硼酸表面微陣列系統的發展及應用｜國立清華大學博碩士論文庫

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研究生：	陳穆麟 Chen, Mu-Lin
論文名稱：	硼酸表面微陣列系統的發展及應用 Development of Boronic Acid Surface Based Microarray System and Its Applications
指導教授：	林俊成 Lin, Chun-Cheng
口試委員:
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2009
畢業學年度：	97
語文別：	英文
論文頁數：	219
中文關鍵詞：	微陣列、硼酸、具方向性醣蛋白微陣列、醣微陣列、醣金奈米粒子、訊號放大系統
外文關鍵詞：	microarray, boronic acid, oriented glycoprotein array, carbohydrate array, glyco-gold nanoparticle, signal amplification system
相關次數：	點閱：1 下載：0
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近年來，微陣列技術已經被發展成為一種高通量的檢測工具，並且已經廣泛的運用於生物分子交互作用的探討以及生醫技術應用，藉以解決基因質體學、蛋白質體學、以及醣質體學上之問題。除此之外，具有專一性的結合配對更可以以微陣列的模式來進行醫學檢測、環境監控、以及毒性物質偵測等等。為了要建立各種不同的生物分子的微陣列系統，已經有各種不同用於固定的微陣列表面官能基被廣泛的研究，然而目前為止沒有任何一樣表面官能基可以適用於全部的生物分子。因此一個容易建立且容易固定生物分子探針的新式表面工具，其可減少生物探針的處理以及可提供共價鍵固定仍然是必要的目標。
苯基硼酸以及其衍生物已知在水溶液下會與含順式二醇形成可逆環狀酯，而多氫氧基化合物例如甘油及醣體因具有許多如此的結構，因此硼酸長久以來已經被使用來達成醣類追蹤的工具並應用於醣類感測器、多醣體偵測、以及醣胜肽與醣蛋白的濃富化與純化等等。然而就我們所知，目前硼酸並沒有應用於生物晶片的研究。有鑑於此，在此篇論文我們結合了硼酸的醣類追蹤特性及生物晶片的優點首創具有醣類追蹤能力的微陣列晶片表面，並應用於醣蛋白方向性共價鍵固定化來保持蛋白質活性，以及共價鍵固定之醣晶片系統來提升醣體在晶片表面上之保持能力。
為了探討蛋白質的固定化，硼酸被用來追蹤Fc融合凝集素以及抗體上座落於Fc domain的醣鏈，以達到方向性固定的目標。經由比較，我們證明具方向性固定的醣蛋白具有較高的結合訊號。而由硼酸共價鍵且方向性固定的醣蛋白其相較於蛋白質G (protein G)非共價鍵且方向性固定的醣蛋白具有較高的結合訊號。
為了建立簡單實用且具有共價固定能力的醣晶片表面，我們選用已商品化的化合物〝間-氨基苯基硼酸〞做為我們的包覆試劑，利用雙NHS活性酯長鏈與牛血清蛋白包覆的晶片進行連結，建立親水性硼酸晶片表面，再用以製造具有共價鍵固定的醣微陣列。經由共價鍵固定，我們證明醣類小分子可以被固定於晶片表面且只要具有0.5 kDa即具有與凝集素辨認的能力。除此之外，我們也成功的利用三層牛血清蛋白包覆表面來成功的減輕表面物理吸附的能力，使我們可以輕易的觀測到硼酸對醣體共價鍵固定所帶來的影響。我們證明了硼酸表面的共價鍵固定醣微陣列相較於沒有共價鍵固定的醣微陣列可以在強烈清洗下有較好的滯留能力。
另外，由於硼酸對於抗體具有方向性固定的能力，我們也建立了抗體微陣列來進行毒物偵測。我們選用一個低毒性的蓖麻毒素替代物〝RCA120〞做為我們的毒物樣板，並用半乳醣官能基化的金奈米粒子做追蹤，最後用銀染技術做放大以達到裸眼偵測的目標。在此我們為了增進靈敏度，我們更開發了金奈米粒子專一性聚集的訊號放大系統，將靈敏度提升至毒物濃度只需aM，且不需要光學儀器即可偵測。

In recent decades, microarray has now been emerged as a high throughput screening tool for expanding biomedical application, such as biomolecular interactions of genomics, proteomics, and more recently in glycomics. The well-known specific binding event can be further developed for clinical diagnostic, environmental monitor, and so on in microarray format. To fabricate various kinds of microarray, there are varieties of surface functional groups available for immobilization of bio-molecules. Even so, none of them could be suitable for immobilization of all kinds of bio-molecules so far. Therefore, a new surface tool, which can be easily constructed and provides a new strategy for probe immobilization that minimizes probe destruction and allows covalent bond formation, are urgently demanded.
