Design,synthesis And Application Of Fluorescent Probe For Biothiols

Small molecular biological thiols(biothiols),such as cysteine(Cys),homocysteine(Hcy),and reduced glutathione(GSH)are important thiol molecules in the body because of their versatility in a variety of physiology and pathology.The important role in the process has attracted much attention.It is of great significance to develop tools that can perform real-time visualization of biothiols.1.Using BODIPY as the fluorophore and nitroolefin as the reactive moiety,probe GZB-1was designed and synthesized.The fluorescent switch of the probe could be regulated using the PET effect by the different reactivity between sulfhydryl group and nitroolefin.The probe responds quickly to thiols,and the detection limit for GSH is as low as 11 n M.Despite the inability to selectively distinguish biothiols with different structures,the probe is still excellent cell membrane permeability and can be used for fluorescence imaging of endogenous biothiols in He La cells and zebrafish.2.Using coumarin as the fluorophore and 1-phenylprop-2-yn-1-one as the reactive moiety,probe GZB-2 was designed and synthesized.The selectivity of biothiols with different structures was realized based on the different intramolecular rates of smile rearrangement reaction after the Michael addition reaction between the mercapto group in biothiol and the 1-phenylprop-2-yn-1-one moiety.The detection limit of probe GZB-2 for Cys is 230 n M.At the same time,the probe GZB-2 also has good cell permeability and can be used for monitoring the fluctuation imaging of endogenous Cys in Hep G2 cells.