基于环糊精的超分子囊泡体系及功能响应
摘要
超分子自组装可以形成多种形式的分子有序组合体,囊泡是其中的一种。囊泡是由双亲分子组成的闭合双层膜。囊泡能够同时增溶亲水性和亲油性的物质,因此在生物膜模拟、药物的封装和靶向释放、纳米粒子的合成以及作微反应器等方面都有着重要的应用价值。环糊精是一系列环状低聚糖的总称,它是由6、7、8或更多个D-吡喃葡萄糖单元,通过α-1,4糖苷键连接而成的“锥筒”状分子,分别称为α-CD,β-CD,γ-CD等。环糊精内腔疏水,外腔亲水以及具备的手性微环境,能够选择性的包合多种有机、无机分子,形成各种各样的包合物,进而组装成各种功能体,如凝胶、轮烷和囊泡等。基于环糊精为主体构建的超分子囊泡因其良好的生物相容性,得到越来越多的关注。由环糊精制备的超分子囊泡主要分为两大类,一类是通过对母体环糊精进行共价键的修饰得到两亲性的环糊精表面活性剂,然后再经过后处理得到囊泡体系。一类是通过非共价键作用形成的包合物来得到囊泡体系。后者因其可控性等优点得到越来越多的青睐。
本论文主要由三部分组成,其内容如下：
1.2-O-羧甲基-β-环糊精与二茂铁衍生物在水溶液中的微观聚集形态的研究及混合溶剂对囊泡的影响。本文选用2-O-羧甲基-β-环糊精作为主体分子,1,6-双二茂铁甲基己二胺做为客体分子,通过两者之间的超分子作用力制得了一种新型的囊泡体系。并进一步研究了甲醇、乙醇、异丙醇和叔丁醇对该囊泡体系的影响。最后讨论并提出了囊泡生成和解体的机理模型。
2.2-O-(4-羟基丁酰)-β-环糊精与甲基橙的包合物在水溶液中的微观聚集形态的研究及对pH的响应。本文首次研究了关于甲基橙-环糊精包合物的微观聚集形态。最后,本文研究并讨论了甲基橙与2-O-(4-羟基丁酰)-β-环糊精的包合物形成囊泡的机理以及对pH值的响应特性。
3.功能性主客体分子的合成及潜在应用的初步探索。一方面合成了N-二茂铁甲基十二胺,培养出了该化合物的晶体,并对晶体的结构进行了解析。另一方面探索用工业方法合成了一种新型环糊精醚胺化合物2-O-丙胺基-β-环糊精,以此化合物为中间体合成了三种新型的环糊精衍生物：2-O-丙胺基邻甲基苯甲酰胺-β-环糊精、2-O-丙胺基萘乙酰胺-β-环糊精和2-O-[(N-蒽醌基)丙胺基]-β-环糊精。并用这三种环糊精衍生物作为荧光传感器对阿莫西林、氨苄西林和辛伐他汀进行了荧光测试。
本论文的主要创新点如下：
(1)首次系统的研究了醇的含量对以环糊精为主体的超分子囊泡的影响。并且比较了不同的醇,由于疏水链的不同,以及分子量的不同对囊泡体系的影响。对于扩展囊泡的应用范围有一定的指导意义。
(2)首次研究了环糊精衍生物与甲基橙包合物在水溶液中的微观聚集形态。并研究了该囊泡体系对pH的响应特性。
(3)培养出了具有长的柔性链的二茂铁衍生物的晶体,并对其结构进行了解析。
(4)首次探索用工业方法合成荧光传感器。并将合成得到的传感器进行了药物分子的识别,取得了一定的效果。对于拓展荧光传感器的工业化有一定的参考价值。
The self-assembly of supramolecule can form various forms of assemblies, and vesicles are one of them. Vesicles, which are made up of amphiphiles, are closed bilayers and can solubilize the hydrophilic and lipophilic substances simultaneously. Therefore they can be used in biofilm-simulation, packaging and targeted release of drugs, synthesis of nanoparticles as well as micro-reactors.Cyclodextrins (CDs) are cyclic molecules which conventionally consist of six (a-), seven (P-) and eight (y-) glucose units linked by a-1-4 glycosidic linkages.They have hydrophilic outer surfaces and hydrophobic inner cavities, and can form inclusion complexes by binding organic or inorganic guest molecules based on supramolecular interaction.A number of novel supramolecular assemblies have been designed, such as gels, otaxanes and vesicles.Vesicles based on CDs inclusion complexes have gained much attention for their good biocompatibility. Vesicles prepared from CDs can be divided into two types:one is based on the amphiphilied CDs modified by covalent bond, and the other is based on the supramolecular amphiphiles.The latter attract more attention for their controllability.
