双亲短肽的超分子自组装及其在仿生中的应用
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摘要
自然界中，生物体经过亿万年物竞天择、适者生存的自然选择与进化，形成诸多结构精妙且具有特殊功能的天然生物材料。然而生物系统是一个非常复杂的体系，所以人们希望利用仿生的概念使用简单的超分子自组装体系来模拟复杂的生物体，理解其复杂机理，进而从自然界获得设计材料的启发，突破传统观念，用超分子自组装的方法构建出具有实际应用价值的特殊功能的仿生材料。以模拟生物体结构和功能为基础的仿生矿化和人工仿酶是仿生领域非常重要的两个研究方向。
在各种生物活性分子中，以多肽自组装体作为构筑基元的仿生体系，由于其具有良好的生物相容性、体内易降解吸收和分子识别特性，引起了仿生学家们极大的兴趣。本论文选择简单的寡肽单体—苯丙二肽及其Fmoc保护衍生物作为构筑基元，以其超分子自组装形成的纳米聚集体如纳米线、螺旋纳米线和纳米管等作为载体，在仿生学思想的指导下，分别研究其在仿生矿化和人工仿酶领域所展示的优异性质。具体研究结果如下：
1）基于肽自组装的仿生矿化：我们制备了Fmoc-FFECG双亲五肽自组装纳米线，并以此纳米线作为有机模板，诱导Ag成核、取向生长，形成具有独特性质的银纳米粒子矿化五肽纳米线的无机有机杂化纳米复合材料。银纳米粒子矿化后的五肽纳米线复合物（Ag-PepNFs）具有高效、广泛的抗菌效果，因而其可作为高效的抗菌材料应用在临床及环境等领域，进一步扩展仿生矿化材料的应用范围。
2）基于肽自组装的人工仿酶体系：通过模拟胰凝乳蛋白酶催化三联体的结构，我们设计合成了Fmoc-FFDHS双亲五肽螺旋纳米线水解酶模型（Helix-PepNFs），该螺旋纳米线上的催化三联体对催化水解底物PNPA起到了一定的促进作用，但由于Asp和Ser参与了形成螺旋纳米线的分子间氢键的自组装，减弱了其形成催化三联体的概率，致使水解酶活力提高有限。作为该体系的改进，我们制备了Fmoc-FFH双亲三肽自组装纳米线水解酶模型，该纳米线亲水表面分布大量的可作为水解酶活性中心的组氨酸，因而其可作为水解酶活性中心。我们进一步通过共组装的方法把不同比例的胍基引入到纳米线中,利用胍基结合稳定碳酸酯水解产生的四面体过渡态，成功地将催化中心、结合位点和稳定过渡态等催化基元富集于同一超分子自组装纳米线聚集体中，得到了最佳活力的纳米线水解酶模型。
3）基于肽自组装的人工仿酶改进体系：为了改进上述所构建的纳米线酶模型，我们以芳香苯丙二肽（FF）自组装形成的纳米管作为构筑水解酶模型的载体，以与苯丙二肽（FF）骨架具有相似结构的FFH作为催化中心、以FFR作为稳定过渡态结合位点，将二者按不同比例共组装至苯丙二肽纳米管中，成功制备了催化中心和结合位点比例可调的最佳纳米管水解酶模型，实现了各催化基元在空间上的最佳匹配。这一方法是其它化学合成水解酶模型很难达到的，为合理设计超分子高效水解酶模拟物提供了新的思路。
Biomimetics - the science of imitating nature - is a growing multidisciplinaryfield by using the tools of molecular biology，chemistry and nanotechnology, which isnow leading to the fabrication of novel materials with remarkable mechanicalproperties. Through billions of years of evolution nature have produced extremelyefficient materials, which become an increasing source of inspiration for scientists.However, the biological systems are usually extremely complex, so scientists want tomake comparatively simple models to understand their complex mechanism.Furthermore, to mimic the syntheses of these materials, researchers not only emulateparticular biological architecture or system, but importantly to abstract the guidingprinciples and ideas and use such knowledge for the preparation of new syntheticmaterials and devices. Biomimetic mineralization and artificial enzyme are two criticalresearch topics in the field of biomimetic systems.
One of most unique and fascinating features of natural biomineralizationprocesses is the controlled growth and hierarchical organization of inorganic mineralsalong with organic materials. Such marvels of nature give excellent physicochemicalproperties to natural biomaterials and provide inspiration for the synthesis of novelfunctional nanomaterials to chemists and materials scientists. For example, naturalbones with excellent mechanical properties are a kind of organic/inorganic hybridmaterials with organic collagen nanofibrils and inorganic calcium phosphatenanocrystals hierarchically organized on a nanoscale. By mimicking natural systems,one may gain insights into biomineralization mechanisms, and synthesize inorganic–organic hybrid materials with potentially interesting functions for applications in nano-and biotechnology. To further expand the scope of application of biomimetic materials,we prepared silver mineralization on self-assembled peptide nanofibers for long termantimicrobial effect.
