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

doi:10.1021/acs.macromol.5b00173

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	942-949
Number of pages	8
Journal	Macromolecules
Volume	48
Issue number	4
DOIs	https://doi.org/10.1021/acs.macromol.5b00173
State	Published - Feb 24 2015

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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

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.",

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AU - Borchmann, Dorothee E.

AU - Tarallo, Rossella

AU - Avendano, Sarha

AU - Falanga, Annarita

AU - Carberry, Tom P.

AU - Galdiero, Stefania

AU - Weck, Marcus

PY - 2015/2/24

Y1 - 2015/2/24

N2 - 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.

AB - 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.

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

Abstract

ASJC Scopus subject areas

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