The glucose‐responsive behavior of a block copolymer featuring boronic acid and glycine. Issue 3 (26th September 2018)

• Record Type: Journal Article
• Authors: Gaballa, Heba; Shang, Jiaojiao; Meier, Sabrina; Theato, Patrick
• Is Part Of: Journal of polymer science. Volume 57:Issue 3(2019)
• Page Start: 422
• Page End: 431
• Publication Date: 2018-09-26
• Subjects: activate ester -- boronic acid polymers -- glucose responsive polymers -- post‐polymerization modification -- RAFT polymerization; 547
• DOI: 10.1002/pola.29226
• Languages: English
• ISSNs: 0887-624X

Abstract

ABSTRACT: Glucose responsive block copolymer featuring boronic acid as a glucose responsive moiety and glycine are reported. The first block is polymerized through reversible addition–fragmentation chain transfer (RAFT) polymerization and the resulting poly( N ‐acryloylmorpholine)113 (PAcM) is employed as a macro‐chain transfer agent for chain extension with pentafluorophenyl acrylate (PFPA) yielding a well‐defined PAcM113 ‐ block ‐poly(pentafluorophenyl acrylate)84 (PPFPA). The PPFPA block is then reacted with functional (3‐aminomethyl) phenyl boronic acid and glycine via post‐polymerization modification and the structure of the block copolymer is confirmed by proton nuclear magnetic resonance (NMR), 19 F NMR, Fourier transform infrared, and gel permeation chromatography. By copolymerizing glycine into the polymer backbone, the relative p K a of the block copolymer is significantly lowered. The block copolymer can self‐assemble into core–shell micelles in aqueous solution and disassemble in response to glucose at the physiological pH. Furthermore, the encapsulation and release of Nile red (NR) as a hydrophobic model drug is studied under the physiological pH. The influence of the glucose concentration on the NR release from the polymeric micelles is demonstrated. These results suggested that the glucose‐responsive poly[(AcM)113 ‐ b ‐(3‐(aminomethyl)phenylboronic acid hydrochloride(‐ co ‐Gly)84 ] block copolymer has potential applications as a glucose‐responsive polymer for insulin delivery. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem.2019, 57, 422–431 Abstract : Amphiphilic glucose responsive block copolymers containing boronic acid as a glucose‐responsive moiety and glycine are prepared by RAFT and post‐polymerization modification. The block copolymer poly[(AcM)113 ‐ b‐ poly[(3‐(aminomethyl)phenylboronic acid hydrochloride‐ co ‐Gly)]84 can self‐assemble into micelles and disassemble in response to glucose at the physiological pH. Nile red is loaded into the polymeric micelles and demonstrated controlled release in the presence of glucose.