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化学进展 2022, Vol. 34 Issue (3): 593-608 DOI: 10.7536/PC210340 前一篇   后一篇

• 综述 •

分子印迹荧光传感构建及应用

田浩1,2, 李子木1,2, 汪长征1,*(), 许萍1, 徐守芳2,*()   

  1. 1 北京建筑大学城市雨水系统与水环境教育部重点实验室 北京 100044
    2 临沂大学材料科学与工程学院功能高分子实验室 临沂 276005
  • 收稿日期:2021-03-23 修回日期:2021-05-22 出版日期:2022-07-29 发布日期:2021-07-29
  • 通讯作者: 汪长征, 徐守芳
  • 基金资助:
    国家自然科学基金项目(21777065); 山东省高等学校青年创新团队(2019KJA021); 山东省自然科学基金(ZR2020KE002)
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Construction and Application of Molecularly Imprinted Fluorescence Sensor

Hao Tian1,2, Zimu Li1,2, Changzheng Wang1(), Ping Xu1, Shoufang Xu2()   

  1. 1 Key Laboratory of Urban Storm Water System and Water Environment, Beijing University of Civil Engineering and Architecture,Beijing 100044, China
    2 Laboratory of Functional Polymers, School of Materials Science and Engineering, Linyi University,Linyi 276005, China
  • Received:2021-03-23 Revised:2021-05-22 Online:2022-07-29 Published:2021-07-29
  • Contact: Changzheng Wang, Shoufang Xu
  • Supported by:
    National Natural Science Foundation of China(21777065); Youth Innovation Project for Colleges of Shandong Province(2019KJA021); Natural Science Foundation of Shandong Province(ZR2020KE002)

构建一个高灵敏、高选择性检测痕量分析物的传感器广受科研工作者关注。分子印迹技术由于具有高选择性识别、高容量吸附、快速结合、热稳定性以及低成本等优点,已广泛应用于传感构建领域。以分子印迹聚合物为识别单元,结合荧光传感技术所构建的分子印迹荧光传感器在环境污染物痕量检测方面成为研究重点。本文主要介绍分子印迹聚合物的制备方法,总结分子印迹荧光传感器的构建机理和分子印迹荧光传感器在金属离子、有机小分子以及生物大分子检测方面的应用。重点探讨分子印迹传感器在不同数量的荧光团下检测一种或多种目标分析物的方法,包括单一荧光团检测单一目标物、比率荧光检测单一目标物以及分子印迹荧光传感的多元检测。基于以上分析和总结,提出分子印迹荧光传感器的当前挑战和发展前景。

关键词： 分子印迹, 荧光传感, 单发射型, 比率型, 双目标型

The construction of a highly sensitive, highly selective sensor for detecting trace analytes has received wide attention from scientific researchers. Molecularly imprinted technology has been widely used in the field of sensor construction due to its highly selective recognition, high-capacity adsorption, fast binding, thermal stability, and low cost. The molecularly imprinted fluorescent sensor constructed with molecularly imprinted polymer as the identification unit combined with fluorescent sensing technology has become a research focus in the detection of environmental pollutants traces. This article mainly introduces the preparation methods of molecularly imprinted polymers. The construction mechanism of molecularly imprinted fluorescent sensors and the application of molecularly imprinted fluorescent sensors in the detection of metal ions, small organic molecules, and biomacromolecules are summarized. The molecularly imprinted sensors to detect one or more target analytes under different numbers of fluorophores are elaborated, including single-target single-fluorophore detection, single-target ratiometric fluorescence detection, and multiplex detection with molecularly imprinted fluorescence sensor. Finally, the current challenges of molecularly imprinted fluorescent sensors and the prospects of molecularly imprinted fluorescent sensors are proposed to accelerate the development of molecularly imprinted fluorescent sensors and to further develop multifunctional molecularly imprinted fluorescent sensors with a wide range of applications.

