Design,Synthesis And Visualization Of High Selection,Sensitivity,and Biocompatibility BODIPY

Fluorescence analysis is an important technique in drug analysis which has the merit of good selectivity and less sample consumption,has been widely used in chemistry,medicine,environment and other related fields.Fluorescent dye is a key tool for realizing fluorescence analysis.As a new type of fluorescent dye,BODIPY has the properties of outstanding photophysical activity,stable chemical structure,large molar absorption coefficient,and easy to structural modification.These performances make it play an important role in the field of fluorescent probes.It is important that the modification is of great significance to the research in biochemistry,medicine and environmental monitoring.Therefore,research on BODIPY structural modification was conducted.In this paper,the structural modification,property optimization,physical modification was conducted on the bases of BODIPY core and designed three series of BODIPY derivatives,through characterizing,and realizing identification of amino acids and ions.Cell imaging and biocompatibility were explored.The main innovative findings which are obtained in this paper are as follows:（1）Design,synthesis and activity of o,m,p phthalaldehyde-BODIPY series 1:In this part,the ortho,meta,and para-dibenzaldehyde are connected to the BODIPY,which the asymmetric N≡C-CH₂-BF structure was formed,and three BODIPY probes（BDP 1～BDP 3）were synthesized.The physical,chemical and biocompatibility of the derivatives are explored separately.It is interesting to find that the results were achieved as expected.It is showed that in terms of photophysical properties,the maximum absorption wavelength(λ_abs)was at the range of 627～636 nm,and the maximum fluorescence emission(λ_em)was at the range of 647～654 nm.In the THF/H₂O（volume ratio=2:1）,derivatives all show a good response to glycine.The fluorescence can quench by the the amino acid-BODIPY complex formation through the PET mechanism by the aldehyde recognition group.In the presence of different ions,derivatives all have an obvious quenching effect on glycine.In cell imaging experiments,BDPs have obtained ideal targeted results and are expected to be visual fluorescent probes with amino acid recognition.（2）Design,synthesis and activity exploration of chalcone-BODIPY series 2:In this part,the BODIPY core is combined with the drug intermediate chalcone-polydiethoxyacetaldehyde group and four fluorescent BODIPYs core,and two new derivatives（BDP 4,BDP 5）are finally prepared.In this paper,the photophysical activity of the products was investigated,and it showed that in methanol solution,the maximum emission and absorption wavelength of BDPs was at 524 nm and 530 nm,respectively.Relative to the raw material,both the maximum absorption and emission peak of synthesized products got a redshift.In addition,biocompatibility studies have achieved desirable results.Ideal anti-proliferative on He La cancer cell line(IC₅₀=63±5.67)was observed when treated with BDP 5.The apoptosis-inducing effect of compound BDP 5（0.55%）was better than that of the reference drug berberine（0.26%）.Finally,the ideal imaging results of the new derivatives were obtained on the confocal imaging technology.What’s more,BDP 4 and BDP 5 have good spectral performance and biocompatibility,be and it is expected to ideal fluorescence imaging tools.（3）Design,synthesis and activity exploration of pyridine quaternary ammonium salt-BODIPY series 3:In this part,pyridinium chloride salt is introduced into BODIPY core to prepare water-soluble BODIPY derivatives BDP 6 and BDP 7.The ethylenediamine acts as a bridge connecting the core and hydrophilic group,and the hydrophilic group of the quaternary ammonium salt further enhances the solubility in an aqueous medium.It shows that BDP 6 and BDP 7 have obvious antibacterial and anticancer activities.In ion titration experiments,BODIPY derivatives showed H₂S recognition,which provides a new possibility for the realization of highly selective fluorescent probes.Therefore,this article successfully synthesized a series of promising water-soluble BODIPY new fluorescent probes.