Synthesis And Application Of Several Fluorescent Probes Of Hypochlorite

Hypochlorous acid(HClO)/hypochlorite(ClO~-)is an important biological reactive oxygen species(ROS),which play a very unique function in physiological as well as pathological aspects.It is widely used in disinfection and cleaning products because of its strong oxidizing properties.However,it will cause human diseases when excessive presence in the human body or excessive inhalation in life.Quantitative determination of HClO/ClO~-is thus highly important.The advent of fluorescent probe technology has made it possible to detect HClO/ClO~-easily and rapidly.Fluorescent probes have attracted extensive attention from researchers because of their advantages of rapidity,high sensitivity,low detection limit and simple preparation.In this thesis,we designed HClO/ClO~-as the detection object,and synthesized four kinds of organic small molecule probes.Based on the structural characterization,we explored the binding mechanism of the probes and conducted the study of biological imaging.The main contents of the thesis are as follows:(1)A Schiff-base probe 1 has been synthesized by1,3,3-trimethyl-2-(formylmethylene)indoline and diaminomaleonitrile.In HEPES(50m M,p H=7.4)solution,by adding HClO/ClO~-to probe 1,the color changed from yellow to colorless,and the specific“naked eye”detection of HClO/ClO~-could be realized.In addition,probe 1 was applied to detect HClO/ClO~-inreal water samples.(2)Probe 2 was a simple ratio fluorescent probe obtained by the condensation of benzo[h]chromene aldehyde with p-toluenesulfonyl hydrazide.In DMSO/PBS(2/8,v/v,10 m M,p H=7.0)solution,Probe 2 exhibited high selectivity and sensitivity toward HClO/ClO~-,and showed a large emission shift(50 nm).In addition,probe 2can also be used to detect HClO/ClO~-in He La cells.(3)Probe 3,as a“Turn-on”fluorescent probe based on rhodanine derivatives,which has the characteristics of moderate water-solubility,high selectivity and low detection limit(23 n M).More importantly,probe 3 displays excellent imaging capability in He La cells as well as very low toxicity and was successfully applied to image HClO/ClO~-in living cells.(4)Probe 4,a novel porous polymeric fluorescent MOF-based probe by post-functionally modifying ZIF-90,which has the characteristics of water stability,porous structures and functional sites.On the basis of the unique oxidative activity of HClO/ClO~-boronate,resulting in the turn-off fluorescence behavior.Probe 4 exhibited high selectivity,high sensititivity(detection limit:12.5 n M)and fast response to HClO/ClO~-.In addition,the probe 4 was successfully used to image HClO/ClO~-in the Mitochondria of live cells.In this thesis,there are 61 figures,4 tables,and 103 references.