The main content of the paper was showed as follows:
1.The study of micro-aggregation based on complex of 2-O-carboxymethyl P-cyclodextrin and ferrocene derivatives in aqueous solution and the effects of mixed solvent on the vesicles. Here, a new vesicle system was prepared based on supramolecular interactions between modified P-CDs (carboxymethyl-p-cyclodextrin, CM-P-CD) and ferrocenyl derivatives (N, N'-bis (ferrocenylmethylene) diaminohexane). The vesicles were studied in water, mixtures of water and alcohols, as well as organic solvents.The mechanism of vesicle formation and dissolution was discussed and proposed.
2.The study of micro-aggregation based on complex of 2-0-(y-hydroxybutyric)-β-cyclodextrin and methyl orange in aqueous solution and pH-responsive properties of the vesicle-like particles.Here, the micro-aggregation based on complex of 2-O-(y-hydroxybutyric)-β-cyclodextrin and methyl orange in aqueous solution was studied for the first time.Then the mechanism and pH-responsive properties of the vesicle-like particles was discussed.
3.The synthesis of functional host-guest molecules and the study of potential application of them.On the one hand, N-(Ferrocenylmethyl)dodecan-1-amine was designed and synthesized and then its crystal structure was grown and analyzed;On the other hand, three new fluorescent sensors base on (3-cyclodextrin were synthesized in industrial method, and then they were used in recognition in amoxicillin, ampicillin and simvastatin.
Main innovations of the thesis:
(1)The effect of alcohols on the vesicles made by cyclodextrins was studied for the first time.The effect of the concentration and alky chain of the alcohols on vesicles was discussed.This research will extend the application of vesicles based on cyclodextrins.
(2)The micro-aggregation based on complex of 2-O-(y-hydroxybutyric)-β-cyclodextrin and methyl orange in aqueous solution was studied for the first time and pH-responsive properties of the vesicle-like particles were discussed.
(3)A crystal of ferrocene derivative with a long flexible chain was obtained and its structure was studied.
(4) Three fluorescent sensors were synthesized in industrial method for the first time and used in identification of amoxicillin ampicillin and simvastatin.The study will extend the application of sensors in industry.
本论文主要由三部分组成,其内容如下：
1.2-O-羧甲基-β-环糊精与二茂铁衍生物在水溶液中的微观聚集形态的研究及混合溶剂对囊泡的影响。本文选用2-O-羧甲基-β-环糊精作为主体分子,1,6-双二茂铁甲基己二胺做为客体分子,通过两者之间的超分子作用力制得了一种新型的囊泡体系。并进一步研究了甲醇、乙醇、异丙醇和叔丁醇对该囊泡体系的影响。最后讨论并提出了囊泡生成和解体的机理模型。
2.2-O-(4-羟基丁酰)-β-环糊精与甲基橙的包合物在水溶液中的微观聚集形态的研究及对pH的响应。本文首次研究了关于甲基橙-环糊精包合物的微观聚集形态。最后,本文研究并讨论了甲基橙与2-O-(4-羟基丁酰)-β-环糊精的包合物形成囊泡的机理以及对pH值的响应特性。
3.功能性主客体分子的合成及潜在应用的初步探索。一方面合成了N-二茂铁甲基十二胺,培养出了该化合物的晶体,并对晶体的结构进行了解析。另一方面探索用工业方法合成了一种新型环糊精醚胺化合物2-O-丙胺基-β-环糊精,以此化合物为中间体合成了三种新型的环糊精衍生物：2-O-丙胺基邻甲基苯甲酰胺-β-环糊精、2-O-丙胺基萘乙酰胺-β-环糊精和2-O-[(N-蒽醌基)丙胺基]-β-环糊精。并用这三种环糊精衍生物作为荧光传感器对阿莫西林、氨苄西林和辛伐他汀进行了荧光测试。
本论文的主要创新点如下：
(1)首次系统的研究了醇的含量对以环糊精为主体的超分子囊泡的影响。并且比较了不同的醇,由于疏水链的不同,以及分子量的不同对囊泡体系的影响。对于扩展囊泡的应用范围有一定的指导意义。
(2)首次研究了环糊精衍生物与甲基橙包合物在水溶液中的微观聚集形态。并研究了该囊泡体系对pH的响应特性。
(3)培养出了具有长的柔性链的二茂铁衍生物的晶体,并对其结构进行了解析。
(4)首次探索用工业方法合成荧光传感器。并将合成得到的传感器进行了药物分子的识别,取得了一定的效果。对于拓展荧光传感器的工业化有一定的参考价值。
