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Synthesis of Water-Soluble Calix[n]arenes and Spectrometric Studies on Its Inclusion Interaction to Several Kinds of Drugs

Author: LuQin
Tutor: ZhouYunYou
School: Anhui Normal University
Course: Analytical Chemistry
Keywords: water-soluble calixarenes acridines, quinolones vitamins fluorescence spectra inclusion interaction
CLC: TQ460.1
Type: Master's thesis
Year: 2006
Downloads: 121
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Abstract


Water-soluble calixarenes are a kind of important calixarenes, which have been one of the current scientific fronts due to their well characteristics on molecular recognition, catalyst and biological activities. In this work, two most popular water-soluble calixarenes─p-sulfonated calix[4]arene (SC4A), p-sulfonated calix[6]arene (SC6A) were synthesized and chosen as research objects, the inclusion interaction between them and several kinds of drugs, such as acridines, quinolones and vitamins were investigated by fluorescence spectrometry and absorption spectrometry. On the one hand, the research extends the molecular recognition range of p-sulfonated calix[n]arenes (n=4, 6) towards guest molecules; developes new methods and techniques for determination of drugs based on supramolecular inclusion complexation. On the other hand, the work provides useful supports in theory for water-soluble calixarenes as novel drug carriers. The content consists of following five chapters:In chapter 1, first a general introduction to the origin of calixarenes and the progress of their application on molecular recognition were presented. Second, the application of water-soluble calixarenes on molecular recognition and the interaction between them and bio-active compounds were summarized. Finally, based on the concerning updated development and our experiment conditions, the research proposal for this thesis was presented.In chapter 2, p-tert-butyl calix[4, 6]arene, debutyl calix[4, 6]arene and p-sulfonated calix[4, 6]arene were prepared according to literatures and identified by 1HNMR. Preliminary study of the inclusion behavior of SC4A towards acridine and 9-amino-acridine was performed. The main driving force for the formation of inclusion complex and the inclusion pattern were deduced.In chapter 3, the inclusion behavior of SC4A and SC6A towards five quinolones was investigated in detail. The various factors affecting the inclusion process such asβ-cyclodextrin, surfactants, ionic strength and ethanol were examined particularly. Based on supramolecular inclusion complex, a novel sensitive spectrofluorimetric method for determination of lomefloxacin was developed and was applied successfully to determination of lomefloxacin in pharmaceutical formulations. The inclusion constants of SC4A and SC6A towards five quinolones were estimated by non-linear least squares method, and the inclusion pattern was proposed with the help of 1H NMR research.In chapter 4, the inclusion interaction of SC4A and SC6A towards several

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