Applications of molecularly imprinted polymers for determination of antibiotics residues

doi:10.3724/SP.J.1123.2019.07007

Abstract

Abstract:

Abuse of antibiotics as well as antibiotic residues cause great harm to living beings and the environment. However, determination of antibiotics is quite difficult owing to the low residue level and multiple categories presence in the complicated matrices. Proper sample pretreatment is usually imperative for coupling with chromatographic analysis toward the sensitive determination of antibiotic residues. Molecularly imprinted polymers (MIPs) possess the binding sites complementary to the target (template) molecules in shape, size, and type of functional groups. Hence, MIPs can selectively recognize and effectively enrich the target analytes as well as eliminate matrix interferences. For this reason, they have been widely applied in the sample pretreatment of antibiotics. In this review, several challenges encountered with the use of MIPs and the possible solutions are proposed. Besides, advances in the applications of MIPs for the sample pretreatment of antibiotics since 2016 are summarized, mainly including conventional solid phase extraction (SPE), dispersive solid phase extraction (DSPE), magnetic solid phase extraction (MSPE), matrix solid phase dispersion (MSPD), solid phase microextraction (SPME) and stir bar sorptive extraction (SBSE). Some new imprinting strategies for the preparation of MIPs to be used in the field of antibiotics are highlighted, such as multi-template imprinting, multi-functional monomer imprinting, dummy imprinting, stimuli-responsive imprinting and hydrophilic imprinting. Finally, an outlook on the preparation and pretreatment application of MIPs for antibiotics is presented.

Key words: solid phase extraction (SPE), sample pretreatment, imprinting strategy, molecularly imprinted polymers (MIPs), antibiotics, review

WANG Liyan, WANG Jia'nan, LI Jinhua, CHEN Lingxin. Applications of molecularly imprinted polymers for determination of antibiotics residues[J]. Chinese Journal of Chromatography, 2020, 38(3): 265-277.

Figures/Tables 4

Fig. 1 Sample pretreatment applications and new imprinting strategies of MIPs for antibiotics MIPs: molecularly imprinted polymers; DSPE: dispersive solid phase extraction; MSPE: magnetic solid phase extraction; MSPD: matrix solid phase dispersion; SBSE: stir bar sorptive extraction.

Table 1 Applications of MIPs for the sorptive extraction of antibiotics

Fig. 2 Schematic illustration for preparation of (a) multi-template[88], (b) dummy template, (c) magnetic-responsive and (d) thermo-responsive MIPs

Fig. 3 Schematic illustration for the preparation of photo-responsive magnetic MIPs[105] TEOS: tetraethoxysilane; MPS: 3-methacryloxypropyltrimethoxysilane; MAPASA: 4-[(4-methacryloyloxy) phenylazo] benzenesulfonic acid.