Natural enzymes are large biomacromolecues with extreme molecular complexity, but their mechanism of catalysis is frequently simple with only a few amino acidsinvolved in catalysis. Hence, it is inherently possible to make a comparatively simplemodel of an active site and obtain selective catalysis. Although artificial enzymesconstructed by chemical and genetic strategies previously have demonstrated highcatalytic activity, some disadvantages still remain in such efficient enzyme models. Onthe one hand, catalytic factors are commonly combined into one scaffold throughcovalent chemical methods, which have the limitation of complicated synthetic routes,expensive cost and low productivity. On the other hand, it is difficult to construct theoptimum artificial enzyme via altering the molar ratio of the catalytic factors as it is afixed value. To address this problem，we construct supramolecular models of enzymesbased on peptide with diverse topological structures such as nanofibers, helicalnanofiners and nanotube. These supramolecular models of enzyme based on peptideoffer obvious advantages of ease of fabrication, good biocompatibility, inexpensiveproduction, molecular-recognition capability, and functional flexibility.
Among various biological systems, the self-assembly of peptide-based buildingblocks into ordered nanostructures has drawn much attention. Bioactive peptides are atype of suitable building blocks as the objects for fabricating such nanostructuralmaterials because they can be easily synthesized, engineered and modified chemicallyor functionalized biologically. In this research, the diphenylalanine peptide (FF) and itsFmoc-protected derivative were employed as the building blocks which self-assembledinto diverse topological structures such as nanofibers, helical nanofiners and nanotubes.These topological structures were used as scaffolds for application in biomimeticmineralization and artificial enzyme mimic.The research results are as followed:
1) We apply peptide nanofibers self-assembled from Fmoc-FFECG as templatesto guide the growth of Ag nanocrystals along with peptide nanofibers. Amphipathicpeptide, Fmoc-FFECG, contain both hydrophobic and hydrophilic moieties. Thehydrophobic group promotes aggregation, which could be used to combineencapsulation of hydrophobic drugs for drug delivery. While the hydrophilic groupdisplay numerous carboxylic acid and thiol groups on peptide nanofiber surface, whichcan serve as nucleation sites for the growth of inorganic materials and metal bindingsites, respectively. In comparison to the traditional Ag-containing materials with silicaor polymer, Ag mineralized peptide nanofibers (Ag–PepNFs) offer obvious advantagesof the ease of fabrication, good biocompatibility, inexpensive production,molecular-recognition capability, and functional flexibility. More importantly, the tubular nanocomposite proves to possess an effective and long-term antibacterialactivity against both Gram-positive and negative bacteria.
2) As artificial enzyme mimic. On the one hand, by simulating the catalytic triadstructure of chymotrypsin, we designed and synthesized peptide Fmoc-FFDHS, whichself- assembled to helical nanofibers (Helix-PepNFs) in aqueous solution. The catalytictriad (Asp, His and Ser) were introduced into helical nanofibers and improved enzymeactivity. On the other hand, as the improvement of the system, we apply peptidenanofibers self-assembled from Fmoc- FFH as catalyst center to hydrolase substratePNPA. We further introduced different proportions of guanidine（Fmoc-FFR）into thenanofibers by co-assembly method. In particular, the optimum artificial enzymemodels PepNFs-His-Argmaxwere achieved through changing the molar ratio of catalystcenter and stabilizing the transition state (Fmoc- FFH and Fmoc- FFR). The highactivity of PepNFs-His-Argmaxis attributed to the match degree among the catalyticfactors. This simple preparation process and better match of catalytic factors, theco-assembly nanofibers models may make the preparation of efficient artificial enzymemodels more eassy.
3) For the enzyme model of PepNFs-His-Argmax, catalytic centers are combinedinto nanofibers through covalent chemical methods, which have the difficulty toconstruct the optimum artificial enzyme models via altering the molar ratio of thecatalytic factors as it is a fixed value. Thus, as an improvement, we applied peptidenanotubes self-assembled from diphenylalanine peptide (FF) as scaffold toco-assemble with FFH as the catalytic center and FFR as stable transition state bindingsites. In particular, the optimum artificial enzyme models FFNTs-His-Argmaxwereachieved through changing the molar ratio of catalyst center and stabilizing thetransition state (FFH and FFR). Among all the enzyme models we designed in thiswork, FFNTs-His-Argmaxshowed the highest enzyme activity. It is noted that not onlythe specific substrate binding ability but also the better match among the catalyticfactors play an important role in designing a desirable artificial enzyme model.
