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Chemical Research in Chinese Universities

, Volume 35, Issue 5, pp 929–936 | Cite as

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

  • Xin Chen
  • Chunsheng XiaoEmail author
  • Xuesi ChenEmail author
Article
  • 48 Downloads

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 nano-particles 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.

Keywords

Click chemistry Aggregation-induced emission nanoprobe PEGylation Bioimaging Self-assembly 

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Supplementary material

40242_2019_9077_MOESM1_ESM.pdf (662 kb)
Synthesis of PEGylatedSalicylaldehydeAzinevia Metal-free ClickChemistry for Cellular Imaging Applications

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH 2019

Authors and Affiliations

  1. 1.Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchunP. R. China
  2. 2.University of Chinese Academy of SciencesBeijingP. R. China
  3. 3.Jilin Biomedical Polymers Engineering Laboratory, Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchunP. R. China

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