Contents

1 Introduction

2 Fluorescence sensing principle and fluorophore type

3 Construction of molecularly imprinted fluorescence sensor

3.1 Molecularly imprinted single emission fluorescence detection

3.2 Molecular imprinting ratiometric fluorescence detection

3.3 Molecularly imprinted multiplex fluorescence detection

4 Application of molecularly imprinted fluorescence sensor

4.1 Detection of metal ions

4.2 Detection of small organic molecules

4.3 Detection of biomacromolecules

5 Conclusion and outlook

Key words: molecularly imprinted, fluorescence sensing, single emission peak type, ratiometric fluorescence type, double target type
()
图1 分子印迹聚合物制备原理[3]
Fig.1 Preparation principle of molecularly imprinted polymers. Copyright 2006, John Wiley and Sons[3]
表1 不同制备分子印迹聚合物方法的优缺点比较
Table 1 Comparison of advantages and disadvantages of different methods for preparing molecularly imprinted polymers
Polymerization mechanism Polymerization method Advantage Disadvantage ref
Radical Polymerization Bulk polymerization Simple operation, high purity of MIPs MIPS has an irregular shape, and larger sizes require grinding 6
Suspension polymerization MIPs is spherical and can be made in one step The effect of MIPs is poor, template is difficult to elute completely 7
Precipitation polymerization Simple operation process, easy control of particle size and morphology of polymer Requires a large amount of solvent and long polymerization time 8
Emulsion polymerization Easily form monodisperse polymers The whole process cycle is relatively long, and the molecular imprinting efficiency is low 9
Reversible addition-
fragmentation chain transfer
(RAFT)		 Wide range of monomers; no interference
from organometallic catalysts;
simple operation		 Requires chain transfer agent and chain terminator; residual impurities are difficult to remove 10
Atom transfer radical
polymerization
(ATRP)		 Mild polymerization conditions; simple operation; high controllability Large amount of catalyst; toxic initiator 11
Sol-gel polymerization Sol-gel method Synthesis at room temperature,
environmentally friendly reaction solvent		 There are fewer choices of types of functional monomers and crosslinker that can be used 12
Self-polymerization of
dopamine		 Self-polymerization of dopamine method With many non-covalent functional groups, easy to be further modified Poor controllability 13
图2 荧光纳米颗粒掺杂到不同形貌的分子印迹聚合物中所制备的分子印迹荧光传感器:(A)实心均质;(B)介孔均质;(C)核壳结构;(D)空心介孔结构;(E)核壳介孔结构
Fig.2 Molecularly imprinted fluorescent sensors prepared by doping fluorescent nanoparticles into molecularly imprinted polymers with different morphologies: (A) solid homogeneous; (B) mesoporous homogeneous; (C) core-shell structure; (D) hollow mesoporous structure; (E) core-shell mesoporous structure
图3 基于硼酸酯亲合力夹心法测定和纳米粒子信号放大的“信号开”荧光传感器的制备过程,以及对HRP检测的示意图[82]
Fig.3 Schematic illustration of the preparation of turn-on MIFS and detection of HRP based on boranate affinity sandwich assay and nanoparticle signal amplification[82]. Copyright 2020, Elsevier
图4 具有参比信号的介孔结构的比率分子印迹荧光传感器的制备过程,以及与目标分析物结合时相应的荧光颜色变化:(A)红色和绿色碲化镉QDs为比率荧光团[90];(B)碲化镉QDs为靶标敏感荧光团,血卟啉为参比荧光团[92]
Fig.4 The preparation process of a ratiometric molecularly imprinted fluorescence sensor with a mesoporous structure with a reference signal, and the corresponding fluorescence color change when the target analyte is recombined. (A) Red and green cadmium telluride quantum dots are ratiometric fluorophores[90]. Copyright 2015, Royal Society of Chemistry. (B) Cadmium telluride quantum dots are the target sensitive fluorophores, and hematoporphyrin is the reference fluorophores[92]. Copyright 2015, Elsevier
图5 具有两个可逆信号的介孔结构的比率分子印迹荧光传感器的制备过程,以及目标分析物重新结合时相应的荧光颜色变化:(A)金纳米颗粒和CDs为比率荧光团[94];(B)CDs和QDs为比率荧光团[95]
