Free radical polymerization (FRP) is widely used in industrial processes as an efficient and versatile method to engineer polymeric nanoparticles (PNPs) of controlled size, narrowly distributed, and of well-defined surface properties. Functional Poly(ε-caprolactone) (PCL) and poly(lactic acid) (PLA) can be utilized as macromonomers in FRP in combination with a co-polymerizable poly(ethylene glycol) (PEG), to achieve aqueous dispersions of PNPs composed of a hydrophobic polyester core and a hydrophilic PEG shell of tuneable size. For several industrial and biological applications, PNPs also need surface functionalization to provide specific physicochemical characteristics, including stimuli-responsiveness, and bioactivity. In this work, a flexible “grafting through” strategy based on Ring opening polymerization (ROP) and FRP was proposed to obtain engineered polyester-PEG nanoparticles functionalized with acrylate groups on the hydrophilic shell. The presence of acrylates allows a versatile surface functionalization through Michael-type addition with a thiolated ligand (peptide), in aqueous solution under physiological pH, with the advantage of high conversion and absence of reaction side products. A cysteine-containing cyclic RGD was used as model peptide for conjugation, due to its potential application as ligand for endothelial cells. Results indicated that active cell targeting can be achieved by using this surface functionalization approach.

Engineered polyester-PEG nanoparticles prepared through a “grafting through” strategy and post-functionalization via Michael type addition

CELENTANO, WANDA;BATTISTELLA, JONATHAN;Silvestri, Ilaria Proietti;Bruni, Riccardo;Huang, Xiaoyi;Ordanini, Stefania;Cellesi, Francesco
2018

Abstract

Free radical polymerization (FRP) is widely used in industrial processes as an efficient and versatile method to engineer polymeric nanoparticles (PNPs) of controlled size, narrowly distributed, and of well-defined surface properties. Functional Poly(ε-caprolactone) (PCL) and poly(lactic acid) (PLA) can be utilized as macromonomers in FRP in combination with a co-polymerizable poly(ethylene glycol) (PEG), to achieve aqueous dispersions of PNPs composed of a hydrophobic polyester core and a hydrophilic PEG shell of tuneable size. For several industrial and biological applications, PNPs also need surface functionalization to provide specific physicochemical characteristics, including stimuli-responsiveness, and bioactivity. In this work, a flexible “grafting through” strategy based on Ring opening polymerization (ROP) and FRP was proposed to obtain engineered polyester-PEG nanoparticles functionalized with acrylate groups on the hydrophilic shell. The presence of acrylates allows a versatile surface functionalization through Michael-type addition with a thiolated ligand (peptide), in aqueous solution under physiological pH, with the advantage of high conversion and absence of reaction side products. A cysteine-containing cyclic RGD was used as model peptide for conjugation, due to its potential application as ligand for endothelial cells. Results indicated that active cell targeting can be achieved by using this surface functionalization approach.
cRGD peptide; Free radical polymerization; Michael type addition; Polymeric nanoparticles; Ring opening polymerization; Chemistry (all); Environmental Chemistry; Biochemistry; Chemical Engineering (all); Polymers and Plastics; Materials Chemistry2506 Metals and Alloys
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/1071924
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