抗原决定基印迹材料及其应用
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摘要
基于抗体-抗原原理的蛋白质印迹材料对蛋白质的分离纯化、药物转运和细胞成像等具有十分重要的意义.其中抗原决定基印迹材料具有模板易得、构象稳定、空间位阻小等优点受到越来越多的关注和得到广泛的应用.本文重点综述了抗原决定基印迹材料的最新制备方法(包括抗原决定基本体印迹、抗原决定基接枝表面印迹、抗原决定基限域表面印迹、基于协同作用的抗原决定基表面印迹技术)以及在肽段、蛋白及细胞识别方面的应用.最后总结了抗原决定基印迹技术面临的主要问题和未来的发展方向.
As artificial antibodies, protein-imprinted materials offer many advantages such as long-term storage stability, potential reusability, resistance to harsh environments and low cost. However, they suffer from obvious disadvantages, when whole proteins are used as templates. First, it is difficult to retain the native conformation of template proteins during the polymerization process. Second, it is unavailable to obtain pure proteins, especially low abundance proteins as the templates. Third, the relatively large imprinted sites are able to bind a range of smaller non-targets, resulting in reduced selectivity. Epitopes are the regions within the structures of globular proteins that can be classified as antigenic determinants. The epitope's structural specificity usually represents the entire protein. And, they can be easily obtained through artificial synthesis. Currently, as an alternative to the target protein, epitopes have been successfully employed as templates to fabricate the recognition sites for several proteins. Compared with protein templates, epitope templates are much more robust and stable during the imprinting process. Moreover, epitope templates could be obtained in large scale with low cost, even for the rare proteins. In this review, we critically and comprehensively survey recent advances and applications in epitope imprinting.The epitope imprinting techniques have been developed into several formats, epitope bulk imprinting, grafted epitope surface imprinting, constrained epitope surface imprinting and synergic epitope surface imprinting according to how the template is presented in the imprinted materials. For the epitope bulk imprinting, binding sites were formed throughout a bulk material. The grafted epitope surface imprinting is achieved by immobilizing epitope on the film or particle surface and then polymerizing with monomers and crosslinkers to form a state-of-the-art recognition sites on the polymer or silica surface. In the constrained epitope surface imprinting, the epitope is confined between the matrix support and the final polymer matrix. Then the matrix support is removed to expose the recognition sites, usually by simply peeling imprinted polymer from the matrix or dissolving the matrix. To improve the affinities and selectivity, additional affinities were integrated into the epitope imprinted surface, which results in the technique of synergic epitope surface imprinting.More recently, application of epitope-imprinted materials has also increased substantially with the rapid development of the life sciences, although they are not as widely used as whole protein molecule imprinting. These are demonstrated in the aspect of the peptide recognition, protein recognition and cell recognition. Finally, we summarized the remaining challenges arising from the intrinsic properties of epitope imprinting, and proposed its future development direction.
As artificial antibodies, protein-imprinted materials offer many advantages such as long-term storage stability, potential reusability, resistance to harsh environments and low cost. However, they suffer from obvious disadvantages, when whole proteins are used as templates. First, it is difficult to retain the native conformation of template proteins during the polymerization process. Second, it is unavailable to obtain pure proteins, especially low abundance proteins as the templates. Third, the relatively large imprinted sites are able to bind a range of smaller non-targets, resulting in reduced selectivity. Epitopes are the regions within the structures of globular proteins that can be classified as antigenic determinants. The epitope's structural specificity usually represents the entire protein. And, they can be easily obtained through artificial synthesis. Currently, as an alternative to the target protein, epitopes have been successfully employed as templates to fabricate the recognition sites for several proteins. Compared with protein templates, epitope templates are much more robust and stable during the imprinting process. Moreover, epitope templates could be obtained in large scale with low cost, even for the rare proteins. In this review, we critically and comprehensively survey recent advances and applications in epitope imprinting.The epitope imprinting techniques have been developed into several formats, epitope bulk imprinting, grafted epitope surface imprinting, constrained epitope surface imprinting and synergic epitope surface imprinting according to how the template is presented in the imprinted materials. For the epitope bulk imprinting, binding sites were formed throughout a bulk material. The grafted epitope surface imprinting is achieved by immobilizing epitope on the film or particle surface and then polymerizing with monomers and crosslinkers to form a state-of-the-art recognition sites on the polymer or silica surface. In the constrained epitope surface imprinting, the epitope is confined between the matrix support and the final polymer matrix. Then the matrix support is removed to expose the recognition sites, usually by simply peeling imprinted polymer from the matrix or dissolving the matrix. To improve the affinities and selectivity, additional affinities were integrated into the epitope imprinted surface, which results in the technique of synergic epitope surface imprinting.More recently, application of epitope-imprinted materials has also increased substantially with the rapid development of the life sciences, although they are not as widely used as whole protein molecule imprinting. These are demonstrated in the aspect of the peptide recognition, protein recognition and cell recognition. Finally, we summarized the remaining challenges arising from the intrinsic properties of epitope imprinting, and proposed its future development direction.
