苯丙素类化合物环糊精超分子体系研究
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摘要
第一章环糊精具有独特的内疏水外亲水大环穴腔结构,能通过静电、氢键、疏水等作用识别离子和分子客体。本章简单介绍了环糊精的发展历史、结构特点和分子识别作用,简述了其在药物领域的研究进展、分子模拟的特点及在超分子领域的相关应用。
第二章合成了羟丙基-β-环糊精与咖啡酸固态包合物,借助红外光谱和差示扫描量热谱对其进行了表征。详细探讨了浓度、pH值、温度等因素对包合过程的影响。结果表明:二者形成化学计量1:1包合物,pH=3.0时包合常数达到最大值,为580L/mol。进一步利用核磁共振技术研究了包合机理:羟丙基-β-环糊精能调节自身空腔大小,从而使咖啡酸的苯环和部分烯键插入其疏水空腔,而羧基部分则伸出空腔进入极性较强的水溶剂中。
第三章采用荧光光谱法比较研究了阿魏酸与β-环糊精、羟丙基-β-环糊精在水溶液中的包合作用,结果表明:酸性介质中羟丙基-β-环糊精对阿魏酸的包合效果较好,包合常数达到最大值,为560L/mol。利用核磁共振氢谱和分子模拟研究了阿魏酸与β-环糊精和羟丙基-β-环糊精包合作用的空间构型,结果表明:阿魏酸从β-环糊精小口端进入其空腔,阿魏酸与羟丙基-β-环糊精作用的取向则相反。苯环和部分烯键位于环糊精腔内,-COOH处在环糊精的腔外。
第四章采用紫外光谱、荧光光谱、一维和二维核磁共振谱、分子模拟方法研究了三种苯丙素类化合物与β-环糊精的相互作用机理,结果表明:阿魏酸、咖啡酸和绿原酸与β-环糊精形成包合物后,体系的紫外吸收光谱出现减色效应,荧光光谱出现荧光增强效应和蓝移效应;从一维、二维核磁图谱和分子模拟的结果可知,客体分子都是其位阻相对较小的一端从β-环糊精的小口端进入环糊精的空腔内,包合位置基本一致,经过能量对比得到了最稳定的包合模式。
第五章采用饱和水溶液法和研磨法制备了阿魏酸、咖啡酸和绿原酸和不同环糊精的固体包合物,比较了它们的产率、借助红外和差示扫描量热光谱对它们进行了表征、并详细考察了几种包合物的溶解性、稳定性和抗氧化性等理化性质的变化。结果表明:包合物对光、热的稳定性得到改善,溶解度得到提高,抗氧化性显著增强。
Chapter 1:The unique cavity structure of cyclodextrin can recognize ions and molecules via electrostatic,hydrogen-bonding,hydrophobic interactions. This chapter reviewed the history,structural feature and recognition interaction of cyclodextrin and the application of cyclodextrin on medicine, and made a brief description of the feature of molecular modeling and its correlative application in the domain of supramolecular.
Chapter 2:The solid inclusion compounds of caffeic acid with Hydroxypropyl-β-cyclodextrin were characterized via IR spectra and DSC curves.Experimental conditions including concentrations of Hydroxypropyl-β-cyclodextrin,media acidity and temperature were investigated for the inclusion formation in aqueous in detail.The results showed that the stoichiometry was 1:1 and the maximum association constant was 580L/mol at pH 3.0.According to the NMR results,the Hydroxypropyl-β-cyclodextrin was found to be able to adjust its conformation to fit the size of caffeic acid,and the lipophilic aromatic ring and the portion of ethylene penetrated into the hydrophobic cavity of Hydroxypropyl-β-cyclodextrin,the -COOH group was exposed outside the Hydroxypropyl-β-cyclodextrin cavity.
Chapter 3:The interaction of ferulic acid withβ-cyclodextrin was compared with that of hydroxypropyl-β-cyclodextrin.Experimental conditions including concentrations of the two cyclodextrins and media acidity were investigated for the inclusion formation in detail.The results suggested that the interaction of ferulic acid with hydroxypropyl-β-cyclodextrin is much stronger than that withβ-cyclodextrin at any pH studied,the maximum association constant was 560L/mol at pH 3.0 Based on the NMR data,FA was entrapped inside the hydrophobic core ofβ-CD with the lipophilic aromatic ring and portion of ethylene from the narrow-diameter side which was opposite to FA/HP-β-CD.phenol and methoxy groups were in and the -COOH group was out the cavity ofβ-cyclodextrin.
Chapter 4:The mechanism of the interaction between the Phenyl-crylic acid andβ-cyclodextrin were discussed by UV-Vis,fluorescence spectroscopy and nuclear magnetic resonance spectroscopy(NMR).As a result,the UV-Vis spectroscopy appeared the effect of lose lusture,fluorescence spectroscopy appeared the opposite effect of einstein shift.According to the result of NMR and molecular modeling,all the object moleculars which part the resistance was weak penetrated the cavum ofβ-CD from the narrow side.
Chapter 5:Water-soluble inclusion compounds of ferulic acid、caffeic acid and chlorogenic acid withβ-cyclodextrin and hydroxypropyl-β-cyclodextrin were prepared by two methods:complexation in solution and complexation by kneading,compared the inclusion ratio of these complexes,characterized via IR spectra and DSC technique.The solubilization,antioxidation and stabilization of inclusion compounds were investigated in detail. Experimental results on the stability of these inclusion compounds against light and heat proved the benefits.The water solubility and antioxidation of the inclusion compounds were improved obviously.
