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通过席夫碱反应,从无忧树种子中提取的聚(N-异丙基丙烯酰胺)/半乳甘露聚糖的热响应接枝共聚物。

Poly(N-isopropylacrylamide)/galactomannan from Delonix regia seed thermal responsive graft copolymer via Schiff base reaction.

机构信息

Department of Organic and Inorganic Chemistry, Federal University of Ceará, Brazil.

Department of Physiology and Pharmacology, Federal University of Ceará, Brazil.

出版信息

Int J Biol Macromol. 2021 Jan 1;166:144-154. doi: 10.1016/j.ijbiomac.2020.10.121. Epub 2020 Oct 22.

Abstract

Aminated poly(N-isopropylacrylamide) (PNIPAm-NH) was grafted onto oxidized galactomannan polysaccharide extracted from Delonix regia (OXGM) via Schiff base reaction by a simple, rapid synthetic route, deprived of the use of organic solvents. Grafting was confirmed by FTIR and H NMR and the self-organizing ability of the obtained nanoparticle copolymers was investigated by dynamic light scattering (DLS). The minimum concentration required for self-organization (CAC) at 25 °C was higher than at 50 °C. Lower critical solution temperature (LCST) was in the range 34-40 °C, depending on both inserted PNIPAm-NH molar mass and on the presence of reduced imine bond. Synthesized copolymers are promising candidates for drug delivery as they show good cell viability, particle size around 250 nm and transition temperature closer to that of human body. Reaction success points out to the possibility of use free aldehyde groups of oxidized polysaccharide, not used in the copolymerization, to form a pro-drug with substances that possess NH groups in their structure, such as doxorubicin.

摘要

通过席夫碱反应,将胺化的聚(N-异丙基丙烯酰胺)(PNIPAm-NH)接枝到从无忧树中提取的氧化半乳甘露聚糖多糖(OXGM)上,该方法简单、快速,无需使用有机溶剂。通过傅里叶变换红外光谱(FTIR)和核磁共振(H NMR)证实了接枝,通过动态光散射(DLS)研究了所得纳米粒子共聚物的自组织能力。在 25°C 下自组织所需的最小浓度(CAC)高于在 50°C 下的 CAC。低临界溶液温度(LCST)在 34-40°C 范围内,这取决于插入的 PNIPAm-NH 摩尔质量和还原亚胺键的存在。合成的共聚物是药物输送的有前途的候选物,因为它们表现出良好的细胞活力、粒径约为 250nm 且转变温度更接近人体温度。反应的成功指出了使用氧化多糖中未在共聚合中使用的游离醛基的可能性,以与具有 NH 基团的结构的物质(如阿霉素)形成前药。

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