Membranotropic peptide-functionalized poly(lactide)- graft -poly(ethylene glycol) brush copolymers for intracellular delivery

Dorothee E. Borchmann, Rossella Tarallo, Sarha Avendano, Annarita Falanga, Tom P. Carberry, Stefania Galdiero, Marcus Weck

Research output: Contribution to journalArticle

Abstract

A biodegradable delivery scaffold based on poly(lactide)-graft-poly(ethylene glycol) (PLA-g-PEG) is introduced and tested in vitro. The use of a functional ring-opening polymerization initiator (containing a masked aldehyde) on an azido PEG-lactide monomer combines two known methodologies to afford functionalized PLA. The resulting copolymer features two compatible functional groups and decreased hydrophobicity due to the PEG. The functional groups are capable of performing high-yielding orthogonal postpolymerization reactions, namely strain-promoted azide-alkyne click chemistry and reductive amination. PLA-g-PEG was functionalized with a fluorescent dye (7-nitrobenzoxadiazole, NBD) and a cell internalization peptide, gH625. The resulting delivery vehicle was investigated for cell uptake with HeLa cells, showing that the gH625 conjugation exhibited enhanced cellular uptake and localization in close proximity to the nuclei. The presented methodology is a new approach toward targeted delivery.

Original languageEnglish (US)
Pages (from-to)942-949
Number of pages8
JournalMacromolecules
Volume48
Issue number4
DOIs
StatePublished - Feb 24 2015

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Brushes
Grafts
Peptides
Polyethylene glycols
Copolymers
Functional groups
Amination
Alkynes
Azides
Ring opening polymerization
Hydrophobicity
Aldehydes
Fluorescent Dyes
Scaffolds
Dyes
Monomers
poly(lactide)

ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Cite this

Membranotropic peptide-functionalized poly(lactide)- graft -poly(ethylene glycol) brush copolymers for intracellular delivery. / Borchmann, Dorothee E.; Tarallo, Rossella; Avendano, Sarha; Falanga, Annarita; Carberry, Tom P.; Galdiero, Stefania; Weck, Marcus.

In: Macromolecules, Vol. 48, No. 4, 24.02.2015, p. 942-949.

Research output: Contribution to journalArticle

Borchmann, Dorothee E. ; Tarallo, Rossella ; Avendano, Sarha ; Falanga, Annarita ; Carberry, Tom P. ; Galdiero, Stefania ; Weck, Marcus. / Membranotropic peptide-functionalized poly(lactide)- graft -poly(ethylene glycol) brush copolymers for intracellular delivery. In: Macromolecules. 2015 ; Vol. 48, No. 4. pp. 942-949.
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