Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application

doi:10.1007/s40242-019-9077-6

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (5): 929-936.doi: 10.1007/s40242-019-9077-6

Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application

CHEN Xin^1,2, XIAO Chunsheng^1,3, CHEN Xuesi^1,3

1. Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China;
3. Jilin Biomedical Polymers Engineering Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

收稿日期:2019-03-20 出版日期:2019-10-01 发布日期:2019-09-24
通讯作者: XIAO Chunsheng, CHEN Xuesi E-mail:xiaocs@ciac.ac.cn;xschen@ciac.ac.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.51573184, 51520105004), the Science and Technology Development Program of Jilin Province, China(No.2019010322JH) and the Fund of Youth Innovation Promotion Association of CAS, China(No.2017266).

Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application

CHEN Xin^1,2, XIAO Chunsheng^1,3, CHEN Xuesi^1,3

1. Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China;
3. Jilin Biomedical Polymers Engineering Laboratory, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

Received:2019-03-20 Online:2019-10-01 Published:2019-09-24
Contact: XIAO Chunsheng, CHEN Xuesi E-mail:xiaocs@ciac.ac.cn;xschen@ciac.ac.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.51573184, 51520105004), the Science and Technology Development Program of Jilin Province, China(No.2019010322JH) and the Fund of Youth Innovation Promotion Association of CAS, China(No.2017266).

摘要/Abstract

摘要： In this work, two kinds of PEGylated salicylaldehyde azine(SA) polymers were prepared and investigated for cellular imaging applications. First, a diazido derivative of SA was synthesized and subsequently PEGylated with polyethylene glycol monomethyl ether(mPEG) by metal-free azide-alkyne 1,3-dipolar cycloaddition reaction. The formed triazole group in mPEG-SA was then converted into cationic triazolium group by N-alkylation reaction. Both the synthesized polymers, mPEG-SA and N-alkylated mPEG-SA, showed good dispersibility in water, but differences in self-assembly of nanostructures. The mPEG-SA with triazole groups self-assembled into micelles, while the N-alkylated mPEG-SA with triazolium groups self-assembled into vesicles. Furthermore, mPEG-SA and N-alkylated mPEG-SA nanoparticles showed bright fluorescence due to the aggregation of AIE-active SA molecules in the nanoparticles and could be successfully used as fluorescent nanoprobes for bioimaging applications in HeLa cancer cells. Finally, both the synthesized polymers showed minimal cytotoxicity and low hemolytic activity. Therefore, these PEGylated SA polymers proved to be promising bioimaging nanoprobes or traceable drug delivery vehicles.

关键词: Click chemistry, Aggregation-induced emission nanoprobe, PEGylation, Bioimaging, Self-assembly

Abstract: In this work, two kinds of PEGylated salicylaldehyde azine(SA) polymers were prepared and investigated for cellular imaging applications. First, a diazido derivative of SA was synthesized and subsequently PEGylated with polyethylene glycol monomethyl ether(mPEG) by metal-free azide-alkyne 1,3-dipolar cycloaddition reaction. The formed triazole group in mPEG-SA was then converted into cationic triazolium group by N-alkylation reaction. Both the synthesized polymers, mPEG-SA and N-alkylated mPEG-SA, showed good dispersibility in water, but differences in self-assembly of nanostructures. The mPEG-SA with triazole groups self-assembled into micelles, while the N-alkylated mPEG-SA with triazolium groups self-assembled into vesicles. Furthermore, mPEG-SA and N-alkylated mPEG-SA nanoparticles showed bright fluorescence due to the aggregation of AIE-active SA molecules in the nanoparticles and could be successfully used as fluorescent nanoprobes for bioimaging applications in HeLa cancer cells. Finally, both the synthesized polymers showed minimal cytotoxicity and low hemolytic activity. Therefore, these PEGylated SA polymers proved to be promising bioimaging nanoprobes or traceable drug delivery vehicles.

Key words: Click chemistry, Aggregation-induced emission nanoprobe, PEGylation, Bioimaging, Self-assembly

CHEN Xin, XIAO Chunsheng, CHEN Xuesi. Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application[J]. 高等学校化学研究, 2019, 35(5): 929-936.

CHEN Xin, XIAO Chunsheng, CHEN Xuesi. Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application[J]. Chemical Research in Chinese Universities, 2019, 35(5): 929-936.

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Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application

Synthesis of PEGylated Salicylaldehyde Azine via Metal-free Click Chemistry for Cellular Imaging Application

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