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化学进展 2022, Vol. 34 Issue (5): 1124-1135 DOI: 10.7536/PC210604 前一篇   后一篇

• 综述 •

水相识别分子印迹聚合物在样品预处理中的应用

周天瑜1,2,3, 王彦博1,4, 赵翌琳5, 李洪吉1,2,3, 刘春波1,2,3,*(), 车广波1,2,3,*()   

  1. 1.吉林师范大学 环境友好材料制备与应用教育部重点实验室 长春 130103
    2.吉林师范大学 环境科学与工程学院 四平 136000
    3.吉林师范大学 吉林省高校环境材料与污染控制重点实验室 四平 136000
    4.吉林师范大学 化学学院 四平 136000
    5.吉林省晴天环保科技处理中心有限公司 长春 130519
  • 收稿日期:2021-06-07 修回日期:2021-07-07 出版日期:2021-07-29 发布日期:2021-07-29
  • 通讯作者: 刘春波, 车广波
  • 基金资助:
    国家自然科学基金项目(22004047); 国家自然科学基金项目(21906062); 吉林省科技厅项目(20180623042TC); 吉林省人力资源和社会保障厅项目(2017956); 吉林省生态环境厅项目(2019-01-07); 吉林省发展和改革委员会项目(2021C036-7); 吉林省教育厅项目(JJKH20200427KJ)
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The Application of Aqueous Recognition Molecularly Imprinted Polymers in Sample Pretreatment

Tianyu Zhou1,2,3, Yanbo Wang1,4, Yilin Zhao5, Hongji Li1,2,3, Chunbo Liu1,2,3(), Guangbo Che1,2,3()   

  1. 1. Key Laboratory of Preparation and Application of Environmental Friendly Materials, Ministry of Education, Jilin Normal University,Changchun 130103, China
    2. College of Environmental Science and Engineering, Jilin Normal University,Siping 136000, China
    3. Key Laboratory of Environmental Materials and Pollution Control, The Education Department of Jilin Province, Jilin Normal University,Siping 136000, China
    4. College of Chemistry, Jilin Normal University,Siping 136000, China
    5. Jilin Qingtian Environmental Protection Technology Processing Center Co., Ltd, Changchun 130519, China
  • Received:2021-06-07 Revised:2021-07-07 Online:2021-07-29 Published:2021-07-29
  • Contact: Chunbo Liu, Guangbo Che
  • Supported by:
    National Natural Science Foundation of China(22004047); National Natural Science Foundation of China(21906062); Project of Department of Science & Technology of Jilin Province(20180623042TC); Project of Human Resources and Social Security Department of Jilin Province(2017956); Project of Ecological Environment Department of Jilin Province(2019-01-07); Project of Jilin Province Development and Reform Commission(2021C036-7); Project of Education Department of Jilin Province(JJKH20200427KJ)

分子印迹聚合物(MIPs)是模拟抗原-抗体识别机制,人工构筑的对目标物具有专一识别性的材料,构建具有优异水相识别能力的MIPs是分子印迹领域长期面临的挑战。近年来水相识别MIPs以其优异的抗基质干扰和水中识别能力,引起了分析化学家、材料学家和环境学家的广泛关注。本文综述了近年来水相识别MIPs在样品预处理中的应用研究。首先,简要介绍了MIPs的构筑原理、优势及面临水相识别困难的挑战。其次,介绍了样品前处理技术及其重要性。再次,结合各类新兴材料和MIPs制备技术,从样品前处理技术的角度(包括固相萃取、分散固相萃取、磁固相萃取、固相微萃取、管尖固相萃取和搅拌棒吸附萃取)全面总结了水相识别MIPs在含水样品分析中的应用,并结合材料性能和分析参数讨论了各类方法的分析优势。最后,分别从水相识别MIPs构建和预处理两方面提出了该领域面临的挑战和未来的发展趋势。