引文
1 Chen L,Wang X,Lu W,et al.Molecular imprinting:Perspectives and applications.Chem Soc Rev,2016,45:2137-2211
2 Yang K,Zhang L,Liang Z,et al.Protein-imprinted materials:Rational design,application and challenges.Anal Bioanal Chem,2012,403:2173-2183
3 Liu J,Deng Q,Tao D,et al.Preparation of protein imprinted materials by hierarchical imprinting techniques and application in selective depletion of albumin from human serum.Sci Rep,2014,4:5487
4 Chen L,Xu S,Li J.Recent advances in molecular imprinting technology:Current status,challenges and highlighted applications.Chem Soc Rev,2011,40:2922-2942
5 Liu L,Yang K,Zhang L,et al.Protein-imprinted material for the treatment of antibiotic-resistant bacteria.Sci Bull,2016,61:1890-1891
6 Rachkov A,Minoura N.Recognition of oxytocin and oxytocin-related peptides in aqueous media using a molecularly imprinted polymer synthesized by the epitope approach.J Chromatogr A,2000,889:111-118
7 Rachkov A,Minoura N.Towards molecularly imprinted polymers selective to peptides and proteins.The epitope approach.BioChim Biophys Acta(BBA)Protein Struct Mol Enzymol,2001,1544:255-266
8 Yang K,Liu J,Li S,et al.Epitope imprinted polyethersulfone beads by self-assembly for target protein capture from the plasma proteome.Chem Commun,2014,50:9521-9524
9 Yang K,Li S,Liu J,et al.Multiepitope templates imprinted particles for the simultaneous capture of various target proteins.Anal Chem,2016,88:5621-5625
10 Nishino H,Huang C S,Shea K J.Selective protein capture by epitope imprinting.Angew Chem Int Ed,2006,45:2392-2396
11 Chen L,Shan Y,Weng Y,et al.Depletion of internal peptides by site-selective blocking,phosphate labeling,and TiO2adsorption for in-depth analysis of C-terminome.Anal Bioanal Chem,2016,408:3867-3874
12 Liu J,Deng Q,Yang K,et al.Macroporous molecularly imprinted monolithic polymer columns for protein recognition by liquid chromatography.JSep Sci,2010,33:2757-2761
13 Whitcombe M J,Chianella I,Larcombe L,et al.The rational development of molecularly imprinted polymer-based sensors for protein detection.Chem Soc Rev,2011,40:1547-1571
14 Helling S,Shinde S,Brosseron F,et al.Ultratrace enrichment of tyrosine phosphorylated peptides on an imprinted polymer.Anal Chem,2011,83:1862-1865
15 Wan L,Chen Z,Huang C,et al.Core-shell molecularly imprinted particles.TrAC Trends Anal Chem,2017,95:110-121
16 Xing R,Wang S,Bie Z,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
17 Bie Z,Chen Y,Ye J,et al.Boronate-affinity glycan-oriented surface imprinting:A new strategy to mimic lectins for the recognition of an intact glycoprotein and its characteristic fragments.Angew Chem Int Ed,2015,54:10211-10215
18 Dechtrirat D,Jetzschmann K J,St?cklein W F M,et al.Protein rebinding to a surface-confined imprint.Adv Funct Mater,2012,22:5231-5237
19 Dechtrirat D,Gajovic-Eichelmann N,Bier F F,et al.Hybrid material for protein sensing based on electrosynthesized MIP on a mannose terminated self-assembled monolayer.Adv Funct Mater,2014,24:2233-2239
20 Jetzschmann K J,Jágerszki G,Dechtrirat D,et al.Vectorially imprinted hybrid nanofilm for acetylcholinesterase recognition.Adv Funct Mater,2015,25:5178-5183
21 Jolly P,Tamboli V,Harniman R L,et al.Aptamer-MIP hybrid receptor for highly sensitive electrochemical detection of prostate specific antigen.Biosens Bioelectron,2016,75:188-195
22 Gao R,Mu X,Hao Y,et al.Combination of surface imprinting and immobilized template techniques for preparation of core-shell molecularly imprinted polymers based on directly amino-modified Fe3O4nanoparticles for specific recognition of bovine hemoglobin.J Mater Chem B,2014,2:1733-1741
