硼亲和可控定向表面分子印迹技术研究进展
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摘要
分子印迹是一项模拟靶向生物分子特异性识别能力的仿生分子识别技术,因其识别选择性好、制备简单、价格低廉等优势而被广泛应用.发展至今,已有多种先进的印迹方法被报道,包括表面印迹、表位印迹、乳液印迹等,克服了传统本体印迹方法中存在的许多问题,也使分子印迹技术在许多应用领域成为理想的抗体替代品.由于糖抗体极为稀缺,因此发展出针对糖类化合物的分子印迹技术显得尤为重要,而硼亲和可控定向表面分子印迹技术的提出为解决该问题提供了极有力的技术支持.该技术是一项可控、通用、高效的分子印迹技术,几乎适用于各种类型的基质材料和所有糖类化合物的印迹.它的提出不仅进一步丰富了分子印迹技术的应用范围,更是从方法学上将分子印迹技术推向了一个新的高度,因此具有重要的现实与科学意义.本文介绍了硼亲和可控定向表面分子印迹技术的主要制备方法、原理、应用及其最新研究进展,提出了该技术目前存在的若干问题并展望其未来可能的发展方向.
Biomolecules, like antibody, aptamer and lectin, are still the main force for applications involved in selective separation and recognition. However, these biomolecules are usually suffered from many inevitable problems, such as hard to prepare,high cost, poor stability, as well as limited quantities. Molecular imprinting technique(MIT) as a robust biomimetic molecular recognition strategy to mimic the targeting ability of antibody and enzyme plays a significant role in many areas,including chemical separation, biosensing, catalysis, disease diagnosis, etc. Scientists have pay a lot of attention to developing advanced imprinting approaches to enable MIT adapt many more possible applications. Several user-friendly molecular imprinting methods, such as surface imprinting, epitope imprinting and emulsion imprinting, are hence developed to meet the high analytical requirements. Even so, facile MITs with wide-range versatility and high imprinting efficiency are extremely limited, which restrict the applicability of MIT.Boronate affinity-based controllable oriented surface imprinting(BACOSI) allows for easy and efficient preparation of molecularly imprinted polymers specific to saccharide compounds, which covering glycoproteins, glycopeptides, glycans and monosaccharides. In this paper, the principle, preparation process, applications and recent developments of BACOSI are briefly introduced. Three steps, namely template immobilization, oriented imprinting and template removal, are included in this approach. Template molecules(glycoprotein, glycopeptide, glycan or monosaccharide) immobilized on the surface of boronic-acid-functionalized substrate by virtue of boronate affinity interaction, followed by controllable selfpolymerization of biocompatible monomer(s) to form an imprinting layer on the template-anchored substrate with tailored thickness in terms of molecule size of templates, and then the templates are effectively removed under suitable conditions(weak acidic solutions with or without surfactant are often utilized for templates removal). Imprinting in this approach is performed in a precise-controllable manner permitting the thickness of the imprinting layer to be fine-tuned via adjusting the imprinting time. This manner not only simplifies the imprinting procedure but also makes the approach widely applicable to a large range of sugar-containing biomolecules. Most of all, it can provide a guidance for design and preparation of other biomimetic molecular recognition materials, and a new level in methodology of MIT has been promoted by the presentation of this approach.In addition, some issues and future prospects of BACOSI are also presented in this paper based on our previous researches. From the viewpoint of preparation mechanism, template anchoring of BACOSI highly relies on the boronate affinity effect between boronic acid and cis-diol groups, thus it does not work for non-cis-diol-containing compounds.Exploiting some other means for template immobilization or template-anchoring-free imprinting modes is benefit for extending the application scope of BACOSI. Likewise, ideal biocompatibility and the ability of targeting are also significant for biological applications, for instance, cell imaging, clinical diagnosis and therapy.(Nevertheless, available aqueous phase polymerization for BACOSI is very limited, and its non-specific effect is also cannot be ignored when used for clinical analysis. The further study and exploration of imprinting system with negligible non-specific effect and suitable for the biomedical analysis is the key to form practical imprinting technology). In summary, BACOSI strategy just opens the pathway for the research and application based on facile and versatile imprinting technique in the future, there is still a long distance from being ready for use on industrial production and commercialization.
