荧光传感为导向的几种环糊精衍生物的键合及组装行为
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摘要
超分子化学是当代化学的前沿领域和热门学科,尤其以环糊精为媒介构筑功能超分子组装体为最重要分支之一。首先,为了研究以环糊精为模块构筑分子组装体的驱动力,本文考察了天然α-环糊精在液相以及固相对模型客体分子的键合行为。其次,本文利用化学修饰桥联环糊精与水溶性卟啉构筑具有光学行为的超分子组装体,并考察了主体与卟啉客体之间的FRET行为,论证了大分子聚集体在构筑光学活性组装体中的优势。进一步,环糊精作为生物相容性良好的主体大环主体在生物学领域得到广泛应用,本文修饰了几种天然环糊精并探讨了其在生物学领域的应用。具体研究内容如下：
1.简要地介绍了超分子化学的概况,对环糊精化学、基于环糊精的能量转移体系、以环糊精为受体的分子识别和分子组装所取得的主要成果和最新进展进行了综述。
2.利用"click"化学合成了氟硼荧修饰的桥联全甲基化-β-环糊精,该主体化合物与水溶性卟啉在溶液中自组装行成1D线性聚集体,通过光谱实验观察到组装体内部高效的FRET行为,随着全甲基化-β-环糊精的加入组装体解聚并伴随能量转移效率的降低,进而利用化学计算和分子模拟的手段阐述了大分子聚集体在能量转移效率上体现出优势的原因。
3.考察了天然α-环糊精与两个偶氮吡啶同分异构体的在液相与固相中络合行为,并说明了主体与客体分子之间在液相与固相包结的驱动力区别；进一步,单晶衍射结果表明,同分异构体的细微差别造成主客体在固态下包结模式的巨大差异,客体分子经历了从液相到固相的部分释放过程。
4.合成了罗丹明内酰胺修饰的天然β-环糊精,首次发现了有机客体分子驱动边臂开环的过程,并初步探索了该主体分子在脂肪氨基酸传感中的应用。
5.通过吡啶二甲酸修饰的天然β-环糊精与稀土金属铽(Ⅲ)较强的键合能力以及环糊精空腔与精胺修饰的金刚烷客体分子强络合作用构筑了类树枝状的基因载体,考察了该基因载体对质粒DNA的凝聚行为并初步探讨了该基因载体在生物学中的应用。
Supramolecular chemistry is a frontier research field and hotpot subject in current chemistry, where construction of functional supramolecular assembly mediated by cyclodextrin is one of the most impotant branches. In this text, the binding behavior between native a-cyclodextrin and model guest molecules either in aqueous or solid state were investigated in order to illustrate the driving forces during the assembly process. Moreover, chromatophore modified permethyl-β-cyclodextrins was synthesized and a 1D linear assembly was logically arrayed between this modified permethyl-β-cyclodextrins and sulphonated porphyrins, where FRET behavior was observed from chromatophore to prphyrin. Further, cyclodextrin was comprehensively used in biology due to its benign biocompatible and in this text several modified native cyclodextrin was synthesized and explored their usage in this field. The major contents of this thesis are as follows:
1. The general aspect of supramolecular chemistry was described briefly, and the cyclodextrin chemistry, energy transfer systems based on cyclodextrin and new progress and important achievement on molecular recognition and assembly of cyclodextrin were reviewed respectively.
2. BODIPY bridged permethyl-β-cyclodextrins was synthesized successfully via "click" chemistry and the formation of 1D supramolecular assembly between this host compound and water soluble porphyrin was intuitionistic constructed. The FRET behavior within this assembly was observed and the differences in energy transfer efficiency between the assembly and the 1:1 inclusion compound was elaborated by the method of computation and molecular simulation.
3. The compelexation between native a-cyclodextrin and two azopyridine isomers were investigated either in aqueous solution or solid state, and the different driving forces during the process of host complexation with guest molecules were illustrated. Further, the trival differences among guest isomers will lead to the huge different packing mode of inclusion compound in solid state, guest molecules was partially released during the phase transfer from solution to solid.
