A novel and simple imidazo[1,2-a]pyridin fluorescent probe for the sensitive and selective imaging of cysteine in living cells and zebrafish.

Abstract Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play many crucial physiological roles in organisms. Their abnormal levels can cause and indicate various diseases. In the present study, a small-molecule fluorescent probe 2-(imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) was designed, synthesized and characterized by NMR, FT-IR and HRMS. IPPA can selectively detect Cys over other analytes because of an approximately 76 times enhancement in fluorescence intensity. The limit of detection of IPPA for Cys was 0.33 μM. The pseudo-first-order rate constant of the reaction between IPPA and Cys was approximately 10 times that of the reaction between IPPA and Hcy (K Cys 3.18 × 10−3 S−1 vs K Hcy 4.92 × 10−4 S−1), indicating that Cys can be distinguished from Hcy. In addition, IPPA exhibits strong anti-interference ability, small molecular weight, high efficiency, low toxicity and good cell permeability. It was successfully used in imaging HepG2 cells and zebrafish. The fluorescence response of IPPA for calf serum are powerful proofs for practical application. Therefore, IPPA has high potential for bioassay applications. Graphical abstract Image 1 Highlights • 2-(Imidazo[1,2-a]pyridin-2-yl)phenyl acrylate (IPPA) is a novel fluorescent probe. • IPPA can detect Cys over Hcy, GSH and other analytes. • IPPA can selectively detect as low as 0.33 μM of Cys in DMSO/HEPES buffer. • IPPA has been successfully utilized to image living cells and zebrafish. [ABSTRACT FROM AUTHOR]