第二章合成了羟丙基-β-环糊精与咖啡酸固态包合物,借助红外光谱和差示扫描量热谱对其进行了表征。详细探讨了浓度、pH值、温度等因素对包合过程的影响。结果表明:二者形成化学计量1:1包合物,pH=3.0时包合常数达到最大值,为580L/mol。进一步利用核磁共振技术研究了包合机理:羟丙基-β-环糊精能调节自身空腔大小,从而使咖啡酸的苯环和部分烯键插入其疏水空腔,而羧基部分则伸出空腔进入极性较强的水溶剂中。
第三章采用荧光光谱法比较研究了阿魏酸与β-环糊精、羟丙基-β-环糊精在水溶液中的包合作用,结果表明:酸性介质中羟丙基-β-环糊精对阿魏酸的包合效果较好,包合常数达到最大值,为560L/mol。利用核磁共振氢谱和分子模拟研究了阿魏酸与β-环糊精和羟丙基-β-环糊精包合作用的空间构型,结果表明:阿魏酸从β-环糊精小口端进入其空腔,阿魏酸与羟丙基-β-环糊精作用的取向则相反。苯环和部分烯键位于环糊精腔内,-COOH处在环糊精的腔外。
第四章采用紫外光谱、荧光光谱、一维和二维核磁共振谱、分子模拟方法研究了三种苯丙素类化合物与β-环糊精的相互作用机理,结果表明:阿魏酸、咖啡酸和绿原酸与β-环糊精形成包合物后,体系的紫外吸收光谱出现减色效应,荧光光谱出现荧光增强效应和蓝移效应;从一维、二维核磁图谱和分子模拟的结果可知,客体分子都是其位阻相对较小的一端从β-环糊精的小口端进入环糊精的空腔内,包合位置基本一致,经过能量对比得到了最稳定的包合模式。
第五章采用饱和水溶液法和研磨法制备了阿魏酸、咖啡酸和绿原酸和不同环糊精的固体包合物,比较了它们的产率、借助红外和差示扫描量热光谱对它们进行了表征、并详细考察了几种包合物的溶解性、稳定性和抗氧化性等理化性质的变化。结果表明:包合物对光、热的稳定性得到改善,溶解度得到提高,抗氧化性显著增强。
Chapter 1:The unique cavity structure of cyclodextrin can recognize ions and molecules via electrostatic,hydrogen-bonding,hydrophobic interactions. This chapter reviewed the history,structural feature and recognition interaction of cyclodextrin and the application of cyclodextrin on medicine, and made a brief description of the feature of molecular modeling and its correlative application in the domain of supramolecular.
Chapter 2:The solid inclusion compounds of caffeic acid with Hydroxypropyl-β-cyclodextrin were characterized via IR spectra and DSC curves.Experimental conditions including concentrations of Hydroxypropyl-β-cyclodextrin,media acidity and temperature were investigated for the inclusion formation in aqueous in detail.The results showed that the stoichiometry was 1:1 and the maximum association constant was 580L/mol at pH 3.0.According to the NMR results,the Hydroxypropyl-β-cyclodextrin was found to be able to adjust its conformation to fit the size of caffeic acid,and the lipophilic aromatic ring and the portion of ethylene penetrated into the hydrophobic cavity of Hydroxypropyl-β-cyclodextrin,the -COOH group was exposed outside the Hydroxypropyl-β-cyclodextrin cavity.
Chapter 3:The interaction of ferulic acid withβ-cyclodextrin was compared with that of hydroxypropyl-β-cyclodextrin.Experimental conditions including concentrations of the two cyclodextrins and media acidity were investigated for the inclusion formation in detail.The results suggested that the interaction of ferulic acid with hydroxypropyl-β-cyclodextrin is much stronger than that withβ-cyclodextrin at any pH studied,the maximum association constant was 560L/mol at pH 3.0 Based on the NMR data,FA was entrapped inside the hydrophobic core ofβ-CD with the lipophilic aromatic ring and portion of ethylene from the narrow-diameter side which was opposite to FA/HP-β-CD.phenol and methoxy groups were in and the -COOH group was out the cavity ofβ-cyclodextrin.
Chapter 4:The mechanism of the interaction between the Phenyl-crylic acid andβ-cyclodextrin were discussed by UV-Vis,fluorescence spectroscopy and nuclear magnetic resonance spectroscopy(NMR).As a result,the UV-Vis spectroscopy appeared the effect of lose lusture,fluorescence spectroscopy appeared the opposite effect of einstein shift.According to the result of NMR and molecular modeling,all the object moleculars which part the resistance was weak penetrated the cavum ofβ-CD from the narrow side.
Chapter 5:Water-soluble inclusion compounds of ferulic acid、caffeic acid and chlorogenic acid withβ-cyclodextrin and hydroxypropyl-β-cyclodextrin were prepared by two methods:complexation in solution and complexation by kneading,compared the inclusion ratio of these complexes,characterized via IR spectra and DSC technique.The solubilization,antioxidation and stabilization of inclusion compounds were investigated in detail. Experimental results on the stability of these inclusion compounds against light and heat proved the benefits.The water solubility and antioxidation of the inclusion compounds were improved obviously.
引文
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