The Synthesis Of BODIPY Fluorescent Probes And Studies On The Biological Detection

Due to the advantages of Fluorescence analysis with low cost,simple operation,high selectivity,good sensitivity and fast response time,so it has been widely used in the field of biomedical research.Closely related fluorescent imaging methods allow the temporal and spatial monitoring of reactive and transient intracellular species,and tissue or cell destruction are not required.BODIPY?4,4-difluoro-4-bora-3a,4a-diaza-s-indacene?derivatives may be favored fluorophores as fluorescent sensors.In this dissertation,we report a series of BODIPY-based fluorescent probes for detection of various of intracellular species based on the worthy qualities of BODIPY.We explore the detection mechanism and exploit it for intracellular detection and imaging through fluorescence microscopy imaging.Details of this dissertation were as follows:?1?A water-soluble copolymer T1,consisting of N-isopropylacrylamide?NIPAM?and derivative of BODIPY units as thermoresponsive and polarity sensitive fluorescent signaling parts,respectively,has been synthesized.The copolymer exhibits weak fluorescence at temperature low than 35°C in aqueous solution,whereas the red fluorescence intensity increases 10 folds in temperature up to 47°C.The prepared nanothermometer was used in application for the fluorescent temperature sensing in living cells.?2?We has developed a phenyl-selenium-substituted BODIPY fluorescent turn-off sensor H1 for the purpose to achieve excellent selectivity and sensitivity for H₂S detection based on the substitution reaction of phenylselenide group at the 3-position with H₂S,the excess addition of hydrogen sulfide promoted the further substitution reaction and was accompanied by a further decrease in fluorescence emission intensity.This sensor demonstrated remarkable performance with 49-fold red colour fluorescence intensity decrease and specific fluorescent response toward H₂S.It was exploited to intracellular H₂S detection and imaging nicely.?3?We has synthesized a fluorescent probe BODIPY-based glyoxal hydrazone?C1?for cysteine based on inhibiting of intramolecular charge transfer?ICT?quenching process upon reaction with the unsaturated aldehyde,which exhibits selective and sensitive colorimetric and fluorimetric response toward cysteine over homocysteine and glutathione with a significant fluorescence enhancement response within 15 min.It was successfully applied to detect and image intracellular cysteine effectively.?4?GS1 was applied for the purpose of achieving two-stage ratiometric fluorescent detection of glutathione based on the two-step thiol-halogen substitution reaction with the sulfhydryl group of glutathione at the 3?mono-substitution?and 3,5-position?disubstitution?.The first stage induced fluorescent color change from green to yellow,excess addition of glutathione caused the second stage fluorescent color change from yellow to red.It exhibits excellent properties with specific colorimetric and ratiometric fluorescent change to glutathione over cysteine and homocysteine.Further application to cellular ratiometric fluorescence imaging indicated that the probe was highly responsive to the glutathione in cells.?5?Two fluorescent,m-nitrophenol substituted BODIPY G1 and G2 for ratiometric fluorescent glutathione detection is based on the two-step nucleophilic aromatic substitution of the nitrophenol groups by glutathione.Probe with one nitrophenol group G1 showed ratiometric fluorescent color change from green to yellow.Addition of excess glutathione caused ratiometric fluorescent color change from yellow to reddish orange.Probe with two nitrophenol groups G2 shows single stage ratiometric fluorescent detection to GSH.The two Probes exhibit excellent properties with specific ratiometric fluorescent response to glutathione over other sulfur nucleophiles.We applied the probes in cellular ratiometric fluorescence imaging for intracellular glutathione successfully.