Construction And Detection Of Two-component Fluorescence Probe For Monosaccharides And Glycosides

The study for monosaccharides and glycosides is one of the topic project in the interdisciplinary field of chemical, material and medicine sciences. In the dissertation work, based on the property of boronic acid and diol units forming cyclic boronate esters, some two-component fluorescence probes with fluorescent dyes and quenchers are designed and prepared. The interactions of these probes with monosaccharides, forsythoside A, forsythin and phillygenin are investigated by fluorescence analysis technique. Additionally, due to Lewis bases and boronic acid generating boronate, the interactions of the probe with common anions are also studied. And the detail research contents are as follows:1) Based on the characteristics of conjugated polyelectrolyte with strong capture ability and amplification signal for light, a polyelectrolyte with fluorene groups is synthesized as a fluorescent reported unit and constructed a fluorescent probe with m-BBV. According to the designed mechanism, the enhancement of fluorescence intensity of the probe is observed with the introduction of monosaccharides. Additionally, the concentration of saccharides in the diabetic blood can be detected by the probe. Furthermore, the interactions of the probe with three main ingredients of Fructus Forsythiae are also studied. The results show that the three ingredients can lead to the intensity reduction of the probe, and the interaction of the probe with forsythoside A is the most prominent.2) A new type quencher S-BINOLPB with boronic acids is designed and synthesized. In the quencher, the boronic acid group is linked directly with pyridine ring, which will promote the transfer of charge from B- to N+. Compared with viologen BBVs, the type quencher can more efficiently bind with saccharides and glycosides. The interaction of HPTS/S-BINOLPB probe with seven monosaccharides are investigated by fluorescence technique. The results display that the probe has very high sensitivity for these monosaccharides. Additionally, the concentration of saccharides in the diabetic blood can be detected by the probe. Furthermore, the probe can discriminate three main ingredients of Fructus Forsythiae (Phillygenin, Forsythin and Forsythoside A). Due to many diol units of forsythoside A, the intensity enhancement of the probe is the most obvious.3) In order to develop the type quenchers and determine their properties, seven quenchers with boronic acid groups and pyridine salts are designed and prepared. These quenchers have different charges, boronic acid groups and space structures. Through the fluorescence quenching technique, the interactions of these quenchers with HPTS are studied. The results show that the quenching actions are enhanced with the increase of charges and boronic acid groups. Upon introduction D-glucose into these probes, which are combined with HPTS and quenchers respectively, the most remarkable enhancement of fluorescence intensity in these probes is the TCTB/HPTS. Next, the probe of TCTB/HPTS has all high response signal with other monosaccharides and can be applied to detect the concentration of saccharides in diabetic blood. Similarly, the main ingredients of Fructus Forsythiae also are recognized by the probe. The work may provide a new way for detecting the ingredients of Chinese Medicine by fluorescence technique.4) A specific fluorescent probe for anions is constructed based on the property of boronic acid and cyanide anion forming boronate. The novel sensing probe is a two-component probe, which is comprised of a water-soluble conjugated polyelectrolyte (PBPYRSO3Na) and a boronic acid subsituted pyridine salt (TCTB). In the probe, the polyelectrolyte is used as a fluorescent signal unit, and the pyridine boronic acid acts as receptor and quencher. The two-component probe shows a fluorescence reversible "off-on" response toward cyanide and phosphate anions based on different binding ways. Furthermore, this optical probe may provide a method for the development of highly sensitive and selective fluorescence probes for cyanide, phosphate anions and other analytes.