Du Yuting, Wang Hongliang, Zhao Sanhu, Guo Minmin, Yang Xiaojing
Department of Chemistry, Xinzhou Normal University, Xinzhou, Shanxi 034000, China.
Department of Chemistry, Xinzhou Normal University, Xinzhou, Shanxi 034000, China.
Bioorg Med Chem. 2025 Nov 1;129:118322. doi: 10.1016/j.bmc.2025.118322. Epub 2025 Jul 18.
Hydrogen sulfide (HS) plays a crucial role in the regulation of various physiological processes within living organisms, including cell signaling, vascular tone modulation, and the inflammatory response. The real-time detection and visualization of HS levels in practical samples hold significant importance for biological analysis. In this study, 3-(benzo[d]thiazol-2-yl)-5-bromo-2-(2,4-dinitrophenoxy)benzaldehyde (DTBH) was designed and synthesized based on the mechanism of excited state intramolecular proton transfer (ESIPT). The probe employs a 2,4-dinitrophenyl ether with an ortho-aldehyde group as the reaction site to test HS. As a result, it exhibits an ultrafast response to HS within only 5 s and demonstrates high absolute fluorescence quantum yield (Φfl) up to 17.63 %. Moreover, DTBH interacts with HS to release its precursor DTB, which leads to a marked enhancement in fluorescence emission with 542 nm. DTBH shows high sensitivity and excellent selectivity for HS over various other analytes. Significantly, the biological imaging investigations in cells demonstrated that DTBH could image endogenous and exogenous HS and provide a promising method for the detection of HS in biological systems.
硫化氢(HS)在生物体内各种生理过程的调节中起着关键作用,包括细胞信号传导、血管张力调节和炎症反应。实际样品中HS水平的实时检测和可视化对于生物分析具有重要意义。在本研究中,基于激发态分子内质子转移(ESIPT)机制设计并合成了3-(苯并[d]噻唑-2-基)-5-溴-2-(2,4-二硝基苯氧基)苯甲醛(DTBH)。该探针采用带有邻位醛基的2,4-二硝基苯基醚作为反应位点来检测HS。结果,它对HS仅在5秒内就表现出超快响应,并显示出高达17.63%的高绝对荧光量子产率(Φfl)。此外,DTBH与HS相互作用释放其前体DTB,这导致在542nm处荧光发射显著增强。DTBH对HS表现出高灵敏度和对各种其他分析物的优异选择性。重要的是,细胞中的生物成像研究表明,DTBH可以对内源性和外源性HS进行成像,并为生物系统中HS的检测提供了一种有前景的方法。