关键词： 分子印迹聚合物, 水相识别, 样品预处理, 亲水, 水兼容

Molecularly imprinted polymers (MIPs) are artificially constructed materials that mimic the recognition mechanism of antigens and antibodies. The construction of MIPs with excellent aqueous recognition capacity has been a long-term challenge in molecular imprinting fields. In recent years, aqueous recognition MIPs have attracted extensive attention from analytical chemists, materials scientists and environmentalists due to their excellent aqueous recognition and anti-matrix interference ability. In this article, we summarize the preparation and application of aqueous recognition MIPs in sample pretreatment in recent years. Firstly, the construction principles, advantages of MIPs and challenges of MIPs in aqueous recognition are briefly introduced. Secondly, sample pretreatment and its importance are introduced. Thirdly, combined with various emerging materials and preparation techniques of MIPs, the application of aqueous recognition MIPs in sample pretreatment is comprehensively summarized from the perspective of sample pretreatment techniques involving solid phase extraction, dispersive solid phase extraction, magnetic solid phase extraction, solid phase microextraction, pipette tip solid phase extraction and stir bar adsorption extraction. Meanwhile, the advantages of various methods in the analysis of water environment samples are discussed in combination with material properties and analytical parameters. Finally, the challenges and future development trends in this field are presented from perspectives of the construction of aqueous recognition MIPs and sample pretreatment.

