臺灣博碩士論文加值系統

奈米材料表面技術為奈米生物工程發展之重要核心。本論文先以量子點生醫技術的發展，介紹此新領域如何在近十年內，由科學技術創新發展成為極具產業利用價值的產品，包含量子點合成、水相改質及官能化及如何賦予生物相容性與生物功能性完整之回顧(第二章)，讓讀者藉由量子點技術演進為例了解奈米生物工程。目前量子點技術發展皆歸功於Alivisatos 和Nie兩位學者實驗室，於1998年所發展出之水相改質技術，此項表面化學技術的揭露，成功媒合物理、化學與生物醫學研究整合。故本論文提出適用於各種疏水奈米材料披覆之兩性高分子設計，作為奈米材料生醫應用之橋樑，文中主要描述以馬來酸酐高分子自動嫁接疏水碳鏈及生物分子(聚乙二醇、半乳糖、生物素等)之製備流程，成功應用於功能性奈米材料(量子點、奈米金、氧化鐵奈米粒子)之水相改質及官能化(第三章)。另外，由於量子點含有有毒重金屬(鎘、鉛)成分，在醫學應用上正受到限制，我們於第二章也回顧了目前綠色(環保)量子點的發展，通常指所使用的奈米材料具有環境安全性、生物相容性、無毒性重金屬及可調控的螢光，更重要的，它必須克服未來臨床應用及環境健康所帶來長期毒性問題。因此本論文亦發展新型螢光金奈米團簇以填補半導體量子點之不足，第四章將充分介紹此新型螢光金奈米團簇之合成、水相改質及生物接枝，並包含成功標定細胞之範例。總之，本博士論文主要提出奈米生醫探針設計之通用技術，提昇奈米材料生醫應用之價值，提供臨床生醫研究重要工具。

Surface modification on nanomaterials is the core technology to develop nanobioengineering. Firstly, the thesis reviews the current progress of nanobiotechnology using quantum dots as examples, including synthesis, phase transfer, surface modification, biocompatibility and in vivo application. The reader can get full images how quantum dots become commercial available products from laboratory. Alivisatos and Nie et al, two most famous pioneering groups, have introduced a powerful interface technology adapting physicist, chemist, and biomedical researcher using quantum dots from 1998. Based on these pioneering works, the thesis propose a general amphiphilic polymer design for coating different kinds of nanomaterials, bridging the biological application of nanomaterials. The poly(maleic anhydride) are found as excellent backbone polymer of which can link hydrophobic alkyl chain as well as (bio-)molecules (polyethylene glycol, galactose, biotin, fluorescein and etc.) through a spontaneous amidation. Hydrophobic nanomaterials not only become water-soluble but get surface functionality right after polymer coating. Secondly, the quantum dots containing toxic ions have restricted their broad application in biomedical research, especially in clinics. The development of “greener” quantum dots, compatible to environments and human body, might solve the current crisis of traditional quantum dots. The thesis also introduces novel fluorescent gold nanoclusters from synthesis, ligand exchange, bioconjugation and cell labeling, giving a overall strategy to use fluorescent gold nanoclusters. In a word, general nanoprobes designs have been fully unveiled in this thesis and are expected to bring many biomedical applications.

中文摘要……………………………………………………………………..I
Abstract……………………………………………………………………...II
致謝(Acknowledgment)…………………………………………………...III
Table of Contents…………………………………………………………...VI
Figure Index………………………………………………………………...V
Supporting Figure Index…………………………………………………..VI

