Design,Synthesis And Properties Of Several Reaction-Based Hydrogen Peroxide Fluorescent Probes

Hydrogen peroxide(H₂O₂)can effectively regulate many important life activities of cells.Therefore,monitoring the H₂O₂ content in biological samples has important application value for the diagnosis and treatment of diseases.Reaction-based fluorescent probes have outstanding advantages such as high sensitivity,simple operation,and high temporal and spatial resolution.At present,a variety of fluorescent probes for the detection of H₂O₂ have been developed.In this paper,based on literature research,three hydrogen peroxide fluorescent probes were designed and synthesized.The main research contents are as follows:(1)Based on 2-Chloro-4,6-dimethylpyrimidine,a pyrimidine-like H₂O₂ fluorescence was finally synthesized by introducing an electron-donating group N,N-dimethylaminophenyl and a recognition group selenomorpholine.The structure of the probe Pyrimidine-Se was described by NMR,HRMS(ESI)and single crystal X-ray diffraction,and the structure optimization and energy level analysis were carried out by Density functional theory(DFT)calculation.The results showed that in PBS buffer(10 m M,p H=7.4),the probe showed high selectivity and sensitivity to H₂O₂,and its fluorescence was significantly enhanced(40 times)after reacting with H₂O₂,and the Stokes shift was 155 nm.The detection limit is 1.3?M.The probe can detect not only H₂O₂in water,but also H₂O₂ in Argentine bloodfin larvae.(2)Based on 4-bromo-1,8-naphthalenedicarboxylic acid anhydride,a naphthalimide-based H₂O₂fluorescent probe MNG was finally synthesized by introducing ethylmorpholine and recognition group selenomorpholine.Its structure was analyzed by NMR,HRMS(ESI)and single crystal X-ray diffraction,and the structure optimization and energy level analysis were carried out by DFT calculation.The results showed that in PBS buffer(10 m M,p H=7.4),the probe showed high selectivity and sensitivity to H₂O₂,the fluorescence was significantly enhanced(45 times)after reacting with H₂O₂,the Stokes shift was 135 nm,and the detection The LOD is 61 n M.The probe can detect not only H₂O₂ in water,but also H₂O₂ in MCF-7 cells.MNG was also able to image and assess drug-induced organ damage in Argentine bloodfin larvae.(3)Based on 2-substituted benzothiazoles,a thiazole-based H₂O₂ fluorescent probe BBS was synthesized by introducing the recognition group arylboronic acid pinacol ester.The structure was characterized by NMR,HRMS(ESI)and single crystal X-ray diffraction,and the structure optimization and energy level analysis were carried out by DFT calculation.The results showed that in PBS buffer(10 m M,p H=7.4,30%DMSO),the probe showed high selectivity and sensitivity to H₂O₂,with a Stokes shift of 70 nm and a detection limit of 132 n M.The probe can also detect endogenous and exogenous H₂O₂ in MCF-7 cells.