In situ gelation using amine-containing copolymer and dialkyne crosslinker via amino-yne click chemistry

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姓名

阮高玟(Nguyen Cao Tuong Vi) 查詢紙本館藏

畢業系所

生醫科學與工程學系

論文名稱

(In situ gelation using amine-containing copolymer and dialkyne crosslinker via amino-yne click chemistry)

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摘要(中)

隨著生物醫學應用的增長，可注射水凝膠是最有趣的領域之一，不僅在組織工程中，而且在藥物遞送應用中也引起了越來越多的關注。此外，交聯劑在水凝膠的形成、性能和應用中也發揮著重要作用。與化學交聯水凝膠相比，物理交聯水凝膠的機械性能較低，短期內穩定性較差。然而，一些化學交聯水凝膠具有苛刻的反應條件、潛在的毒性以及對環境條件（例如溫度、pH 值和離子強度）的難以響應，這限制了它們在某些領域的應用。在本研究中，合成了由 2-甲基丙烯酰氧基乙基磷酰膽鹼 (MPC) 和 2-甲基丙烯酸氨基乙酯鹽酸鹽 (AE) 組成的兩性離子共聚物，用於在聚乙二醇二丙酸酯 (DA-PEG) 的存在下製備可注射水凝膠，這是一種化學交聯劑。交聯劑 DA-PEG 交聯劑是一種同型雙功能 PEG，它包含兩個具有高反應性的炔烴官能團。交聯劑的活化炔基將通過氨基-炔點擊反應與共聚物 p(MPC-AE)xy 的氨基動態連接。 p(MPC-AE)xy 的凝膠時間、機械性能、平衡溶脹和降解性研究了p(MPC-AE)xy_DA-PEG水凝膠。該水凝膠在2小時內形成水凝膠並顯示出高溶脹率、自癒合和活力特性。此外，烯胺鍵的形成在誘導 pH 響應水凝膠中起著重要作用。在酸性條件下，烯胺和亞胺鍵之間的可逆機制誘導了 p(MPC-AE)xy_DA-PEG 水凝膠的溶膠-凝膠轉變行為。基於上述優點，p(MPC-AE)xy_DA-PEG 水凝膠是一種潛在的材料，可用於生物醫學領域，例如組織工程和治療劑遞送.

摘要(英)

With the growth of biomedical applications, in situ forming hydrogel is one of the most interesting fields that has attracted increasing attention not only in tissue engineering but also in drug delivery applications. In addition, cross-linkers also play an important role in the formation, properties, and applications of hydrogels. In comparison to chemically cross-linked hydrogels, physically cross-linked hydrogels provide lower mechanical properties and are less stable in the short term. However, some chemical cross-linking hydrogels have harsh reaction conditions, potential toxicity, and difficult responses to environmental conditions (e.g., temperature, pH, and ionic strength), which limit their application in some fields. In this research, zwitterionic copolymers consisting of 2-methacryloyloxyethyl phosphorylcholine (MPC) and 2-aminoethyl methacrylate hydrochloride (AE) were synthesized for preparing injectable hydrogels with the presence of dipropiolate ester of polyethylene glycol (DA-PEG), which is a chemical cross-linker. The DA-PEG crosslinker is a homobifunctional PEG that contains two alkyne functional groups that have high reactivity properties. The activated alkyne groups of the crosslinker will be dynamically linked with amino groups of the copolymer p(MPC-AE)xy via the amino-yne click reaction.The gelation time, mechanical properties, equilibrium swelling, and degradability of p(MPC-AE)xy_DA-PEG hydrogel were investigated.The hydrogel formed a hydrogel within 2 hours and showed a high swelling ratio, self-healing, and viability properties. In addition, the formation of enamine bonds plays an important role in inducing the pH response hydrogel. In acid conditions, a reversible mechanism between enamine and imine bonds induced the sol-gel transition behavior of the p(MPC-AE)xy_DA-PEG hydrogel.Based on the foregoing benefits, the p(MPC-AE)xy_DA-PEG hydrogel is a potential material for use in biomedical fields such as tissue engineering and therapeutic agent delivery.

關鍵字(中)

★ 炔烴
★ 2-甲基丙烯酰氧乙基磷酰膽鹼
★ 2-甲基丙烯酸氨基乙酯鹽酸鹽
★ 點擊聚合
★ 水凝膠
★ 交聯劑

關鍵字(英)

★ alkynes
★ 2-methacryloyloxyethyl phosphorylcholine
★ 2-aminoethyl methacrylate hydrochloride
★ click polymerization
★ hydrogel
★ crosslinker

論文目次

CHINESE ABSTRACT i
ABSTRACT ii
LIST OF FIGURE vi
LIST OF TABLES ix
LIST OF ABBREVIATIONS x
Chapter I: INTRODUCTION 1
1.1 Hydrogel background 1
1.2 Formation mechanism of hydrogels 3
1.2.1. Physical crosslinker 3
1.2.2. Chemical crosslinker 5
1.3. Self-healing hydrogel 6
1.4 Click polymerization 7
1.4.1 Amino-yne click polymerization 9
1.4.2 Spontaneous amino-yne click polymerization 10
1.5. Biocompatibility material 11
1.5.1 Zwitterionic monomer 11
1.5.2. Phosphorylcholine (PC) material 12
1.5.3 Poly(ethylene glycol) 13
1.6 Tissue engineering application of hydrogel 14
1.6.1 Hydrogel Design Considerations For Cell Encapsulation 15
1.6.2 Encapsulated hydrogel degradability 16
1.7. Injectable hydrogel 16
CHAPTER II: RESEARCH OBJECTIVES 18
CHAPTER III: MATERIALS AND METHODS 19
3.1 Materials 19
3.2 Synthesis dialkyne poly ethylene glycol crosslinker 19
3.3. Synthesis (2-Methacryloyloxyethyl phosphorylcholine)-co-(2-aminoethyl methacrylate hydrochloride) polymer 19
3.4. In Situ Hydrogel Formation 20
3.5 Compressive mechanical test 22
3.6 Swelling capacity 22
3.7 Degradation test 22
3.8 Self-healing test 23
3.9 Cytotoxicity tests 23
3.10 Cell encapsulation 23
IV. RESULT 25
4.1 Synthesis dialkyne poly ethylene glycol crosslinker 25
4.2. Synthesis (2-Methacryloyloxyethyl phosphorylcholine)-co-(2-aminoethyl methacrylate hydrochloride) polymer 27
4.3 In Situ Hydrogel Formation and Gelation time 30
4.4 Gelation time 31
4.5 Compressive mechanical test 33
4.6 Swelling capacity 37
4.7 Degradation of hydrogel 38
4.8 Self-healing test 40
4.9 Cytotoxicity tests 42
4.10 Enapsulation hydrogel 43
CHAPTER 5: CONCLUSION 48
CHAPTER 6: FUTURE WORK 49
REFERRENCE 50

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指導教授

黃俊仁李宇翔(Chun-Jen Huang Yu-Hsiang Lee)

審核日期

2022-1-19

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