在各种生物活性分子中，以多肽自组装体作为构筑基元的仿生体系，由于其具有良好的生物相容性、体内易降解吸收和分子识别特性，引起了仿生学家们极大的兴趣。本论文选择简单的寡肽单体—苯丙二肽及其Fmoc保护衍生物作为构筑基元，以其超分子自组装形成的纳米聚集体如纳米线、螺旋纳米线和纳米管等作为载体，在仿生学思想的指导下，分别研究其在仿生矿化和人工仿酶领域所展示的优异性质。具体研究结果如下：
1）基于肽自组装的仿生矿化：我们制备了Fmoc-FFECG双亲五肽自组装纳米线，并以此纳米线作为有机模板，诱导Ag成核、取向生长，形成具有独特性质的银纳米粒子矿化五肽纳米线的无机有机杂化纳米复合材料。银纳米粒子矿化后的五肽纳米线复合物（Ag-PepNFs）具有高效、广泛的抗菌效果，因而其可作为高效的抗菌材料应用在临床及环境等领域，进一步扩展仿生矿化材料的应用范围。
2）基于肽自组装的人工仿酶体系：通过模拟胰凝乳蛋白酶催化三联体的结构，我们设计合成了Fmoc-FFDHS双亲五肽螺旋纳米线水解酶模型（Helix-PepNFs），该螺旋纳米线上的催化三联体对催化水解底物PNPA起到了一定的促进作用，但由于Asp和Ser参与了形成螺旋纳米线的分子间氢键的自组装，减弱了其形成催化三联体的概率，致使水解酶活力提高有限。作为该体系的改进，我们制备了Fmoc-FFH双亲三肽自组装纳米线水解酶模型，该纳米线亲水表面分布大量的可作为水解酶活性中心的组氨酸，因而其可作为水解酶活性中心。我们进一步通过共组装的方法把不同比例的胍基引入到纳米线中,利用胍基结合稳定碳酸酯水解产生的四面体过渡态，成功地将催化中心、结合位点和稳定过渡态等催化基元富集于同一超分子自组装纳米线聚集体中，得到了最佳活力的纳米线水解酶模型。
3）基于肽自组装的人工仿酶改进体系：为了改进上述所构建的纳米线酶模型，我们以芳香苯丙二肽（FF）自组装形成的纳米管作为构筑水解酶模型的载体，以与苯丙二肽（FF）骨架具有相似结构的FFH作为催化中心、以FFR作为稳定过渡态结合位点，将二者按不同比例共组装至苯丙二肽纳米管中，成功制备了催化中心和结合位点比例可调的最佳纳米管水解酶模型，实现了各催化基元在空间上的最佳匹配。这一方法是其它化学合成水解酶模型很难达到的，为合理设计超分子高效水解酶模拟物提供了新的思路。
Biomimetics - the science of imitating nature - is a growing multidisciplinaryfield by using the tools of molecular biology，chemistry and nanotechnology, which isnow leading to the fabrication of novel materials with remarkable mechanicalproperties. Through billions of years of evolution nature have produced extremelyefficient materials, which become an increasing source of inspiration for scientists.However, the biological systems are usually extremely complex, so scientists want tomake comparatively simple models to understand their complex mechanism.Furthermore, to mimic the syntheses of these materials, researchers not only emulateparticular biological architecture or system, but importantly to abstract the guidingprinciples and ideas and use such knowledge for the preparation of new syntheticmaterials and devices. Biomimetic mineralization and artificial enzyme are two criticalresearch topics in the field of biomimetic systems.
One of most unique and fascinating features of natural biomineralizationprocesses is the controlled growth and hierarchical organization of inorganic mineralsalong with organic materials. Such marvels of nature give excellent physicochemicalproperties to natural biomaterials and provide inspiration for the synthesis of novelfunctional nanomaterials to chemists and materials scientists. For example, naturalbones with excellent mechanical properties are a kind of organic/inorganic hybridmaterials with organic collagen nanofibrils and inorganic calcium phosphatenanocrystals hierarchically organized on a nanoscale. By mimicking natural systems,one may gain insights into biomineralization mechanisms, and synthesize inorganic–organic hybrid materials with potentially interesting functions for applications in nano-and biotechnology. To further expand the scope of application of biomimetic materials,we prepared silver mineralization on self-assembled peptide nanofibers for long termantimicrobial effect.
