α-Acetal, ω-alkyne poly(ethylene oxide) as a versatile building block for the synthesis of glycoconjugated graft-copolymers suited for targeted drug delivery
[en] α-Acetal, ω-alkyne poly(ethylene oxide) was synthesized as building block of glycoconjugated poly(ε-caprolactone)-graft-poly(ethylene oxide) (PCL-g-PEO) copolymers. The alkyne group is indeed instrumental for the PEGylation of a poly(α-azido-ε-caprolactone-co-ε-caprolactone) copolymer by the Huisgen’s 1,3 dipolar cycloaddition, i.e., a click reaction. Moreover, deprotection of the acetal end-group of the hydrophilic PEO grafts followed by reductive amination of the accordingly formed aldehyde with an aminated sugar is a valuable strategy of glycoconjugation of the graft copolymer, whose micelles are then potential. A model molecule (fluoresceinamine) was first considered in order to optimize the experimental conditions for the reductive amination. These conditions were then extended to the decoration of the graft copolymer micelles with mannose, which is a targeting agent of dendritic cells and macrophages. The bioavailability of the sugar units at the surface of micelles was investigated by surface plasmon resonance (SPR). The same question was addressed to nanoparticles stabilized by the graft copolymer. Enzyme linked lectin assay (ELLA) confirmed the availability of mannose at the nanoparticle surface.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Freichels, Hélène; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Alaimo, David ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Auzély-Velty, Rachel; Université Joseph Fourier, Grenoble, France > Institut de Chimie Moléculaire de Grenoble > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
α-Acetal, ω-alkyne poly(ethylene oxide) as a versatile building block for the synthesis of glycoconjugated graft-copolymers suited for targeted drug delivery
Publication date :
09 September 2012
Journal title :
Bioconjugate Chemistry
ISSN :
1043-1802
eISSN :
1520-4812
Publisher :
American Chemical Society, Washington, United States - District of Columbia
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