of conducting polymer polyaniline,” J Polym Eng., vol 33, no 9, pp 785–792 53 Martins, M C L., C Fonseca, M A Barbosa, and B D Ratner (2003), “Albumin adsorption on alkanethiols self-assembled monolayers on gold electrodes studied by chronopotentiometry,” Biomaterials, vol 24, no 21, pp 3697–3706 54 Masdarolomoor, F (2006), “Novel nanostructured conducting polymer systems based on sulfonated polyaniline,” 55 Mayes, A G and M J Whitcombe (2005), “Synthetic strategies for the generation of molecularly imprinted organic polymers,” Adv Drug Deliv Rev., vol 57, no 12, pp 1742–1778 56 Meng, Z., Q Zhang, M Xue, D Wang, and A Wang (2012), “Removal of 2,4,6-trinitrotoluene from ‘pink water’ using molecularly-imprinted absorbent,” Propellants, Explos Pyrotech., vol 37, no 1, pp 100–106 57 Molapo, K M., P M Ndangili, R F Ajayi, G Mbambisa, S M Mailu, N Njomo, M Masikini, P Baker, and E I Iwuoha (2012), “Electronics of conjugated polymers (I): Polyaniline,” Int J Electrochem Sci., vol 7, no 12, pp 11859–11875 58 Mungroo, N A and S Neethirajan (2014), “Biosensors for the detection of 72 antibiotics in poultry industry-A Review,” Biosensors, vol 4, no 4, pp 472– 493 59 Nagata, T and H Oka (1996), “Detection of residual chloramphenicol, florfenicol, and thiamphenicol in yellowtail fish muscles by capillary gas chromatography-mass spectrometry,” J Agric Food Chem., vol 44, no 5, pp 1280–1284 60 Naidu, P R (1966), “Infrared Spectroscopic Study of Hydrogen Bonding: Hydrogen Bond Association of Phenols With Dioxan,” Aust J Chem, vol 19, pp 2393–2395 61 Nam-Trung Nguyen (2012), Micromixers: Fundamentals, Design and Fabrication, 2nd ed 62 Nezhadali, A., L Mehri, and R Shadmehri (2018), “Determination of methimazole based on electropolymerized-molecularly imprinted polypyrrole modified pencil graphite sensor,” Mater Sci Eng C, vol 85, pp 225–232 63 Nguy, T P., T Van Phi, D T N Tram, K Eersels, P Wagner, and T T N Lien (2017), “Development of an impedimetric sensor for the label-free detection of the amino acid sarcosine with molecularly imprinted polymer receptors,” Sensors Actuators, B Chem., vol 246, pp 461–470 64 Oka, H., Y Ito, and H Matsumoto (2000), “Chromatographic analysis of tetracycline antibiotics in foods.,” J Chromatogr A, vol 882, no 1–2, pp 109– 33, Jun 65 Piletsky, S A., N W Turner, and P Laitenberger (2006), “Molecularly imprinted polymers in clinical diagnostics-Future potential and existing problems,” Med Eng Phys., vol 28, no 10, pp 971–977 66 Puoci, F., G Cirillo, M Curcio, O I Parisi, F Iemma, and N Picci (2011), “Molecularly imprinted polymers in drug delivery: state of art and future perspectives,” Expert Opin Drug Deliv., vol 8, no 10, pp 1379–1393 73 67 Rassie, C., R A Olowu, T T Waryo, L Wilson, A Williams, P G Baker, and E I Iwuoha (2011), “Dendritic 7T-polythiophene electro-catalytic sensor system for the determination of polycyclic aromatic hydrocarbons,” Int J Electrochem Sci., vol 6, no 6, pp 1949–1967 68 Reeves, T (2011), Chemical Analysis of Antibiotic Residues in Food Hoboken, NJ, USA: John Wiley & Sons, Inc 69 Rezende, C P., L F Souza, M P Almeida, P G Dias, M H Diniz, and J C Garcia (2012), “Optimisation and validation of a quantitative and confirmatory method for