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

Wanda Celentano, Jonathan Battistella, Ilaria Proietti Silvestri, Riccardo Bruni, Xiaoyi Huang, Min Li, Piergiorgio Messa, Stefania Ordanini, Francesco Cellesi

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)164-173
Number of pages10
JournalReactive and Functional Polymers
Volume131
DOIs
Publication statusPublished - Oct 1 2018

Fingerprint

Polyesters
polymerization
Polymerization
Nanoparticles
Polyethylene glycols
free radical
Free radical polymerization
Free Radicals
peptide
Peptides
ligand
Acrylates
Ligands
shell
Conversion Disorder
bioactivity
Ethylene Glycol
Surface Properties
Ring opening polymerization
Endothelial cells

Keywords

  • cRGD peptide
  • Free radical polymerization
  • Michael type addition
  • Polymeric nanoparticles
  • Ring opening polymerization

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Biochemistry
  • Chemical Engineering(all)
  • Polymers and Plastics
  • Materials Chemistry

Cite this

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; Li, Min; Messa, Piergiorgio; Ordanini, Stefania; Cellesi, Francesco.

In: Reactive and Functional Polymers, Vol. 131, 01.10.2018, p. 164-173.

Research output: Contribution to journalArticle

Celentano, Wanda ; Battistella, Jonathan ; Silvestri, Ilaria Proietti ; Bruni, Riccardo ; Huang, Xiaoyi ; Li, Min ; Messa, Piergiorgio ; Ordanini, Stefania ; Cellesi, Francesco. / Engineered polyester-PEG nanoparticles prepared through a “grafting through” strategy and post-functionalization via Michael type addition. In: Reactive and Functional Polymers. 2018 ; Vol. 131. pp. 164-173.
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