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Synthesis Of Novel Selenium-containing Fluorescent Probe Based On 1,8-Naphthalimide And Its Specific Detection And Application To H2S

Posted on:2020-05-09Degree:MasterType:Thesis
Country:ChinaCandidate:Y Z LiFull Text:PDF
GTID:2491305714957279Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Hydrogen sulfide(H2S)is the third important gas signal molecule after nitric oxide(NO)and carbon monoxide(CO)in living organisms.Therefore,the identification and quantitative detection of H2S in vivo and in biological environment is undoubtedly of great significance.The fluorescent probe technology has fast response,high sensitivity and easy operation.As the core of the fluorescent probe,the 1,8-naphthalimide block has stable molecular chemical properties,high fluorescence quantum yield,large Stockes shift,and good light stability,easy modification and the characteristics of ICT luminescence mechanism.The design,synthesis and application of 1,8-naphthalimide structural molecules have become the frontier and hotspot of discipline research.Diselenoether compounds and ebselen are well known glutathione peroxidases(GPx)mimics,both are capable of nucleophilic addition reactions with sulfhydryl-containing small molecules in the organism.The reaction of the diselenide compound with hydrogen sulfide or biothiol is based on the cleavage of the diselenide bond,and the reaction of ebselen is based on the cleavage of the Se-N bond.Based on this principle,we designed and synthesized three new types six of new selenium-containing fluorescent probe molecules,using selenium ether and ebseline as reaction sites and 1,8-naphthalimide as fluorophore to carry out specific fluorescence recognition and detection of H2S.1.The first series of target molecules:(1)Based on the ICT mechanism,the fluorophore1,8-naphthalimide with excellent fluorescence activity and large emission wavelength was used as the core unit,two target molecules DSHN(1-2)were designed and synthesized by hydrazide bond and diaryl selenide.The structures were successfully characterized.(2)The target molecules are all turn-on fluorescent probes.With the addition of H2S,the fluorescence signal are continuously enhanced,the solution changes from colorless to pale yellow,which achieves the effect of naked eye recognition.(3)Specific high-selective fluorescence detection and recognition of H2S is obtained.In the experiment,14 substances(including anions,amino acids and redox small molecules)were choosed to be explored.The results showed that other anions,redox molecules and thiol-containing biothiols do not respond to the detection and have no interference.(4)The cell level research was performed using this type target molecule.The results show that it has good cell membrane permeability,low cytotoxicity and can be applied to cell imaging,indicating that the target molecule can be used as fluorescence probs to detect and identify of exogenous source of H2S.2.The second and third series of target molecules:(1)In order to compare the effect of intramolecular spacers on the detection of H2S,the Se-N bond of ebselen was used as thereaction site.The second-type fluorescent probes EPHN(1-2)and the third-type fluorescent probes EHN(1-2)were synthesized through two modes and their structures were character-ized.(2)The results of the fluorescence recognition of H2S show that both types of targetmolecules can selectively detect H2S,and it is successfully applized in the actual living water sample.The spacer part of the target molecule has little influence on the sensitivity of theprobe molecule.This result demonstrates that the both types of target molecules are expected to be fluorescent probes for H2S.(3)The cell level research was also performed and theresults show that EPHN1 has good cell membrane permeability,low cytotoxicity and can be applied to cell imaging.
Keywords/Search Tags:H2S, Fluorescent Probe, 1,8-naphthalimide, Diselenides, Ebselen Derivative
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