自组装多肽的修饰方法及其应用

doi:10.6023/cjoc202104020

摘要/Abstract

自组装多肽是指能够在一定条件下, 通过π-π堆积、静电相互作用等分子间作用力, 形成组装体的多肽类材料. 此类材料具有良好的生物相容性和可控性, 能够形成颗粒、纤维和凝胶等纳米结构, 发挥特定的形貌学功能, 广泛应用在生物医学等领域. 为了满足药物递送、疾病诊疗等需求, 需要在多肽上进行修饰. 由于多肽的组装特性及其自身的生物功能, 修饰后的组装肽在组装能力和生物医学应用方面更具有优势, 所以如何进行自组装肽的功能化修饰一直是研究热点. 多肽修饰位点一般在两端的羧基和氨基, 以及氨基酸侧链上的活性基团. 为了降低修饰难度或避免影响目标分子的生物活性, 可以通过连接单元来修饰某些功能基团. 因此根据修饰方法可以分为直接修饰和间接修饰. 综述了近期自组装多肽的功能化修饰方法及相关应用.

关键词: 多肽修饰, 自组装, 合成方法, 生物应用

Self-assembly peptide is a kind of peptide material that can form assembly under certain conditions due to the intermolecular forces such as π-π stacking and electrostatic interaction. This class of material exhibits good biocompatibility and controllability, and can form nanostructures such as granules, fibers and gels, which play a specific morphologic function and are widely used in biomedicine and other fields. In order to meet the needs of drug delivery, disease diagnosis and regulation of hydrophilic hydrophobic balance of peptides, it is necessary to perform modification for peptides. Due to the assembly characteristics of peptides and their biological functions, modified peptides have more advantages than the unmodified ones. Thus, functional modification for self-assembly peptides has been investigated intensively in recent years. The modification sites in peptide are usually the carboxyl and amino groups at both ends, as well as the active groups on the amino acid side chain. However, it is difficult for some molecules to react with peptides directly. Accordingly, two modification methods, i.e. direct and indirect modifications, have been developed in research. In this paper, the recent functionalization methods of self-assembly peptides and relevant applications are reviewed.

Key words: peptide modification, self-assembly, synthetic method, biological application

引用此文

任涵, 李茹祥, 陈志坚, 李莉莉, 王浩. 自组装多肽的修饰方法及其应用[J]. 有机化学, 2021, 41(10): 3983-3994.

Han Ren, Ruxiang Li, Zhijian Chen, Lili Li, Hao Wang. Modification Methods and Applications of Self-Assembly Peptides[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3983-3994.

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图/表 10

图1. 多肽直接、间接修饰示意图

Figure 1. Schematic diagram of direct and indirect modification of peptide

图2. 多肽氨基端修饰喜树碱的合成方法及应用

Figure 2. Synthesis and application of conjugating camptothecin at the amino end of peptide

图3. NBD的氨基酸改性及修饰方法

Figure 3. Amino acid modification and modification methods of NBD

图4. 近红外菁类染料Cy-Cl的合成方法及修饰多肽的方法

Figure 4. Synthesis of near infrared cyanine dye Cy-Cl and its modification of peptide

图5. BP分子的合成方法及修饰多肽的方法

Figure 5. Synthesis of BP and modification of peptide

图6. 氨基端改性的烷基链NH2-Gly-(C16)2的合成方法及修饰多肽的方法

Figure 6. Synthesis of amino terminal modified alkyl chain NH2-Gly-(C16)2 and modification of peptide

图7. 糖酪氨酸的合成方法及修饰多肽的方法

Figure 7. Methods for synthesis of glycotyrosine and modification of peptide

图8. 磷酸的酪氨酸改性及修饰多肽的合成方法

Figure 8. Tyrosine modification of phosphoric acid and synthesis of modified peptide

图9. 利用叠氮-炔基的点击化学反应对多肽进行修饰

Figure 9. Modification of polypeptides by click reaction between azide and alkyne groups

图10. 通过引入酸酐将姜黄素修饰在多肽上的方法

Figure 10. Curcumin modified on polypeptide by introducing anhydride

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