磺基甜菜鹼基自組裝單分子層的形成、穩定性和抗污染性的比較研究

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薩明(Mohamed Amin Salah Abbas Sayed Ahmed) 查詢紙本館藏

畢業系所

生醫科學與工程學系

論文名稱

磺基甜菜鹼基自組裝單分子層的形成、穩定性和抗污染性的比較研究
(Comparative study in formation,stability and fouling resistance of sulfobetaine-based self-assembled monolayers)

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摘要(中)

非特異性蛋白質吸附是生物醫學應用中最重要的問題，例如植入式
醫療器械。此外，自組裝單層的降解受到廣泛關注，因為它被認為
是決定這些系統適用性的關鍵因素。研究中，發現很多對不同血液
成分具有高抗污性的穩定塗層材料，並且提出不同策略作為增強自
組裝單層的穩定性的解決方案。在這項工作中，我們合成了三種磺
基甜菜鹼基單體; （單硫醇）3 - [（11-巰基-十一烷基）-N，N-二
甲基 - 氨基] - 丙烷-1-磺酸“SB-硫醇”，（二硫化物）硫辛酸 -
磺基乙烷“SBSS”和（二硫醇）二氫脂質酸 - 磺基甜菜鹼“SB-二
硫醇”，並比較了它們的自組裝單層的構成，穩定性和抗吸附性。
將SBSS 還原成SB-二硫醇導致更高的覆蓋率，對不同蛋白質的抗吸
附性，更高的阻斷電子轉移能力和對解吸電壓掃描的有效穩定性，
如表面等離子體共振（SPR）形成測試所示，並進行蛋白質抗吸附性
試驗和電化學分析。儘管SB-二硫醇在潤濕性方面表現出與SB-硫醇
相似的能力，並且對不同蛋白質具有抗吸附性，但前者在”接觸角
分析”，”厚度分析”，”表面等離子體共振分析”和”電化學分
析”中所有的穩定性測試顯示出更好的特性。這項研究將使我們對
類似兩性離子自組裝單層與金和鄰近部分的相互作用有所了解，並
有望為未來的許多應用奠定基礎。

摘要(英)

Non-specific protein adsorption is the most important problem in
biomedical applications, such as implantable medical devices.1 In addition,
the degradation of self-assembled monolayers has received a broad
attention as it is regarded a key factor that determines the applicability of
these systems into many applications. Many studies have been introduced
to give stable coating materials with high fouling resistance against
different blood components and different strategies have been proposed as
a solution to enhance the stability of the self-assembled monolayers.2 In
this work, we synthezied three sulfobetaine-based monomers; (monothiol)
3-[(11-mercapto-undecyl)-N,N-dimethyl-amino]-propane-1-sulfonic acid
“SB-thiol“, (disulfide) lipoic acid-sulfobetiane “SBSS“ and (dithiol)
dihydrolipoic acid-sulfobetaine “SB-dithiol“, and compared the formation,
stability and fouling resistance of their self-assembled monolayers. The
reduction of SBSS into SB-dithiol3 resulted in a higher coverage, a better
fouling resistance against different proteins, a higher capability to block
electron transfer and an effective stability against desorption voltage sweep
as was shown by the Surface Plasmon Resonance (SPR) formation test,
protein fouling resistance test and the electrochemical analysis
respectively. Although SB-dithiol exhibited a similar behavior to SB-thiol
in the wetting properties and the fouling resistance against different
proteins, the former showed a privilege in all the stability tests “contact
angle analysis”, “thickness analysis”, “Surface Plasmon Resonance
analysis” and electrochemical analysis. This study will develop our
understanding of the interactions of analogues zwitterionic SAMs with
gold and adjacent moities, and it is expected to put the basis for many future
applications.

關鍵字(中)

★ 磺酸甜菜鹼
★ 抗吸附性
★ 兩性離子自組裝單層

關鍵字(英)