Natural enzymes are large biomacromolecues with extreme molecular complexity, but their mechanism of catalysis is frequently simple with only a few amino acidsinvolved in catalysis. Hence, it is inherently possible to make a comparatively simplemodel of an active site and obtain selective catalysis. Although artificial enzymesconstructed by chemical and genetic strategies previously have demonstrated highcatalytic activity, some disadvantages still remain in such efficient enzyme models. Onthe one hand, catalytic factors are commonly combined into one scaffold throughcovalent chemical methods, which have the limitation of complicated synthetic routes,expensive cost and low productivity. On the other hand, it is difficult to construct theoptimum artificial enzyme via altering the molar ratio of the catalytic factors as it is afixed value. To address this problem，we construct supramolecular models of enzymesbased on peptide with diverse topological structures such as nanofibers, helicalnanofiners and nanotube. These supramolecular models of enzyme based on peptideoffer obvious advantages of ease of fabrication, good biocompatibility, inexpensiveproduction, molecular-recognition capability, and functional flexibility.
Among various biological systems, the self-assembly of peptide-based buildingblocks into ordered nanostructures has drawn much attention. Bioactive peptides are atype of suitable building blocks as the objects for fabricating such nanostructuralmaterials because they can be easily synthesized, engineered and modified chemicallyor functionalized biologically. In this research, the diphenylalanine peptide (FF) and itsFmoc-protected derivative were employed as the building blocks which self-assembledinto diverse topological structures such as nanofibers, helical nanofiners and nanotubes.These topological structures were used as scaffolds for application in biomimeticmineralization and artificial enzyme mimic.The research results are as followed:
1) We apply peptide nanofibers self-assembled from Fmoc-FFECG as templatesto guide the growth of Ag nanocrystals along with peptide nanofibers. Amphipathicpeptide, Fmoc-FFECG, contain both hydrophobic and hydrophilic moieties. Thehydrophobic group promotes aggregation, which could be used to combineencapsulation of hydrophobic drugs for drug delivery. While the hydrophilic groupdisplay numerous carboxylic acid and thiol groups on peptide nanofiber surface, whichcan serve as nucleation sites for the growth of inorganic materials and metal bindingsites, respectively. In comparison to the traditional Ag-containing materials with silicaor polymer, Ag mineralized peptide nanofibers (Ag–PepNFs) offer obvious advantagesof the ease of fabrication, good biocompatibility, inexpensive production,molecular-recognition capability, and functional flexibility. More importantly, the tubular nanocomposite proves to possess an effective and long-term antibacterialactivity against both Gram-positive and negative bacteria.
2) As artificial enzyme mimic. On the one hand, by simulating the catalytic triadstructure of chymotrypsin, we designed and synthesized peptide Fmoc-FFDHS, whichself- assembled to helical nanofibers (Helix-PepNFs) in aqueous solution. The catalytictriad (Asp, His and Ser) were introduced into helical nanofibers and improved enzymeactivity. On the other hand, as the improvement of the system, we apply peptidenanofibers self-assembled from Fmoc- FFH as catalyst center to hydrolase substratePNPA. We further introduced different proportions of guanidine（Fmoc-FFR）into thenanofibers by co-assembly method. In particular, the optimum artificial enzymemodels PepNFs-His-Argmaxwere achieved through changing the molar ratio of catalystcenter and stabilizing the transition state (Fmoc- FFH and Fmoc- FFR). The highactivity of PepNFs-His-Argmaxis attributed to the match degree among the catalyticfactors. This simple preparation process and better match of catalytic factors, theco-assembly nanofibers models may make the preparation of efficient artificial enzymemodels more eassy.
3) For the enzyme model of PepNFs-His-Argmax, catalytic centers are combinedinto nanofibers through covalent chemical methods, which have the difficulty toconstruct the optimum artificial enzyme models via altering the molar ratio of thecatalytic factors as it is a fixed value. Thus, as an improvement, we applied peptidenanotubes self-assembled from diphenylalanine peptide (FF) as scaffold toco-assemble with FFH as the catalytic center and FFR as stable transition state bindingsites. In particular, the optimum artificial enzyme models FFNTs-His-Argmaxwereachieved through changing the molar ratio of catalyst center and stabilizing thetransition state (FFH and FFR). Among all the enzyme models we designed in thiswork, FFNTs-His-Argmaxshowed the highest enzyme activity. It is noted that not onlythe specific substrate binding ability but also the better match among the catalyticfactors play an important role in designing a desirable artificial enzyme model.
引文
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