刺激-响应型蛋白质分子印迹材料的研究进展
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摘要
蛋白质分子印迹技术在蛋白组学、生命科学、生物传感、药学研究及生物样品纯化等领域具有广泛的应用价值并备受关注.不过,由于其分子量较大,蛋白质分子印迹材料在应用中还存在蛋白质的传输扩散效率较低及吸附脱附较难等缺陷.而新出现的刺激-响应型蛋白质分子印迹材料可对外界刺激做出反应,并可进一步通过调控分子印迹材料与生物大分子之间的相互作用来实现目标蛋白质的高效快速捕获及释放,因此其具有重要的应用前景.本文综述了近20年来刺激-响应型蛋白质分子印迹材料的研究进展,并概述了其制备方法、聚合物单体种类、刺激-响应类型及机理,还进一步阐明了刺激-响应型蛋白质分子印迹技术的未来发展方向.
To date, molecular imprinting(MIP) materials towards proteins have been utilized in a wide range of applications encompassing the fields of samples purification, proteomics, life science, biosensor, pharmaceutical research and drug delivery. Although tremendous progress has been made in MIP technique field, the large size of macromolecules would lead to low transmission and diffusion efficiency during MIP processes, and further cause difficult in adsorption and desorption of target proteins. Therefore, great challenges still remain to be addressed, especially in the design of unique and advanced MIP materials towards macromolecules. More recently, stimuli-responsive MIP materials have attracted considerable interest because they can respond to external stimuli while modulating their affinities for the target proteins and endowing switchable capacities of the binding/releasing processes. In this review, an overview of different stimuli-responsive MIP materials towards proteins developed from 1998 to now, especially the synthetic methods, monomer species, intelligent modulating principle and application has been provided. Moreover, the future of intelligent stimuli-responsive MIP materials for target proteins is expounded. In the first section, the classical MIP fabrication process and mechanism of MIP materials have been described: template incubating with the function monomers, polymerization and template removing. Then the fundamental properties of classical MIP materials including high selectivity, stability and excellent reusability without loss of activity have been discussed. However, the MIP materials are mainly utilized as adsorbents for extraction of the small molecules. When it comes to template with large molecules, such as proteins, the MIP materials suffered from the lower diffusion efficiency and needed harsh elution conditions. Therefore, to approach challenges, new materials-the stimuli-responsive MIP materials should be explored. In the second section, several methods for synthesis of stimuli-responsive MIP materials have been introduced in detail, including bulk polymerization, emulsion polymerization, precipitation polymerization, suspension polymerization and surface imprinting method. Moreover, the advantages and shortcomings of each method and its application have been summarized. Combination of MIP materials with stimuli-responsive properties has attracted significant research interest. In the third section, a general summary of stimuli-responsive MIP technology has been made, including the design of thermo/pH sensitive MIP materials and its application in proteins analysis. Finally, this review performs prospect for the future development of stimuli-responsive MIP technology including the limitation in theoretical study, synthesis method and commercial products. The stimuli-responsive MIP materials have displayed great potential anyhow in several applications including drug delivery and environmental protection owing to their versatility properties.