Biomolecules, like antibody, aptamer and lectin, are still the main force for applications involved in selective separation and recognition. However, these biomolecules are usually suffered from many inevitable problems, such as hard to prepare,high cost, poor stability, as well as limited quantities. Molecular imprinting technique(MIT) as a robust biomimetic molecular recognition strategy to mimic the targeting ability of antibody and enzyme plays a significant role in many areas,including chemical separation, biosensing, catalysis, disease diagnosis, etc. Scientists have pay a lot of attention to developing advanced imprinting approaches to enable MIT adapt many more possible applications. Several user-friendly molecular imprinting methods, such as surface imprinting, epitope imprinting and emulsion imprinting, are hence developed to meet the high analytical requirements. Even so, facile MITs with wide-range versatility and high imprinting efficiency are extremely limited, which restrict the applicability of MIT.Boronate affinity-based controllable oriented surface imprinting(BACOSI) allows for easy and efficient preparation of molecularly imprinted polymers specific to saccharide compounds, which covering glycoproteins, glycopeptides, glycans and monosaccharides. In this paper, the principle, preparation process, applications and recent developments of BACOSI are briefly introduced. Three steps, namely template immobilization, oriented imprinting and template removal, are included in this approach. Template molecules(glycoprotein, glycopeptide, glycan or monosaccharide) immobilized on the surface of boronic-acid-functionalized substrate by virtue of boronate affinity interaction, followed by controllable selfpolymerization of biocompatible monomer(s) to form an imprinting layer on the template-anchored substrate with tailored thickness in terms of molecule size of templates, and then the templates are effectively removed under suitable conditions(weak acidic solutions with or without surfactant are often utilized for templates removal). Imprinting in this approach is performed in a precise-controllable manner permitting the thickness of the imprinting layer to be fine-tuned via adjusting the imprinting time. This manner not only simplifies the imprinting procedure but also makes the approach widely applicable to a large range of sugar-containing biomolecules. Most of all, it can provide a guidance for design and preparation of other biomimetic molecular recognition materials, and a new level in methodology of MIT has been promoted by the presentation of this approach.In addition, some issues and future prospects of BACOSI are also presented in this paper based on our previous researches. From the viewpoint of preparation mechanism, template anchoring of BACOSI highly relies on the boronate affinity effect between boronic acid and cis-diol groups, thus it does not work for non-cis-diol-containing compounds.Exploiting some other means for template immobilization or template-anchoring-free imprinting modes is benefit for extending the application scope of BACOSI. Likewise, ideal biocompatibility and the ability of targeting are also significant for biological applications, for instance, cell imaging, clinical diagnosis and therapy.(Nevertheless, available aqueous phase polymerization for BACOSI is very limited, and its non-specific effect is also cannot be ignored when used for clinical analysis. The further study and exploration of imprinting system with negligible non-specific effect and suitable for the biomedical analysis is the key to form practical imprinting technology). In summary, BACOSI strategy just opens the pathway for the research and application based on facile and versatile imprinting technique in the future, there is still a long distance from being ready for use on industrial production and commercialization.
