Design, Synthesis And Identification Of Multi-signal Functional Molecular Probes Based On Xanthene And Its Derivatives

Recently, fluorescent probes, with the excellent properties of high specifity and sensitivity, wide responding range, accurate rapid real-time response, clear visibility response and well environmental and biological compatibility, have become more and more important in tracking of the heterogeneous recognition behaviors and the information expression from the internal status of the complicated biological and environmental systems. It has become an indispensable technical methods with broad application prospects in the areas of modern environmental science, material science, food science, information science, pharmacology and physiology, cell biology and molecular geneticsCurrently, the research of fluorescent probes is coming to the trendcy of the thorough in mechanism and diversification in molecular function as well as the inclined to practical applications in the field of environmental and life science. Xanthene and related derivatives, including rhodamine and fluorescein, have become the most extensively used model in construction of novel photosensitive fluorescent probes with excellent optical properties. Research breakthroughs in this field are constantly emerging.Based on the summarization of reported works and our previous resrarches, two types of xanthene based probes with wonderful recognition performances were designed and synthesized in the present work on the basis structure of xanthene hydrazide and xanthene acyl chloride. Our studies were carried out as follows:1. The produce of fluorescence and related parameters were introduced. The recent progress in detection of metal ions, pH, commen anions, reactive oxygen species, reactive nitrogen species, thiols, proteins and nucleic acids were reviewed.2. Based on the structure of rhodamin B hydrazide, nine unreported probes la-li with cinnamyl aldehyde Schiff base functional group were designed and synthesized. The chemical structures were characterized. The recognition properties of the probes toward Cu2+ and the effect of different substituent group were then investigated. In addition, we also explored the recognition mechanism and the application potential of the probes in cell imaging of Cu2+ in human cervical cancer cells, mouse fibroblast cells and bacteria-EPS-mineral aggregates.3. Based on the thiophile property of Hg2+, the structure of rhodamin B thiohydrazide was contructured and nine unreported probes 2a-2i with cinnamyl aldehyde Schiff base functional group were then designed, synthesized and characterized. The recognition properties toward Hg2+ and the effect of substituent group were then studied detailedly. The recognition mechanism and the application potential of the probes in cell imaging of Hg2+ in mouse fibroblast cells were also invesitgated.4. Based on the structure of rhodamin B acyl chloride, three probes BJA-BJC with five-membered spiro ring and phenylhydrazines functional group were designed and synthesized. The X-ray single crystal and 2D NMR spectra were used to classify the isomeride of the five-and six-membered structures. The recognition properties, the recognition mechanism and the application potential of the probes in cell imaging of Cu2+ in mouse fibroblast cells have also been carried out.5. Based on the structure of rhodamin B acyl chloride, three probes JA-JC with six-membered spiro ring and hydrazinobenzothiazole functional group were designed and synthesized. To distinguish the isomeride of the five- and six-membered structures, we also use the X-ray single crystal in combination with 2D NMR spectra. We also took deep investigation in the recognition properties and the recognition mechanism. The application properties of the probes in cell imaging of Hg2+ in human cervical cancer cells, mouse fibroblast cells and bacteria-EPS-mineral aggregates have also been successfully performed.