To date, molecular imprinting(MIP) materials towards proteins have been utilized in a wide range of applications encompassing the fields of samples purification, proteomics, life science, biosensor, pharmaceutical research and drug delivery. Although tremendous progress has been made in MIP technique field, the large size of macromolecules would lead to low transmission and diffusion efficiency during MIP processes, and further cause difficult in adsorption and desorption of target proteins. Therefore, great challenges still remain to be addressed, especially in the design of unique and advanced MIP materials towards macromolecules. More recently, stimuli-responsive MIP materials have attracted considerable interest because they can respond to external stimuli while modulating their affinities for the target proteins and endowing switchable capacities of the binding/releasing processes. In this review, an overview of different stimuli-responsive MIP materials towards proteins developed from 1998 to now, especially the synthetic methods, monomer species, intelligent modulating principle and application has been provided. Moreover, the future of intelligent stimuli-responsive MIP materials for target proteins is expounded. In the first section, the classical MIP fabrication process and mechanism of MIP materials have been described: template incubating with the function monomers, polymerization and template removing. Then the fundamental properties of classical MIP materials including high selectivity, stability and excellent reusability without loss of activity have been discussed. However, the MIP materials are mainly utilized as adsorbents for extraction of the small molecules. When it comes to template with large molecules, such as proteins, the MIP materials suffered from the lower diffusion efficiency and needed harsh elution conditions. Therefore, to approach challenges, new materials-the stimuli-responsive MIP materials should be explored. In the second section, several methods for synthesis of stimuli-responsive MIP materials have been introduced in detail, including bulk polymerization, emulsion polymerization, precipitation polymerization, suspension polymerization and surface imprinting method. Moreover, the advantages and shortcomings of each method and its application have been summarized. Combination of MIP materials with stimuli-responsive properties has attracted significant research interest. In the third section, a general summary of stimuli-responsive MIP technology has been made, including the design of thermo/pH sensitive MIP materials and its application in proteins analysis. Finally, this review performs prospect for the future development of stimuli-responsive MIP technology including the limitation in theoretical study, synthesis method and commercial products. The stimuli-responsive MIP materials have displayed great potential anyhow in several applications including drug delivery and environmental protection owing to their versatility properties.
引文
1 Zaidi S A.Latest trends in molecular imprinted polymer based drug delivery systems.RSC Adv,2016,6:88807-88819
2 Chen L X,Wang X Y,Lu W H,et al.Molecular imprinting:Perspectives and applications.Chem Soc Rev,2016,45:2137-2211
3 Haupt K,Mosbach K.Molecularly imprinted polymers and their use in biomimetic sensors.Chem Rev,2000,100:2495-2504
4 Hirayama K,Sakai Y,Kameoka K,et al.Preparation of a sensor device with specific recognition sites for acetaldehyde by molecular imprinting technique.Sens Actuators B,2002,86:20-25
5 Lavignac N,Allender C J,Brain K R.Current status of molecularly imprinted polymers as alternatives to antibodies in sorbent assays.Anal Chim Acta,2004,510:139-145
6 Ye L,Mosbach K.Molecularly imprinted microspheres antibody binding mimics.React Funct Polym,2001,48:149-157
7 Inoue Y,Kuwahara A,Ohmori K,et al.Fluorescent molecularly imprinted polymer thin films for specific protein detection prepared with dansyl ethylenediamine-conjugated O-acryloyl L-hydroxyproline,Biosens Bioelectron,2013,48:113-119