23 Li Q,Yang K,Liang Y,et al.Surface protein imprinted core-shell particles for high selective lysozyme recognition prepared by reversible additionfragmentation chain transfer strategy.ACS Appl Mater Interfaces,2014,6:21954-21960
24 Shiomi T,Matsui M,Mizukami F,et al.A method for the molecular imprinting of hemoglobin on silica surfaces using silanes.Biomaterials,2005,26:5564-5571
25 Gao R,Kong X,Wang X,et al.Preparation and characterization of uniformly sized molecularly imprinted polymers functionalized with core-shell magnetic nanoparticles for the recognition and enrichment of protein.J Mater Chem,2011,21:17863-17871
26 Liu J,Yang K,Deng Q,et al.Preparation of a new type of affinity materials combining metal coordination with molecular imprinting.Chem Commun,2011,47:3969-3971
27 Li Q,Yang K,Li S,et al.Preparation of surface imprinted core-shell particles via a metal chelating strategy:Specific recognition of porcine serum albumin.Microchim Acta,2016,183:345-352
28 Gao F X,Ma X T,He X W,et al.Smart surface imprinting polymer nanospheres for selective recognition and separation of glycoprotein.Colloids Surfs A-Physicochem Eng Aspects,2013,433:191-199
29 Tretjakov A,Syritski V,Reut J,et al.Molecularly imprinted polymer film interfaced with Surface Acoustic Wave technology as a sensing platform for label-free protein detection.Anal Chim Acta,2016,902:182-188
30 Wu G,Li J,Qu X,et al.Template size matched film thickness for effectively in situ surface imprinting:A model study of glycoprotein imprints.RSC Adv,2015,5:47010-47021
31 Tamboli V K,Bhalla N,Jolly P,et al.Hybrid synthetic receptors on MOSFET devices for detection of prostate specific antigen in human plasma.Anal Chem,2016,88:11486-11490
32 Li S,Yang K,Liu J,et al.Surface-imprinted nanoparticles prepared with a His-tag-anchored epitope as the template.Anal Chem,2015,87:4617-4620
33 Yang K,Huang X,Zhu M,et al.Combining RAFT polymerization and thiol-ene click reaction for core-shell structured polymer@BaTiO3nanodielectrics with high dielectric constant,low dielectric loss,and high energy storage capability.ACS Appl Mater Interfaces,2014,6:1812-1822
34 Liu J,Yang K,Qu Y,et al.An efficient approach to prepare boronate core-shell polymer nanoparticles for glycoprotein recognition via combined distillation precipitation polymerization and RAFT media precipitation polymerization.Chem Commun,2015,51:3896-3898
35 Dine E J,Ferjaoui Z,Roques-Carmes T,et al.Efficient synthetic access to thermo-responsive core/shell nanoparticles.Nanotechnology,28:125601
36 Coumes F,BeautéL,Domurado D,et al.Self-assembly of well-defined triblock copolymers based on poly(lactic acid)and poly(oligo(ethylene glycol)methyl ether methacrylate)prepared by ATRP.RSC Adv,2016,6:53370-53377
37 Zhou T,J?rgensen L,Mattebjerg M A,et al.Molecularly imprinted polymer beads for nicotine recognition prepared by RAFT precipitation polymerization:A step forward towards multi-functionalities.RSC Adv,2014,4:30292-30299
38 Linares A V,Vandevelde F,Pantigny J,et al.Polymer films composed of surface-bound nanofilaments with a high aspect ratio,molecularly imprinted with small molecules and proteins.Adv Funct Mater,2009,19:1299-1303
39 Tang A,Duan L,Liu M,et al.An epitope imprinted polymer with affinity for kininogen fragments prepared by metal coordination interaction for cancer biomarker analysis.J Mater Chem B,2016,4:7464-7471
