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The Study of Building of Drug/Cyclodextrins Supramolecular System and Their Applied Properties

Author: SunXinChao
Tutor: YangBo
School: Kunming University of Science and Technology
Course: Medicinal Chemistry
Keywords: β-cyclodextrin complex artemether scutellarin binding
CLC: TQ460.1
Type: Master's thesis
Year: 2009
Downloads: 57
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Abstract


Recently, cyclodextrins (CDs) have been widely used in pharmaceutical, chemical industry, agriculture, consumer goods and bio-technology and other fields around home and abroad. Cyclodextrins can be chemically modified to give us a variety of derivatives, not only to expand its original molecular binding ability, but also to change its molecular selectivity. The molecular recognition and assembly of chemical modified cyclodextrins have become the significant topic of supramolecular chemistry. In order to reveal mechanism of the molecular recognition and their potential application in drug delivery system, firstly, complex and de-clathration of perilla frufescens seed oil-β-cyclodextrin was carried out. The infrared spectroscopy (IR), thermal analysis (TGA-DSC) method were used to verify the solid inclusion complex. Secondly, the inclusion complexes of artemether and hydroxypropyl P-cyclodextrin was prepared by the the insoluble and active drug artemether and hydroxypropylβ-cyclodextrin. High-Performance Liquid Chromatography was used to detected the inclusion complex. And then, five kinds of modified cyclodextrins were synthetized. The synthetized cyclodextrins derivatives were used to design and synthesis the binding complexes of scutellarin and cyclodextrin. The water solubility of the binding complexes was studied, as well as. The paper included the following sections.(1) A brief description of research progress and important achievements of supramolecular chemistry, molecular recognition of cyclodextrin and its derivatives with natural medicines, drug carrier of cyclodextrin conjugations.(2) Solid inclusion complexes of theβ-cyclodextrin with perilla seed oil which was extracted with hexane, was prepared by solution method. The complexes was verified by IR and TGA-DSC. TGA curves and DSC curves proved that inclusion complex was formed and the thermal stability was enhanced. De-clathration curves showed that the De-clathration rate of inclusion complex reduced, and the stability was enhancement. The results showed that perilla seed oil andβ-CD formed 1:1 inclusion complexes. The De-clathration was carried out by soxhlet extraction, as a result the De-clathration was got, which proved the feasibility of the De-clathration. Perilla seed oil-β-cyclodextrin inclusion was prepared in this way. The inclusion of artemether and hydroxypropyl (3-cyclodextrin was prepared. The inclusion was verified by High-Performance Liquid Chromato-graphy. The results showed that the content of artemethe in inclusion fully meet the requirement of experiment.(4) Five kinds ofβ-cyclodextrin derivatives which structural charcterization were verified by NMR, IR and so on, were synthesized. The results showed that the synthesis method was correct. And the target intermediate could be synthesized in this way.(5) In three different ways, the conjugations of scutellarin and cyclodextrins was synthesized, using the prepared derivatives of cyclodextrin as the intermediate. The structural characterization of the compound we synthesized was verified by NMR and IR. And the water solubility of the compound was studied, as well. The results showed that conjugations of scutellarin and cyclodextrins had prospects of prodrug.

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