A novel quinoline-BODIPY fluorescent probe for fast sensing biothiols via hydrogen bonds assisted-deprotonation mechanism and its application in cells and zebrafish imaging

A novel quinoline BODIPY fluorescent probe Q-BODIPY was designed. Probe Q-BODIPY combined 8-hydroxyquinoline-BODIPY with 2,4-dinitrobenzenesulfonyl group as a new biothiols-detection fluorescent probe. After addition of biothiols, probe Q-BODIPY responds to Cys quickly and displays a manifest fluorescent signal at 521 nm with quantum yield increased from 0.02 to 0.16 and detection limit was determined to be 33 nM with great goodness of fit at 0.98. Furthermore, The response of probe Q-BODIPY with Cys also could be observed with “naked eyes” in 3 min. The cleavage of the suphonate accelerated by hydrogen bonds was proposed according the theoretical calculation and acid-base interaction. Additionally, The probe works excellently within a wide pH range of 5.9–10.1 and was used for selective imaging of biothiols in HepG2 cells and zebrafish. These results indicated that the probe could fast sensing different biothiols via different reaction rate of probe Q-BODIPY with these three type of biothiols, which result from hydrogen bonds assistance mechanism, and provide a functional tool for reflecting the changes of biothiols.