residues of macrolide antibiotics and lincomycin in kidney by liquid chromatography coupled to mass spectrometry,” Food Addit Contam - Part A Chem Anal Control Expo Risk Assess., vol 29, no 4, pp 587–595 70 Robert M Silverstein, Francis X Webster, D J K (2005), “Spectrometric identification of organic compounds,” Journal of Molecular Structure p 512 71 Rostami, A and M S Taylor (2012), Polymers for anion recognition and sensing, vol 33, no 72 Rostamizadeh, K., M Vahedpour, and S Bozorgi (2012), “Synthesis, characterization and evaluation of computationally designed nanoparticles of molecular imprinted polymers as drug delivery systems,” Int J Pharm., vol 424, no 1–2, pp 67–75 73 Sainz, R., A M Benito, M T Martinez, J F Galindo, J Sotres, A M Baro, B Corraze, O Chauvet, A B Dalton, R H Baughman, and W K Maser (2005), “A soluble and highly functional polyaniline-carbon nanotube composite,” Nanotechnology, vol 16, no 74 Schirhagl, R., D Podlipna, P A Lieberzeit, and F L Dickert (2010), “Comparing biomimetic and biological receptors for insulin sensing,” Chem Commun., vol 46, no 18, pp 3128–3130 75 Schweitz, L., L I Andersson, and S Nilsson (1997), “Capillary 74 Electrochromatography with Predetermined Selectivity Obtained through Molecular Imprinting,” Anal Chem., vol 69, no 6, pp 1179–1183 76 Shimano, J Y and A G MacDiarmid (2001), “Polyaniline, a dynamic block copolymer: Key to attaining its intrinsic conductivity?,” Synth Met., vol 123, no 2, pp 251–262 77 Sniegocki, T., A Posyniak, and J Zmudzki (2006), “Validation of the gas chromatography-mass spectrometry method for the determination of chloramphenicol residues in milk,” … -Veterinary Inst …, pp 353–357 78 Song, E and J.-W Choi (2013), “Conducting Polyaniline Nanowire and Its Applications in Chemiresistive Sensing,” Nanomaterials, vol 3, no 3, pp 498–523 79 Steinke, J., A Chemistry, and C Street (1995), “Imprinting of Synthetic Polymers Using Molecular Templates” 80 Syu, M J., T C Chiu, C Y Lai, and Y S Chang (2006), “Amperometric detection of bilirubin from a micro-sensing electrode with a synthetic bilirubin imprinted poly(MAA-co-EGDMA) film,” Biosens Bioelectron., vol 22, no SPEC ISS., pp 550–557 81 Takagishi, T and I M Klotz (1972), “Macromolecule‐small molecule interactions; introduction of additional binding sites in polyethyleneimine by disulfide cross–linkages,” Biopolymers, vol 11, no 2, pp 483–491 82 Takeuchi, T and J Haginaka (1999), “Separation and sensing based on molecular recognition using molecularly imprinted polymers,” J Chromatogr B Biomed Sci Appl., vol 728, no 1, pp 1–20 83 Thinh, T Q (2016), “Fabrication of Immunosensor For Detection of Poultry Virus”, Master thesis, Hanoi University of Science and Technology 84 Thongchai, W., B Liawruangath, S Liawruangrath, and G M Greenway (2010), “A microflow chemiluminescence system for determination of 75 chloramphenicol in honey with preconcentration using a molecularly imprinted polymer,” Talanta, vol 82, no 2, pp 560–566 85 Trchová, M and J Stejskal (2011), “Polyaniline: The infrared spectroscopy of conducting polymer nanotubes (IUPAC Technical Report),” Pure Appl Chem., vol 83, no 10, pp 1803–1817 86 Van Tuan, C., T Q Huy, N Van Hieu, M A Tuan, and T Trung (2013), “Polyaniline