近年來，免疫磁性奈米粒子和生物晶片這類的生醫材料受到相當多的重視，並廣泛應用於生物分子交互作用的探討及生醫技術應用。然而目前所常用的免疫磁性奈米粒子大多不具有抗體位向性和共價性交聯，導致免疫磁性奈米粒子萃取活性較低。在本論文第二章節中，欲設計結合硼酸和光親和性分子的磁性奈米粒子，利用硼酸親和力及光化學束縛來製備同時具有位向性和共價鍵連結的Fc融合凝集素Siglec-2及抗血清澱粉樣蛋白A抗體(anti-SAA mAb)，同時也證明免疫磁性奈米粒子在血清中的穩定性，以及將其應用於萃取細胞膜醣蛋白。相較於傳統隨機固化法，位向專一性的蛋白質活性會比隨機固化的方式高出許多。
本論文第三和第四章節中，將探討無銅離子自身催化的疊氮化物-炔烴環加成反應（CuAAC）。CuAAC已成為化學連接或生物偶聯中一種強大的偶聯策略，然而，由於銅離子的毒性或銅催化劑的干擾，在生物共軛方面的應用受到限制。因此，我們探討了氧化亞銅奈米粒子(Cu2O NP)的表面螯合催化作用，發現Cu2O NP作為固相載體容納功能分子的同時也能兼具CuAAC的催化劑的作用。此無銅離子策略能將表面銅螯合的炔烴和各種疊氮基經由簡易的混合反應有效地結合在一起，其中包含了醣體小分子以及抗體大分子。我們也將此策略應用至細胞標記上，先透過修飾於Cu2O NP上的配體引導至細胞上，再以無銅離子自身催化作用將香豆素螢光基團標記於細胞。無銅離子自身催化策略提供了一種具有潛力的且生物相容的方法，可用於製造生醫診斷奈米材料，或是進一步用於生物學上研究，且無需使用任何金屬離子和無明顯毒性。
接著，我們將無銅離子自身催化的策略應用至微陣列晶片上。我們製備了一種銀銅塗層(Ag @ Cu2O)的玻璃晶片，將銀與銅奈米顆粒先後修飾在晶片上，並呈現出雙重功效，包括金屬增強螢光效應(MEF)和無銅離子點擊反應。透過簡易的化學還原方法將金屬沉積在玻璃片上，與矽氧玻璃片相比，其顯示出優異的螢光信號，可達30倍之多。此外，晶片上的銅奈米顆粒可以提供無銅離子非勻相CuAAC點擊反應，在生物感測晶片方面能夠提供更廣泛的應用。我們將Ag @ Cu2O玻片作為氟化物感測器，得到M等級的偵測靈敏度。此外，我們使用BA-tosyl策略位向性地固化PD-L1抗體，進一步應用到這種新開發的玻片中，並顯示出較好的靈敏度和低背景值。在此開發的Ag @ Cu2O晶片提供了一種用於生物學或診斷應用且生物相容的感測平台。

The utilization of immuno-magnetic nanoparticles (MNPs) for the selective capture, enrichment, and separation of specific glycoproteins from complicated biological samples is appealing for the discovery of disease biomarkers. In the second chapter, MNPs were designed and anchored with boronic acid (BA) and photoreactive diazirine (Diaz) groups to obtain permanently tethered Fc-fused Siglec-2 and antiserum amyloid A (SAA) mAb with the assistance of reversible boronate affinity and UV light activation in an orientation-controlled manner. The Siglec-2-Fc-functionalized MNPs showed excellent stability in fetal bovine serum (FBS) and excellent efficiency in the extraction of cell membrane glycoproteins. The anti-SAA mAb-functionalized MNPs maintained active Ab orientation and preserved antigen recognition capability in biological samples. Thus, the BA-Diaz-based strategy holds promise for the immobilization of glycoproteins, such as antibodies, with the original protein binding activity maintained, which can provide better enrichment for the sensitive detection of target proteins.
Copper-catalyzed azide-alkyne cycloaddition (CuAAC) is ubiquitous across the organic and biological sciences in chemical ligation or bioconjugation. However, applications toward bioconjugation were limited owing to the toxicity or undesired interruption from Cu-containing catalysts. In the third chapter, we highlighted our discovery of surface chelating catalytic effect by copper nanoparticles (Cu2O NP), which Cu2O NP played a role of solid support to accommodate functional molecules as well as a catalyst to achieve CuAAC subsequently. This self-catalyzed CuAAC strategy combines surface Cu-chelating alkynes with azido-glycans and azido-Ab simply and in good efficiency. Moreover, we incorporate sulfonamide and 3-O-Carbamoylmannose affinity ligands on Cu2O NP for targeting A549 and MCF-7 cell surface receptor of protein respectively. The intracellular click reactions were achieved and measured by reacting with azido-coumarin, which lighted-on upon alkyne-azide cycloaddition. These examples featured not only simple azido compounds and macromolecules such as an antibody, but also live cell targeting and imaging. We believe the new exploration presented herein will be a practical concept to build up methodologies for universal bioconjugation purposes and also with great potential for diverse metal surface catalyzes.
In the forth chapter, we fabricated an Ag@Cu2O slide with silver and Cu2O coated on microarray device and demonstrated its dual function including metal enhanced fluorescence (MEF) effect and self-catalyzed CuAAC click reaction. The metals were deposited on glass slides by optimized chemical reduction method which showed excellent fluorescent readout signal up to 30-fold better than on silicon slide. Besides, the Cu2O on the slide exhibited a copper ion-free heterogeneous CuAAC click reaction which showed a broader application toward biological sensing on chips. We demonstrated Ag@Cu2O slide as a fluoride sensor with better sensitivity, and an antibody microarray by using BA-tosyl strategies to immobilize antibodies in an oriented manner with lower background signal. The Ag@Cu2O microarray which we developed herein represents a practical and biocompatible sensing platform for biological or diagnostic applications.

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