Design,synthesis And Application Of Fluorescent Probes Based On 1,8-naphthalimide

Chemical sensors are a class of compounds that can specifically combine with the analyte under test to produce significant optical,electromagnetic,and electrical signals.As a kind of chemical sensor,fluorescence probe has been widely used in the detection of anions,cations,redox substances and biological enzymes due to its superior sensitivity,good selectivity and the advantages of being able to be used in biological tissue imaging.Among them,naphthalimide and its derivatives are widely used in the design and synthesis of novel fluorescent probes due to their simple structure,high photostability,large Stokes shift,high quantum yield,and easy chemical modification.The main work of this thesis is to design and synthesize two naphthalimide-based fluorescent probes NADCN and NAOO for the detection of hydrazine hydrate and peroxynitrite respectively.Their optical properties were studied by ultraviolet and fluorescence spectroscopy,and could be used for the detection of target analyte with high sensitivity and good selectivity in biological samples.We have successfully synthesized 2 novel fluorescent probes for the detection of hydrazine(N₂H₄)and peroxynitrite(ONOO^-).A novel fluorescent probe NADCN with naphthalimide as fluorophore and malononitrile as recognition group was designed and was used to detect hydrazine hydrate(N₂H₄).NADCN showed high sensitivity and good selectivity to N₂H₄with a detection limit of 28 n M(0.9 ppb).The detection of N₂H₄by NADCN is not disturbed by various potential interfering substances(especially amine derivatives).Cytotoxicity experiments showed that NADCN was almost nontoxic to cells even at a concentration of up to 30??.In addition,NADCN was successfully applied to detect N₂H₄ in Raw264.7 macrophage cells.A novel naphthalimide based probe NAOO was designed and synthesized.The experimental results showed that NAOO could identify ONOO^-in a sensitive and rapid manner with a detection limit as low as 15 n M and showed good selectivity for a range of other bio-related species including ROS/RNS,biothiols,anions and cations.Cytotoxicity experiments showed that probe NAOO is almost non-toxic to cells even at a concentrations as high as 30?M.In addition,NAOO could sensitively and rapidly detect endogenous ONOO^-in Raw 264.7 macrophage cells.And NAOO has the potential to target lysosomes and can be used for the detection of ONOO^-in lysosomes.