It is well known that phenyl boronic acid (BA) and its derivatives can form cyclic boronate esters with vicinal cis-diols and polyols, such as glycerol and carbohydrates, even under aqueous conditions. Accordingly, BA has been employed for achieving glyco-targeting such as carbohydrate biosensors, polysaccharide detection, separation or enrichment of glycoprotein and glycopeptide, and so on. However, to our knowledge, it has not been attempted to use as chips. In this thesis, we take advantage of BA to fabricate oriented protein microarray and covalent polysaccharide microarray to improve accessibility of proteins and retention of polysaccharide on slide surface.
To improve the protein conjugation on solid support, BA was used to site-specifically assemble Fc-fused lectin and antibody from its Fc domain for maintaining the best activity on the solid surface. We demonstrated that the protein activity can be conserved when protein molecule is oriented in an optimal manner on the BA surface. In addition, m-aminophenylboronic acid was used to easily construct covalent microarray of oligosaccharide and polysaccharide of molecular weight at least 0.5 KDa. The triple BSA layers surface was successfully applied to generate hydrophilic BA surfaces to significantly alleviate nonspecific adsorption for elucidation of covalent effect upon the carbohydrate. We demonstrated that BA based oligosaccharide microarrays offer better retention of carbohydrates on supports over non-covalent attachment during more stringent washing conditions.
Furthermore, owing to its potential application in glycoprotein microarrays, we employed antibody microarray to detect RCA120, a low-toxic “ricin” surrogate, by using galactose-gold nanoparticle (g-AuNP) and in combination with silver enhancement by the naked eye. To enhance the detection sensitivity, we developed a method to generate and amplify the signal of a antibody microarray using AuNP-based agglutination to give a new ultrasensitive assay with detection sensitivity at the attomolar (aM) level that doesn’t required any optical instrument for readout.

Content...........................................................................................................................i
Acknowledgement.......................................................................................................vii
List of Figure.................................................................................................................ix
List of Scheme..............................................................................................................xv
List of Tables................................................................................................................xv
Abbreviations..............................................................................................................xvi
Abstract.......................................................................................................................xix
Chapter 1. Introduction of Microarray
1 General Introduction of Microarray Fabrication......................................................1
1.1 Introduction of Microarray................................................................................1
1.2 Principle of Microarray.....................................................................................1
1.3 Microarray Construction...................................................................................4
1.3.1 The Substrate of Microarray.......................................................................4
1.3.2 Glass Slide Cleaning, Coating and Activating...........................................5
1.3.2.1 Glass Slide Cleaning...........................................................................5
1.3.2.2 So-Gel Based Coating of Glass Slide..................................................8
1.3.2.3 Chemistry of Surface Modification...................................................11
1.3.2.4 Fabrication of Microarray..................................................................12
1.4 Detection Strategy: Signal Generation and Amplification..............................15
1.4.1 The Label Based Signal Generation.........................................................15
1.4.2 Signal Amplification................................................................................18
2 Immobilization Strategies of Carbohydrate Microarray.........................................22
2.1 Introduction of Carbohydrate Microarray.......................................................22
2.2 Immobilization Strategies................................................................................23
2.2.1 The Modified, Noncovalent, and Oriented Strategies..............................26
2.2.2 The Modified, Covalent, and Oriented Strategies....................................27
2.2.3 The One Step Modified, Covalent, and Oriented Strategies....................30
2.2.4 The Unmodified, Covalent, and Random Strategies................................30
2.2.5 The Unmodified, Covalent, and Oriented Strategies...............................31
2.2.6 The Unmodified, Noncovalent, ans Random Strategies..........................31
3 Immobilization Strategies of Protein Microarray...................................................35
3.1 Introduction of Protein Microarray..................................................................35
3.2 Strategies for Protein Immobilization.............................................................37
3.2.1 Physical Adsorption.....................................................................................39
