Synthesis And Properties Of Acrylate Porphyrin Fluorescent Molecular Probes

Cysteine is a non-protein thiol in human cells and plays a very important role in human physiology.The traditional method of detecting small molecule biomercaptan has the disadvantages of complex detection process,low sensitivity,poor stability of fluorophore and short fluorescence lifetime.In this thesis,four kinds of porphyrin fluorescence moleculer probes with porphyrin as fluorophore and acrylate as recognition group were designed and synthesized by using these characteristics of porphyrin and acrylate groups.The thiol-containing Cys was detected using this type of probe.The details are as follows:(1)Via the Adler-Longo method,Pyrrole,p-hydroxybenzaldehyde,benzaldehyde,p-methylbenzaldehyde,p-methoxybenzaldehyde,and thiophene-2-carbaldehyde are used as raw materials.Reaction to give 5-(4-hydroxyphenyl)-10,15,20-triphenyl porphyrin(Ph1);5-(4-hydroxyphenyl)-10,15,20-tri-(4-methylphenyl)porphyrin(Ph2);5-(4-hydroxyphenyl)-10,15,20-tri-(4-methoxyphenyl)porphyrin(Ph3);5-(4-hydroxyphenyl)-10,15,20-tri-(2-thio phene)porphyrin(Ph4).Synthesis of acrylate porphyrins by the preparation of asymmetric hydroxy porphyrins and acryloyl chloride under the action of triethylamine:5-(4-acrylate phenyl)-10,15,20-triphenyl porphyrin(P1);5-(4-acrylate phenyl)-10,15,20-tri-(4-methyp helnyl)porphyrin(P2);5-(4-acrylate phenyl)-10,15,20-tri-(4-methoxyphenyl)porphyrin(P3);5-(4-acrylate phenyl)-10,15,20-tri-(2-thiophen)porphyrin(P4).he target compounds were characterized by FTIR,UV-visible,~1H NMR and elemental analyses.The characterization data of the compounds was consistent with the assigned formula.(2)The quantitative detection effects of fluorescent molecular probes P1,P2,P3,and P4on Cys were investigated by fluorescence spectroscopy,The optimum conditions of Cys quantitative detection using the above four fluorescent molecular probes,the detection impact of specificity and interfering substances were explored.The linear range of the probe P1 for detection of Cys is 0.1~2.0?mol/L,The linear range of the probes P2,P3 for detection of Cys is all 0.1~2.5?mol/L,The linear range of the probe P4 for detection of Cys is 0.05~2.5?mol/L.The results showed that the method is feasible of the four acrylate porphyrin fluorescent molecular probes for quantitative detecting cysteine,good stability,simple operation and high sensitivity.