Contents

1 Introduction

2 Sample pretreatment techniques

2.1 Solid phase extraction

2.2 Dispersive solid phase extraction

2.3 Magnetic solid phase extraction

2.4 Solid phase microextraction

2.5 Pipette tip solid phase extraction

2.6 Stir bar adsorption extraction

2.7 Membrane protected solid phase extraction

3 Conclusion and outlook

Key words: molecularly imprinted polymers, aqueous recognition, sample pretreatment, hydrophilic, water compatible
()
图1 MIPs的制备流程图
Fig. 1 The preparation scheme of MIPs
表1 水相识别MIPs在样品前处理中应用实例及相应分析参数
Table 1 The preparation of aqueous-recognition MIPs for samples pretreatment and corresponding analytical parameters
Preparation of aqueous-recognition MIPs Target Sample Analytical method LOD Linear range RSD% Re% ref
MIPs surface-grafted dense poly
(2hydroxyethyl methacrylate) brushes		 Propranolol Undiluted bovine
serum		 DSPE-HPLC-UV 0.002 μmol·L-1 0.01~100 μmol·L-1 2.3~3.7 85.2~97.4 18
Hydrophilic MIPs constructed by
natural polysaccharide		 Cyclic adenosine
monophosphate		 Winter jujube MSPE-HPLC-UV 5 ng·mg-1 0.02~3.0 mg· mL-1 - - 19
Phenolic condensation with hydrophilic small molecule Plant hormones Bean sprouts SPE-HPLC-UV 0.014 mg·kg-1 0.07~2.86 mg ·kg-1 <5.3 90.2~99.1 20
Radical polymerization Tyloside Milk SPE-UV 0.026 μg·mL-1 1~20 μg·mL-1 5 92 27
Non-covalent bulk polymerization Spiramycin Water and goat milk SPE-HPLC-UV 24.1 μg·kg-1 24~965 μg· kg-1 5 90 28
Bifunctional monomers of 1-allyl-3-
vinylimidazole chloride and 2-hydroxyethyl
methacrylate		 Quinolone antibiotics Water, soil and pork SPE-HPLC-UV 0.11 μg·L-1 0.0000029~0.0000147
μg· L-1		 9.65 87.3~102.5 31
Bulk polymerization Pirmica Water SPE-HPLC-MS/MS - - 5.07 76.8~96.4 32
Noncovalent imprinting Carbamazepine and
oxcarbazepine		 Urine and blood SPE-HPLC-UV 0.488~0.515μg·L-1 1~500 μg·L-1 3 72~98 33
Noncovalent molecular imprinting Ceftazidime Serum and urine MISPE-HPLC-DAD 7 μg·L-1 25~800 μg·L-1 4.1 94~99 36
Combination of computational model and
molecular imprinting technique		 Chenodeoxycholic acid Crude bile SPE-HPLC-UV - - - 94.1~96.1 38
Green organic solvent free strategy molecular imprinting technology Cardiovascular drugs Urine DSPE-HPLC-DAD 0.1~0.2 μg·L-1 0.3~100 μg· L-1 <4 90.5~102.5 45
RAFT strategy Fluoroquinolones Milk and river water DSPE-HPLC-UV 0.93~2.87 μg·L-1 - <5.3 80.7~105.9 46
RAFTPP strategy Bisphenol A Drinks DSPE-HPLC-DAD 3.75 nmol·L-1 - <6.08 80.7~108.2 47
One step swelling method Thiomycin Milk and river water MSPE-HPLC-UV 10.4 μg·L-1 - 2.8~3.8 96.5~101.1 55
One pot condensation of resorcinol,
melamine and formaldehyde		 Triazines Environmental water MSPE-HPLC-MS/MS 0.02~0.07 μg·L-1 0.65~333.33 μg·L-1 ≤7 85~101 60
One pot condensation Triazines Environmental water MSPE-HPLC-MS/MS 0.007~0.068 μg·L-1 0.25~50 μg ·L-1 <9 88~100 61
Two step template immobilization strategy combined with surface imprinting Chlorophenols Environmental water MSPE-HPLC-UV 0.056~0.102 μg·L-1 0.5~100 μg· L-1 2.0~5.4 91~100 62
Methods of multicomponent copolymerization Tetracyclines Animal derived food SPME-HPLC-UV 0.38~0.72 μg·kg-1 5~1000 μg·L-1 3.1~7.9 77.3~104.4 69
Ccocaine imprinted polymer on the surface of magnetite nanoparticles Cocaine and its
metabolites		 Plasma MSPE-HPLC-MS/MS 0.013~0.36 ng·L-1 - 1~10 91~102 70
Sol-gel Paraquat Environmental water, vegetable MIP-SB-HPLC-UV 8.2 ng·L-1 ,0.02~
0.85 mg·kg-1		 100~10 000 ng·L-1 ≤7.6 70.0~96.1 82
Emulsion polymerization Triazines Tea MPSPE-HPLC-MS/MS 0.09~0.18 ng·g-1 0.5~250 ng·g-1 - 81~104 86
Bulk polymerization Synthetic cannabinoids Urine MIP-MPSPE-SPME-UHPLC-MS/MS 0.032~0.75 mg·L-1 5.0~20 g·L-1 <8 86~106 88
Bulk polymerization Indole-3-butyric acid Mung bean MIP-MPSPE-SPME-HPLC-FD 0.075 mg·kg-1 5~20 mg· L-1 <2.13 88.9~106.4 89
图2 SPE过程示意图
Fig. 2 Schematic diagram of SPE
图3 MIPs结合DSPE过程示意图
Fig. 3 Schematic diagram of MIPs combined with DSPE
图4 MMIPs结合MSPE过程示意图
Fig. 4 Schematic diagram of MMIPs combined with MSPE
图5 MIPs结合MPSPE示意图
Fig. 5 Schematic illustration of the MIPs combined with MPSPE
表2 各种前处理方法优缺点对比
Table 2 Comparison of advantages and disadvantages of various pretreatment methods
SPE DSPE MSPE SPME PT-SPE SBPE MPSPE
Advantages High enrichment factor
Flexibility
Method mature		 No need of
package
Wide application
range
Adsorbent particle
size freedom
Large volume
sample analysis		 No need of package and centrifugation
Wide application
range
Adsorbent particle
size freedom
Operation-simple, time-saving and
labor-saving
Large volume sample
analysis		 Clean extraction
Ease of
automation
Low consumption
of sample,
adsorbent and
solvent
Cheapness		 Low consumption
of sample,
adsorbent and
solvent
Cheapness		 High extraction
efficiency
Simple extraction
process
Green extraction		 High extraction
efficiency
Simple extraction
process
Suitable for
complex samples
analysis
Wide applications
range
Disadvantages Channeling or
blockage of
column
Solvent consumption
Operation complex		 Adsorbents-deteriorated in
complex samples
Residual of sorbent in sample solution
Operation complex		 Adsorbents-
deteriorated in
complex sample
Require magnetic
adsorbent
Residual of sorbent in sample solution		 Device complex
High cost
Fragile device		 Leakage of
adsorbent
Blocking
pipe-tip
Incompatible with
solid samples		 Blocking stir bar
Incompatible with
solid samples
Complex construction process of stir bar
Fragile device		 Complex construction process of device
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