References

1	Zhang Q , Xin Q , Zhu J M , et al. Environmental Chemistry, 2014, 33 (7): 1075
1	章强, 辛琦, 朱静敏, et al. 环境化学, 2014, 33 (7): 1075
2	Zhang Q Q , Ying G G , Pan C G , et al. Environ Sci Technol, 2015, 49: 6772
3	World Health Organization. Global Action Plan on Antimicrobial Resistance. Geneva: World Health Organization, 2015
4	Bitas D , Samanidou V . Molecules, 2018, 23 (2): 316
5	Chen L X , Xu S F , Li J H . Chem Soc Rev, 2011, 40: 2922
6	Chen L X , Wang X Y , Lu W H , et al. Chem Soc Rev, 2016, 45: 2137
7	Li J H , Wen Y Y , Chen L X . Chinese Journal of Chromatography, 2013, 31 (3): 181
7	李金花, 温莹莹, 陈令新色谱, 2013, 31 (3): 181
8	Zhang K G , Hu Y L , Hu Y F . Chinese Journal of Chromatography, 2012, 30 (12): 1220
8	张凯歌, 胡玉玲, 胡玉斐, et al. 色谱, 2012, 30 (12): 1220
9	Huang S Y , Xu J Q , Zheng J T , et al. Anal Bioanal Chem, 2018, 410 (17): 3991
10	Mohsenzadeh M S , Mohammadinejad A , Mohajeri S A . Food Addit Contam A, 2018, 35 (10): 1959
11	Lofgreen J E , Ozin G A . Chem Soc Rev, 2014, 43: 911
12	Wang S S , She Y X , Hong S H , et al. J Hazard Mater, 2019, 367: 686
13	Xu S F , Chen L X , Li J H , et al. J Hazard Mater, 2012, 237/238: 347
14	Xu S F , Li J H , Chen L X . J Mater Chem, 2011, 21: 4346
15	Xu S F , Chen L X , Li J H , et al. J Mater Chem, 2011, 21: 12047
16	Zhang Z , Xu S F , Li J H , et al. J Agric Food Chem, 2012, 60: 180
17	Fu J Q , Wang X Y , Li J H , et al. RSC Adv, 2016, 6: 44087
18	Liu D , Song N Z , Feng W , et al. RSC Adv, 2016, 6 (14): 11742
19	Rozaini M N , Semail N , Saad B , et al. Talanta, 2019, 199: 522
20	Takeuchi T , Sunayama H . Chem Commun, 2018, 54 (49): 6243
21	Madikizela L M , Tavengwa N T , Tutu H , et al. Trends Environ Anal Chem, 2018, 17: 14
22	Zhu G F , Cheng G H , Wang L , et al. J Sep Sci, 2019, 42 (3): 725
23	Awino J K , Gunasekara R W , Zhao Y . J Am Chem Soc, 2016, 138: 9759
24	Xing R R , Wang S S , Bie Z J , et al. Nat Protoc, 2017, 12: 964
25	Chen Y , Li X L , Yin D Y , et al. Chem Commun, 2015, 51: 10929
26	Feng M X , Wang G N , Yang K . Food Control, 2016, 69: 171
27	Fonte A B , Castro G R , María L . J Liq Chromatogr R T, 2018, 41 (15/16): 881
28	He X P , Tan L J , Wu W , et al. J Sep Sci, 2016, 39: 2204
29	Shao H K , Zhou H B , Zhang T T , et al. J Chromatogr A, 2019, 1588: 33
30	Ma J Q , Yu X H , Jia C L , et al. Journal of Food Safety and Quality, 2018, 9 (3): 540
30	马俊琴, 于小慧, 贾翠玲, et al. 食品安全质量检测学报, 2018, 9 (3): 540
31	Wang X X , Zhou Y Q , Niu Y L , et al. Int J Anal Chem, 2019, 2019: 1
32	Tang Y W , Li M , Gao X , et al. Microchim Acta, 2016, 183: 589
33	Wang G N , Yang K , Liu H Z , et al. Anal Methods, 2016, 8 (27): 5511
34	Song Y P , Zhang L , Wang G N , et al. Food Control, 2017, 82: 233
