Abstract

Hybrid 2-(2-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)vinyl)-1,3-dimethyl-1H-benzo[d]imidazol-3-ium iodide compounds (LHZD-1 ∼ 3) were synthesized by Knoevenagel condensation reaction. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS spectroscopy. The fluorescence property of LHZD-1 ∼ 3 varied with the substituent groups such as -Br, -H and -OMe in the benzimidazolium skeleton. The probe LHZD-1 showed remarkable selectivity for the bisulfite ion over other common anions and biotins, which outputted the obvious color change in both absorption (462 nm to 400 nm) and emission (580 nm to 480 nm) spectra. The probe LHZD-1 showed the lysosome positioning action in Hela cells. This study not only provides a way for optimizing coumarin-benzimidazolium probes but also holds considerable promise in detection of bisulfite ion in organelles.

摘要

杂化2-（2-（2-（7-（二乙氨基）-2-氧代-2H-铬-3-基）乙烯基）-1,3-二甲基-1H-苯并[ d ]咪唑-3-碘化碘化合物（LHZD- 1〜3）通过Knoevenagel缩合反应合成。它们的结构通过¹ H NMR，¹³ C NMR和HRMS光谱确认。LHZD-1〜3的荧光性质随苯并咪唑骨架中的-Br，-H和-OMe等取代基而变化。LHZD-1探针对亚硫酸氢根离子具有比其他常见阴离子和生物素显着的选择性，在吸收光谱（462 nm至400 nm）和发射光谱（580 nm至480 nm）中均产生明显的颜色变化。探头LHZD-1在Hela细胞中显示了溶酶体定位作用。这项研究不仅为优化香豆素-苯并咪唑鎓探针提供了一种方法，而且在细胞器中亚硫酸氢根离子的检测方面具有广阔的前景。