3.2.2 The Bioaffinity Tag for Immobilization...................................................40
3.2.3 Immobilization by Photochemistry..........................................................42
3.2.3.1 Arylazide...........................................................................................44
3.2.3.2 Diazirines..........................................................................................45
3.2.3.3 Benzophenones..................................................................................45
3.2.3.4 Nitrobenzyl........................................................................................46
3.2.3.5 Heterobifunctional Photolinkers.......................................................46
3.2.3.6 Photolabeling for Bioaffinity Immobilization..................................47
3.2.4 Protein Side Chain Functional Groups Based Chemistry........................47
3.2.4.1 Immobilization via Amine................................................................48
3.2.4.1.1 Amide Bond Formation by Activated Ester...............................48
3.2.4.1.2 Imine -Based Chemistry for Conjugation..................................50
3.2.4.1.3 Thiourea Formation by Isothiocyanate......................................51
3.2.4.1.4 Amino-alcohol Formation by Epoxy Groups.............................51
3.2.4.2 Thiol Reactive Chemistry..................................................................52
3.2.4.2.1 Michael Addition by Maleimide................................................53
3.2.4.2.2 Disulfide Bond Formation by Pyridyl Disulfide........................53
3.2.4.2.3 Michael Addition by Vinyl Sulfone...........................................53
3.2.4.2.4 Thiol Reactive Labeling for Bioaffinity Immobilization...........54
3.2.4.3 Carboxyl Reactive Chemistry...........................................................56
3.2.4.3.1 Amide Bond Formation by Amine.............................................56
3.2.4.3.2 Carboxyl Reactive Labeling for Bioaffinity Immobilization….56
3.2.5 Site-specific Tag Fusion Protein by Recombinant Technology…………57
3.2.5.1 Oriented Bioaffinity Immobilization by Biologically Active Fusion Proteins.............................................................................................58
3.2.5.2 Oriented Covalent Immobilization by Biologically Active Fusion Proteins.............................................................................................59
3.2.5.3 Oriented Immobilization by Intein Tag Fusion.................................60
3.3 Antibody Immobilization Strategies...............................................................65
3.3.1 Targeting the Carbohydrate Moiety.........................................................66
3.3.2 Protein A/Protein G-Mediated Immobilization........................................67
4 Boronic Acid Based Immobilization through Carbohydrate Targeting.................68
4.1 Introduction of Boronic Acid..........................................................................68
4.2 Boronic Acid–Diol Complexation..................................................................72
4.3 Overview of BA Applications.........................................................................74
4.4 Boronic Acid Based Immobilization of Glycoprotein.....................................90
Chapter 2. Fabrication of an Oriented Fc-Fused Lectin Microarray through Boronate Formation
1 Introduction............................................................................................................93
2 Results and Discussion...........................................................................................96
2.1 Fc-fused Lectin Microarray by Random Schiff’s Base Formation for Probing Reishi Polysaccharide Interactions.................................................................96
2.2 Fabrication of Fc-fused Dectin-1 Microarray through Covalent and Site-specific Immobilization by Boronate formation....................................97
2.3 Immobilization of Fc-fused Dectin-1 on Glass Surface via Non-covalent and Site-specific Immobilization by Fc-receptor Modified Surface...................111
2.4 Comparison of Site-specific Immobilization and Random Schiff’s Base Formation....................................................................................................114
3 Conclusion............................................................................................................122
4 Materials and Methods.........................................................................................122
4.1 Fc-fused Lectins and Microarray Reagents...................................................122
4.2 Fc-fused Fluorescent Recombinant Protein Expression and Purification.....123
4.3 General Procedure for Microarray Fabrication.............................................123
4.4 Fabrication of BA Microarray for the Binding Test of Polysaccharide F3-biotin.......................................................................................................124
4.5 The Polysaccharide F3-biotin Microarray Fabricated through Boronate Formation.....................................................................................................125
4.6 Chemical Competition Assay for Selection of Capping Reagent for BA-based Slide..............................................................................................................125
4.7 Background Noise Suppression of Dextran..................................................125
4.8 Carbohydrate Competition Assay..................................................................126
