The Synthesis And Properties Of Fluorescent Probes Based On BODIPY Derivatives

In recent years,the fluorescent probes combined with fluorescence imaging can be easily used in the detection of target molecules in biological system and its biological process monitoring.The technology become indispensable molecular tools to modern life science and disease diagnosis in areas.At the same time,convenient for operating,the sensitivity and selectivity highly,can be widely used in food,environment and other fields.Boron-dipyrrolemethene(BODIPY)with high molar extinction coefficient,excellent photostabilit and high fluorescence quantum yield is ideal fluorophores for fluorescent probe.So,in this thesis,the BODIPY core as fluorescent matrix design BODIPY derivatives were synthesized B1 and B2.Test results showed that the probe can not only specific identification of cysteine(Cys)and homocysteine(Hcy),and can further through the differences of reaction kinetics distinguish Cys and Hcy.Our studies are carried out as follows:In chapter 1,we presented the research background of this thesis and described the structure of fluorescent probe molecules and their recognition mechanism.According to reaction mechanism of probe and biological mercaptan had summarized simple classification.For this thesis design,synthesis and application of small molecule probe establish the literature basis.In chapter 2,we designed and synthesized two novel BODIPY derivatives(B1,B2)which were characterized by MS,NMR and elemental analysis.In chapter 3,we described a turn-on BODIPY-based probe B1 that was used to detect Cys in real samples.The probe B1 displays highly selective detection of Cys over other biological thiols such as Hcy and GSH.The probe can be applied to the quantification of Cys with a linear range covering from 0.2 to 30 ?M and the detection limit is 0.05 ?M.The experiment results show that the response behavior of B1 towards Cys is p H independent in the neutral range from 6.0 to 8.0 and the response of B1 toward Cys is fast response time less than 5 min.Moreover,the fluorescence sensing mechanism(PET)of the probe is fully demonstrated by MS,1H NMR spectra and DFT calculations.Finally,the probe is applied for detection of Cys in living cells with encouraging results.In chapter 4,we focused on introducing a turn-on BODIPY-based NIR probe B2 that is used to detect Cys in real samples.The emission of the probe at 708 nm.It displays highly sensitive fluorescent response toward Cys The probe can be applied to the quantification of Cys with a linear range covering from 0.2 to 30 ?M and the detection limit is 0.05 ?M.Moreover,the experiment results show that the response behavior of B2 towards Cys is p H independent in the neutral range from 6.0 to 9.0.The response of B2 toward Cys is fast(response time is less than 5 min)and the probe is chemically reversible.Furthermore,the PET mechanism of probe B2 towards Cys is supported by MS,1H NMR spectra and DFT calculations.Finally,the probe is applied for detection of Cys in living cells and tissue with encouraging results.