ROMP synthesis of benzaldehyde-containing amphiphilic block polynorbornenes used to conjugate drugs for pH-responsive release

嬉戏 共聚物 两亲性 胶束 苯甲醛 化学 聚合 结合 组合化学 侧链 高分子化学 药物输送 聚合物 有机化学 复分解 催化作用 水溶液 数学分析 数学
作者
Guirong Qiu,Li Zhao,Xiong Liu,Qiuxia Zhao,Fangfei Liu,Yue Liu,Yewu Liu,Haibin Gu
出处
期刊:Reactive & Functional Polymers [Elsevier]
卷期号:128: 1-15 被引量:25
标识
DOI:10.1016/j.reactfunctpolym.2018.03.010
摘要

The development of novel polymer carriers, which have well-defined structures and desired conjugative abiltiy to therapeutic agents, is still an urgent requirement in the field of polymer–drug conjugates (PDCs) used for stimuli-responsive drug delivery systems. Herein, we present the controlled synthesis of a novel amphiphilic polynorbornene-based block copolymer, side-chain containing hydrophobic functionalizable benzaldehyde groups and hydrophilic dentritic triethylene glycol (TEG) moieties, by the ring-opening metathesis polymerization (ROMP) using the 3rd generation Grubbs catalyst 1 as the initiator. The obtained copolymer can self-assemble into spherical micelles with the average size of 84 nm in water, and its remarkable ability as the polymer carrier to fabricate PDCs was fully confirmed by the efficient covalently Schiff-base linking of its side-chain benzaldehyde groups to amino groups of model drugs including O-benzylhydroxylamine (BHA), 1-hexadecanamine, tryptophan and benzocaine. Notably, torispherical micelles with the average size of 90 nm were also obtained by the self-assembly of the formed polymer-BHA conjugate, and the pH-triggered release of BHA molecules from the micelles was observed at acidic environments (for example, pH 4.0 and 2.5). Therefore, the present polynorbornene block copolymer is expected to find potential applications in the stimuli-responsive drug delivery systems as a promising polymer carrier to form PDCs via acid-responsive Schiff-base linkage with amino-containing drugs such as doxorubicin, daunorubicin, epirubicin and pirarubicin.
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