★ Sulfobetaine
★ fouling resistance
★ zwitterionic self-assembled monolayers

論文目次

Abstract…………………...……………………………....….………... (II)
Table of contents……….……………………………….…..……....... (IV)
List of figures……………………………………………………….. (VIII)
List of Tables…………………………………………………………. (XI)
Chapter 1. Literature review………………......……………..…...….… (1)
1.1 Introduction …………………………….……………..…….…….. (1)
1.2 SAMs and Organic Surfaces …………….……………….….…….. (3)
1.2.1 SAMs of mercaptans on gold surfaces…………..……..… (4)
1.3 Preparation of SAMs ……………….………………...…….……… (6)
1.3.1 Why Is Gold the Standard ………...……..….…….……… (7)
1.3.2 The cleanliness of the Substrate ……….........……...……... (8)
1.3.3 Concentration of SAMs …....……….……….………...….. (9)
1.3.4 Temperature ………...……..….……………..…………..... (9)
1.4 Applications of SAMs on Thin Metal Films……..……...….…….. (10)
1.4.1 SAMs as Barriers to Electron Transport ……..…....… ….(11)
1.4.1.1 SAMs for Electrochemistry ………..……... ….(11)
1.4.2 SAMs for Biochemistry and Biology….…………....… … (12)
1.4.2.1 Designing SAMs to be Model Biological
Surfaces………..…………………….......... ….(13)
1.5 Protein-resistant surfaces…………………………...…….…........ (14)
V
1.5.1 Ethylene glycol………………………...……….........… (15)
1.5.2 Zwitterionic coating….……...………...……..............… (16)
1.6 Removing SAMs from surfaces……………………….…...…...... (18)
1.6.1 Electrochemical Desorption of SAMs………..………… (19)
1.6.2 Photooxidation of SAMs...……..……….…………….... (20)
Chapter 2. Research objectives …………………………………....…. (21)
Chapter 3. Materials and Methods ……………………….....…..….… (23)
3.1 Materials ………………………………………………..……..…. (23)
3.2 Methods ………………………………………………..……..….. (23)
3.2.1 Synthesis of SB-thiol ……………...…………...………... (23)
3.2.2 Synthesis of SBSS and SB-dithiol....…………....………. (25)
3.2.3 Thin film preparation……………....…………..………… (26)
3.2.4 Water contact angle measurement.....…………...………. (26)
3.2.5 SPR measurement………………......…………...………. (27)
3.2.6 Electrochemical Analysis………......…………..………... (28)
3.2.7 Ellipsometry measurement………...…………..……….... (28)
3.2.8 UV-aging Test………….…………..…………...…….…. (29)
3.2.9 SEIRA Spectroscopy………………...…………...…….... (29)
Chapter 4. Results……………... ………………...……………......… (30)
4.1 Characterization of SB-thiol, SBSS and SB-dithiol………........... (30)
4.1.1 Mass spectra measurements ….…...…………...………... (30)
4.1.2 Analysis of 1H NMR spectra……...…………...………...... (31)
VI
4.1.3 XPS Surface Elemental Analysis …...…………...…….........(34)
4.1.4 Wettabilities of the Films …………...…………...….…….. (36)
4.1.5 Thicknesses of the Films …………...…………...……….... (37)
4.1.6 Surface Enhanced Infra-Red Analysis (SEIRA) .…..……... (37)
4.1.7 Protein Fouling Resistance ……………...….....………....... (39)
4.2 The SPR Formation Test…………..……………………......……. (40)
4.3 The Stability Tests ………………………………………..……. ..(41)
4.3.1 UV-Oxidation “Contact angle Analysis”………...…..…….. (41)
4.3.2 UV-Oxidation “Thickness Analysis”….………...……….... (42)
4.3.3 UV-Oxidation “SPR Analysis”…………………...………... (43)
4.3.4 Electrochemical Analysis….………...…………...……….... (44)
Chapter 5. Discussion …………….………………………………….. (46)
5.1 Characterization of SB-thiol, SBSS and SB-dithiol………....... ….(46)
5.1.1 XPS Surface Elemental Analysis …...…………...……….... (46)
5.1.2 Wettabilities of the Films …………...…………...……….... (46)
5.1.3 Thicknesses of the Films …………...…………...………...... (47)
5.1.4 Surface Enhanced Infra-Red Analysis (SEIRA) .….…..….. .(47)
5.1.5 Protein Fouling Resistance ……………...….....………….... (48)
5.2 The SPR Formation Test…………..……………………......……. (48)
5.3 The Stability Tests ………………………………………..……… (49)
5.3.1 UV-Oxidation tests…………………..………...……….... ….(49)
5.3.2 Electrochemical Analysis….………...…………...……….... .(50)
Chapter 6. Conclusions ……………………………………………… (52)
Chapter 7. Future Work ……………………………………………… (53)
Bibliography ………………………...………………………………. (54)

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指導教授

黃俊仁(Chun-Jen Huang)

審核日期

2019-1-22

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