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Lipase-catalyzed synthesis of oxidation-responsive poly(ethylene glycol)-b-poly(beta-thioether ester) amphiphilic block copolymers

机译:脂肪酶催化合成的氧化响应聚(乙二醇)-B-聚(β-硫醚酯)两亲嵌段共聚物

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摘要

A series of novel oxidation-responsive amphiphilic diblock copolymers with beta-thioether ester groups were synthesized via the one-step lipase-catalyzed polycondensation of methyl 3-((2-hydroxyethyl)thio)propanoate (MHETP) with monomethoxy poly(ethylene glycol) (mPEG) using immobilized lipase B from Candida antarctica (CALB) as the catalyst. The amphiphilic poly(ethylene glycol)-b-poly(beta-thioether ester) (mPEG-b-PTE) diblock copolymers could self-assemble to form nanosized micelles in aqueous solution with low critical micelle concentration (CMC). The micelles were able to undergo a H2O2-triggered disassembly due to the oxidizable thioether groups and degradable ester groups in the hydrophobic PTE core. The oxidation-responsive behaviour of the micelles was further investigated by dynamic light scattering (DLS) and transmission electron microscopy (TEM). Nile Red, a hydrophobic model drug, was encapsulated into the polymeric micelles and showed fast release upon the addition of H2O2. Cell cytotoxicity tests indicated that the micelles had low cytotoxicity toward HeLa cells. The oxidation-insensitive poly(ethylene glycol)-b-poly(epsilon-caprolactone) (mPEG-b-PCL) diblock copolymer was also prepared for comparison. All these findings demonstrated the potential of mPEG-b-PTE diblock copolymers as a promising oxidation-responsive nanocarrier for controlled drug delivery.
机译:通过用单甲氧基聚(乙二醇)的一步脂肪酶催化的丙酸甲酯(MHETP)的一步脂肪酶催化的缩聚合成具有β-硫醚酯基的一系列新的氧化响应式两亲二嵌段共聚物。用单甲氧基聚(乙二醇) (MPEG)使用来自Candida抗野胶(CALB)的固定化脂肪酶B作为催化剂。两亲硅(乙二醇)-B-聚(β-硫醚酯)(MPEG-B-PTE)二嵌段共聚物可以自组装成在具有低临界胶束浓度(CMC)的水溶液中形成纳米粒子胶束。由于可氧化的硫醚基团和疏水性PTE核中的可降解酯基,胶束能够经历H 2 O 2触发的拆卸。通过动态光散射(DLS)和透射电子显微镜(TEM)进一步研究胶束的氧化响应性能。尼罗红,一种疏水模型药物被包封成聚合物胶束,并在加入H 2 O 2时显示出快速释放。细胞细胞毒性试验表明胶束对HeLa细胞具有低细胞毒性。还制备了氧化不敏感聚(乙二醇)-B-聚(ε-己内酯)(MPEG-B-PCL)二嵌段共聚物进行比较。所有这些发现证明了MPEG-B-PTE二嵌段共聚物的潜力作为受控药物递送的有前途的氧化响应纳米载体。

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  • 来源
    《RSC Advances》 |2016年第14期|共10页
  • 作者单位

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

    Sichuan Univ Coll Chem Minist Educ Key Lab Green Chem &

    Technol Chengdu 610064 Peoples R China;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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