一锅合成PEG-（氨基酸）嵌段共聚物组装具有PEG可分离功能的聚合物胶束,ACS Biomaterials Science & Engineering

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一锅合成PEG-（氨基酸）嵌段共聚物组装具有PEG可分离功能的聚合物胶束
ACS Biomaterials Science & Engineering ( IF 5.4 ) Pub Date : 2019-02-05 , DOI: 10.1021/acsbiomaterials.8b01549
Takuya Miyazaki ₁ , Kazunori Igarashi ₂ , Yu Matsumoto ₂ , Horacio Cabral ₁

Affiliation

由聚（乙二醇）（PEG）和聚（氨基酸）（PAA）链段组成的嵌段共聚物显示出开发生物相容性纳米结构的杰出特征。尽管合成PEG-PAA的常规方法可以很好地控制聚合度和多分散性，但这些协议涉及几个步骤，这增加了时间和成本，并减少了可能的嵌段共聚物设计的数量。在这项研究中，我们通过进行环氧乙烷（EO）和有机碱促进的氨基酸的N-羧基酐（NCA）的顺序开环聚合（ROP），开发了一种PEG-PAA嵌段共聚物的一锅法合成方法1,1,3,3-四甲基胍（TMG）作为催化剂。该程序是有效地用于合成PEG-聚（苄基-升-谷氨酸盐（PEG-PBLG）和PEG-聚（1-赖氨酸）（PEG-PLL）的分子量分布较窄，与通过胺端基PEG引发NCA的ROP的常规方法合成的嵌段共聚物相当。所得的嵌段共聚物在PEG和PAA链段之间存在酯键，该酯键可以在生理条件下逐渐水解，有利于提高生物相容性。此外，我们证实一锅法PEG-PBLG在水性条件下自组装成胶束，与传统PEG-PBLG制备的胶束相比，它具有可比的血液循环和生物分布。这些结果表明，我们的一锅法合成方法在制备可水解的PEG-PAA中用于构建超分子组装体具有很高的潜力。

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One-Pot Synthesis of PEG–Poly(amino acid) Block Copolymers Assembling Polymeric Micelles with PEG-Detachable Functionality

Block copolymers composed of poly(ethylene glycol) (PEG) and poly(amino acids) (PAA) segments have shown exceptional features for developing biocompatible nanostructures. While the conventional methods for synthesizing PEG–PAA provide excellent control of the degree of polymerization and polydispersity, these protocols involve several steps, which increase the time and costs, and reduce the number of possible block copolymer designs. In this study, we developed a one-pot synthetic method for PEG–PAA block copolymers by doing sequential ring-opening polymerizations (ROP) of ethylene oxide (EO) and the N-carboxyanhydrides (NCAs) of amino acids promoted by the organic base 1,1,3,3-tetramethylguanidine (TMG) as the catalyst. The procedure was effectively used to synthesize PEG-poly(benzyl-l-glutamate) (PEG–PBLG) and PEG-poly(l-Lysine) (PEG–PLL) with narrow molecular weight distribution, comparable to that of block copolymers synthesized by the conventional method initiating the ROP of NCA by amine-terminated PEG. The resulting block copolymers present an ester bond between the PEG and the PAA segments, which can be gradually hydrolyzed in physiological conditions, being advantageous for improving the biocompatibility. Besides, we confirmed that the one-pot PEG–PBLG self-assembled into micelles in aqueous conditions, which showed comparable blood circulation and biodistribution to the micelles prepared from conventional PEG–PBLG. These results indicate the high potential of our one-pot synthetic approach for preparing hydrolyzable PEG–PAAs for constructing supramolecular assemblies.

更新日期：2019-05-23

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