pH-Responsive benzaldehyde-functionalized PEG-based polymeric nanoparticles for drug delivery: Effect of preparation method on morphology, dye encapsulation and attachment

Peter Smyth, Thomas J Gibson, Gavin Irvine, Gemma Black, Daniel Lavery, Mona Semsarilar, Christopher J Scott, Efrosyni Themistou

Research output: Contribution to journalArticle

Abstract

Functionalized, pH-responsive and biocompatible polymeric nanoparticles have attracted the interest of manyresearchers working on novel pharmaceutical formulations. Here, in an effort to develop an efficient drug delivery formulation, all these properties are combined in one polymeric nanoparticle system. More specifically,benzaldehyde-functionalized amphiphilic block copolymers based on PEG-based oligo(ethylene glycol) methacrylate (OEGMA), benzaldehyde-containingpara-formyl phenyl methacrylate (pFPMA) and pH-responsive 2-(diisopropyl)aminoethyl methacrylate (DPA) monomers are readily prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. pH-Switch and single emulsion-solvent evaporation post-poly-merization processing methods are used to prepare benzaldehyde-functionalized PEGylated pH-responsive nanoparticles with diameters of 180–230 nm. After nanoparticle formation, the benzaldehyde groups on the surface are shown to react with an Alexa Fluor 488 hydroxylamine dye through oxime bond formation, illustrating the potential for these particles to be surface-functionalized with biologically important molecules, suchas fluorescent dyes for tracking their intracellular fate or antibodies for targeted therapy. Encapsulation of Nile Red and rhodamine 6G dyes is performed during the post-polymerization processing step for nanoparticle formation. Nanoparticles with a fluorescent cargo were shown to be successfully internalized in both A2780 ovariancancer and A549 lung epithelial human cellsinvitro, further illustrating the potential for these formulations to beused as triggered release therapeutic drug delivery vehicles.
Original languageEnglish
Article number109471
JournalEuropean Polymer Journal
Volume124
Early online date02 Jan 2020
DOIs
Publication statusEarly online date - 02 Jan 2020

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Drug delivery
Encapsulation
Polyethylene glycols
attachment
delivery
drugs
Coloring Agents
Dyes
dyes
Nanoparticles
nanoparticles
preparation
formulations
polymerization
Polymerization
Hydroxylamine
cargo
Oximes
Ethylene Glycol
Methacrylates

Cite this

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title = "pH-Responsive benzaldehyde-functionalized PEG-based polymeric nanoparticles for drug delivery: Effect of preparation method on morphology, dye encapsulation and attachment",
abstract = "Functionalized, pH-responsive and biocompatible polymeric nanoparticles have attracted the interest of manyresearchers working on novel pharmaceutical formulations. Here, in an effort to develop an efficient drug delivery formulation, all these properties are combined in one polymeric nanoparticle system. More specifically,benzaldehyde-functionalized amphiphilic block copolymers based on PEG-based oligo(ethylene glycol) methacrylate (OEGMA), benzaldehyde-containingpara-formyl phenyl methacrylate (pFPMA) and pH-responsive 2-(diisopropyl)aminoethyl methacrylate (DPA) monomers are readily prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. pH-Switch and single emulsion-solvent evaporation post-poly-merization processing methods are used to prepare benzaldehyde-functionalized PEGylated pH-responsive nanoparticles with diameters of 180–230 nm. After nanoparticle formation, the benzaldehyde groups on the surface are shown to react with an Alexa Fluor 488 hydroxylamine dye through oxime bond formation, illustrating the potential for these particles to be surface-functionalized with biologically important molecules, suchas fluorescent dyes for tracking their intracellular fate or antibodies for targeted therapy. Encapsulation of Nile Red and rhodamine 6G dyes is performed during the post-polymerization processing step for nanoparticle formation. Nanoparticles with a fluorescent cargo were shown to be successfully internalized in both A2780 ovariancancer and A549 lung epithelial human cellsinvitro, further illustrating the potential for these formulations to beused as triggered release therapeutic drug delivery vehicles.",
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AU - Smyth, Peter

AU - Gibson, Thomas J

AU - Irvine, Gavin

AU - Black, Gemma

AU - Lavery, Daniel

AU - Semsarilar, Mona

AU - Scott, Christopher J

AU - Themistou, Efrosyni

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