Chapter 1 Scope of the Thesis………………………………………….1
Reference…………………………………………………………4
Chapter 2 Introduction of Nanobiotechnology: Quantum Dots as an Example................5
Introduction……………………………………………………...7
Quantum Dots: Synthesis and Surface Modification for their Use in Biomedical Research……………………………………...9
Quantum Dots as Cellular Probes………………………………19
Quantum Dots as Biosensors……………………………………26
Quantum Dots as in vivo Probes..................................................30
Synthesis of ‘Greener’ Quantum Dots (GQDs)…………………32
Concluding Remarks…………………………………………….36
References………………………………………………………..37
Chapter 3 Design of an Amphiphilic Polymer for Nanoparticle Coating and Functionalization...53
Introduction……………………………………………………...55
Results and Discussion………………………………………….56
Conclusion……………………………………………………….66
Experiments in Details………………………………………......67
Supporting Figures………………………………………………90
References………………………………………………………..103
Chapter 4 Synthesis, Characterization and Bio-conjugation of Fluorescent Gold Nanoclusters toward Biological Labeling Applications.....107
Introduction……………………………………………………...109
Results and Discussion……………………………………….....111
Conclusion……………………………………………………….120
Experiments in Details…………………………………………..121
Supporting Figures………………………………………………132
References………………………………………………………..149
Chapter 5 Conclusion & Perspective………………………………….155
Appendix List of Publication………………………………………….159


Figure index:
Figure 2-1 The optical properties of colloidal CdSe nanocrystals…………8
Figure 2-2 General strategy for hydrophilic modification of quantum dots ………………………………………………………………….17
Figure 2-3 Red and green fluorescent CdSe/ZnS Qdots with different surface coatings have been ingested by MDA-MB-453S cells…. 23
Figure 3-1 Scheme of the synthesis of the amphiphilic polymer and the coating of nanoparticles……………………………………………56
Figure 3-2 PEG molecules with amino-terminal (Mw = 5000 g/mol) were incorporated by amidation in the amphiphilic polymer so that 0%, 0.25%, 0.5% and 1% of the anhydride rings are reacted with the PEG………………………………………………………..59
Figure 3-3 Au particles with no (Au-0), exactly one (Au-1-bio), and exactly two (Au-2-bio) biotin-PEG molecules per particle were run with 1% agarose gel electrophoresis…………………………62
Figure 3-4 Au nanoparticles have been transferred to aqueous solution by embedding them in an amphiphilic polymer shell………….64
Figure 3-5 Au particles have been transferred to aqueous solution by an amphiphilic polymer coating in which 1% of the anhydride rings were use to link fluoresceinamine………………………….65
Figure 4-1 Prototype of water-soluble fluorescent Au nanoclusters (AuNC@DHLA).................................................................................111
Figure 4-2 General strategy to fabricate water-soluble fluorescent Au nanoclusters (AuNC@DHLA)..........................................................112
Figure 4-3 Absorption, PL, PLE of fluorescent Au nanoclusters…………...114
Figure 4-4 PEGylation and biotinylation of fluorescent Au nanoclusters (AuNC@DHLA) resolved in gel electrophoresis………………..116
Figure 4-5 Detection of endogenous-biotin within cell using the nanobioconjugates of which fluorescent Au nanoclusters conjugated with avidin (AuNC@DHLA-Avidin).........................119
Figure 4-6 The uptake of fluorescent Au nanoclusters (AuNC@DHLA) by human aortic endothelial cells…………………………………….120