引文
1 Shi H,Tsai W B,Garrison M D,et al.Template-imprinted nanostructured surfaces for protein recognition.Nature,1999,398:593-597
2 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
3 Hoshino Y,Kodama T,Okahata Y,et al.Peptide imprinted polymer nanoparticles:A plastic antibody.J Am Chem Soc,2008,130:15242-15243
4 Wang H J,Zhou W H,Yin X F,et al.Template synthesized molecularly imprinted polymer nanotube membranes for chemical separations.J Am Chem Soc,2006,128:15954-15955
5 Pan X,He X,Liu Z.Molecularly imprinted mesoporous silica nanoparticles for specific extraction and efficient identification of Amadori compounds.Anal Chim Acta,2018,1019:65-73
6 Haupt K,Mosbach K.Molecularly imprinted polymers and their use in biomimetic sensors.Chem Rev,2000,100:2495-2504
7 Li J,Li Y,Zhang Y,et al.Highly sensitive molecularly imprinted electrochemical sensor based on the double amplification by an inorganic prussian blue catalytic polymer and the enzymatic effect of glucose oxidase.Anal Chem,2012,84:1888-1893
8 Wulff G.Enzyme-like catalysis by molecularly imprinted polymers.Chem Rev,2002,102:1-27
9 Ye J,Chen Y,Liu Z.A boronate affinity sandwich assay:An appealing alternative to immunoassays for the determination of glycoproteins.Angew Chem Int Ed,2014,53:10386-10389
10 Kurczewska J,Ceg?owski M,Pecyna P,et al.Molecularly imprinted polymer as drug delivery carrier in alginate dressing.Mater Lett,2017,201:46-49
11 Zaidi S A.Molecular imprinted polymers as drug delivery vehicles.Drug Deliv,2014,23:2262-2271
12 Panagiotopoulou M,Salinas Y,Beyazit S,et al.Molecularly imprinted polymer coated quantum dots for multiplexed cell targeting and imaging.Angew Chem Int Ed,2016,55:8244-8248
13 Hoshino Y,Koide H,Urakami T,et al.Recognition,neutralization,and clearance of target peptides in the bloodstream of living mice by molecularly imprinted polymer nanoparticles:A plastic antibody.J Am Chem Soc,2010,132:6644-6645
14 Cecchini A,Raffa V,Canfarotta F,et al.In vivo recognition of human vascular endothelial growth factor by molecularly imprinted polymers.Nano Lett.2017,17:2307-2312
15 Hashemi-Moghaddam H,Rahimian M,Niromand B.Molecularly imprinted polymers for solid-phase extraction of sarcosine as prostate cancer biomarker from human urine.Bull Korean Chem Soc,2013,34:2330-2334
16 Gao D,Zhang Z,Wu M,et al.A surface functional monomer-directing strategy for highly dense imprinting of TNT at surface of silica nanoparticles.J Am Chem Soc,2007,129:7859-7866
17 Lu C H,Zhang Y,Tang S F,et al.Sensing HIV related protein using epitope imprinted hydrophilic polymer coated quartz crystal microbalance.Biosens Bioelectron,2012,31:439-444
18 Shen X,Ye L.Molecular imprinting in Pickering emulsions:A new insight into molecular recognition in water.Chem Commun,2011,47:10359-10361
19 Shen X,Zhou T,Ye L.Molecular imprinting of protein in Pickering emulsion.Chem Commun,2012,48:8198-8200
20 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
21 Li D,Chen Y,Liu Z.Boronate affinity materials for separation and molecular recognition:Structure,properties and applications.Chem Soc Rev,2015,44:8097-8123
22 Liu Z,He H.Synthesis and applications of boronate affinity materials:From class selectivity to biomimetic specificity.Acc Chem Res,2017,50:2185-2193
23 Wang S,Ye J,Bie Z,et al.Affinity-tunable specific recognition of glycoproteins via boronate affinity-based controllable oriented surface imprinting.Chem Sci,2014,5:1135-1140
24 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
25 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,2014,86:959-966
26 Yin D,Wang S,He Y,et al.Surface-enhanced Raman scattering imaging of cancer cells and tissues via sialic acid-imprinted nanotags.Chem Commun,2015,51:17696-17699
27 Wang S,Yin D,Wang W,et al.Targeting and imaging of cancer cells via monosaccharide-imprinted fluorescent nanoparticles.Sci Rep,2016,6:22757
28 Wang S,Wen Y,Wang Y,et al.Pattern recognition of cells via multiplexed imaging with monosaccharide-imprinted quantum dots.Anal Chem,2017,89:5646-5652