35	Negarian M , Mohammadinejad A , Mohajeri S A . Food Chem, 2019, 288: 29
36	Cai T P , Ma M H , Liu H C , et al. J Liq Chromatogr R T, 2019, 42 (13/14): 459
37	Mayor M A G , Gonzalez G P , Martinez R M G . Food Chem, 2017, 221: 721
38	Song X Q , Zhou T , Liu Q Y , et al. Food Chem, 2016, 208: 169
39	Zhou T , Yang H C , Jin Z , et al. J Sep Sci, 2016, 39: 1339
40	Tian Y , Wang Y , Wu S S , et al. Int J Anal Chem, 2018
41	Wang W W , Luo Z M , Guo P Q , et al. Anal Lett, 2017, 50 (8): 1276
42	Royen G V , Dubruel P , Weyenberg S V , et al. J Chromatogr B, 2016, 1025: 48
43	Urraca J L , Chamorro-Mendiluce R , Orellana G , et al. Anal Bioanal Chem, 2016, 408: 1843
44	Victoria S , Maria K , Abuzar K , et al. Anal Chim Acta, 2016, 914: 62
45	Moreno-González D , Hamed A M , García-Campana A M , et al. Talanta, 2017, 171: 74
46	Zhu G F , Li W W , Wang L , et al. J Chromatogr A, 2019, 1592: 38
47	Lian Z R , Wang J T . Mar Pollut Bull, 2016, 111 (1/2): 411
48	Li G Y , Zha J , Niu M C , et al. Appl Clay Sci, 2018, 162: 409
49	Lian Z R , Wang J T . Mar Pollut Bull, 2018, 133: 750
50	Mtolo S P , Mahlambi P N , Madikizela L M . Water Sci Technol, 2019, 79 (2): 356
51	Hammam M A , Abdel-Halim M , Madbouly A , et al. Microchem J, 2019, 148: 51
52	Du K L , Luo Z M , Guo P Q . J Sep Sci, 2016, 39: 483
53	Li X X , Row K H . RSC Adv, 2017, 7 (28): 16997
54	Chen X , Ye N . RSC Adv, 2017, 7 (54): 34077
55	Ji S L , Li T F , Yang W , et al. Microchim Acta, 2018, 185 (3): 203
56	Du W , Sun M , Guo P Q , et al. Food Chemistry, 2018, 259: 73
57	Yao R , Yu Z , Wu M M , et al. Anal Methods, 2018, 10 (45): 5416
58	Li J H , Dong R C , Wang X Y , et al. RSC Adv, 2015, 5: 10611
59	Wu X Q , Wang X Y , Lu W H , et al. J Chromatogr A, 2016, 1435: 30
60	Peng H L , Luo M , Xiong H , et al. J Chromatogr A, 2016, 1442: 30
61	Peng R F , Zhou Z Q , Wang Q , et al. J Chromatogr A, 2019, 1597: 28
62	Xu Y , Zhao Q , Jiang L Y , et al. Environ Sci Pollut Res, 2017, 24: 9174
63	Hu Y F , Wang C , Li X D , et al. Electrophoresis, 2017, 38 (19): 2462
64	Huang W H , Kong Y , Yang W M , et al. J Polym Res, 2016, 23: 94
65	Xu Y , Li J N , Jiang L Y , et al. Environ Sci Pollut Res, 2018, 25: 16121
66	Sun J J , Zhang F F , Liang X M . Chinese Journal of Chromatography, 2018, 36 (8): 723
66	孙佳佳, 章飞芳, 梁鑫淼色谱, 2018, 36 (8): 723
67	Liu L J , Yang B C , Zhang F F , et al. Anal Methods, 2017, 9 (20): 2990
68	Ding J , Zhang F S , Zhang X P , et al. J Chromatogr B, 2016, 1021: 221
69	Qin D , Wang J T , Ge C Z , et al. Microchim Acta, 2019, 186: 428
70	Kunsa-Ngiem S , Sutthivaiyakit P , Lowmunkhong P , et al. J Environ Sci Heal B, 2018, 53 (11): 738