The self-assembly of supramolecule can form various forms of assemblies, and vesicles are one of them. Vesicles, which are made up of amphiphiles, are closed bilayers and can solubilize the hydrophilic and lipophilic substances simultaneously. Therefore they can be used in biofilm-simulation, packaging and targeted release of drugs, synthesis of nanoparticles as well as micro-reactors.Cyclodextrins (CDs) are cyclic molecules which conventionally consist of six (a-), seven (P-) and eight (y-) glucose units linked by a-1-4 glycosidic linkages.They have hydrophilic outer surfaces and hydrophobic inner cavities, and can form inclusion complexes by binding organic or inorganic guest molecules based on supramolecular interaction.A number of novel supramolecular assemblies have been designed, such as gels, otaxanes and vesicles.Vesicles based on CDs inclusion complexes have gained much attention for their good biocompatibility. Vesicles prepared from CDs can be divided into two types:one is based on the amphiphilied CDs modified by covalent bond, and the other is based on the supramolecular amphiphiles.The latter attract more attention for their controllability.
The main content of the paper was showed as follows:
1.The study of micro-aggregation based on complex of 2-O-carboxymethyl P-cyclodextrin and ferrocene derivatives in aqueous solution and the effects of mixed solvent on the vesicles. Here, a new vesicle system was prepared based on supramolecular interactions between modified P-CDs (carboxymethyl-p-cyclodextrin, CM-P-CD) and ferrocenyl derivatives (N, N'-bis (ferrocenylmethylene) diaminohexane). The vesicles were studied in water, mixtures of water and alcohols, as well as organic solvents.The mechanism of vesicle formation and dissolution was discussed and proposed.
2.The study of micro-aggregation based on complex of 2-0-(y-hydroxybutyric)-β-cyclodextrin and methyl orange in aqueous solution and pH-responsive properties of the vesicle-like particles.Here, the micro-aggregation based on complex of 2-O-(y-hydroxybutyric)-β-cyclodextrin and methyl orange in aqueous solution was studied for the first time.Then the mechanism and pH-responsive properties of the vesicle-like particles was discussed.
3.The synthesis of functional host-guest molecules and the study of potential application of them.On the one hand, N-(Ferrocenylmethyl)dodecan-1-amine was designed and synthesized and then its crystal structure was grown and analyzed;On the other hand, three new fluorescent sensors base on (3-cyclodextrin were synthesized in industrial method, and then they were used in recognition in amoxicillin, ampicillin and simvastatin.
Main innovations of the thesis:
(1)The effect of alcohols on the vesicles made by cyclodextrins was studied for the first time.The effect of the concentration and alky chain of the alcohols on vesicles was discussed.This research will extend the application of vesicles based on cyclodextrins.
(2)The micro-aggregation based on complex of 2-O-(y-hydroxybutyric)-β-cyclodextrin and methyl orange in aqueous solution was studied for the first time and pH-responsive properties of the vesicle-like particles were discussed.
(3)A crystal of ferrocene derivative with a long flexible chain was obtained and its structure was studied.
(4) Three fluorescent sensors were synthesized in industrial method for the first time and used in identification of amoxicillin ampicillin and simvastatin.The study will extend the application of sensors in industry.
引文
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[1]Szejtli,J.,Introduction and general overview of cyclodextrin chemistry, Chem. Rev.,1998,98,1743-1754
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