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Design,Synthesis And Application Of Fluorescent Probe Based On Pyridyl-porphyrin

Posted on:2023-11-20Degree:MasterType:Thesis
Country:ChinaCandidate:H WangFull Text:PDF
GTID:2531307091498364Subject:Engineering
Abstract/Summary:PDF Full Text Request
Fluorescence analysis is to detect the substance qualitatively or quantitatively through the change of fluorescence signal.Compared with traditional detection methods such as electron probe method,spectrum method and mass spectrometry,fluorescence analysis has the advantages of simple operation,high sensitivity,strong selectivity and less damage.Porphyrins have excellent properties such as large Stokes shift,long emission wavelength and good photothermal stability.They are often used in the design and synthesis of fluorescent probes.They are widely used in biomolecular detection,photodynamic therapy and so on.In view of the many excellent characteristics of porphyrins,in this paper,we constructed two fluorescent probes based on pyridyl porphyrins to detect nerve agent simulants and target GSH in cancer cells.The main contents and results of this paper are as follows:(1)Based on the principle of intramolecular charge transfer(ICT),we designed and synthesized a fluorescent probe 5-(4-pyridyl)-10,15,20-tris(phenyl)porphyrin(TPy P)for the detection of diethyl chlorophosphate(DCP).When the probe molecule is in the DCP environment,DCP will react rapidly with the pyridine group and pyrrole group of the fluorescent probe.This reaction process enhances the ICT effect,the color changes from pink to bright green,and the red fluorescence decreases.When triethylamine is added to the upper solution,the color and fluorescence of the reaction solution quickly return to the original state,and then the reversible detection and analysis of nerve agent simulant is realized.Further,the probe molecule and methyl polyacrylate were mixed in dichloromethane solution and deposited on the filter paper to make the detection test paper,which realized the detection of the vapor state of nerve agent simulant.Finally,the probe can detect the nerve agent simulant in liquid and gas phases..(2)Using the porphyrin molecular platform,we constructed a porphyrin based cancer cell targeting nanoprobe.In this system,2,4-dinitrofluorobenzene reacts with monopyridyl porphyrin to obtain positively charged porphyrin molecules,and the ability of porphyrin to fluorescence and produce singlet oxygen(1O2)is reduced.The ability to attract the negative charge of 1O2porphyrin in the preparation of nano porphyrin based on the electrostatic charge and the negative charge of1O2porphyrin in the preparation of cancer cells is further reduced.Once the nanoprobe enters the cancer cells with hyaluronic acid overexpression,the hyaluronidase in the cells catalyzes the degradation of the nanoprobe and releases positively charged porphyrin molecules.Then,2,4-dinitrophenyl in porphyrin molecules reacts with GSH in cells to release monopyridyl porphyrin molecules.Under red light irradiation,porphyrin photosensitive molecules release 1O2to induce cell apoptosis and further enhance the effect of photodynamic therapy.
Keywords/Search Tags:Pyridyl porphyrin, Nerveagent, Fluorescent nanoprobe, Glutathione, Singlet oxygen
PDF Full Text Request
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