29 Yin D,Li X,Ma Y,et al.Targeted cancer imaging and photothermal therapy via monosaccharide-imprinted gold nanorods.Chem Commun,2017,53:6716-6719
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 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
32 Shinde S,El-Schich Z,Malakpour A,et al.Sialic acid-imprinted fluorescent core-shell particles for selective labeling of cell surface glycans.J Am Chem Soc,2015,137:13908-13912
33 Kunath S,Panagiotopoulou M,Maximilien J,et al.Cell and tissue imaging with molecularly imprinted polymers as plastic antibody mimics.Adv Healthcare Mater,2015,4:1322-1326
34 Ma R T,Ha W,Chen J,et al.Highly dispersed magnetic molecularly imprinted nanoparticles with well-defined thin film for the selective extraction of glycoprotein.J Mater Chem B,2016,4:2620-2627
35 Sun X Y,Ma R T,Chen J,et al.Synthesis of magnetic molecularly imprinted nanoparticles with multiple recognition sites for the simultaneous and selective capture of two glycoproteins.J Mater Chem B,2018,6:688-696
36 Wang C,Wang Q,Zhong M,et al.Boronic acid based imprinted electrochemical sensor for rutin recognition and detection.Analyst,2016,141:5792-5798
37 Tu X,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
38 Muhammad P,Tu X,Liu J,et al.Molecularly imprinted plasmonic substrates for specific and ultrasensitive immunoassay of trace glycoproteins in biological samples.ACS Appl Mater Interfaces,2017,9:12082-12091
39 Liu J,Yin D,Wang S,et al.Probing low-copy-number proteins in a single living cell.Angew Chem Int Ed,2016,55:13215-13218
40 Huang J,Wu Y,Cong J,et al.Selective and sensitive glycoprotein detection via a biomimetic electrochemical sensor based on surface molecular imprinting and boronate-modified reduced graphene oxide.Senss Actuators B-Chem,2018,259:1-9
41 Muhammad P,Liu J,Xing R,et al.Fast probing of glucose and fructose in plant tissues via plasmonic affinity sandwich assay with molecularlyimprinted extraction microprobes.Anal Chim Acta,2017,995:34-42
42 Bie Z,Xing R,He X,et al.Precision imprinting of glycopeptides for facile preparation of glycan-specific artificial antibodies.Anal Chem,2018,90:9845-9852
2 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
3 Hoshino Y,Kodama T,Okahata Y,et al.Peptide imprinted polymer nanoparticles:A plastic antibody.J Am Chem Soc,2008,130:15242-15243
4 Wang H J,Zhou W H,Yin X F,et al.Template synthesized molecularly imprinted polymer nanotube membranes for chemical separations.J Am Chem Soc,2006,128:15954-15955
5 Pan X,He X,Liu Z.Molecularly imprinted mesoporous silica nanoparticles for specific extraction and efficient identification of Amadori compounds.Anal Chim Acta,2018,1019:65-73
6 Haupt K,Mosbach K.Molecularly imprinted polymers and their use in biomimetic sensors.Chem Rev,2000,100:2495-2504
7 Li J,Li Y,Zhang Y,et al.Highly sensitive molecularly imprinted electrochemical sensor based on the double amplification by an inorganic prussian blue catalytic polymer and the enzymatic effect of glucose oxidase.Anal Chem,2012,84:1888-1893
8 Wulff G.Enzyme-like catalysis by molecularly imprinted polymers.Chem Rev,2002,102:1-27
9 Ye J,Chen Y,Liu Z.A boronate affinity sandwich assay:An appealing alternative to immunoassays for the determination of glycoproteins.Angew Chem Int Ed,2014,53:10386-10389
10 Kurczewska J,Ceg?owski M,Pecyna P,et al.Molecularly imprinted polymer as drug delivery carrier in alginate dressing.Mater Lett,2017,201:46-49
11 Zaidi S A.Molecular imprinted polymers as drug delivery vehicles.Drug Deliv,2014,23:2262-2271
12 Panagiotopoulou M,Salinas Y,Beyazit S,et al.Molecularly imprinted polymer coated quantum dots for multiplexed cell targeting and imaging.Angew Chem Int Ed,2016,55:8244-8248
13 Hoshino Y,Koide H,Urakami T,et al.Recognition,neutralization,and clearance of target peptides in the bloodstream of living mice by molecularly imprinted polymer nanoparticles:A plastic antibody.J Am Chem Soc,2010,132:6644-6645
14 Cecchini A,Raffa V,Canfarotta F,et al.In vivo recognition of human vascular endothelial growth factor by molecularly imprinted polymers.Nano Lett.2017,17:2307-2312
