以Michael加成化學接枝雙離子材料於聚多巴胺表面之研究

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劉家榆(Chia-yu Liu) 查詢紙本館藏

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生物醫學工程研究所

論文名稱

以Michael加成化學接枝雙離子材料於聚多巴胺表面之研究
(Development of Zwitterionic Biointerfaces on Polydopamine via Michael Addition Chemistry)

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摘要(中)

超親水雙離子材料具有和聚乙二醇(polyethylene glycol, PEG)相同的抗生物汙染(anti-biofouling)特性，因此被應用於生醫材料的表面修飾。在這研究中，我們提出一種建構抗非特異性吸附表面的新方法，以Michael addition方式，將雙離子材料接枝於聚多巴胺表面，使其具有1. 超親水性；2. 抵抗生物吸附；3. 可用於多樣基材表面修飾；4. 製備簡單與5. 多功能性。多巴胺因同時具有鄰苯二酚和胺基被證實能黏附於各種基材表面，形成聚多巴胺層，此化學結構中，俱有一級胺與二級胺官能基，可與甲基丙烯酸磺基甜菜鹼(Sulfobetaine methacrylate, SBMA)和丙烯醯胺磺基甜菜鹼(Sulfobetaine acrylamide, SBAA)雙離子單體藉由Michael addition接枝於表面，達到良好的抗生物汙染特性。
因此這項研究要先形成帶有大量的活性胺基官能基的聚多巴胺表面，並且藉由Michael addition反應使胺基和帶有乙烯基單體進行1，4加成，而將單體接枝於聚多巴胺表面，並應用於各種基板修飾。這裡我們比較三種抗吸附單體分別為SBAA、SBMA和聚乙二醇單甲醚甲基丙烯酸酯(poly(ethylene glycol) methacrylate, PEGMA)，並接枝於聚多巴胺表面使其達抗生物汙染之特性。利用水接觸角和X射線光電子能譜了解單體接枝於聚多巴胺的親水性質、表面元素組態和鍵結機制。並藉由綠膿桿菌、大腸桿菌和表皮葡萄球菌細菌貼附，比較不同密度的丙烯醯胺基和甲基丙烯酸接枝於聚多巴胺和具有不同抗生物汙染程度。其中，在XPS結果，於pDA18的塗層上接枝，其效果比於pDA3有更好的單體接枝率。在pDA18 SBAA修飾條件下，表面水接觸角可小於5度；細菌貼附實驗結果，可分別抵抗93%、94.2%和98%的綠膿桿菌、大腸桿菌和表皮葡萄球菌的貼附。最後，利用聚多胺還原銀奈米粒子特性結合抗生物汙染塗層，發展出同時具有銀奈米粒子殺菌功效和SBAA抗細菌貼附的複合式塗層，此表面可抵抗90%大腸桿菌貼附，而貼附於表面的細菌98%為死菌。本研究的最終目的是發展了一種新的修飾方法，可於各種機材表面進行改質而達到抗生物汙染的功能，並且開發多功能生物界面，並期待應用於醫療器材表面塗層，以提升其生物相容性與使用安全性。

摘要(英)

Superhydrophilic zwitterionic materials are recognized as a new class of antifouling materials as an alternative to poly(ethylene glycol) (PEG) for uses of biomedical device in complex conditions. In this study, we aim to develop establish a new grafting method based on polydopamine via Michael addition approach to avoid nonspecific adsorption. The developed coatings exhibit multiple functions, including 1. superhydrophilicity, 2. antifouling properties, 3. substrate-independent modification, 4. facile preparation, and 5. versatility. Dopamine contains both amine and catechol functional groups, which enables to deposit on all kinds of substrates. Sulfobetaine acrylamide (SBAA), Sulfobetaine methacrylate (SBMA) are zwitterionic monomer, which have been demonstrated with their excellent antifouling properties in a polymer brush form. Therefore, the purpose of this work is to graft SB moieties onto polydopamine (pDA) coatings containing abundant amine groups to react with vinyl groups of monomers via the Michael addition to achieve substrate-independent surface modification. We employed three monomers, i.e. SBAA, SBMA, and poly(ethylene glycol) methacrylate (PEGMA) to react with pDA. To develop an antifouling coating, an appropriate preparation strategy is highly determinant for the sufficient grafting density of fouling-resistant groups, i.e. SB and PEG. Surface characterization techniques with the contact angle goniometer, and X-ray photoelectron spectroscopy (XPS) were utilized to explore the surface hydration, chemical states and bonding mechanism of the grafted pDA films. To examine the antifouling properties of the coatings, they were brought to contact with bacteria solutions containing P. aeruginosa, E. coli, and S. epidermidis followed by observing under fluorescence optical microscope. The results indicated that the fouling levels were determined by the grafting densities of monomers on pDA surfaces. In XPS result, pDA18 coating condition grafting densities of monomer is higher than pDA3 coating condition. In pDA18 SBAA coating condition, the contact angle is less than 5 degree. According to the bacterial anti-fouling results, pDA18 SBAA coating can resistance 93%, 94.2% and 98% of P. aeruginosa, E. coli, and S. epidermidis, respectively. This can be modulated by the reaction activities of methacrylate and acrylamide with amine groups on pDA. In addition, silver particles formed in the pDA layers were applied to kill 98% adsorbed bacteria, enabling multiple functions of adlayers. The work paves a new avenue to developing the new functional bioinspired antifouling interface in a substrate-independent fashion.