40 Yang F,Lin S,Dong X.An artificial receptor synthesized by surface-confined imprinting for the recognition of acetylation on histone H4 K16.Chem Commun,2015,51:7673-7676
41 Yang X,Dong X,Zhang K,et al.A molecularly imprinted polymer as an antibody mimic with affinity for lysine acetylated peptides.J Mater Chem B,2016,4:920-928
42 Nematollahzadeh A,Lindemann P,Sun W,et al.Robust and selective nano cavities for protein separation:An interpenetrating polymer network modified hierarchically protein imprinted hydrogel.J Chromatogr A,2014,1345:154-163
43 Nematollahzadeh A,Sun W,Aureliano C S A,et al.High-capacity hierarchically imprinted polymer beads for protein recognition and capture.Angew Chem Int Ed,2011,50:495-498
44 Kryscio D R,Peppas N A.Surface imprinted thin polymer film systems with selective recognition for bovine serum albumin.Anal Chim Acta,2012,718:109-115
45 Chevalier Y,Bolzinger M A.Emulsions stabilized with solid nanoparticles:Pickering emulsions.Colloids Surfaces A Physicochem Eng Aspects,2013,439:23-34
46 Shen X,Ye L.Interfacial molecular imprinting in nanoparticle-stabilized emulsions.Macromolecules,2011,44:5631-5637
47 Shen X,Zhou T,Ye L.Molecular imprinting of protein in Pickering emulsion.Chem Commun,2012,48:8198-8200
48 Zhou T,Zhang K,Kamra T,et al.Preparation of protein imprinted polymer beads by Pickering emulsion polymerization.J Mater Chem B,2015,3:1254-1260
49 Zhang X,Hu X,Guan P,et al.Immunostimulating peptide interfacial imprinted magnetic microspheres synthesized via Pickering emulsion polymerization.J Mater Sci,2016,52:4713-4726
50 Yang J,Li Y,Wang J,et al.Molecularly imprinted polymer microspheres prepared by Pickering emulsion polymerization for selective solid-phase extraction of eight bisphenols from human urine samples.Anal Chim Acta,2015,872:35-45
51 Li S,Yang K,Zhao B,et al.Epitope imprinting enhanced IMAC(EI-IMAC)for highly selective purification of His-tagged protein.J Mater Chem B,2016,4:1960-1967
52 Li S,Yang K,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
53 Emgenbroich M,Borrelli C,Shinde S,et al.A phosphotyrosine-imprinted polymer receptor for the recognition of tyrosine phosphorylated peptides.Chem Eur J,2008,14:9516-9529
54 Chen J,Shinde S,Koch M H,et al.Low-bias phosphopeptide enrichment from scarce samples using plastic antibodies.Sci Rep,2015,5:11438
55 Shogren-Knaak M,Ishii H,Sun J M,et al.Histone H4-K16 acetylation controls chromatin structure and protein interactions.Science,2006,311:844-847
56 Grunstein M.Histone acetylation in chromatin structure and transcription.Nature,1997,389:349-352
57 Yang X,Dong X,Zhang K,et al.Molecularly Imprinted polymer as antibody mimic with affinity for lysine acetylated peptides.J Mater Chem B,2015,4:920-928
58 Tan L,Yu Z,Zhou X,et al.Antibody-free ultra-high performance liquid chromatography/tandem mass spectrometry measurement of angiotensin Iand II using magnetic epitope-imprinted polymers.J Chromatogr A,2015,1411:69-76
59 Yang Y Q,He X W,Wang Y Z,et al.Epitope imprinted polymer coating CdTe quantum dots for specific recognition and direct fluorescent quantification of the target protein bovine serum albumin.Biosens Bioelectron,2014,54:266-272
60 Li D Y,Zhang X M,Yan Y J,et al.Thermo-sensitive imprinted polymer embedded carbon dots using epitope approach.Biosens Bioelectron,2016,79:187-192
61 Li L,Lu Y,Bie Z,et al.Photolithographic boronate affinity molecular imprinting:A general and facile approach for glycoprotein imprinting.Angew Chem Int Ed,2013,52:7451-7454