Supporting Figure Index:
Figure S3-1 Conceptual scheme of polymer design…………………………..90
Figure S3-2 Polymer coating of Au nanoparticles…………………………….90
Figure S3-3 Scheme of polymer coating procedure…………………………...91
Figure S3-4 Discrete PEGylation of polymer-coated quantum dots (QD)….91
Figure S3-5 Discrete PEGylation test of polymer-coated iron oxide nanoparticles (FeNP)……………………………………………….92
Figure S3-6 Discrete PEGylation test of polymer-coated gold nanoparticles (AuNP)………………………………………………………………92
Figure S3-7 Discrete PEGylation test of fluorescein-polymer micelles……..93
Figure S3-8 Absorption and photoluminescence (PL) of fluorescein-polymer micelles……………………………………..93
Figure S3-9 Different mPEG5k-polymer coatings with gold nanoparticles..94
Figure S3-10 Agglutination effect of galactosylated gold nanoparticles……..94
Figure S3-11 Sugar effects on agglutinated gold nanoparticles (AuNP)……..95
Figure S3-12 4% biotinylated gold nanoparticles (AuNP)……………………..96
Figure S3-13 Absorption and photoluminescence (PL) of fluorescein-polymer gold nanoparticles…………………………96
Figure S3-14 Polymer-coated Au and CdSe/ZnS nanoparticles conjugated with PEG molecules of different molecular weight…………….97
Figure S3-15 Isolation of 1- or 2-biotin functionalized nanoparticles………...97
Figure S3-16 Assembly of 0-, 1- or 2-Biotin gold nanoparticles (Au-x-bio) with streptavidin…………………………………………………...98
Figure S3-17 Assembly of 0-, 1- or 2-biotin gold nanoparticles (Au-x-bio) with neutravidin and avidin………………………………………99
Figure S3-18 Assembly of 0-, 1- or 2-biotin gold nanoparticles (Au-x-bio) with streptavidin-FITC…………………………………………….100
Figure S3-19 Assembly of 0-, 1- or 2-biotin gold nanoparticles (Au-x-bio) with neutrAvidin-FITC…………………………………………….101
Figure S3-20 Assembly of 1-biotin nanoparticles with streptavidin………….102
Figure S4-1 Etching of Au nanoparticles that had been purified with methanol precipitation……………………………………………..132
Figure S4-2 Etching of Au nanoparticles that had not been purified with methanol precipitation……………………………………………..133
Figure S4-3 Fluorescent Au nanoclusters………………………………………134
Figure S4-4 TEM imaging of different synthetic stage of fluorescent Au nanoclusters…………………………………………………………135
Figure S4-5 Size exclusion chromatography (SEC) elution profiles of fluorescent Au nanoclusters (AuNC@DHLA) compared with PEG standards………………………………………………………136
Figure S4-6 Gel electrophoresis of fluorescent gold nanoclusters (AuNC@DHLA) and gold nanoparticles (AuNP@DHLA)..........137
Figure S4-7 Absorption spectrum of Au nanoparticles and nanoclusters in organic and aqueous phase………………………………………..138
Figure S4-8 Absorption, photoluminescence (PL) and photoluminescence excitation (PLE) of fluorescent Au nanoclusters (AuNC@DHLA).................................................................................139
Figure S4-9 Solid-state photoluminescence (PL) and photoluminescence excitation (PLE) of fluorescent Au nanoclusters (AuNC@DHLA).................................................................................140
Figure S4-10 Quantum yield of the fluorescent gold gold nanoclusters (AuNC@DHLA).................................................................................141
Figure S4-11 Photostability of fluorescent Au nanoclusters (AuNC@DHLA) compared to semiconductor quantum dots (polymer coated QD 520 from Invitrogen) and organic fluorophores (fluorescein, rhodamine 6G)………………………………………142
Figure S4-12 Illustration of the conjugation of fluorescent Au nanoclusters (AuNC@DHLA) with biomolecules………………………………143
Figure S4-13 Gel electrophoresis for probing of the bioconjugation of fluorescent Au nanoclusters (AuNC@DHLA)...............................144
Figure S4-14 Probing of the biotinylated fluorescent Au nanoclusters………145
Figure S4-15 Gel electrophoresis of fluorescent Au nanoclusters with covalently attached avidin………………………………………...146
Figure S4-16 Uptake of fluorescent Au nanoclusters by HAEC cells………...147
Figure S4-17 Labeling of endogenous biotin within a human hepatoma (HepG2) cell lines with fluorescent Au nanoclusters (FANCs) and controls…………………………………………………………148

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11.Lin CAJ, Liedl T, Sperling RA, Fernandez-Arguelles MT, Costa-Fernandez JM, Pereiro R, Sanz-Medel A, Chang WH, Parak WJ 2007 Bioanalytics and biolabeling with semiconductor nanoparticles (quantum dots). Journal of Materials Chemistry 17(14):1343-1346.
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13.Lin CAJ, Yang TY, Lee CH, Huang SH, Sperling RA, Zanella M, Wang HH, Shen JL, Yeh HI, Parak WGJ, Chang WH 2008 Synthesis, Characterization and Bio-conjugation of Fluorescent Gold Nanoclusters toward Biological Labeling Applications. to be submitted.


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Chapter 3:
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