15 Hashemi-Moghaddam H,Rahimian M,Niromand B.Molecularly imprinted polymers for solid-phase extraction of sarcosine as prostate cancer biomarker from human urine.Bull Korean Chem Soc,2013,34:2330-2334
16 Gao D,Zhang Z,Wu M,et al.A surface functional monomer-directing strategy for highly dense imprinting of TNT at surface of silica nanoparticles.J Am Chem Soc,2007,129:7859-7866
17 Lu C H,Zhang Y,Tang S F,et al.Sensing HIV related protein using epitope imprinted hydrophilic polymer coated quartz crystal microbalance.Biosens Bioelectron,2012,31:439-444
18 Shen X,Ye L.Molecular imprinting in Pickering emulsions:A new insight into molecular recognition in water.Chem Commun,2011,47:10359-10361
19 Shen X,Zhou T,Ye L.Molecular imprinting of protein in Pickering emulsion.Chem Commun,2012,48:8198-8200
20 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
21 Li D,Chen Y,Liu Z.Boronate affinity materials for separation and molecular recognition:Structure,properties and applications.Chem Soc Rev,2015,44:8097-8123
22 Liu Z,He H.Synthesis and applications of boronate affinity materials:From class selectivity to biomimetic specificity.Acc Chem Res,2017,50:2185-2193
23 Wang S,Ye J,Bie Z,et al.Affinity-tunable specific recognition of glycoproteins via boronate affinity-based controllable oriented surface imprinting.Chem Sci,2014,5:1135-1140
24 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
25 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,2014,86:959-966
26 Yin D,Wang S,He Y,et al.Surface-enhanced Raman scattering imaging of cancer cells and tissues via sialic acid-imprinted nanotags.Chem Commun,2015,51:17696-17699
27 Wang S,Yin D,Wang W,et al.Targeting and imaging of cancer cells via monosaccharide-imprinted fluorescent nanoparticles.Sci Rep,2016,6:22757
28 Wang S,Wen Y,Wang Y,et al.Pattern recognition of cells via multiplexed imaging with monosaccharide-imprinted quantum dots.Anal Chem,2017,89:5646-5652
29 Yin D,Li X,Ma Y,et al.Targeted cancer imaging and photothermal therapy via monosaccharide-imprinted gold nanorods.Chem Commun,2017,53:6716-6719
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 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
32 Shinde S,El-Schich Z,Malakpour A,et al.Sialic acid-imprinted fluorescent core-shell particles for selective labeling of cell surface glycans.J Am Chem Soc,2015,137:13908-13912
33 Kunath S,Panagiotopoulou M,Maximilien J,et al.Cell and tissue imaging with molecularly imprinted polymers as plastic antibody mimics.Adv Healthcare Mater,2015,4:1322-1326
34 Ma R T,Ha W,Chen J,et al.Highly dispersed magnetic molecularly imprinted nanoparticles with well-defined thin film for the selective extraction of glycoprotein.J Mater Chem B,2016,4:2620-2627
35 Sun X Y,Ma R T,Chen J,et al.Synthesis of magnetic molecularly imprinted nanoparticles with multiple recognition sites for the simultaneous and selective capture of two glycoproteins.J Mater Chem B,2018,6:688-696
36 Wang C,Wang Q,Zhong M,et al.Boronic acid based imprinted electrochemical sensor for rutin recognition and detection.Analyst,2016,141:5792-5798
37 Tu X,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
38 Muhammad P,Tu X,Liu J,et al.Molecularly imprinted plasmonic substrates for specific and ultrasensitive immunoassay of trace glycoproteins in biological samples.ACS Appl Mater Interfaces,2017,9:12082-12091
39 Liu J,Yin D,Wang S,et al.Probing low-copy-number proteins in a single living cell.Angew Chem Int Ed,2016,55:13215-13218
40 Huang J,Wu Y,Cong J,et al.Selective and sensitive glycoprotein detection via a biomimetic electrochemical sensor based on surface molecular imprinting and boronate-modified reduced graphene oxide.Senss Actuators B-Chem,2018,259:1-9
41 Muhammad P,Liu J,Xing R,et al.Fast probing of glucose and fructose in plant tissues via plasmonic affinity sandwich assay with molecularlyimprinted extraction microprobes.Anal Chim Acta,2017,995:34-42
42 Bie Z,Xing R,He X,et al.Precision imprinting of glycopeptides for facile preparation of glycan-specific artificial antibodies.Anal Chem,2018,90:9845-9852