Glucose-Sensitivity of Boronic Acid Block Copolymers at Physiological pH

Debashish Roy; Brent S Sumerlin

doi:10.1021/mz300047c

Glucose-Sensitivity of Boronic Acid Block Copolymers at Physiological pH

ACS Macro Lett. 2012 May 15;1(5):529-532. doi: 10.1021/mz300047c. Epub 2012 Apr 9.

Authors

Debashish Roy¹, Brent S Sumerlin¹

Affiliation

¹ Department of Chemistry and Center for Drug Discovery, Design, and Delivery, Southern Methodist University, 3215 Daniel Avenue, Dallas, Texas 75275-0314, United States.

PMID: 35607054
DOI: 10.1021/mz300047c

Abstract

Well-defined boronic acid block copolymers were demonstrated to exhibit glucose-responsive disassembly at physiological pH. A boronic acid-containing acrylamide monomer with an electron-withdrawing substituent on the pendant phenylboronic acid moiety was polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to yield a polymer with a boronic acid pK_a = 8.2. Below this value, a block copolymer of this monomer with poly(N,N-dimethylacrylamide) self-assembled into aggregates. Addition of base to yield a pH > pK_a or addition of glucose at pH = 7.4 resulted in aggregate dissociation that may prove promising for controlled delivery applications under physiological relevant conditions.