合成及鑑定含羧酸螢光劑及具螢光劑中孔分子篩

Synthesis and characterization of carboxylic fluorescence dyes and mesoporous silica materials with dye

曾善美(Shan-Mei Tseng)

指導教授 ： 鄭吉豐

中原大學/理學院/奈米科技碩士學位學程/碩士(2013年)

https://doi.org/10.6840/cycu201301099

摘要

本論文以合成及鑑定含羧酸基螢光劑作為研究之對象，進行研究。用來標定細胞的螢光劑多選用於市售的5(6)-羧基螢光黃(5(6)-Carboxyfluorescein,簡稱FAM)與含-NCS官能基的FITC，但兩者都非常昂貴，因此本研究利用Friedel-Crafts reaction可以成功的合成出含羧酸基螢光劑，且價格低廉。第一種是F，這是一般常見用於生物標定之染料，它會發出特定之綠色螢光。第二種染料為B會發橘黃色螢光。第三種123會發出黃綠色螢光。第四種G會發黃色螢光。
另外以生物細胞之標定為研究目標，選用含螢光染料之奈米孔洞材料作為研究之對象，進行研究。相較於一般合成含染料之奈米孔洞材料，以染料作為起始物進行改質、修飾。將改質後染料鍵結於修飾過後之奈米孔洞材料上。本論文將採用不同方式合成含染料之奈米孔洞材料，利用Friedel-Crafts反應於奈米孔洞材料表面上固相合成及鍵結所需之染料。本論文使用以具有高度生物相容性之二氧化矽奈米孔洞材料作為基材，一為奈米尺寸孔洞材料MSN(Mesoporous Silica Nanoparticle)，孔洞及顆粒大小約為2.6 nm及70 nm;另一為SBA-15奈米中孔洞分子篩，孔洞及顆粒大小約為10 nm及400 nm。利用其高表面積與孔洞性質，使染料之鍵結提高，孔洞性也能使染料對外界環境更加敏感。將以合成具有螢光性質之奈米孔洞材料。此合成方法不但稀有，不需使用含特殊官能基之昂貴染料，合成所需之染料。在生物細胞標定之應用上也具實際效果。選用生物標定螢光物質是Rh123，這是一般常見用於生物標定之染料，它會發出特定之黃綠色螢光。

關鍵字

螢光 ； 染料 ； 中孔洞

並列摘要

Abstract
Commercially available 5(6)-Carboxyfluorescein with NCS-functional groups is very expensive and has a fixed green fluorescence. Therefore, four inexpensive fluorescent agents containing additional carboxylic acid groups were prepared via Friedel-Crafts reaction. The first dye is F, which emits green fluorescence and commonly used in biological labeling. B is the second dye and emits the orange fluorescence. The third 123 emits yellow-green fluorescence and last G emits yellow fluorescence.
Nano-sized nanoporous materials tethering carboxylic indicators were prepared via direct-synthesis and co-condensation. Indicators with carboxylic group were synthesized on nanoporous materials via Friedel-Crafts reaction. These nanoporous materials with indicators can be used for trace of biological cells.Two kinds of nanosized nanoporous material were synthesized. One was MSN (mesoporous silica nanoparticle) with porosity of 2.6 nm and particle size of 70 nm. Another was SBA-15NPs (SBA-15 nanoparticles) having 10 nm porous and 400 nm particle size. Indicators on MSN and SBA-15NPs were bonded after synthesis.
Rh123 was bonded on the surface of nanoporous nanoparticles via in-situ Friedel-Crafts reaction and emits strong yellow-green fluorescence. The characteristic fluorescence intensity variation with various pH values in solution was monitored by photography and fluorescence spectroscopy. MSNs with indicators were effectively endocytosed into cells as cell markers.
Synthesized nanoporous materials with indicators via Friedel-Crafts reaction are inexpensive, simple and rare as compared to commercially available dyes. Synthesis of different indicators can be achieved by simply adding different reactants. In addition, Silica as the component of the synthesized nanomaterial has high biocompatibility and stability. Thus, mesoporous nanoparticles with indicators can be applied not only as a cell maker but also a medicine carrier.

並列關鍵字

Mesoporous silica ； fluorescent ； dye

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