71	Liu H C , Zhou Y Q , Qi Y X , et al. J Liq Chromatogr R T, 2018, 41 (13/14): 868
72	Wei S L , Li J W , Liu Y , et al. J Chromatogr A, 2016, 1473: 19
73	Lv Y K , Zhang J , Li M Z , et al. Anal Methods, 2016, 8 (19): 3982
74	Wang G N , Zhang L , Song Y P , et al. J Chromatogr B, 2017, 1065/1066: 104
75	Wang S S , Zhang J F , Li C Y , et al. J Sep Sci, 2018, 41 (12): 2604
76	Hu Y L , Wang Y Y , Chen X G , et al. Talanta, 2010, 80: 2099
77	Lian H X , Hu Y L , Li G K . J Sep Sci, 2014, 37: 106
78	Barahona F , Albero B , Tadeo J L , et al. J Chromatogr A, 2019, 1587: 42
79	Mirzajani R , Kardani F . J Pharmaceut Biomed, 2016, 122: 98
80	Liu Y H , Yang Q X , Chen X T , et al. Talanta, 2018, 204: 238
81	Hu Y L , Li J W , Li G K . J Sep Sci, 2011, 34: 1190
82	Xu Z G , Song C Y , Hu Y L , et al. Talanta, 2011, 85: 97
83	Yang K , Wang G N , Liu H Z , et al. J Chromatogr B, 2017, 1046: 65
84	Tang T , Wei F D , Wang X , et al. J Chromatogr B, 2018, 1076: 8
85	Lu W H , Wang X Y , Wu X Q , et al. J Chromatogr A, 2017, 1483: 30
86	Song X L , Li J H , Xu S F , et al. Talanta, 2012, 99: 75
87	Ostovan A , Ghaedi M , Arabi M , et al. ACS Appl Mater Inter, 2018, 10: 4140
88	Lu W H , Liu J , Li J H , et al. Analyst, 2019, 144: 1292
89	Xie Y F , Hu Q , Zhao M Y , et al. Food Anal Method, 2017, 11 (2): 374
90	Kechagia M , Samanidou V , Kabir A , et al. J Sep Sci, 2018, 41 (3): 723
91	Ma W W , Row K H . J Sep Sci, 2019, 42 (3): 642
92	Wang L Y , Li J H , Wang J N , et al. J Colloid Interf Sci, 2019, 541: 376
93	Cai X Q , Li J H , Zhang Z , et al. ACS Appl Mater Inter, 2014, 6: 305
94	Li Z W , Lei C , Wang N , et al. J Chromatogr B, 2018, 1100/1101: 113
95	Xu Y , Tang Y H , Zhao Y Y , et al. J Colloid Interf Sci, 2018, 515: 18
96	Xu S F , Lu H Z , Li J H , et al. ACS Appl Mater Inter, 2013, 5: 8146
97	Fu Z Z , Zeng Y , Li Z W , et al. Acta Agriculturae Zhejiangensis, 2018, 30 (2): 314
97	付珍珍, 曾月, 李增威, et al. 浙江农业学报, 2018, 30 (2): 314
98	Song X Q , Zhou T , Li J F , et al. J Sep Sci, 2018, 41 (5): 1138
99	Song X Q , Zhou T , Li J F , et al. Molecules, 2018, 23 (5): 1172
100	Meng J , Wang X . J Chem, 2019
101	Hu Z H , Wang Y F , Omer A M . Int J Biol Macromol, 2018, 107 (A): 453
102	Mao Y L , Niu Y F , Wu J F , et al. Chinese Journal of Analytical Chemistry, 2016, 44 (6): 915
102	毛艳丽, 牛云峰, 吴俊峰, et al. 分析化学, 2016, 44 (6): 915
103	Wang H W , Liu Y Q , Wei S L , et al. Anal Bioanal Chem, 2016, 408: 589
104	Huang W H , Qing Y J , Wang N W , et al. Mater, 2018, 11 (11): 2067
105	Chen F F , Dong Y H , Zhao Y X . J Sep Sci, 2016, 39: 4866
106	Zhu G F , Cheng G H , Wang P Y , et al. Talanta, 2019, 200: 307
107	Zhao X L , Wang J Y , Wang J P , et al. J Chromatogr A, 2018, 1574: 9