62 Bi X,Liu Z.Facile preparation of glycoprotein-imprinted 96-well microplates for enzyme-linked immunosorbent assay by boronate affinity-based oriented surface imprinting.Anal Chem,2013,86:959-966
63 Bi X,Liu Z.Enzyme activity assay of glycoprotein enzymes based on a boronate affinity molecularly imprinted 96-well microplate.Anal Chem,2014,86:12382-12389
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2 Yang K,Zhang L,Liang Z,et al.Protein-imprinted materials:Rational design,application and challenges.Anal Bioanal Chem,2012,403:2173-2183
3 Liu J,Deng Q,Tao D,et al.Preparation of protein imprinted materials by hierarchical imprinting techniques and application in selective depletion of albumin from human serum.Sci Rep,2014,4:5487
4 Chen L,Xu S,Li J.Recent advances in molecular imprinting technology:Current status,challenges and highlighted applications.Chem Soc Rev,2011,40:2922-2942
5 Liu L,Yang K,Zhang L,et al.Protein-imprinted material for the treatment of antibiotic-resistant bacteria.Sci Bull,2016,61:1890-1891
6 Rachkov A,Minoura N.Recognition of oxytocin and oxytocin-related peptides in aqueous media using a molecularly imprinted polymer synthesized by the epitope approach.J Chromatogr A,2000,889:111-118
7 Rachkov A,Minoura N.Towards molecularly imprinted polymers selective to peptides and proteins.The epitope approach.BioChim Biophys Acta(BBA)Protein Struct Mol Enzymol,2001,1544:255-266
8 Yang K,Liu J,Li S,et al.Epitope imprinted polyethersulfone beads by self-assembly for target protein capture from the plasma proteome.Chem Commun,2014,50:9521-9524
9 Yang K,Li S,Liu J,et al.Multiepitope templates imprinted particles for the simultaneous capture of various target proteins.Anal Chem,2016,88:5621-5625
10 Nishino H,Huang C S,Shea K J.Selective protein capture by epitope imprinting.Angew Chem Int Ed,2006,45:2392-2396
11 Chen L,Shan Y,Weng Y,et al.Depletion of internal peptides by site-selective blocking,phosphate labeling,and TiO2adsorption for in-depth analysis of C-terminome.Anal Bioanal Chem,2016,408:3867-3874
12 Liu J,Deng Q,Yang K,et al.Macroporous molecularly imprinted monolithic polymer columns for protein recognition by liquid chromatography.JSep Sci,2010,33:2757-2761
13 Whitcombe M J,Chianella I,Larcombe L,et al.The rational development of molecularly imprinted polymer-based sensors for protein detection.Chem Soc Rev,2011,40:1547-1571
14 Helling S,Shinde S,Brosseron F,et al.Ultratrace enrichment of tyrosine phosphorylated peptides on an imprinted polymer.Anal Chem,2011,83:1862-1865
15 Wan L,Chen Z,Huang C,et al.Core-shell molecularly imprinted particles.TrAC Trends Anal Chem,2017,95:110-121
16 Xing R,Wang S,Bie Z,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
17 Bie Z,Chen Y,Ye J,et al.Boronate-affinity glycan-oriented surface imprinting:A new strategy to mimic lectins for the recognition of an intact glycoprotein and its characteristic fragments.Angew Chem Int Ed,2015,54:10211-10215
18 Dechtrirat D,Jetzschmann K J,St?cklein W F M,et al.Protein rebinding to a surface-confined imprint.Adv Funct Mater,2012,22:5231-5237
19 Dechtrirat D,Gajovic-Eichelmann N,Bier F F,et al.Hybrid material for protein sensing based on electrosynthesized MIP on a mannose terminated self-assembled monolayer.Adv Funct Mater,2014,24:2233-2239
20 Jetzschmann K J,Jágerszki G,Dechtrirat D,et al.Vectorially imprinted hybrid nanofilm for acetylcholinesterase recognition.Adv Funct Mater,2015,25:5178-5183
21 Jolly P,Tamboli V,Harniman R L,et al.Aptamer-MIP hybrid receptor for highly sensitive electrochemical detection of prostate specific antigen.Biosens Bioelectron,2016,75:188-195
