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肽和糖肽树枝状大分子及其类似的树枝状结构及其在生物医学中的应用。

Peptide and glycopeptide dendrimers and analogous dendrimeric structures and their biomedical applications.

机构信息

Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 166 10, Prague 6, Czech Republic.

出版信息

Amino Acids. 2011 Feb;40(2):301-70. doi: 10.1007/s00726-010-0707-z. Epub 2010 Aug 3.

DOI:10.1007/s00726-010-0707-z
PMID:21058024
Abstract

The size of information that can be stored in nucleic acids, proteins, and carbohydrates was calculated. The number of hexamers for peptides is 64,000,000 (20(6)) and seems to be impressive in comparison with 4,096 (4(6)) hexanucleotides, but the number of isomers of hexasaccharides is 1.44 × 10(15). Carbohydrates are therefore the best high-density coding system. This language has been named glycocode resp. sugar code. In comparison with peptide dendrimers, the amount of information carried by glycopeptide dendrimers or glycodendrimers is therefore much higher. This is reflected by the variability of structures and functions (activities). This review is about the broad area of peptide and glycopeptide dendrimers. The dendrimeric state and physicochemical properties and general consequences are described, together with a cluster effect. The impact of cluster effect to biological, chemical, and physical properties is discussed. Synthesis of dendrimers by convergent and divergent approaches, "Lego" chemistry, ligation strategies, and click chemistry is given with many examples. Purification and characterization of dendrimers by chromatographic methods, electromigration methods, and mass spectrometry are briefly mentioned. Different types of dendrimers with cyclic core, i.e. RAFTs, TASPs and analogous cyclic structures, carbopeptides, carboproteins, octopus glycosides, inositol-based dendrimers, cyclodextrins, calix[4]arenes, resorcarenes, cavitands, and porphyrins are given. Dendrimers can be used for creation of libraries, catalysts, and solubilizing agents. Biocompatibility and toxicity of dendrimers is discussed, as well as their applications in nanoscience, nanotechnology, drug delivery, and gene delivery. Carbohydrate interactions of glycopeptide dendrimers (bacteria, viruses, and cancer) are described. Examples of dendrimers as anti-prion agents are given. Dendrimers represent a fast developing area which partly overlaps with nanoparticles and nanotechnologies.

摘要

对核酸、蛋白质和碳水化合物的信息存储能力进行了计算。肽的六联体数量为 6400 万(20(6)),与 4096 个(4(6))六核苷酸相比似乎令人印象深刻,但六糖的异构体数量为 1.44×10(15)。因此,碳水化合物是最好的高密度编码系统。这种语言被命名为糖码。与肽树突相比,糖肽树突或糖树突所携带的信息量要高得多。这反映在结构和功能(活性)的可变性上。本文综述了肽和糖肽树突的广泛领域。描述了树突状态和物理化学性质以及一般后果,包括聚类效应。讨论了聚类效应对生物、化学和物理性质的影响。通过收敛和发散方法、“乐高”化学、连接策略和点击化学合成树突,并给出了许多例子。简要提到了通过色谱方法、电泳方法和质谱法对树突进行的纯化和表征。给出了不同类型的具有环状核心的树突,即 RAFTs、TASPs 和类似的环状结构、碳肽、碳蛋白、章鱼糖苷、肌醇基树突、环糊精、杯芳烃、杯芳烃、 Cavitands 和卟啉。树突可用于创建文库、催化剂和增溶剂。讨论了树突的生物相容性和毒性,以及它们在纳米科学、纳米技术、药物传递和基因传递中的应用。描述了糖肽树突的碳水化合物相互作用(细菌、病毒和癌症)。还给出了作为抗朊病毒剂的树突的例子。树突是一个快速发展的领域,部分与纳米粒子和纳米技术重叠。

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