8 Chen W,Ma Y,Pan J M,et al.Molecularly imprinted polymers with stimuli-responsive affinity:Progress and perspectives.Polymers,2015,7:1689-1715
9 Jing T,Gao X,Wang P,et al.Determination of trace tetracycline antibiotics in foodstuffs by liquid chromatography-tandem mass spectrometry coupled with selective molecular-imprinted solid-phase extraction.Anal Bioanal Chem,2009,393:2009-2018
10 Pérez-Moral N,Mayes A G.Novel MIP formats.Bioseparation,2001,10:287-299
11 Tan C J,Tong Y W.Preparation of superparamagnetic ribonuclease a surface-imprint particles for protein recognition in aqueous media.Anal Chem,2007,79:299-306
12 Pan G,Zhang Y,Guo X,et al.An efficient approach to obtaining water-compatible and stimuli-responsive molecularly imprinted polymers by the facile surface-grafting of functional polymer brushes via RAFT polymerization.Biosens Bioelectron,2010,26:976-982
13 Gonzato C,Pasetto P,Bedoui F,et al.On the effect of using RAFT and FRP for the bulk synthesis of acrylic and methacrylic molecularly imprinted polymers.Polym Chem,2014,5:1313-1322
14 Liu S,Yan H,Wang M,et al.Water-compatible molecularly imprinted microspheres in pipette tip solid-phase extraction for simultaneous determination of five fluoroquinolones in eggs.J Agr Food Chem,2013,61:11974-11980
15 Carter S R,Rimmer S.Molecular recognition of caffeine by shell molecular imprinted core-shell polymer particles in aqueous media.Adv Mater,2002,14:667-670
16 Haginaka J.Molecularly imprinted polymers as affinity-based separation media for sample preparation.J Sep Sci,2009,32:1548-1565
17 Li Y,Dong C,Chu J,et al.Surface molecular imprinting onto fluorescein-coated magnetic nanoparticles via reversible addition fragmentation chain transfer polymerization:A facile three-in-one system for recognition and separation of endocrine disrupting chemicals.Nanoscale,2011,3:280-287
18 Wu P,He Y,Wang H F.Conjugation of glucose oxidase onto Mn-doped ZnS quantum dots for phosphorescent sensing of glucose in biological fluids.Anal Chem,2010,82:1427-1433
19 Choong C L,Bendall J S,Milne W I.Carbon nanotube array:A new MIP platform.Biosens Bioelectron,2009,25:652-656
20 Yoshikawa M,Tharpa K,Dima S O.Molecularlt imprinted membranes:Past,present,and future.Chem Rev,2016,116:11500-11528
21 Ji S L,Li N,Shen Y,et al.Poly(amino acid)-based thermoresponsive molecularly imprinted magnetic nanoparticles for specific recognition and release of lysozyme.Anal Chim Acta,2016,909:60-66
22 Ran D,Wang Y,Jia X,et al.Bovine serum albumin recognition via thermosensitive molecular imprinted macroporous hydrogels prepared at two different temperatures.Anal Chim Acta,2012,723:45-53
23 Miyata T,Jige M,Nakaminami T,et al.Tumor marker-responsive behavior of gels prepared by biomolecular imprinting.Proc Natl Acad Sci USA,2006,103:1190-1193
24 Chen Z Y,Hua Z D,Xu L,et al.Protein-responsive imprinted polymers with specific shrinking and rebinding.J Mol Recognit,2008,21:71-77
25 Chen Z Y,Xu L,Liang Y,et al.pH-sensitive water-soluble nanospheric imprinted hydrogels prepared as horseradish peroxidase mimetic enzymes.Adv Mater,2010,22:1488-1492
26 Pan G,Guo Q,Cao C,et al.Thermo-responsive molecularly imprinted nanogels for specific recognition and controlled release of proteins.Soft Matter 2013,9:3840-3850
27 Qin L,He X W,Yuan X,et al.Molecularly imprinted beads with double thermosensitive gates for selective recognition of proteins.Anal Bioanal Chem,2011,399:3375-3385
28 Li S W,Yang K G,Deng N,et al.Thermoresponsive epitope surface-imprinted nanoparticles for specific capture and release of target protein from human plasma.ACS Appl Mater Interfaces,2016,8:5747-5751
29 Li N,Qi L,Shen Y,et al.Novel oligo(ethylene glycol)-based molecularly imprinted magnetic nanoparticles for thermally modulated capture and release of lysozyme.ACS Appl Mater Interfaces,2014,6:17289-17295
30 Zhang M M,Qiao J,Qi L.Dual-functional polymer-modified magnetic nanoparticles for isolation of lysozyme.Anal Chim Acta,2018,1035:70-76