Fig.5 The preparation process of a ratiometric molecularly imprinted fluorescence sensor with two reversible signals of mesoporous structure, and the corresponding fluorescence color change when the target analyte is recombined. (A) Gold nanoparticles and carbon dots are ratiometric fluorophores[94]. Copyright 2017, Elsevier. (B) Carbon dots and quantum dots are ratio fluorophores[95]. Copyright 2019, Royal Society of Chemistry
图6 三元检测示意图:荧光颜色表现出黄绿色-黄色-紫色-蓝色的荧光色演变,从而可以肉眼可视化检测BHb[96]
Fig.6 Schematic diagram of ternary detection. The fluorescent color shows the evolution of yellow-green-yellow-purple-blue fluorescence color, which can visually detect BHb with the naked eye[96]. Copyright 2019, American Chemical Society
图7 双参比离子印迹比率荧光传感器的制备以及 Pb2+和Ag+检测的响应机制示意图。在预聚合中,CDs与Ag+混合,而Au NCs与Pb2+混合,形成官能团-模板离子螯合物[104]
Fig.7 The preparation of the dual-reference ion imprinting ratiometric fluorescence sensor and the schematic diagram of the response mechanism of Pb2+ and Ag+ detection. In the pre-polymerization process, CDs are mixed with Ag+, while Au NCs are mixed with Pb2+ to form a functional group-template ion chelate[104]. Copyright 2019, Elsevier
图8 蓝色和红色CDs双通道检测Cr3+和 Pb2+[106]
Fig.8 Two-channel detection of Cr3+ and Pb2+ with blue and red carbon dots[106]. Copyright 2019, American Chemical Society
表2 分子印迹荧光传感器在不同领域检测中的应用
Table 2 Application of molecularly imprinted fluorescence sensors in detection of different fields
Detection field Fluorescent material Sensor type Target substance Detection matrix Linear range Detection limit ref
Metal ion CDs, Au NCs Double reference
type		 Pb2+, Ag+ Real water 50 ~ 900 nmol/L
0.2 ~ 12.5 nmol/L		 26 nmol/L
86 nmol/L		 104
Amino modified CDs, carboxyl modified CDs Double reference
type		 Cu2+, Fe3+ Real water 0.5 ~ 50 μmol/L
1 ~ 100 μmol/L		 130 nmol/L
340 nmol/L		 105
ZnSe QDs Microfluidic paper
chip		 Cd2+, Pb2+ Real water 1 ~ 70 μg/L
1 ~ 60 μg/L		 0.245 μg/L
0.335 μg/L		 103
Blue and red CDs Two-channel detection Cr3+, Pb2+ Real water 0.1 ~ 6.0 μmol/L
0.1 ~ 5.0 μmol/L		 27 nmol/L
34 nmol/L		 106
Blue and red CDs Two-channel detection Cr6+, Cr3+ Real water 0.01 ~ 10.0 μmol/L
0.1 ~ 15.0 μmol/L		 3.8 nmol/L
46 nmol/L		 107
CdTe QDs Microfluidic paper
chip		 Cu2+, Hg2+ Real water 0.11 ~ 58.0 μg/L
0.26 ~ 34.0 μg/L		 0.035 μg/L
0.056 μg/L		 101
CQDs Single emission
quenching		 Cu2+ Tap Water 0.25 ~ 2 mg /L
3 ~ 10 mg /L		 2.86μmol/L 109
Organic molecules CQDs, CdTe QDs Ratiometric type Dopamine Human serum 0.2853~ 5 μmol/L 0.2853μmol/L 110
3-(anthracen-9-
ylmethyl)-1-vinyl-1H-
imidazol-3-ium chloride		 Single emission
quenching		 P-nitroaniline Wastewater 10-8 ~ 10 mol/L 9 nmol/L 111
ZnS QDs Single emission
quenching		 Sparfloxacin Biological serum 0.05~ 2.0 μg/mL 0.012 μg/mL 112
Nitrogen-doped CDs Single emission
quenching		 Aspirin Human urine and saliva 0.9~ 9.0 mg/L 0.198 mg/L 113
CQDs Single emission
quenching		 Tetracycline Real water 1.0 ~ 60 μmol/L 0.17 μmol/L 114
Calcium fluoride CDs Ratiometric type 5-Hydroxymethyl-
furfural		 Honey 0.1~ 6.0 μg/mL 0.043 μg/mL 115
CQDs, CdTe QDs Ratiometric type Sulfadiazine Real water
and milk		 0.25~ 20 μmol/L 0.042 μmol/L 116
Biomacromolecule ATTO 647N Signal amplification Porcine serum
albumin		 Porcine serum 0.25~ 5 nmol/L 40 pmol/L 117
Cadmium telluride QDs Single emission
quenching		 Myoglobin Human serum 7.39 ~ 291.3 pg/mL 3.08 pg/mL 118
Silanized CDs Single emission
quenching		 Bovine hemoglobin Bovine serum 0.31~ 1.55μmol/L 1.55μmol/L 119
ZnS QDs Single emission
quenching		 Lysozyme Real biologic
sample		 0.1 ~ 1μmol/L 10.2 nmol/L 120
CdTe QDs Single emission
quenching		 Myoglobin Human serum 0.304 ~ 571 pg/mL 0.045 pg/mL 121
Green and red
CdTe QDs		 Ratiometric type Bovine hemoglobin Bovine urine 0.050 ~ 3.0μmol/L 9.6 nmol/L 93
Tetra(4-
carboxyphenyl)
porphyrin		 Signal amplification Horseradish peroxidase Urine 10-4 ~ 10 mg/L 0.042 μg/L 82
Phycocyanin and CdTe QDs Ratiometric type Phycocyanin Seawater 0 ~ 1.8 μmol/L 3.2 nmol/L 122
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分子印迹荧光传感构建及应用