22 Gao R,Mu X,Hao Y,et al.Combination of surface imprinting and immobilized template techniques for preparation of core-shell molecularly imprinted polymers based on directly amino-modified Fe3O4nanoparticles for specific recognition of bovine hemoglobin.J Mater Chem B,2014,2:1733-1741
23 Li Q,Yang K,Liang Y,et al.Surface protein imprinted core-shell particles for high selective lysozyme recognition prepared by reversible additionfragmentation chain transfer strategy.ACS Appl Mater Interfaces,2014,6:21954-21960
24 Shiomi T,Matsui M,Mizukami F,et al.A method for the molecular imprinting of hemoglobin on silica surfaces using silanes.Biomaterials,2005,26:5564-5571
25 Gao R,Kong X,Wang X,et al.Preparation and characterization of uniformly sized molecularly imprinted polymers functionalized with core-shell magnetic nanoparticles for the recognition and enrichment of protein.J Mater Chem,2011,21:17863-17871
26 Liu J,Yang K,Deng Q,et al.Preparation of a new type of affinity materials combining metal coordination with molecular imprinting.Chem Commun,2011,47:3969-3971
27 Li Q,Yang K,Li S,et al.Preparation of surface imprinted core-shell particles via a metal chelating strategy:Specific recognition of porcine serum albumin.Microchim Acta,2016,183:345-352
28 Gao F X,Ma X T,He X W,et al.Smart surface imprinting polymer nanospheres for selective recognition and separation of glycoprotein.Colloids Surfs A-Physicochem Eng Aspects,2013,433:191-199
29 Tretjakov A,Syritski V,Reut J,et al.Molecularly imprinted polymer film interfaced with Surface Acoustic Wave technology as a sensing platform for label-free protein detection.Anal Chim Acta,2016,902:182-188
30 Wu G,Li J,Qu X,et al.Template size matched film thickness for effectively in situ surface imprinting:A model study of glycoprotein imprints.RSC Adv,2015,5:47010-47021
31 Tamboli V K,Bhalla N,Jolly P,et al.Hybrid synthetic receptors on MOSFET devices for detection of prostate specific antigen in human plasma.Anal Chem,2016,88:11486-11490
32 Li S,Yang K,Liu J,et al.Surface-imprinted nanoparticles prepared with a His-tag-anchored epitope as the template.Anal Chem,2015,87:4617-4620
33 Yang K,Huang X,Zhu M,et al.Combining RAFT polymerization and thiol-ene click reaction for core-shell structured polymer@BaTiO3nanodielectrics with high dielectric constant,low dielectric loss,and high energy storage capability.ACS Appl Mater Interfaces,2014,6:1812-1822
34 Liu J,Yang K,Qu Y,et al.An efficient approach to prepare boronate core-shell polymer nanoparticles for glycoprotein recognition via combined distillation precipitation polymerization and RAFT media precipitation polymerization.Chem Commun,2015,51:3896-3898
35 Dine E J,Ferjaoui Z,Roques-Carmes T,et al.Efficient synthetic access to thermo-responsive core/shell nanoparticles.Nanotechnology,28:125601
36 Coumes F,BeautéL,Domurado D,et al.Self-assembly of well-defined triblock copolymers based on poly(lactic acid)and poly(oligo(ethylene glycol)methyl ether methacrylate)prepared by ATRP.RSC Adv,2016,6:53370-53377
37 Zhou T,J?rgensen L,Mattebjerg M A,et al.Molecularly imprinted polymer beads for nicotine recognition prepared by RAFT precipitation polymerization:A step forward towards multi-functionalities.RSC Adv,2014,4:30292-30299
38 Linares A V,Vandevelde F,Pantigny J,et al.Polymer films composed of surface-bound nanofilaments with a high aspect ratio,molecularly imprinted with small molecules and proteins.Adv Funct Mater,2009,19:1299-1303
