Construction And Application Of Novel Thiophene And Pyridine Modified BODIPY Dyes

Mitochondria play an important role in regulating cell redox potential and signal transduction,regulating cell differentiation and apoptosis,gene expression and transmembrane transport.It is part of the most vital organelles in cell life.Studies have shown that changes in the number,distribution,structure and function of mitochondria are associated with neurodegenerative diseases?such as Alzheimer's disease,Parkinson's disease?,metabolic diseases?such as obesity,type II diabetes?,and neurodegenerative diseases?such as Alzheimer's disease,Parkinson's disease?,Cardiovascular disease and cancer and other diseases are closely related.Therefore,it is of great biological significance to trace the morphological changes of mitochondria in order to deeply study the life activities of objects.In the near infrared region?650-900 nm?,the absorption,scattering and spontaneous fluorescence background of the tissue is much smaller than that of the visible region.The near infrared dyes have significant advantages in resisting background interference,biological safety and sensitivity of detection,etc.It is particularly suitable for the construction of fluorescent probes and nondestructive monitoring in living organisms?zebra fish,mice,etc.?.Therefore,there is still a lot of work to do in order to build the near infrared fluorescent dyes with the ability of targeting mitochondria.As a sensitive non-invasive detection technique,fluorescent probes have been largely used in biological detection and mechanism research.Since the frequent use of Pd in modern synthetic chemistry and medicine may result in trace residue of Pd in water or pharmaceutical and chemical products,the threshold of Pd in pharmaceutical products is strictly limited to 5 ppm.by the European Drug Assessment Agency?EMEA?.On the other hand,Pd exists in biological cells in the form of Pd²⁺,which can be binding to a variety of bioactive molecules?such as proteins,amino acids,DNA or RNA,etc.?may be harmful to a variety of life processes and lead to a series of diseases.Therefore,the detection and monitoring of the concentration of Pd²⁺in biological cells is of great biological significance in the study of life phenomena and the diagnosis of diseases.In order to solve that problem that the BODIPY dye has a short wavelength,poor water solubility and no sub-organelle targeting property.in that structure of BODIPY or Aza-BODIPY,we transform the connection site,and transform the connection mode of the BIPY framework and the BODIPY framework?1-2-base,1-2-3-base and 1-4-group?,and the BODIPY-like dye with different structure is synthesized through different synthetic routes,And the part of the BODIPY dye is subjected to quaternary salt precipitation.The method is mainly based on two points:firstly,the wavelength of the dye is red by the ICT mechanism,so that the structure requirement of the preparation of the near-infrared dye can be met,and the molecular weight of the BODIPY is not small;and the second point,In the first quarter of the period,the red shift of the absorption and the fluorescence emission can significantly improve the water solubility of the dye,and the dye has the mitochondrial targeting ability at the same time.12 new BODIPY dyes,10 new BODIPY dyes,10 new BODIPY dyes and 6 polyurethane salt-modified BODIPY dyes were synthesized,and their relevant spectrum tests were carried out,and it was found that due to the ICT mechanism,The absorption of the modified BODIPY dye and the fluorescence emission wavelength of the modified BODIPY dye are red-shift,and the wavelength of the dye after the salt-modified BODIPY-based dye is further red-shifted.There are a lot main uses of fluorescent dyes,such as fluorescence probe detection,biological tissue staining,photodynamic therapy and so on.If the research direction of our research group is always used for fluorescence probe detection,we first designed a new recognition group alkyne group fluorescence probe to detect Pd²⁺expectation alkyne group as a new recognition group can have excellent performance compared with the traditional recognition group propargyl group.Therefore,water-soluble carboxy BODIPY dye was selected as a model compound to verify the correctness and applicability of the mechanism.A new fluorescence probe based on meso-Carboxyl BODIPY,with 1,3,5,7-tetramethyl-BODIPY as fluorescent group and butterfly ester as recognition group was developed to detect Pd²⁺,and its response time,sensitivity,selectivity,anti-interference,pH stability and the ability to detect Pd²⁺in A549 cells were tested and evaluated.It was found that the alkynyl group was similar to the commonly used propargyl recognition group,and the alkynyl group could still be used for the detection of Pd²⁺.However,the response speed looks forward.