4. Rohdamine derivative modified nativeβ-cyclodextrin was synthesized and organic compound driving this compound from ring-closed to ring-opened state was firstly discovered. Futher usage of this compound to sensor of amphatic amino acid was investigated.
5. A gene vector was constructed by 2,6-pyridinedicaboxylic acid modified cyclodextrin, Tb(Ⅲ) and spermine modified admatane. The condensation of pDNA induced by this gene vector was investigated through several methods and its usage in biology was investigated for the first stage.
1.简要地介绍了超分子化学的概况,对环糊精化学、基于环糊精的能量转移体系、以环糊精为受体的分子识别和分子组装所取得的主要成果和最新进展进行了综述。
2.利用"click"化学合成了氟硼荧修饰的桥联全甲基化-β-环糊精,该主体化合物与水溶性卟啉在溶液中自组装行成1D线性聚集体,通过光谱实验观察到组装体内部高效的FRET行为,随着全甲基化-β-环糊精的加入组装体解聚并伴随能量转移效率的降低,进而利用化学计算和分子模拟的手段阐述了大分子聚集体在能量转移效率上体现出优势的原因。
3.考察了天然α-环糊精与两个偶氮吡啶同分异构体的在液相与固相中络合行为,并说明了主体与客体分子之间在液相与固相包结的驱动力区别；进一步,单晶衍射结果表明,同分异构体的细微差别造成主客体在固态下包结模式的巨大差异,客体分子经历了从液相到固相的部分释放过程。
4.合成了罗丹明内酰胺修饰的天然β-环糊精,首次发现了有机客体分子驱动边臂开环的过程,并初步探索了该主体分子在脂肪氨基酸传感中的应用。
5.通过吡啶二甲酸修饰的天然β-环糊精与稀土金属铽(Ⅲ)较强的键合能力以及环糊精空腔与精胺修饰的金刚烷客体分子强络合作用构筑了类树枝状的基因载体,考察了该基因载体对质粒DNA的凝聚行为并初步探讨了该基因载体在生物学中的应用。
Supramolecular chemistry is a frontier research field and hotpot subject in current chemistry, where construction of functional supramolecular assembly mediated by cyclodextrin is one of the most impotant branches. In this text, the binding behavior between native a-cyclodextrin and model guest molecules either in aqueous or solid state were investigated in order to illustrate the driving forces during the assembly process. Moreover, chromatophore modified permethyl-β-cyclodextrins was synthesized and a 1D linear assembly was logically arrayed between this modified permethyl-β-cyclodextrins and sulphonated porphyrins, where FRET behavior was observed from chromatophore to prphyrin. Further, cyclodextrin was comprehensively used in biology due to its benign biocompatible and in this text several modified native cyclodextrin was synthesized and explored their usage in this field. The major contents of this thesis are as follows:
1. The general aspect of supramolecular chemistry was described briefly, and the cyclodextrin chemistry, energy transfer systems based on cyclodextrin and new progress and important achievement on molecular recognition and assembly of cyclodextrin were reviewed respectively.
2. BODIPY bridged permethyl-β-cyclodextrins was synthesized successfully via "click" chemistry and the formation of 1D supramolecular assembly between this host compound and water soluble porphyrin was intuitionistic constructed. The FRET behavior within this assembly was observed and the differences in energy transfer efficiency between the assembly and the 1:1 inclusion compound was elaborated by the method of computation and molecular simulation.
3. The compelexation between native a-cyclodextrin and two azopyridine isomers were investigated either in aqueous solution or solid state, and the different driving forces during the process of host complexation with guest molecules were illustrated. Further, the trival differences among guest isomers will lead to the huge different packing mode of inclusion compound in solid state, guest molecules was partially released during the phase transfer from solution to solid.
4. Rohdamine derivative modified nativeβ-cyclodextrin was synthesized and organic compound driving this compound from ring-closed to ring-opened state was firstly discovered. Futher usage of this compound to sensor of amphatic amino acid was investigated.
5. A gene vector was constructed by 2,6-pyridinedicaboxylic acid modified cyclodextrin, Tb(Ⅲ) and spermine modified admatane. The condensation of pDNA induced by this gene vector was investigated through several methods and its usage in biology was investigated for the first stage.
引文
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