Efstathiou, Spyridon, Ma, Congkai, Coursari, Despina, Patias, Georgios, Al-Shok, Lucas, Eissa, Ahmed M. and Haddleton, David M. (2022) Functional pH-responsive polymers containing dynamic enaminone linkages for the release of active organic amines. Polymer Chemistry, 13 (16). pp. 2362-2374. doi:10.1039/d2py00167e ISSN 1759-9954.

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Abstract

Dynamic covalent bonds have attracted considerable attention for the development of pH-responsive polymers, however, studies using acid-cleavable enaminone linkages as a means of controlled release are limited. Herein, we report pH-sensitive benzocaine-modified poly(ethylene glycol) monomethyl ether-block-poly[2-(acetoacetoxy)ethyl methacrylate] (mPEGx-b-pAEMAy)/BNZ nanoparticles (NPs) for the aqueous controlled release of benzocaine through enaminone bond cleavage. The system is based on the commercially available monomer 2-(acetoacetoxy)ethyl methacrylate (AEMA) which contains free pendant β-ketoester functionality. Well-defined poly[2-(acetoacetoxy)ethyl methacrylate] (pAEMA) homopolymers and poly[(ethylene glycol) monomethyl ether]-block-poly[2-(acetoacetoxy)ethyl methacrylate] (mPEGx-b-pAEMAy) amphiphilic block copolymers were prepared by photoinduced Cu(II)-mediated RDRP to investigate their modification with propylamine (a model amine) and benzocaine (a primary amine containing API) through an enaminone bond. Block copolymers were prepared via two poly(ethylene glycol) monomethyl ether-2-bromo-2-phenylacetate (mPEGx-BPA, x = 43 or 113) macroinitiators synthesised by esterification which acted as the hydrophilic coronas of the ensuing NPs. The self-assembly of both mPEGx-b-pAEMAy and (mPEGx-b-pAEMAy)/BNZ was assessed in water by the direct dilution approach forming spherical NPs as characterised by dynamic light scattering (DLS) and dry-state transmission electron microscopy (TEM). Finally, the in vitro controlled release of benzocaine from mPEGx-b-pAEMAy/BNZ NPs was examined at different pH environments demonstrating faster release kinetics at lower pH with potential utility in applications with relevant chemical environments.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH):	Polymerization, Polymers, Chemistry, Organic, Amines
Journal or Publication Title:	Polymer Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1759-9954
Official Date:	28 April 2022
Dates:	Date Event 28 April 2022 Published 18 March 2022 Available 16 March 2022 Accepted 7 February 2022 Submitted
Volume:	13
Number:	16
Page Range:	pp. 2362-2374
DOI:	10.1039/d2py00167e
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Open Access (Creative Commons)
Date of first compliant deposit:	30 May 2022
Date of first compliant Open Access:	1 June 2022
RIOXX Funder/Project Grant:	Project/Grant ID RIOXX Funder Name Funder ID EP/V036211/1 [EPSRC] Engineering and Physical Sciences Research Council http://dx.doi.org/10.13039/501100000266 EP/L015307/1 [EPSRC] Engineering and Physical Sciences Research Council http://dx.doi.org/10.13039/501100000266

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