31 Chen J X,Lei S,Xie Y Y,et al.Fabrication of high-performance magnetic lysozyme-imprinted microsphere and its NIR-responsive controlled release property.ACS Appl Mater Interfaces,2015,7:28606-28615
32 Bi X D,Liu Z.Enzyme activity assay of glycoprotein enzymes based on a boronate affinity molecularly imprinted 96-well microplate.Anal Chem,2014,86:12382-12389
33 Tu X Y,Muhammad P,Liu J,et al.Molecularly imprinted polymer-based plasmonic immunosandwich assay for fast and ultrasensitive determination of trace glycoproteins in complex samples.Anal Chem,2016,88:12363-12370
34 Mai B,Fernandes S,Balakrishnan P B,et al.Nanosystems based on mnagnetic nanoparticles and thermo-or pH-responsive polymers:An update and future perspectives.Acc Chem Res,2018,51:999-1013
35 Watanabe M,Akahoshi T,Tabata Y,et al.Molecular specific swelling change of hydrogels in accordance with the concentration of guest molecules.J Am Chem Soc,1998,120:5577-5578
36 Xu S F,Lu H Z,Zheng X W,et al.Stimuli-responsive molecularly imprinted polymers:Versatile functional materials.J Mater Chem C,2013,1:4406-4422
37 Qin L,He X W,Jia M,et al.A thermosensitive monolithic column as an artificial antibody for the on-line selective separation of the protein.Chem Eur J,2011,17:1696-1704
38 Demirel G,?z?etin G,Turan E,et al.pH/Temperature-sensitive imprinted ionic poly(N-tert-butylacrylamide-co-acrylamide/maleic acid)hydrogels for bovine serum albumin.Macromol Biosci,2005,5:1032-1037
39 Qin L,He X W,Zhang W,et al.Macroporous thermosensitive imprinted hydrogel for recognition of protein by metal coordinate interaction.Anal Chem,2009,81:7206-7216
40 Li C X,Ma Y,Niu H,et al.Hydrophilic hollow molecularly imprinted polymer microparticles with photo-and thermoresponsive template binding and release properties in aqueous media.ACS Appl Mater Interfaces,2015,7:27340-27350
41 Matsumoto K,Kawamura A,Miyata T.Conformationally regulated molecular binding and release of molecularly imprinted polypeptide hydrogels that undergo helix-coil transition.Macromolecules,2017,50:2136-2144
42 Wang X L,Yao H F,Li X Y,et al.pH/temperature-sensitive hydrogel-based molecularly imprinted polymers(hydroMIPs)for drug delivery by frontal polymerization.RSC Adv,2016,6:94038-94047
43 Gao F X,Zhao X L,He X W,et al.A pH and temperature dual-responsive macroporous molecularly imprinted cryogel for enhanced recognition capability towards ovalbumin.Anal Methods,2013,5:6700-6708
44 Tang Q,Nie Y T,Gong C B,et al.Photo-responsive molecularly imprinted hydrogels for the detection of melamine in aqueous media.JMater Chem,2012,22:19812-19820
45 Gomy C,Schmitzer A R.Synthesis and photoresponsive properties of a molecularly imprinted polymer.Org Lett,2007,9:20
46 Ma Y,Zhang Y,Zhao M,et al.Efficient synthesis of narrowly dispersed molecularly imprinted polymer microspheres with multiple stimuli-responsive template binding properties in aqueous media.Chem Commun,2012,48:6217-6219
47 Li D J,Chen Y,Liu Z.Boronate affinity materials for separation and molecular recognition:Structure,properties and applications.Chem Soc Rev,2015,44:8097-8123
48 Bi X D,Liu Z.Facile preparation of glycoprotein-imprinted 96-well microplates for enzyme-linked immunosorbent assay by boronate affinity-based oriented surface imprinting.Anal Chem,2014,86:959-966
49 Xing R R,Wang S S,Bie Z J,et al.Preparation of molecularly imprinted polymers specific to glycoproteins,glycans and monosaccharides via boronate affinity controllable-oriented surface imprinting.Nat Protoc,2017,12:964-987
2 Chen L X,Wang X Y,Lu W H,et al.Molecular imprinting:Perspectives and applications.Chem Soc Rev,2016,45:2137-2211
3 Haupt K,Mosbach K.Molecularly imprinted polymers and their use in biomimetic sensors.Chem Rev,2000,100:2495-2504
4 Hirayama K,Sakai Y,Kameoka K,et al.Preparation of a sensor device with specific recognition sites for acetaldehyde by molecular imprinting technique.Sens Actuators B,2002,86:20-25
