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Synthesis of amphiphilic fluorescent copolymers with smart pH sensitivity via RAFT polymerization and their application in cell imaging

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Abstract

In this paper, a fluorescein methacryloyl monomer (named Flu-MA) was firstly fabricated by the esterification reaction of fluorescein and methacryloyl chloride; subsequently, a novel amphiphilic fluorescent copolymer (Flu-PEG) with smart pH sensitivity was successfully prepared by RAFT copolymerizing of Flu-MA and poly(ethylene glycol) monomethacrylate (PEGMA). The result of 1H NMR and FTIR implied that both Flu-MA and PEGMA monomers were successfully incorporated into Flu-PEG copolymers, the molecular weight (M n) of which was about 39,800 with polydispersity index (PDI) as about 1.30. In aqueous solution, Flu-PEG copolymers could self-assemble into fluorescent organic nanoparticles (FONs) with about 200 nm diameters due to high water dispersibility and good fluorescence, respectively, endowed by PEGMA and Flu-MA, the fluorescence intensity of which was high sensitive to pH value of solution. More importantly, due to their high water dispersibility, excellent biocompatibility and good fluorescence, the as-prepared Flu-PEG FONs were high attractive for the application in cell imaging.

Graphical abstract

A novel amphiphilic fluorescent copolymer (Flu-PEG) with smart pH-sensitivity was successfully fabricated by RAFT copolymerizing of Flu-MA and PEGMA, which showed high water dispersibility, uniform size and excellent biocompatibility, making them be highly potential for bioimaging application.

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Acknowledgements

This research was financially supported by the National Science Foundation of China (Nos. 21474057, 21104039, 21134004, 51363016), the National 973 Project (Nos. 2011CB935700), and the Science and Technology Project of Zhongshan City of China (2014A2FC309).

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Authors and Affiliations

  1. College of Chemistry and Biology, Zhongshan Institute, University of Electronic Science and Technology of China, Zhongshan, 528402, People’s Republic of China

    Zengfang Huang

  2. Department of Chemistry, The Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing, 100084, People’s Republic of China

    Zengfang Huang, Xiqi Zhang, Xiaoyong Zhang, Shiqi Wang, Bin Yang, Ke Wang, Jinying Yuan, Lei Tao & Yen Wei

  3. Laboratory of Bio-Inspired Smart Interface Science, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, People’s Republic of China

    Xiqi Zhang

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Correspondence to Zengfang Huang, Lei Tao or Yen Wei.

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Huang, Z., Zhang, X., Zhang, X. et al. Synthesis of amphiphilic fluorescent copolymers with smart pH sensitivity via RAFT polymerization and their application in cell imaging. Polym. Bull. 74, 4525–4536 (2017). https://doi.org/10.1007/s00289-017-1969-3

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  • DOI: https://doi.org/10.1007/s00289-017-1969-3

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