Design,Synthesis And Biological Properties Of Fluorescent Probes For Detection Of H₂S,NO,HClO And Phosgene Based On 1,8-naphthalimide Fluorophore

Hydrogen sulfide(H₂S)is an important reactive sulfur species in cells,nitric oxide(NO)is an important reactive nitrogen species in cells,and hypochlorous acid(HCl O)and phosgene(COCl₂)are important reactive oxygen species in cells.Many reactive sulfur species play important roles in maintaining redox homeostasis,acting as antioxidants and acting as free radical scavengers,while many reactive nitrogen and reactive oxygen species are associated with diseases such as Alzheimer's disease,cancer,diabetes,cardiovascular disease related to pathological processes such as aging.Among them,H₂S has functions such as neuromodulation,vasodilation,and insulin inhibition;NO has functions such as regulating neurotransmission,inhibiting platelet activation,and vasodilation;HCl O plays a role in various physiological and pathological processes such as cell signal transduction,pathogen invasion,and redox balance regulation.plays an important role in.At the same time,abnormal metabolism of H₂S,HCl O,and NO may lead to physiological diseases such as hypertension,heart failure,diabetes,and ischemia-reperfusion.An important and commonly used chemical material,phosgene,is a highly toxic and easily leaking gas.Therefore,it is of great significance to study a simple phosgene detection method for preventing phosgene leakage and terrorist activities.Based on this,in this thesis,three fluorescent probes for highly selective detection of NO,H₂S,HCl O and phosgene were designed,and their photophysical properties and biological applications(cell imaging studies)were explored.1.We designed and synthesized a novel fluorescent probe ZQ-COX2-N based on 1,8-naphthalimide fluorophore to detect H₂S,and its structure was characterized by 1,8-naphthalimide fluorophore.The photophysical properties of the probe ZQ-COX2-N were investigated,and it was found that the probe ZQ-COX2-N exhibited strong green fluorescence emission at 535 nm after the addition of H₂S.The mechanism of the specific detection and recognition of H₂S by the probe ZQ-COX2-N was verified by ESI high-resolution mass spectrometry.The probe ZQ-COX2-N was successfully applied to the fluorescence imaging study of normal cells and cancer cells,and it was found that the probe ZQ-COX2-N could specifically detect H₂S in rat glioblastoma(9L).2.We designed and synthesized a novel fluorescent probe ZQ-N-NH based on1,8-naphthalimide fluorophore for the simultaneous detection of H₂S and NO.Its structure was characterized by H NMR and C NMR spectroscopy.The photophysical properties of the probe ZQ-N-NH were investigated,and it was found that the probe ZQ-N-NH exhibited strong green fluorescence emission at 530 nm after the addition of H₂S and NO.Through ESI high-resolution mass spectrometry,the mechanism of the specific detection and recognition of H₂S and NO by the probe ZQ-N-NH was verified.The probe ZQ-N-NH was successfully applied to the fluorescence imaging study of normal cells and cancer cells,and it was found that the probe ZQ-N-NH could specifically detect H₂S in rat glioblastoma(9L).3.We designed and synthesized a novel fluorescent probe FDOCl-NH-OH based on methylene blue and 1,8-naphthalimide fluorophores for simultaneous detection of HCl O and phosgene.characterization.By studying the photophysical properties of the probe FDOCl-NH-OH,it was found that the probe FDOCl-NH-OH exhibited strong fluorescence emission at 685 nm and 523 nm after the addition of HCl O and phosgene.The probe showed the advantages of rapid response to HCl O and phosgene(less than 30 s for HCl O and less than 60 s for phosgene)and low detection limit(less than 12.76?mol/L for HCl O and less than9.77?mol/L for phosgene).Through ESI high-resolution mass spectrometry,the mechanism of the specific detection and recognition of HCl O and phosgene by the probe FDOCl-NH-OH was verified.