硫化氫螢光探針MaT-cyclen之特性研究

Abstract

本研究設計並合成了一個親水性的硫化氫螢光探針，MaT-cyclen，主要是以一個 cyclen 的結構，修飾上ㄧ個 triazole ring 以及螢光基團所組成，此螢光探針可檢測出特定的生物硫醇，硫化氫； MaT-cyclen 對硫化氫的螢光表現顯示高選擇性，並且此硫化氫螢光探針 MaT-cyclen 具有相當好的水溶性，不需要添加輔助溶劑即可水溶，此硫化氫螢光探針之偵測極限為 1.27 nM，並且此探針在反應前後之螢光量子產率 (Φfl) 差高達7倍左右，表示此探針對於偵測硫化氫相當敏感；此探針與硫化氫反應速度相當快( < 5 sec ) ，且 MaT-cyclen 與 [Cu(MaT-cyclen)2] 皆具有很好的生物相容性，對細胞低毒性，並可應用於 pH 值 5.5 至 10.0 之間，具有相當良好的反應性，不會受到環境中的酸鹼值改變，而影響其螢光效力。

To design a selective and quick response method for monitoring hydrogen sulfide in aqueous media that works under the biological system. However, the applications of bioimaging studies or real sample detection of fluorescent chemosensors for hydrogen sulfide have been rarely reported, and even the reported methods have some disadvantages such as poor solubility in aqueous media and lack of reversible nature. The design of fluorescent sensors for hydrogen sulfide in aqueous solution is a challenging task owing to the strong hydration of anions, which weakens the interactions of the sensors with the target anions. But the displacement method can be used to tackle this hurdle. Based on the above mentioned facts, cyclen based chemosensor ligand, 1-((1-((10-methylanthracen-9-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-1,4,7,10-tetraazacyclododecane (MaT-cyclen) was designed, synthesized and characterized. In this study, MaT-cyclen exhibited high sensitivity and selectivity towards Cu2+ in aqueous medium. MaT-cyclen also exhibited excellent optical properties and formed complex [Cu(MaT-cyclen)2] when combined with CuCl2, which displayed fluorescence ON–OFF behavior. This complex also showed high sensitivity and selectivity for HS- to show fluorescence OFF- ON behavior on the basis of forming CuS. In addition, [Cu(MaT-cyclen)2] displayed rapid response (<5 sec), well reversibility and high sensitivity for recognizing HS− in 100% aqueous medium. Furthermore, its potential utility for biological applications was confirmed by fluorescence imaging of hydrogen sulfide in living cells.