The Chemical Reaction Fluorescence Probe Based On BODIPY For Selective Detection Of Bio-thiols And Thiophenol

Sulfhydryl compounds play a very important role in the body metabolism,industrial production and the natural environment.Biological thiols(cysteine Cys.homocysteine Hcy,glutathione GSH)can be critical parts of many proteins and small molecules in the organism and play an important role in the antioxidant system of cells.The abnormalities of concentration and distribution are closely related to many diseases,the thiophenol and its derivatives are significant intermediates in chemical industry.A large amount of thiophenol wastewater discharged into natural water,will be bound to pollute the water and soil inevitably,and then endanger human health.Therefore,how to selectively detect bio-thiols and thiophenol is of great significance.Based on the BODIPY fluorophore group,the fluorescence probes of GSH and Cys/Hcy and thiophenol were designed and synthesized in combination with the differences of structure and reactivity for sulfhydryl compound.The contents of specific research are as follows:1.The coumarin group was introduced based on monochlorinated BODIPY to synthesize the probe BC for simultaneous detection of cysteine Cys and glutathione GSH.The sulfhydryl group of bio-thiols released blue-fluorescent coumarin as an internal molecule by nucleophilic substitution reaction SNAr,In addition,GSH led to thiol substitution and generated yellow/red BODIPY,while the amino group of Cys/Hcy can be further subjected to the transition of five-or six-membered ring to get amino substituted blue BODIPY through intramolecular rearrangement,whereby the system exhibited a different luminescent color,and achieved simultaneous detection for the GSH and Cys/Hcy.Interestingly,the solution showed white fluorescence at 0.4 mM for GSH.The probe was successfully used for simultaneous imaging of GSH and Cys in living cells.2.By the click reaction,the triphenylphosphine group for mitochondrial localization was introduced at the 3-position of BODIPY,and the fluorescent probe BODIPY-PPh3 was synthesized,which can located in the mitochondria accurately,and reaced with the Cys/Hcy to generate amino substituted products,in contrast to GSH,thiol-substituted product was produced.The different compounds had different emission wavelength,and the selective imaging of GSH in mitochondria was realized.3.By adjusting the capability of push-pull electronic at the 3-position of BODIPY,synthesized and screened the fluorescent probes Amide-BODIPY for selective detection of thiophenol.Under physiological conditions,because of the different reactivity between thiophenol and aliphatic thiol,Amide-BODIPY can occur nucleophilic substitution reaction(SNAr)with thiophenol,red shift of emission spectrum,and aliphatic thiol were almost not reaction.So the selective detection of thiophenol was realized.The probe was successfully used for selective discrimination of thiophenol over aliphatic thiols in the actual water samples and in living cells.4.The new BODIPY derivatives were synthesized according to "O-replace-F"generation ring,and characterized by 1H NMR,13C NMR,HRMS and RSD.The data of spectral test showed that the derivative had a long absorption and emission wavelength,higher quantum yield and good the fluorescence lifetime.So the derivatives can be as the excellent fluorescent dye molecules.