Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Institute of Molecular Science, Shanxi University, Taiyuan 030006, China.
Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China.
Spectrochim Acta A Mol Biomol Spectrosc. 2018 Apr 15;195:16-20. doi: 10.1016/j.saa.2018.01.052. Epub 2018 Jan 19.
Small molecule biothiols, including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play many crucial roles in physiological processes. In this work, we have prepared a nitroolefin-based BODIPY fluorescent probe with excellent water solubility for detection thiols, which displayed ratiometric fluorescent signal for thiols. Incorporation of a nitroolefin unit to the BODIPY dye would transform it into a strong Michael acceptor, which would be highly susceptible to sulfhydryl nucleophiles. This probe shows an obvious ratio change upon response with thiols, an increase of the emission at 517 nm along with a concomitant decrease of fluorescence peak at 573 nm. Moreover, these successes of intracellular imaging experiments in A549 cells indicated that this probe is suitable for imaging of ex-/endogenous thiols in living cells.
小分子生物硫醇，包括半胱氨酸 (Cys)、同型半胱氨酸 (Hcy) 和谷胱甘肽 (GSH)，在生理过程中发挥着许多关键作用。在这项工作中，我们制备了一种基于硝基烯烃的具有优异水溶性的 BODIPY 荧光探针，用于检测硫醇，该探针对硫醇显示出比率荧光信号。将硝基烯烃单元引入 BODIPY 染料中会将其转化为强迈克尔受体，使其极易受到巯基亲核试剂的攻击。该探针与硫醇反应时会发生明显的比率变化，517nm 处的发射强度增加，同时 573nm 处的荧光峰强度降低。此外，在 A549 细胞中的细胞内成像实验的成功表明，该探针适用于活细胞中外源性/内源性硫醇的成像。