關鍵字(中)

★ 抗非特異性吸附
★ 聚多巴胺
★ 兩性離子
★ 聚乙二醇
★ Michael 加成化學

關鍵字(英)

★ anti-biofouling
★ polydopamine
★ zwitterionic
★ poly(ethylene glycol)
★ Michael addition

論文目次

中文摘要 iv
Abstract vi
致謝 viii
圖目錄 xii
表目錄 xv
簡寫對照表 xvi
第一章文獻回顧 1
1-1 醫療植入物之生物汙染 1
1-1-1 異物反應(Foreign Body Response) 1
1-1-2 微生物貼附 2
1-2 抗生物汙染之生物塗層 3
1-2-1聚乙二醇材料 3
1-2-2雙離子材料 5
1-2-2-1 PC類雙離子性分子 7
1-2-2-2 SB類雙離子性分子 8
1-2-2-3 CB類雙離子性分子 10
1-3 表面改質技術 11
1-3-1 原子轉移自由基聚合法 11
1-3-2 自組裝膜之介紹 12
1-4 鄰苯二酚衍生物應用於表面修飾 15
1-4-1貽貝蛋白 15
1-4-2多巴胺分子 15
1-4-3聚多巴胺的形成機制 16
1-5 聚多巴胺表面功能化接枝與應用 19
1-5-1表面接枝胺基、硫醇分子 19
1-5-2表面還原金屬奈米粒子 21
1-6 Michael加成機制 22
第二章研究目的 23
第三章實驗藥品、設備及實驗方法 24
3-1實驗藥品 24
3-2實驗設備 25
3-3實驗方法 25
3-3-1功能性聚多巴胺 (pDA)自組裝膜的製備 26
3-3-2聚甲基丙烯酸乙二醇酯 ( PEGMA )、甲基丙烯酸磺基甜菜鹼(SBMA)、丙烯醯胺磺基甜菜鹼 ( SBAA )接枝方法 26
3-3-3銀奈米粒子表面還原 26
3-3-4銀奈米粒子加丙烯醯胺磺基甜菜鹼 (SBAA)接枝方法 27
3-3-5接觸角測量 27
3-3-6高解析電子能譜儀 (XPS)分析 27
3-3-7 橢圓儀偏振儀後度測量 28
3-3-8細菌貼附測試 28
3-3-9細胞毒性測試 (MTT) 29
第四章實驗結果 30
4-1 pDA接枝PEGMA、 SBMA、 SBAA於二氧化鈦基板 30
4-1-1薄膜的接觸角測量 30
4-1-2 XPS元素組成和薄膜的化學狀態 31
4-1-3 MTT 細胞毒性試驗 35
4-1-4薄膜的抗細菌吸附測試 36
4-2 pDA接枝SBAA於各種基板 39
4-2-1薄膜的接觸角測量 39
4-2-2薄膜的抗細菌貼附測試 40
4-3 pDA還原銀奈米粒子並接枝SBAA 42
4-3-1薄膜的可見光紫外光分光光譜儀量測 42
4-3-2薄膜的抗細菌貼附測試 43
第五章討論 45
5-1 比較聚多巴胺 (pDA)接枝PEGMA、SBMA、SBAA於二氧化鈦基板之差異 45
5-1-1 表面性質-水接觸角 45
5-1-2 表面性質-XPS元素組成和薄膜的化學狀態 46
5-1-3 抗細菌貼附性質 48
5-2 無表面選擇聚多巴胺(pDA)抗沾黏修飾 49
5-3 複合式功能聚多巴胺生物界面 50
第六章結論 51
第七章未來展望 52
第八章參考文獻 52

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指導教授

黃俊仁(Chun-jen Huang)

審核日期

2016-1-28

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