4.9 BA–based Slides for Production of Fc-fused Lectin Microarrays................126
4.10 Comparison of protein A/G layer for Fc-Dectin-1 Microarray...................126
4.11 General Procedure Used for Fabrication of Protein G Layer to Achieve Site-specific Immobilization......................................................................126
4.12 Synthesis of APBA-TEG.............................................................................127
Chapter 3. Boronic Acid Based Oligosaccharide and Polysaccharide Microarray
1 Introduction..........................................................................................................129
2 Results and Discussion.........................................................................................132
2.1 Epoxy-BA Surface for Observation of Covalent Boronate Immobilization………………………………………………………….132
2.2 Triple BSA Coating for Hydrophilic Slide Surface………………………..133
2.3 BSA-BA Surface for Observation of Covalent Boronate Immobilization…135
2.4 BSA-BA Surface Based Oligosaccharide and Polysacchride Microarray.....139
3 Conclusion............................................................................................................142
4 Materials and Methods.........................................................................................143
4.1 Oligosaccharide, Polysaccharide and Microarray Reagents.........................143
4.2 Conditions for Validating the Effect of Covalent Boronate Immobilization on Bifunctional Boronate-Epoxy Slide.............................................................144
4.3 Characterization of BSA Based Aldehyde Slide Surface..............................145
4.4 Conditions for Validating the Effect of Covalent Boronate Immobilization on Hydrophilic BSA Layers Based BA Surface...............................................146
4.5 BSA-BA Based Oligosaccharide and Polysacchride Microarray..................146
Chapter 4. Microarray/Glyconanoparticle-Based Agglutination as an Ultrasensitive Label-Free Method to Detect Lectins
1 Introduction..........................................................................................................148
1.1 Background and Challenge...............................................................................148
1.2 X-Ray Crystal Structural Information of Ricin, and Low Toxic Ricin Surrogate “RCA120”............................................................................................................150
1.3 Present Work: Designing of New Microarray-based Naked Eye Detection Assay for RCA120........................................................................................................152
2 Results and Discussion.........................................................................................154
2.1 Synthesis of Galactose-encapsulated AuNPs and Agglutination Test...........154
2.1.1 Synthesis of Galactose-encapsulated AuNPs (g-AuNP)........................154
2.1.2 Colorimetric Detection of RCA120.........................................................155
2.1.3 Dynamic Light Scattering Studies……………………..........................157
2.2 Conventional Layer-by-Layer Sandwich Assay…........................................159
2.2.1 Detection of RCA120 by Random Immobilized Antibody Microarray...159
2.2.2 Detection of RCA120 by Site-specific Antibody Microarrays through Oriented Boronate Formation...............................................................160
2.3 Galactose-AuNPs/Microarray-Based Silver-enhanced Naked Eye Detection of RCA120............................................................................................................161
2.4 Generality of the Agglutination Method: A tetrameric Plant Lectin, ConA as a Target...........................................................................................................163
3 Conclusion............................................................................................................167
4 Materials and Methods.........................................................................................168
4.1 Reagents........................................................................................................168
4.2 Synthesis of Thiolated Mannose- and Galactose-Derivatives.......................169
4.3 Preparation of Glyco-AuNPs........................................................................170
4.4 Fabrication of Antibody Microarray.............................................................171
4.5 Silver Enhancement………………………………………………………...171
4.6 Immunoassay Principles................................................................................171
4.7 Glyco-AuNP Based Enrichment of RCA120 For Microarray Detection........172
4.8 In situ RCA120 Induced AuNPs Agglutination on Microarray For Detection of RCA120..........................................................................................................173
Chapter 5. Conclusion and Perspective…………………………………………..174
Reference....................................................................................................................178
Publications................................................................................................................206
Appendix....................................................................................................................207
Appendix I: Spectrum of BA Compound……………………………………...……207
Appendix II: TSA Fluorescence Systems…………………………………………..211

                                

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