Synthesis of Poly(N-vinylpyrrolidone)-based polymer bottlebrushes by ATRPA and RAFT polymerization: Toward drug delivery application

Yi Shen Huang, Jem Kun Chen, Shiao Wei Kuo, Ya An Hsieh, Shota Yamamoto, Jun Nakanishi, Chih Feng Huang

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Atom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conductedATRPAof 4-vinylbenzyl 2-bromo-2-phenylacetate (VBBPA) inimer and successfully obtained a linear type poly(VBBPA) (PVBBPA) polyester with benzylic bromides along the backbone. To obtain a novel amphiphilic polymer bottlebrush, however, the lateral ATRP chain extension of PVBBPA with N-vinyl pyrrolidone (NVP) met the problem of quantitative dimerization. By replacing the bromides to xanthate moieties efficiently, we thus observed a pseudo linear first order reversible addition-fragmentation chain transfer (RAFT) polymerization to obtain novel poly(4-vinylbenzyl-2-phenylacetate)-g-poly(NVP) (PVBPA-g-PNVP) amphiphilic polymer bottlebrushes. The critical micelle concentration (CMC) and particle size of the amphiphilic polymer bottlebrushes were characterized by fluorescence spectroscopy, dynamic light scattering (DLS), and scanning electron microscopy (SEM) (CMCs < 0.5 mg/mL; particle sizes = ca. 100 nm). Toward drug delivery application, we examined release profiles using a model drug of Nile red at different pH environments (3, 5, and 7). Eventually, low cytotoxicity and well cell uptake of the Madin-Darby Canine Kidney Epithelial (MDCK) for the polymer bottlebrush micelles were demonstrated.

Original languageEnglish
Article number1079
JournalPolymers
Volume11
Issue number6
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

Keywords

  • Amphiphilic polymer bottlebrush
  • Atom transfer radical polyaddition (ATRPA)
  • Functional polyesters
  • Poly(N-vinylpyrrolidone)
  • Reversible addition-fragmentation chain transfer (RAFT) polymerization

ASJC Scopus subject areas

  • Chemistry(all)
  • Polymers and Plastics

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