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Open AccessArticle

Synthesis of Poly(N-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application

1
Department of Chemical Engineering, National Chung Hsing University, 145 Xingda Road, Taichung 40227, Taiwan
2
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei 10607, Taiwan
3
Department of Materials and Optoelectronic Science, Center of Crystal Research, National Sun Yat-Sen University, Kaohsiung 804, Taiwan
4
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
5
World Premier International Research Center for Materials Nanoarchitectonics (WPI-MANA), National Institute for Materials Science (NIMS), 1-1, Namiki, Tsukuba, Ibaraki 305-0044, Japan
*
Authors to whom correspondence should be addressed.
Polymers 2019, 11(6), 1079; https://doi.org/10.3390/polym11061079
Received: 20 May 2019 / Revised: 19 June 2019 / Accepted: 20 June 2019 / Published: 22 June 2019
(This article belongs to the Special Issue Reversible-Deactivation Radical Polymerization)
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Abstract

Atom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conducted ATRPA of 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. View Full-Text
Keywords: atom transfer radical polyaddition (ATRPA); reversible addition–fragmentation chain transfer (RAFT) polymerization; functional polyesters; poly(N-vinylpyrrolidone); amphiphilic polymer bottlebrush atom transfer radical polyaddition (ATRPA); reversible addition–fragmentation chain transfer (RAFT) polymerization; functional polyesters; poly(N-vinylpyrrolidone); amphiphilic polymer bottlebrush
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    Description: Figure S1. GPC traces for ATRPA of VBBPA (VBBPA/CuBr2/Cu/PMDETA = 50/2/1/6 at 40 °C; [VBBPA]0 = 1.8 M in anisole). Figure S2. FT-IR spectra of (a) PVBBPA and (b) purified NVP dimer obtained after ATRP (NVP/PVBBPA/CuBr/PMDETA = 200/1/1/1 in anisole; PVBBPA: Mn = 11200 and PDI = 1.58; [NVP]0 = 4.0 M). Figure S3. GPC traces for ATRP of PVBBPA with NVP at various reaction times (NVP/PVBBPA/CuBr/PMDETA = 200/1/1/1 in anisole at 80 °C). Figure S4. FT-IR spectra of (a) PVBXPA and (b) PVBPA-g-PNVP (co)polymers.
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Huang, Y.-S.; Chen, J.-K.; Kuo, S.-W.; Hsieh, Y.-A.; Yamamoto, S.; Nakanishi, J.; Huang, C.-F. Synthesis of Poly(N-vinylpyrrolidone)-Based Polymer Bottlebrushes by ATRPA and RAFT Polymerization: Toward Drug Delivery Application. Polymers 2019, 11, 1079.

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