5 Lavignac N,Allender C J,Brain K R.Current status of molecularly imprinted polymers as alternatives to antibodies in sorbent assays.Anal Chim Acta,2004,510:139-145
6 Ye L,Mosbach K.Molecularly imprinted microspheres antibody binding mimics.React Funct Polym,2001,48:149-157
7 Inoue Y,Kuwahara A,Ohmori K,et al.Fluorescent molecularly imprinted polymer thin films for specific protein detection prepared with dansyl ethylenediamine-conjugated O-acryloyl L-hydroxyproline,Biosens Bioelectron,2013,48:113-119
8 Chen W,Ma Y,Pan J M,et al.Molecularly imprinted polymers with stimuli-responsive affinity:Progress and perspectives.Polymers,2015,7:1689-1715
9 Jing T,Gao X,Wang P,et al.Determination of trace tetracycline antibiotics in foodstuffs by liquid chromatography-tandem mass spectrometry coupled with selective molecular-imprinted solid-phase extraction.Anal Bioanal Chem,2009,393:2009-2018
10 Pérez-Moral N,Mayes A G.Novel MIP formats.Bioseparation,2001,10:287-299
11 Tan C J,Tong Y W.Preparation of superparamagnetic ribonuclease a surface-imprint particles for protein recognition in aqueous media.Anal Chem,2007,79:299-306
12 Pan G,Zhang Y,Guo X,et al.An efficient approach to obtaining water-compatible and stimuli-responsive molecularly imprinted polymers by the facile surface-grafting of functional polymer brushes via RAFT polymerization.Biosens Bioelectron,2010,26:976-982
13 Gonzato C,Pasetto P,Bedoui F,et al.On the effect of using RAFT and FRP for the bulk synthesis of acrylic and methacrylic molecularly imprinted polymers.Polym Chem,2014,5:1313-1322
14 Liu S,Yan H,Wang M,et al.Water-compatible molecularly imprinted microspheres in pipette tip solid-phase extraction for simultaneous determination of five fluoroquinolones in eggs.J Agr Food Chem,2013,61:11974-11980
15 Carter S R,Rimmer S.Molecular recognition of caffeine by shell molecular imprinted core-shell polymer particles in aqueous media.Adv Mater,2002,14:667-670
16 Haginaka J.Molecularly imprinted polymers as affinity-based separation media for sample preparation.J Sep Sci,2009,32:1548-1565
17 Li Y,Dong C,Chu J,et al.Surface molecular imprinting onto fluorescein-coated magnetic nanoparticles via reversible addition fragmentation chain transfer polymerization:A facile three-in-one system for recognition and separation of endocrine disrupting chemicals.Nanoscale,2011,3:280-287
18 Wu P,He Y,Wang H F.Conjugation of glucose oxidase onto Mn-doped ZnS quantum dots for phosphorescent sensing of glucose in biological fluids.Anal Chem,2010,82:1427-1433
19 Choong C L,Bendall J S,Milne W I.Carbon nanotube array:A new MIP platform.Biosens Bioelectron,2009,25:652-656
20 Yoshikawa M,Tharpa K,Dima S O.Molecularlt imprinted membranes:Past,present,and future.Chem Rev,2016,116:11500-11528
21 Ji S L,Li N,Shen Y,et al.Poly(amino acid)-based thermoresponsive molecularly imprinted magnetic nanoparticles for specific recognition and release of lysozyme.Anal Chim Acta,2016,909:60-66
22 Ran D,Wang Y,Jia X,et al.Bovine serum albumin recognition via thermosensitive molecular imprinted macroporous hydrogels prepared at two different temperatures.Anal Chim Acta,2012,723:45-53
23 Miyata T,Jige M,Nakaminami T,et al.Tumor marker-responsive behavior of gels prepared by biomolecular imprinting.Proc Natl Acad Sci USA,2006,103:1190-1193
24 Chen Z Y,Hua Z D,Xu L,et al.Protein-responsive imprinted polymers with specific shrinking and rebinding.J Mol Recognit,2008,21:71-77
25 Chen Z Y,Xu L,Liang Y,et al.pH-sensitive water-soluble nanospheric imprinted hydrogels prepared as horseradish peroxidase mimetic enzymes.Adv Mater,2010,22:1488-1492
26 Pan G,Guo Q,Cao C,et al.Thermo-responsive molecularly imprinted nanogels for specific recognition and controlled release of proteins.Soft Matter 2013,9:3840-3850
27 Qin L,He X W,Yuan X,et al.Molecularly imprinted beads with double thermosensitive gates for selective recognition of proteins.Anal Bioanal Chem,2011,399:3375-3385
