汞(II)及次氯酸螢光化學感測分子之設計與合成及於活體細胞的應用

Abstract

本論文以 pyrene 和 coumarin 為螢光基團主體，設計偵測汞離子及次氯酸螢光化學感測分子 PES 和 CHT。 PES 以 bis(ethylsulfane) 基團做為與汞離子的反應辨識端，在各種金屬中具有良好的選擇性與靈敏性偵測汞離子。PES 的螢光很弱 (Φ = 0.01)，而與汞離子作用後使 bis(ethylsulfane) 基團離去，進而產生 27 倍的藍色螢光強度增加 (Φ = 0.27)。PES 在不同濃度汞離子反應所表現出來的螢光強度呈現良好的線性關係，偵測極限約為 55 nM。此外，PES 可在細胞顯影實驗中應用於巨噬細胞偵測汞離子。 第二部分是偵測次氯酸的感測分子 CHT，以 hydrazinecarbothio- amide 基團做為次氯酸的辨識端，在 ROS 和 RNS 中對於次氯酸具有很好的選擇性與靈敏性。CHT 對次氯酸偵測極限為 0.82 μM，在 pH 值 6.0 到 10.0 時有較明顯的偵測效果。最後，在細胞顯影實驗中，可應用於巨噬細胞偵測次氯酸。

In this thesis, pyrene-based and coumarin-based chemsensors, PES and CHT, were designed to detect Hg2+ and hypochlorous acid. PES contains a bis(ethylsulfane) group as a reaction moiety for Hg2+, and exhibits good selectivity and sensitivity over other metals. PES shows weak fluorescence with a quantum yield (Φ=0.01), and 27 fold blue fluorescence enhancement (Φ = 0.27) is produced upon removal of bis(ethylsulfane) by Hg2+. The intensity of PES in the presence of different Hg2+ concentration shows a good linearity with a detection limit of 55 nM. Confocal fluorescence microscopy imaging using RAW 264.7 cells shows that PES can be an effective fluorescent probe for Hg2+ in living cells. In second part, CHT uses hydrazinecarbothioamide group as recognition moiety for HOCl detection, and exhibits good selectivity and sensitivity over other ROS and RNS. The detection limit of CHT for HOCl is 0.82 μM and displays good sensitivity in buffer solution in the pH value of 6.0 to 10.0. Confocal fluorescence microscopy imaging using RAW 264.7 cells shows that CHT could be an efficient fluorescent probe.