指導教授：陳賢燁臺灣大學：化學工程學研究所蔡孟諭Tsai, Meng-YuMeng-YuTsai2014-11-252018-06-282014-11-252018-06-282013http://ntur.lib.ntu.edu.tw//handle/246246/261131The first maleimide-functionalized poly-p-xylylene is synthesized via chemical vapor deposition (CVD) polymerization from 4-N-maleimidomethyl-[2,2]paracyclophane on various substrates. Coated substrates are readily available to perform thiol–maleimide click reaction under mild conditions. Designed surfaces are highlighted in low-protein-fouling modification as well as manipulated attachments and growth of bovine arterial endothelial cells. The availability of the maleimide functionality is further exploited in combination with alkynyl moiety, and the direct synthesis to prepare the multicomponent coating containing the two functionalities is enabled via CVD copolymerization on various substrates. The novel coating is comprised of distinguished anchoring sites of electron-deficient alkynes and unsaturated maleimides and is readily to simultaneously proceed doubled “click” reactions. XPS and IRRAS characterizations have verified the chemical composition for the coatings. The demonstration of synergically doubled bioorthogonal reactions is performed via azide-alkyne click reaction and thiol-maleimide coupling reaction to immobilize fluorescently labeled azides and cystines, respectively, under mild conditions in water and without the need of a catalyst, and no trace of cross-reaction is found. Finally, the multicomponent surface is designed to exhibit distinct biological functions by first immobilizing polyethylene glycols that provide a low fouling state (bioinert) to suppress undesired background perturbance, while at the same time, addressing surface bioactive function is performed by tethering Cys-Arg-Glu-Asp-Val (CREDV) peptides on stent substrate and the adhesion of human umbilical vein endothelial cells (HUVECs) are precisely manipulated.致謝 I 摘要 II Abstract III 圖目錄 VI 表目錄 IX 第一章 緒論 1 1.1 前言 1 1.2 文獻回顧 4 1.3研究動機 15 第二章 馬來醯亞胺基聚對二甲苯之製備及其化學特性分析 18 2.1 藥品及基材之準備 18 2.2馬來醯亞胺基對二甲苯二聚體(4-N-maleimidomethyl-[2.2]paracyclophane)之製備及其特性分析 19 2.3化學氣相沉積聚合法製備馬來醯亞胺基聚對二甲苯poly[(4-N-maleimidomethyl-p-xylylene)-co-(p-xylylene)]鍍膜 24 2.4化學氣相沉積共聚合法製備同時具馬來醯亞胺基及炔基之poly[(4-N-maleimidomethyl-p-xylylene)-co-(4-methyl-propiolate-p-xylylene)-co-(p-xylylene)]共聚物 24 2.5鍍膜之化學特性分析 29 第三章 馬來醯亞胺基聚對二甲苯之表面改質及其應用 35 3.1生物耦合(bioconjugation)技術 35 3.1.1 poly[(4-N-maleimidomethyl-p-xylylene)-co-(p-xylylene)]鍍膜 35 3.1.2 poly[(4-N-maleimidomethyl-p-xylylene)-co-(4-methyl-propiolate-p-xylylene)-co-(p-xylylene)]共聚物 39 3.2蛋白質吸附測試(protein adsorption study) 41 3.2.1 纖維蛋白原(fibrinogen)吸附測試 41 3.2.2 石英晶體微量天秤(QCM)定量分析 43 3.3細胞培養測試(cell culture study) 50 3.3.1 poly[(4-N-maleimidomethyl-p-xylylene)-co-(p-xylylene)]鍍膜之細胞培養測試 50 3.3.2 poly[(4-N-maleimidomethyl-p-xylylene)-co-(4-methyl-propiolate-p-xylylene)-co-(p-xylylene)]共聚物之細胞培養測試 54 第四章 結論與未來展望 60 4.1 結論 60 4.2 未來展望 61 參考資料 65 附錄 682944254 bytesapplication/pdf論文使用權限：不同意授權化學氣相沉積馬來醯亞胺基多功能性鍍膜“點擊”反應生物界面thesishttp://ntur.lib.ntu.edu.tw/bitstream/246246/261131/1/ntu-102-R00524008-1.pdf