Design,Synthesis And Application Of Novel Dicyanisophorone And Bodipy Fluorescent Probes

Fluorescent probes,as a kind of functional dyes,play the important role in chemical sensor and medical field.With the development of the study,the main research direction of fluorescent probe has transformed from traditional detection of heavy mental ions to monitoring active substances involved in vital activity in organism.Nowadays,experts and scholars focus their eyes on monitoring intracellular microenvironment.Therefore,transformation of research direction means new fluorescent probes are supposed to possess better performance,including favorable biocompatibility,near infrared absorption and emission,lower detection limit and satisfactory optical stability.As a result,during the process of designing fluorescent probe,the choice of fluorescent chromophore is of vital importance which directly affects the optical properties of the probe.Dicyanisophorone and BODIPY derivatives appeal to a wide range of interests of researchers over common fluorophores.Dicyanisophorone derivatives which possesses large stokes shift may exhibit near infrared emission so that the resolution of imaging organisms will be improved.BODIPY derivatives have good performance on absorption coefficient,modification site,stability and fluorescence quantum yield.In this paper,we have successfully synthesized three fluorescent probes based above-mentioned fluorophores to detect mercury ion(Hg²⁺)in aquatic environment,recognize peroxynitrite（ONOO^-）in cellular level and trace the viscosity of intracellular microenvironment,respectively.Two different aromatic aldehydes were reacted with dicyanisophorone to generate fluorescent probe Iso-NH2 and Diso-OH.The structures had been conformed via Nuclear Magnetic Resonance Spectrometer and Mass Spectrometer.As a“turn-on”probe,Iso-NH₂ used for Hg²⁺detection possesses favorable properties,including simple synthesis,lower detection limit,satisfactory selectivity,short response time,noticeable color changes and so on.Simple test strip dipped in Iso-NH2 solution had realized fast detection of Hg²⁺in aquatic medium with low cost.The results of optical performance show that Diso-OH,as a“turn-on”fluorescent probe,can specifically recognize ONOO^-in aquatic medium.Diso-OH exhibits good performance,including low detection limit,fast response time,wide p H range,near-infrared emission and so on,which proves Diso-OH has potential to apply to biological application.The results show that,Diso-OH has superior biocompatibility via MTT test and successfully realizes the detection for ONOO^-in cellular level by cell imaging.Besides,we have synthesized a new probe Car-BDP with aggregation-induced emission activity based BODIPY core for the detection of viscosity and the structure has been confirmed by analytical method.The emission wavelength of Car-BDP will be redshifted to the near infrared region during the aggregation state.Car-BDP exhibits fluorescence enhancement in high viscosity medium.Besides,Car-BDP has good stability and hardly suffers from change of p H and environment.MTT test and colocalization experiments show that Car-BDP have satisfactory biocompatibility and specific localization to lysosome.More importantly,Car-BDP has been successfully applied in the detection of endogenous viscosity for long time,which indicates Car-BDP has potential to become a useful tool for diagnosis and treatment of cancer.