Department of Chemistry, Xinzhou Teachers University, Xinzhou 034000, Shanxi, China; Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China.
Institute of Molecular Science, Shanxi University, Taiyuan 030006, China.
Spectrochim Acta A Mol Biomol Spectrosc. 2020 Sep 5;238:118437. doi: 10.1016/j.saa.2020.118437. Epub 2020 May 3.
In view of the importance of hydrogen sulfide (HS) in the organism, a fast, noninvasive method for the detection of HS in situ is needed. Fluorescent probes based on disulfide-bond nucleophilic substitution-addition can selectively detect HS in vivo, which is very popular because it allows quick response for HS, thus it will be a useful tool for monitoring HS in the vivo. We developed a dicyanoisopentanone-based HS fluorescent probe (EW-H) that used a disulfide group as a self-destructive linker reaction site. Under the nucleophilic substitution of HS, the disulfide bond of EW-H was cleaved, and then nucleophilic addition took place intramolecularly to release the fluorophore (at 580 nm). The response to HS, EW-H had high sensitivity (86 nM of the detection limit), large Stokes shift (155 nm) and a fast response time. More importantly, the probe was also applied for bioimaging in HepG2 cells, indicating its potential applications in biological organism.
鉴于硫化氢 (HS) 在生物体中的重要性，需要一种快速、非侵入性的方法来原位检测 HS。基于二硫键亲核取代-加成的荧光探针可以选择性地在体内检测 HS，这非常受欢迎，因为它可以快速响应 HS，因此将成为监测体内 HS 的有用工具。我们开发了一种基于二氰基异戊二烯酮的 HS 荧光探针 (EW-H)，它使用二硫键作为自毁连接反应位点。在 HS 的亲核取代下，EW-H 的二硫键被切断，然后发生分子内亲核加成反应，释放荧光团（在 580nm 处）。对 HS 的响应，EW-H 具有高灵敏度（检测限为 86nM）、大斯托克斯位移（155nm）和快速响应时间。更重要的是，该探针还应用于 HepG2 细胞的生物成像，表明其在生物体内具有潜在的应用。