[1]	ZHOU Ranfeng, ZHANG Huixian, YIN Xiaoli, PENG Xitian. Progress in the application of novel nano-materials to the safety analysis of agricultural products [J]. Chinese Journal of Chromatography, 2023, 41(9): 731-741.
[2]	QU Jian, NI Yuwen, YU Haoran, TIAN Hongxu, WANG Longxing, CHEN Jiping. New pretreatment method for detecting petroleum hydrocarbons in soil: silica-gel dehydration and cyclohexane extraction [J]. Chinese Journal of Chromatography, 2023, 41(9): 814-820.
[3]	GAO Yiyang, DING Yali, CHEN Luyu, DU Fang, XIN Xubo, FENG Juanjuan, SUN Mingxia, FENG Yang, SUN Min. Recent application advances of covalent organic frameworks for solid-phase extraction [J]. Chinese Journal of Chromatography, 2023, 41(7): 545-553.
[4]	XIA Baolin, WANG Shitao, YIN Jingjing, ZHANG Weiyi, YANG Na, LIU Qiang, WU Haijing. Simultaneous determination of 43 antibacterials from nine categories in water using automatic sample loading-solid phase extraction-ultra performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(7): 591-601.
[5]	WANG Yuanyuan, LI Lulu, LÜ Jia, CHEN Yongyan, ZHANG Lan. Determination of 13 halobenzoquinone disinfection by-products in drinking water using solid phase extraction-ultra performance liquid chromatography-triple quadrupole mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(6): 482-489.
[6]	WANG Xuemei, HUANG Lixia, YUAN Na, HUANG Pengfei, DU Xinzhen, LU Xiaoquan. Progress in preparation of hollow nanomaterials and their application to sample pretreatment [J]. Chinese Journal of Chromatography, 2023, 41(6): 457-471.
[7]	WEN Yalun, SHAO Yuchen, ZHAO Xinying, QU Feng. Annual review of capillary electrophoresis technology in 2022 [J]. Chinese Journal of Chromatography, 2023, 41(5): 377-385.
[8]	LI Zhenhuan, HU Xiaojian, LU Yifu, XIE Linna, ZHU Ying. Determination of sixteen antibiotics and four β-agonists in human urine samples using ultra-performance liquid chromatography-tandem mass spectrometry based on high-throughput automatic solid-phase extraction [J]. Chinese Journal of Chromatography, 2023, 41(5): 397-408.
[9]	WU Shaoming, OUYANG Liqun, MENG Peng, HE Menghang, LIN Qin, CHEN Yankai, LIU Wenjing, SU Xiaoming, DAI Ming. Determination of 18 caine anesthetics in animal meat using solid phase extraction combined with ultra-performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(5): 434-442.
[10]	YE Hanzhang, LIU Tingting, DING Yongli, GU Jingjing, LI Yuhao, WANG Qi, ZHANG Zhan’en, WANG Xuedong. Recent advances in the development and application of effervescence-assisted microextraction techniques [J]. Chinese Journal of Chromatography, 2023, 41(4): 289-301.
[11]	HAN Linxue, ZHANG Xu, HU Xiaojian, ZHANG Haijing, QIU Tian, LIN Xiao, ZHU Ying. Determination of 12 typical personal care products in human urine samples by ultra performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(4): 312-322.
[12]	XIE Weiya, ZHU Xiaohan, MEI Hongcheng, GUO Hongling, LI Yajun, HUANG Yang, QIN Hao, ZHU Jun, HU Can. Applications of functional materials-based solid phase microextraction technique in forensic science [J]. Chinese Journal of Chromatography, 2023, 41(4): 302-311.
[13]	LU Huiyuan, WANG Lijuan, ZHANG Jiongkai, ZHANG Chizhong, LI Tianjuan, JI Ruixue, SHEN Weijian. Determination of four fatty acid ethyl esters in olive oil by solid phase extraction-gas chromatography [J]. Chinese Journal of Chromatography, 2023, 41(4): 359-365.
[14]	WANG Jin, YE Kaixiao, TIAN Yan, LIU Ke, LIANG Liuling, LI Qingqian, HUANG Ning, WANG Xinting. Simultaneous determination of 22 antibiotics in environmental water samples by solid phase extraction-high performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(3): 241-249.
[15]	ZHANG Xu, HAN Linxue, QIU Tian, HU Xiaojian, ZHU Ying, YANG Yanwei. Determination of phenoxyacetic herbicides, metabolites of organophosphorus and pyrethroid pesticides in human urine using solid phase extraction coupled with ultra-performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(3): 224-232.