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Methionine-Based pH and Oxidation Dual-Responsive Block Copolymer: Synthesis and Fabrication of Protein Nanogels.
Biomacromolecules ( IF 5.5 ) Pub Date : 2020-09-11 , DOI: 10.1021/acs.biomac.0c00879 Shuqi Dong 1 , Yanfen Jiang 1 , Guoyang Qin 1 , Li Liu 1 , Hanying Zhao 1, 2
Biomacromolecules ( IF 5.5 ) Pub Date : 2020-09-11 , DOI: 10.1021/acs.biomac.0c00879 Shuqi Dong 1 , Yanfen Jiang 1 , Guoyang Qin 1 , Li Liu 1 , Hanying Zhao 1, 2
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In this paper, we synthesized a block copolymer containing pendent thioether functionalities by reversible addition–fragmentation chain transfer polymerization of a tert-butyloxycarbonyl (Boc)-l-methionine-(2-methacryloylethyl)ester (Boc-METMA) monomer using a poly(ethylene glycol) (PEG)-based chain transfer agent. The deprotection of Boc groups resulted in an oxidation and pH dual-responsive cationic block copolymer PEG-b-P(METMA). The block copolymer PEG-b-P(METMA) possessing protonable amine groups was water-soluble at pH < 6.0 and self-assembled to form spherical micelles at pH > 6.0. In the presence of H2O2, the micelles first became highly swollen with time and completely disassembled at last, demonstrating the H2O2-responsive feature because of the oxidation of hydrophobic thioether to hydrophilic sulfoxide. The anticancer drug curcumin (Cur) was entrapped in the polymeric micelles and the Cur-loaded micelles displayed a H2O2-triggered release profile as well as a pH-dependent release behavior, making PEG-b-P(METMA) micelles promising nanocarriers for reactive oxygen species-responsive drug delivery. Taking advantage of the protonated amine groups, the cationic polyelectrolyte PEG-b-P(METMA) formed polyion complex micelles with glucose oxidase (GOx) through electrostatic interactions at pH 5.8. By cross-linking the cores of PIC micelles with glutaraldehyde, the PIC micelles were fixed to generate stable GOx nanogels under physiological conditions. The GOx nanogels were glucose-responsive and exhibited glucose-dependent H2O2-generation activity in vitro and improved storage and thermal stability of GOx. Cur can be encapsulated in the GOx nanogels, and the Cur-loaded GOx nanogels demonstrate the glucose-responsive release profile. The GOx nanogels displayed high cytotoxicity to 4T1 cells and were effectively internalized by the cells. Therefore, these GOx nanogels have potential applications in the areas of cancer starvation and oxidation therapy.
中文翻译：
蛋氨酸基pH和氧化双响应嵌段共聚物：蛋白质纳米凝胶的合成与制备。
在本文中，我们合成了含有侧接由的可逆加成-断裂链转移聚合硫醚官能团的嵌段共聚物叔丁氧基羰（BOC） -升-methionine-（2- methacryloylethyl）酯（BOC-METMA），使用聚单体（乙二醇）（PEG）基链转移剂。Boc基团的脱保护导致氧化和pH双响应阳离子嵌段共聚物PEG- b - P（METMA）。具有质子胺基团的嵌段共聚物PEG- b - P（METMA）在pH ＜6.0下是水溶性的，并在pH＞ 6.0下自组装形成球形胶束。在H 2 O 2存在下，胶束首先随着时间的流逝而高度溶胀，最后完全分解，这表明由于疏水性硫醚氧化为亲水性亚砜而引起的H 2 O 2响应特性。抗癌药姜黄素（Cur）被截留在聚合物胶束中，Cur负载的胶束显示出H 2 O 2触发的释放曲线以及pH依赖的释放行为，这使得PEG- b -P（METMA）胶束有望实现纳米载体用于活性氧反应药物。利用质子化胺基，阳离子聚电解质PEG- b-P（METMA）通过pH 5.8的静电相互作用与葡萄糖氧化酶（GOx）形成聚离子复合胶束。通过将PIC胶束的核心与戊二醛交联，固定PIC胶束以在生理条件下生成稳定的GOx纳米凝胶。GOx纳米凝胶对葡萄糖具有反应性，并在体外具有葡萄糖依赖性H 2 O 2生成活性并改善了GOx的储存和热稳定性。可以将Cur封装在GOx纳米凝胶中，并且加载了Cur的GOx纳米凝胶显示出葡萄糖响应释放曲线。GOx纳米凝胶对4T1细胞显示出高细胞毒性，并被细胞有效内化。因此，这些GOx纳米凝胶在癌症饥饿和氧化疗法领域具有潜在的应用。
更新日期：2020-10-12
中文翻译：
蛋氨酸基pH和氧化双响应嵌段共聚物：蛋白质纳米凝胶的合成与制备。
在本文中，我们合成了含有侧接由的可逆加成-断裂链转移聚合硫醚官能团的嵌段共聚物叔丁氧基羰（BOC） -升-methionine-（2- methacryloylethyl）酯（BOC-METMA），使用聚单体（乙二醇）（PEG）基链转移剂。Boc基团的脱保护导致氧化和pH双响应阳离子嵌段共聚物PEG- b - P（METMA）。具有质子胺基团的嵌段共聚物PEG- b - P（METMA）在pH ＜6.0下是水溶性的，并在pH＞ 6.0下自组装形成球形胶束。在H 2 O 2存在下，胶束首先随着时间的流逝而高度溶胀，最后完全分解，这表明由于疏水性硫醚氧化为亲水性亚砜而引起的H 2 O 2响应特性。抗癌药姜黄素（Cur）被截留在聚合物胶束中，Cur负载的胶束显示出H 2 O 2触发的释放曲线以及pH依赖的释放行为，这使得PEG- b -P（METMA）胶束有望实现纳米载体用于活性氧反应药物。利用质子化胺基，阳离子聚电解质PEG- b-P（METMA）通过pH 5.8的静电相互作用与葡萄糖氧化酶（GOx）形成聚离子复合胶束。通过将PIC胶束的核心与戊二醛交联，固定PIC胶束以在生理条件下生成稳定的GOx纳米凝胶。GOx纳米凝胶对葡萄糖具有反应性，并在体外具有葡萄糖依赖性H 2 O 2生成活性并改善了GOx的储存和热稳定性。可以将Cur封装在GOx纳米凝胶中，并且加载了Cur的GOx纳米凝胶显示出葡萄糖响应释放曲线。GOx纳米凝胶对4T1细胞显示出高细胞毒性，并被细胞有效内化。因此，这些GOx纳米凝胶在癌症饥饿和氧化疗法领域具有潜在的应用。
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