28 Li S W,Yang K G,Deng N,et al.Thermoresponsive epitope surface-imprinted nanoparticles for specific capture and release of target protein from human plasma.ACS Appl Mater Interfaces,2016,8:5747-5751
29 Li N,Qi L,Shen Y,et al.Novel oligo(ethylene glycol)-based molecularly imprinted magnetic nanoparticles for thermally modulated capture and release of lysozyme.ACS Appl Mater Interfaces,2014,6:17289-17295
30 Zhang M M,Qiao J,Qi L.Dual-functional polymer-modified magnetic nanoparticles for isolation of lysozyme.Anal Chim Acta,2018,1035:70-76
31 Chen J X,Lei S,Xie Y Y,et al.Fabrication of high-performance magnetic lysozyme-imprinted microsphere and its NIR-responsive controlled release property.ACS Appl Mater Interfaces,2015,7:28606-28615
32 Bi X D,Liu Z.Enzyme activity assay of glycoprotein enzymes based on a boronate affinity molecularly imprinted 96-well microplate.Anal Chem,2014,86:12382-12389
33 Tu X Y,Muhammad P,Liu J,et al.Molecularly imprinted polymer-based plasmonic immunosandwich assay for fast and ultrasensitive determination of trace glycoproteins in complex samples.Anal Chem,2016,88:12363-12370
34 Mai B,Fernandes S,Balakrishnan P B,et al.Nanosystems based on mnagnetic nanoparticles and thermo-or pH-responsive polymers:An update and future perspectives.Acc Chem Res,2018,51:999-1013
35 Watanabe M,Akahoshi T,Tabata Y,et al.Molecular specific swelling change of hydrogels in accordance with the concentration of guest molecules.J Am Chem Soc,1998,120:5577-5578
36 Xu S F,Lu H Z,Zheng X W,et al.Stimuli-responsive molecularly imprinted polymers:Versatile functional materials.J Mater Chem C,2013,1:4406-4422
37 Qin L,He X W,Jia M,et al.A thermosensitive monolithic column as an artificial antibody for the on-line selective separation of the protein.Chem Eur J,2011,17:1696-1704
38 Demirel G,?z?etin G,Turan E,et al.pH/Temperature-sensitive imprinted ionic poly(N-tert-butylacrylamide-co-acrylamide/maleic acid)hydrogels for bovine serum albumin.Macromol Biosci,2005,5:1032-1037
39 Qin L,He X W,Zhang W,et al.Macroporous thermosensitive imprinted hydrogel for recognition of protein by metal coordinate interaction.Anal Chem,2009,81:7206-7216
40 Li C X,Ma Y,Niu H,et al.Hydrophilic hollow molecularly imprinted polymer microparticles with photo-and thermoresponsive template binding and release properties in aqueous media.ACS Appl Mater Interfaces,2015,7:27340-27350
41 Matsumoto K,Kawamura A,Miyata T.Conformationally regulated molecular binding and release of molecularly imprinted polypeptide hydrogels that undergo helix-coil transition.Macromolecules,2017,50:2136-2144
42 Wang X L,Yao H F,Li X Y,et al.pH/temperature-sensitive hydrogel-based molecularly imprinted polymers(hydroMIPs)for drug delivery by frontal polymerization.RSC Adv,2016,6:94038-94047
43 Gao F X,Zhao X L,He X W,et al.A pH and temperature dual-responsive macroporous molecularly imprinted cryogel for enhanced recognition capability towards ovalbumin.Anal Methods,2013,5:6700-6708
44 Tang Q,Nie Y T,Gong C B,et al.Photo-responsive molecularly imprinted hydrogels for the detection of melamine in aqueous media.JMater Chem,2012,22:19812-19820
45 Gomy C,Schmitzer A R.Synthesis and photoresponsive properties of a molecularly imprinted polymer.Org Lett,2007,9:20
46 Ma Y,Zhang Y,Zhao M,et al.Efficient synthesis of narrowly dispersed molecularly imprinted polymer microspheres with multiple stimuli-responsive template binding properties in aqueous media.Chem Commun,2012,48:6217-6219
47 Li D J,Chen Y,Liu Z.Boronate affinity materials for separation and molecular recognition:Structure,properties and applications.Chem Soc Rev,2015,44:8097-8123
48 Bi X D,Liu Z.Facile preparation of glycoprotein-imprinted 96-well microplates for enzyme-linked immunosorbent assay by boronate affinity-based oriented surface imprinting.Anal Chem,2014,86:959-966
49 Xing R R,Wang S S,Bie Z J,et al.Preparation of molecularly imprinted polymers specific to glycoproteins,glycans and monosaccharides via boronate affinity controllable-oriented surface imprinting.Nat Protoc,2017,12:964-987