Meso-heteroaryl BODIPY dyes as dual-responsive fluorescent probes for discrimination of Cys from Hcy and GSH

Two new BODIPY-based turn-on fluorescent probes (BDP-S-1 and BDP-O-6) contained tetramethyl at 1-, 3-, 5- and 7-positions, as well as O-, or S-aryl substituent at 8-position for the simultaneous and selective detection of Cys and Hcy/GSH from dual emission channels were developed. The spatial steric hindrance of the methyl groups at 1- and 7-positions prevented intramolecular displacement of sulfur with amino group of Hcy but not of Cys. Based on different thiols-induced SNAr substitution-rearrangement reaction with Cys and Hcy/GSH, leading to the corresponding amino-and thiol-BODIPY dyes with distinct photo-physical properties, these probes could simultaneously and selectively detect Cys and Hcy/GSH. With the help of laser scanning confocal microscope, we demonstrated that these probes could simultaneously sense Cys and GSH in Hela cells using multicolor imaging. (C) 2018 Elsevier B.V. All rights reserved.