Synthesis of poly(lactide-co-glycolide-co-ε-caprolactone)-graft-mannosylated poly(ethylene oxide) copolymers by combination of “clip” and “click” chemistries
ring opening metathesis polymerization; click chemistry; copper-mediated Huisgen's cycloaddition; self-assembly in solution; micelle; polymer functionalization
Abstract :
[en] Poly(lactide-co-glycolide) (PLGA) is extensively used in pharmaceutical applications, for example, in targeted drug delivery, because of biocompatibility and degradation rate, which is easily tuned by the copolymer composition. Nevertheless, synthesis of sugar-labeled amphiphilic copolymers with a PLGA backbone is quite a challenge because of high sensitivity to hydrolytic degradation. This Article reports on the synthesis of a new amphiphilic copolymer of PLGA grafted by mannosylated poly(ethylene oxide) (PEO). A novel building block, that is, α-methoxy-ω-alkyne PEO-clip-N-hydroxysuccinimide (NHS) ester, was prepared on purpose by photoreaction of a diazirine containing molecular clip. This PEO block was mannosylated by reaction of the NHS ester groups with an aminated sugar, that is, 2-aminoethyl-α-d-mannopyroside. Then, the alkyne ω-end-group of PEO was involved in a copper alkyne- azide coupling (CuAAC) with the pendent azides of the aliphatic copolyester. The targeted mannose-labeled poly(lactide-co-glycolide-co-ε-caprolactone)-graft-poly(ethylene oxide) copolymer was accordingly formed. Copolymerization of d,l-lactide and glycolide with α-chloro-ε-caprolactone, followed by substitution of chlorides by azides provided the azido-functional PLGA backbone. Finally, micelles of the amphiphilic mannosylated graft copolymer were prepared in water, and their interaction with Concanavalin A (ConA), a glyco-receptor protein, was studied by quartz crystal microbalance. This study concluded to the prospect of using this novel bioconjugate in targeted drug delivery.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Freichels, Hélène; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Pourcelle, Vincent; Université catholique de Louvain (UCL) > Institute of Condensed Matter and Nanosciences (IMCN)
Auzély-Velty, Rachel; Université Joseph Fourier, Grenoble, France > Institut de Chimie Moléculaire de Grenoble > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Marchand-Brynaert, Jacqueline; Université catholique de Louvain (UCL) > Institute of Condensed Matter and Nanosciences (IMCN)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Synthesis of poly(lactide-co-glycolide-co-ε-caprolactone)-graft-mannosylated poly(ethylene oxide) copolymers by combination of “clip” and “click” chemistries
Publication date :
12 March 2012
Journal title :
Biomacromolecules
ISSN :
1525-7797
eISSN :
1526-4602
Publisher :
American Chemical Society, Washington, United States - District of Columbia
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