Quinoline-derived fluorescent probes for the discrimination of Cys from Hcys/GSH and bioimaging in living cells

Development of thiol-specific fluorescent probes with selectivity in different thiol compounds is more practical and significant than those without that capacity. In this work, a new quinoline-derived fluorophore, hydroxyl-substituted quinoline-benzo[d]oxazole 6 with high fluorescence quantum yield is synthesized and esterified with acrylic acid to afford two fluorescent probes, BQA-1 and BQA-2 for selectively discriminating Cys from Hcys/GSH based on conjugate addition-cyclization mechanism. BQA-1 exhibits a large ratiometric fluorescence response toward Cys in aqueous pH 7.4 solution with big emission peak-shifting from 383 nm to 518 nm, over 130 nm. The detection limit is determined to be as low as 0.59 μM. In contrast to BQA-1, BQA-2 whose acrylic ester moiety is further modified with pyridine group, displays a turn-on fluorescence response to Cys with detection limit of 0.98 μM. Both BQA-1 and BQA-2 have relatively weak response to another two biothiols, Hcys and GSH and nearly no response to other nucleophiles. Furthermore, the potential application for the detection of biothiols in living cells has been demonstrated by cell imaging experiment.