Synthesis Of Water-soluble Calixarene Derivatives And Application In Bioanalysis

Supramolecular Chemistry originated from the discovery of crown ethers and was further developed as host-guest chemistry and supramolecular chemistry by D. J. Cram and J. M. Lehn. Calixarene was the representative of the third generation supramolecular. Different functional groups were introduced to the calixarene in this paper. With their different electric, good water solubility and spectral activity of nature, not only water-soluble ability of calixarene was enhanced significantly, but also the application of calixarene derivatives in the spectrum and molecular recognition was enlarged. Water-soluble calixarene derivatives and spectral activity of calixarene derivatives were synthesized in this paper .In order to study the feasibility of the p-sulfoniccalix[8]arene as controlled-release drug delivery agents in pharmaceutical industry, the inclusion behavior between p-sulfoniccalix[8]arene and quinolones or quinolones drugs were investigated. This study demonstrated the potential application of calixarene derivatives in biology and pharmaceutics. There were some paragraphs in this paper as following.The research significance of calixarene, the research of water-soluble calixarene derivatives and azobenzene calixarene derivatives, the applications of calixarene and its derivatives in molecular recognition, the main content and characteristic of this paper were summarized in first paragraph.Tert-butylcalix[n]arene (n=4,8) and intermediate de-tert-butylcalix[n]arene were synthesized with one-step method in the second paragraph, and further benzene sulfonic acid and the acid azo introduced into the off-tert-butyl calixarenes, the synthesis of a calix[8]arene, calix sulfobenzylidene[n]arene (n=4,8). Infrared spectroscopy, ultraviolet spectroscopy, elemental analysis were used to characterize the structure of the synthesized product , the reaction process was tracked using thin layer chromatography, and the purity of the synthesized product was characterized with liquid chromatography. Finally, the product factors in the experiment were discussed.In the third paragraph, the inclusion behavior between p-sulfoniccalix[8]arene and quinolones drugs were investigated by fluorescence spectroscopy. The optimum conditions of forming host-guest systems in aqueous solution were studied.Meanwhile, in order to discuss the mechanism of inclusion process, the various influence on the inclusion process, such as temperature, pH value, concentrations of host and guest compounds, surfactants, organic solvent were also examined. On the base of experimental results, the association constant K and combined ratio (n) were calculated. Subsequently, the addition of bovine serum albumin (BSA) solution into the host-guest system leads to the recovery of fluorescence intensity. It is indicated that BSA may destruct the SC8A-NFLX inclusion complex, and liberate the NFLX into solution.In the fourth paragraph, the inclusion behavior between p-sulfoniccalix[n]arene and phenothiazine methylene blue and toluidine bule with fluorescence spectroscopy and UV absorption spectroscopy. The mechanism of inclusion process between p-sulfoniccalix[n]arene and quinolones drugs were discussed.In the fifth paragraph, the protein in milk was determinated using methylene blue as the probe with fluorescence spectrophotometry of p-sulfoniccalix[6]arene-methylene blue -BSA system. The best formation conditions of the calix [6] arene-methylene blue supramolecular systems were discussed, and a low detection limit, high sensitivity detection method was established. The method was used in real samples and the experiment results were satisfactoryIn the sixth paragraph, the jobs in this paper were summarized and the jobs in future were also discussed.