含氟抗生素光誘發聚合類核黃素及導電高分子的反應與葡萄糖感測應用

洪嘉均

指導教授 ： 王忠茂

國立臺灣師範大學/理學院/化學系/碩士(2011年)

摘要

含氟抗生素Lomefloxacin（簡稱LFLX）在含氧環境中受到UV光照射時會進行脫氟反應，所衍生的碳烯可與氧氣反應，進一步生成高反應性含氧自由基（Reactive oxygen species，簡稱ROS）。有鑒於此，本論文利用黃血鹽、NADH、維生素C與Ru(bpy)32+探討其氧化力，發現其氧化力高達1.0 V。根據此一結果，我們藉以對類核黃素、苯胺及吡咯進行氧化聚合反應。原子力顯微鏡（Atomic force microscopy，簡稱AFM）分析結果顯示：這些具電化學活性單體可被LFLX氧化，而聚合固定於導電玻璃表面。因此，我們也以之製備類核黃素、苯胺及吡咯修飾電極，藉以對過氧化氫進行檢測。實驗結果顯示：聚苯胺修飾電極可降低過氧化氫過電壓。若在這些電極表面再修飾金屬微粒，如白金、銀與銅，發現聚苯胺-銀修飾電極對過氧化氫具有更高檢測能力，我們也藉以製備葡萄糖修飾電極，成功對葡萄糖進行定量分析。

關鍵字

Lomefloxacin ； 高反應性含氧自由基 ； 類核黃素 ； 苯胺 ； 吡咯 ； 過氧化氫 ； 葡萄糖

並列摘要

Fluoroquinolone, such as lomefloxacin (denoted LFLX), are effective antibiotics. In fact, they are also unique photochemical initiators. According to our experiments, as LFLX is exposed to UV irradiation, it can undergo defluorination reaction and transform into carbene. The resulting carbene can interact with oxygen in aqueous solutions to generate reactive oxygen species (ROS) such as hydrogen peroxide. In the light of this, we characterized its oxidation power based on Fe(CN)64-, NADH, ascorbic acid and Ru(bpy)32+. The oxidation potential is equivalent to 1.0 V vs. SCE, which can cause oxidation polymerization for phenothiazine, aniline and pyrrole. According to the transmission electron microscopy (TEM) and atomic force microscopy (AFM), phenothiazine tends to form nanoparticles while the other two turn into nanofibers and nanotubes.
Based on the LFLX-induced photopolymerization reaction, we prepared polymer-modified electrodes for the detection of H2O2. The polyaniline modified electrodes exhibited catalytic potential for the reduction of H2O2. Further with Ag nanoparticles, the electrodes can even be tailored as glucose sensor, showing remarkable response to glucose.

並列關鍵字

Lomefloxacin ； reactive oxygen species ； phenothiazine ； aniline ； pyrrole ； H2O2 ； glucose

參考文獻

13. 呂威良，國立臺灣師範大學化學系碩士論文，2009，氟化奎林酮之光分解反應及其應用探討。

19. Dan Li, Jiaxing Huang and Richard B. Kaner, Acc. Chem. Res., 2009, 42, 135-145.

22. D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res., 2000, 34, 40-48.

3. A. Albini, S. Monti, Chem. Soc. Rev., 2003, 32, 238-250.

7. M. V. Orna, Electrochemistry, Past and Present, 1989, 390, 196-210.