39 Tang A,Duan L,Liu M,et al.An epitope imprinted polymer with affinity for kininogen fragments prepared by metal coordination interaction for cancer biomarker analysis.J Mater Chem B,2016,4:7464-7471
40 Yang F,Lin S,Dong X.An artificial receptor synthesized by surface-confined imprinting for the recognition of acetylation on histone H4 K16.Chem Commun,2015,51:7673-7676
41 Yang X,Dong X,Zhang K,et al.A molecularly imprinted polymer as an antibody mimic with affinity for lysine acetylated peptides.J Mater Chem B,2016,4:920-928
42 Nematollahzadeh A,Lindemann P,Sun W,et al.Robust and selective nano cavities for protein separation:An interpenetrating polymer network modified hierarchically protein imprinted hydrogel.J Chromatogr A,2014,1345:154-163
43 Nematollahzadeh A,Sun W,Aureliano C S A,et al.High-capacity hierarchically imprinted polymer beads for protein recognition and capture.Angew Chem Int Ed,2011,50:495-498
44 Kryscio D R,Peppas N A.Surface imprinted thin polymer film systems with selective recognition for bovine serum albumin.Anal Chim Acta,2012,718:109-115
45 Chevalier Y,Bolzinger M A.Emulsions stabilized with solid nanoparticles:Pickering emulsions.Colloids Surfaces A Physicochem Eng Aspects,2013,439:23-34
46 Shen X,Ye L.Interfacial molecular imprinting in nanoparticle-stabilized emulsions.Macromolecules,2011,44:5631-5637
47 Shen X,Zhou T,Ye L.Molecular imprinting of protein in Pickering emulsion.Chem Commun,2012,48:8198-8200
48 Zhou T,Zhang K,Kamra T,et al.Preparation of protein imprinted polymer beads by Pickering emulsion polymerization.J Mater Chem B,2015,3:1254-1260
49 Zhang X,Hu X,Guan P,et al.Immunostimulating peptide interfacial imprinted magnetic microspheres synthesized via Pickering emulsion polymerization.J Mater Sci,2016,52:4713-4726
50 Yang J,Li Y,Wang J,et al.Molecularly imprinted polymer microspheres prepared by Pickering emulsion polymerization for selective solid-phase extraction of eight bisphenols from human urine samples.Anal Chim Acta,2015,872:35-45
51 Li S,Yang K,Zhao B,et al.Epitope imprinting enhanced IMAC(EI-IMAC)for highly selective purification of His-tagged protein.J Mater Chem B,2016,4:1960-1967
52 Li S,Yang K,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
53 Emgenbroich M,Borrelli C,Shinde S,et al.A phosphotyrosine-imprinted polymer receptor for the recognition of tyrosine phosphorylated peptides.Chem Eur J,2008,14:9516-9529
54 Chen J,Shinde S,Koch M H,et al.Low-bias phosphopeptide enrichment from scarce samples using plastic antibodies.Sci Rep,2015,5:11438
55 Shogren-Knaak M,Ishii H,Sun J M,et al.Histone H4-K16 acetylation controls chromatin structure and protein interactions.Science,2006,311:844-847
56 Grunstein M.Histone acetylation in chromatin structure and transcription.Nature,1997,389:349-352
57 Yang X,Dong X,Zhang K,et al.Molecularly Imprinted polymer as antibody mimic with affinity for lysine acetylated peptides.J Mater Chem B,2015,4:920-928
58 Tan L,Yu Z,Zhou X,et al.Antibody-free ultra-high performance liquid chromatography/tandem mass spectrometry measurement of angiotensin Iand II using magnetic epitope-imprinted polymers.J Chromatogr A,2015,1411:69-76
59 Yang Y Q,He X W,Wang Y Z,et al.Epitope imprinted polymer coating CdTe quantum dots for specific recognition and direct fluorescent quantification of the target protein bovine serum albumin.Biosens Bioelectron,2014,54:266-272
60 Li D Y,Zhang X M,Yan Y J,et al.Thermo-sensitive imprinted polymer embedded carbon dots using epitope approach.Biosens Bioelectron,2016,79:187-192
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