Jiaxing Key Laboratory of Molecular Recognition and Sensing, College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China.
Molecules. 2022 Nov 3;27(21):7499. doi: 10.3390/molecules27217499.
Hydrogen sulfide (HS) as small molecular signal messenger plays key functions in numerous biological processes. The imaging detection of intracellular hydrogen sulfide is of great significance. In this work, a ratiometric fluorescent probe based on an asymmetric BODIPY dye for detection of HS was designed and synthesized. After the interaction with hydrogen sulfide, probe display colorimetric and ratiometric fluorescence response, with its maximum emission fluorescence wavelength red-shifted from 542 nm to 594 nm, which is attributed to the sequential nucleophilic reaction of HS leading to enhanced molecular conjugation after ring formation of the BODIPY skeleton. A special response mechanism has been fully investigated by NMR titration and MS, so that the probe has excellent detection selectivity. Furthermore, probe has low cytotoxicity and fluorescence imaging experiments indicate that it can be used to monitor hydrogen sulfide in living cells.
硫化氢 (HS) 作为小分子信号信使,在许多生物过程中发挥着关键作用。细胞内硫化氢的成像检测具有重要意义。在这项工作中,设计并合成了一种基于不对称 BODIPY 染料的比率荧光探针,用于检测 HS。与硫化氢相互作用后,探针呈现出比色和比率荧光响应,其最大发射荧光波长从 542nm 红移至 594nm,这归因于 HS 的顺序亲核反应导致 BODIPY 骨架环形成后分子共轭增强。通过 NMR 滴定和 MS 充分研究了特殊的响应机制,使探针具有优异的检测选择性。此外,探针具有低细胞毒性,荧光成像实验表明它可用于监测活细胞中的硫化氢。