苯并噻唑
斯托克斯位移
荧光
荧光团
化学
光化学
半胱氨酸
谷胱甘肽
分子内力
亲核加成
亲核细胞
立体化学
有机化学
催化作用
酶
物理
量子力学
作者
Haixian Ren,Fangjun Huo,Yongbin Zhang,Sanhu Zhao,Caixia Yin
标识
DOI:10.1016/j.snb.2020.128248
摘要
ESIPT-based (Excited-State Intramolecular Proton Transfer) fluorescent probes have been popular because of their large stokes shift and environmental sensitivity. In this work, by coupling dicyanoisophorone and benzothiazole with toluene, we built a cysteine (Cys) fluorescent probe containing a near-infrared ESIPT fluorophore, and an acryloyl group as a nucleophilic addition and leaving site. It was found that only Cys enabled nucleophilic addition and release of hydroxy toluene in conjugated system, with a turn-on NIR emission based on ESIPT effect of benzothiazole. The probe SYP exhibited an excellent selectivity for Cys without any interference from H2S and other thiols (glutathione and homocysteine), attributed to the formation of the seven-membered heterocyclic compound favored kinetically. More, the sensing mechanism was proved to be the ESIPT process by 1H-NMR and MS titration experiments. Of course, the probe displayed its practical application by imaging endogenous Cys in cells and mice. This work innovatively proposed a method for designing a near-infrared fluorescent probe specifically for Cys based on the ESIPT mechanism.
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