Borondipyrrolemethene-based fluorescent probe for distinguishing cysteine from biological thiols and its application in cell image

• Published in: Dyes and pigments 2017-04, Vol.139, p.381-387
• Main Authors: Fu, Ya-Jun, Li, Zhi, Li, Chun-Yan, Li, Yong-Fei, Wu, Ping, Wen, Zuo-Heng
• Format: Article
• Language: English
• Subjects: Borondipyrrolemethene; Cell image; Cysteine; Fluorescent probe; Photoinduced electron transfer
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2016.12.033

Biological thiols including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) possess the similar structures, but they play different important biological roles. So the detection and discrimination of these biological thiols are of great importance. To date, a number of fluorescent probes have been developed for detection of biothiols. Unfortunately, it is difficult for the probes in discrimination of Cys from Hcy. In this paper, the borondipyrrolemethene -based fluorescent probe named 1 is successfully synthesized. The probe itself exhibits weak fluorescence because the fluorophore is quenched by the acrylate group through a photoinduced electron-transfer (PET) process. Upon reaction of the probe with cysteine, large fluorescence enhancement is produced. The probe could be applied to the quantification of Cys with a linear range covering from 0.2 to 30 μM and the detection limit is 0.05 μM. Furthermore, the fluorescence enhancement shows high sensitivity towards Cys owing that there is more fast reaction rate between the probe and Cys than that of Hcy. Moreover, the response behavior of 1 towards Cys is pH independent in the neutral range from 6.0 to 8.0 and the response of 1 toward Cys was fast. Finally, the probe has low cytotoxicity and is applied for detection of Cys in living cells with encouraging results. [Display omitted] •A BODIPY-based fluorescent probe (1) is developed for detecting Cys.•The acrylate is selected as recognition group of the probe.•The probe shows high sensitive response to Cys and the detection limit is 0.05 μM.•The probe exhibits high selectivity for Cys over other biological thiols (Hcy).•The probe has been used for detection of Cys in living cells successfully.