生物正交化学
化学
硫化氢
噻吩
组合化学
线粒体
取代基
生物物理学
光化学
立体化学
点击化学
有机化学
生物化学
生物
硫黄
作者
Yinghan Chen,Ruohan Zhao,Cheng Tang,Chun Zhang,Wenyuan Xu,Luyan Wu,Yuqi Wang,Deju Ye,Yong Liang
标识
DOI:10.1002/anie.202112734
摘要
Hydrogen sulfide (H2 S) is an important endogenous gasotransmitter, but the targeted delivery and real-time feedback of exogenous H2 S are still challenging. With the aid of density functional theory (DFT) calculations, we designed a new 1,3-dithiolium-4-olate (DTO) compound, which can react with a strained alkyne via the 1,3-dipolar cycloaddition and the retro-Diels-Alder reaction to generate carbonyl sulfide (COS) as the precursor of H2 S, and a thiophene derivative with turn-on fluorescence. Moreover, the diphenylamino substituent in DTO greatly increases the mitochondrial targeting of this H2 S delivery system. Such a bioorthogonal click-and-release reaction has integrated three functions in one system for the first time: (1) in situ controllable H2 S release, (2) concomitant fluorescence response, and (3) mitochondria-targeted delivery. In addition, we investigated the mitochondrial membrane potential loss alleviation by using this system in H9c2 cells under oxidative stress.
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