A novel hepatocyte-targeting fluorescent probe of rhodamine analogues to detect hypochlorite in lysosomes: Design, synthesis and evaluation

A novel hepatocyte-targeting and lysosomal-targeting fluorescent probe of rhodamine analogues MOR-HOCl-Gal was designed and synthesized. MOR-HOCl-Gal exhibited good sensitivity and selectivity towards ClO-, without interference from other reactive oxygen species, representative anions, and representative cations. MOR-HOCl-Gal could be oxidized by ClO− to generate an instantaneous dicarbonyl diimide, and then hydrolyzed and ring-opened to a conjugated structure with high fluorescence property, which is confirmed by MS, 1HNMR and DFT calculations. Low toxic MOR-HOCl-Gal could distinguish hepatoma cells from other tissue cells, and selectively monitor endogenous and exogenous ClO− in liver lysosomes. The success of MOR-HOCl-Gal imaging in the zebrafish suggests that the aimed probe has the potential to visually monitor the presence of ClO− in vivo, and is expected to become a new effective diagnostic tool for liver related diseases.