Nanowires-Based Electrochemical Immunosensor for Label Free Detection of Japanese Encephalitis Virus,” Anal Lett., vol 46, no 8, pp 1229– 1240 87 V., P M (1931), “Adsorption properties and structure of silica gel,” Zhurnal Fiz khimii, vol 2S, pp 799–804 88 Varanasi, V K (2012), “Molecularly Imprinted Polymers: The Way Forward,” Org Chem Curr Res., vol 01, no 01, pp 1–2 89 Wang, C Y., V Mottaghitalab, C O Too, G M Spinks, and G G Wallace (2007), “Polyaniline and polyaniline – carbon nanotube composite fibres as battery materials in ionic liquid electrolyte,” vol 163, pp 1105–1109 90 Wang, H Y., T Kobayashi, and N Fujii (1996), “Molecular Imprint Membranes Prepared by the Phase Inversion Precipitation Technique,” Langmuir, vol 12, no 20, pp 4850–4856 91 Wang, S., B Xu, Y Zhang, and J X He (2009), “Development of enzymelinked immunosorbent assay (ELISA) for the detection of neomycin residues in pig muscle, chicken muscle, egg, fish, milk and kidney,” Meat Sci., vol 82, no 1, pp 53–58 92 Wang, X Q., B J Xin, and J Xu (2013), “Preparation of conductive PANI/PVA composites via an emulsion route,” Int J Polym Sci., vol 2013 93 Whitcombe, M J and E N Vulfson (2001), “Imprinted polymers,” Adv Mater., vol 13, no 7, pp 467–478 76 94 Whitcombe, M J (2009), “MIPdatabase.” [Online] Available: http://mipdatabase.com/all_items.php [Accessed: 20-Aug-2009] 95 Whitcombe, M J., M E Rodriguez, P Villar, and E N Vulfson (1995), “A New Method for the Introduction of Recognition Site Functionality into Polymers Prepared by Molecular Imprinting: Synthesis and Characterization of Polymeric Receptors for Cholesterol,” J Am Chem Soc., vol 117, no 27, pp 7105–7111 96 Widiastuti, R and Y Anastasia (2014), “Detection of Chloramphenicol Residue in Bovine Meat Using Liquid Chromatography Mass Spectrometry,” vol 19, no 1, pp 74–79 97 Wulff, G (1995), “Molecular Imprinting in Cross‐Linked Materials with the Aid of Molecular Templates— A Way towards Artificial Antibodies,” Angew Chemie Int Ed English, vol 34, no 17, pp 1812–1832 98 Yang, G and F Zhao (2014), “Electrochemical sensor for chloramphenicol based on novel multiwalled carbon nanotubes@molecularly imprinted polymer,” Biosens Bioelectron., vol 64, pp 416–422 99 Ye, L., I Surugiu, and K Haupt (2002), “Scintillation proximity assay using molecularly imprinted microspheres,” Anal Chem., vol 74, no 5, pp 959– 964 100 “Downloaded by UNIV OF CALIFORNIA SAN DIEGO on March , 2016 | http://pubs.acs.org Moats ; Agricultural Uses of Antibiotics ACS Symposium Series ; American Chemical Society : Washington , DC , (1986) Downloaded by UNIV OF CALIFORNIA SAN DIEGO on March ,” pp 142–153 77 ... between template and the imprinting polymer includes covalent bonding, non-covalent bonding, and semi-covalent imprinting  Covalent imprinting: Molecular imprinting via covalent forces is one... residues described in the report includes lincomycin, clindamycin, tilmicosin, erythromycin and tylosin [69] Traditional analytical techniques that dominate the analytical industry as well as... aquaculture includes compounds containing chloramphenicol (CAP) and restricted group residues including compounds in the tetracycline group (doxycycline, oxytetracycline, and tetracycline) So as