Mannosylated poly(ethylene oxide)-b-Poly(epsilon-caprolactone) diblock copolymers: Synthesis, characterization, and interaction with a bacterial lectin
[en] A novel bioeliminable amphiphilic poly(ethylene oxide)-b-poly(epsilon-caprolactone) (PEO-b-PCL) diblock copolymer end-capped by a mannose residue was synthesized by sequential controlled polymerization of ethylene oxide and epsilon-caprolactone, followed by the coupling of a reactive mannose derivative to the PEO chain end. The anionic polymerization of ethylene oxide was first initiated by potassium 2-dimethylaminoethanolate. The ring-opening polymerization of epsilon-caprolactone was then initiated by the omega-hydroxy end-group of PEO previously converted into an Al alkoxide. Finally, the saccharidic end-group was attached by quaternization of the tertiary amine (alpha-end-group of the PEO-b-PCL with a brominated mannose derivative. The copolymer was fully characterized in terms of chemical composition and purity by high-resolution NMR spectroscopy and size exclusion chromatography. Furthermore, measurements with a pendant drop tensiometer showed that both the mannosylated copolymer and the non-mannosylated counterpart significantly decreased the dichloromethane/water interfacial tension. Moreover, these amphiphilic copolymers formed monodisperse spherical micelles in water with an average diameter of similar to 11 nin as measured by dynamic light scattering and cryo-transmission electron microscopy. The availability of mannose as a specific recognition site at the surface of the micelles was proved by isothermal titration microcalorimetry (ITC), using the BclA lectin (from Burkholderia cenocepacia), which interacts selectively with a-D-mannopyranoside derivatives. The thermodynamic parameters of the lectin/mannose interaction were extracted from the ITC data. These colloidal systems have great potential for drug targeting and vaccine delivery systems.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Rieger, Jutta ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Stoffelbach, François; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Cui, Di; Université Joseph Fourier and the Institut de Chimie Moléculaire de Grenoble, France > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Imberty, Anne; Université Joseph Fourier and the Institut de Chimie Moléculaire de Grenoble, France > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Lameignere, E.; Université Joseph Fourier and the Institut de Chimie Moléculaire de Grenoble, France > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Putaux, Jean-Luc; Université Joseph Fourier and the Institut de Chimie Moléculaire de Grenoble, France > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Jérôme, Robert ; Université de Liège - ULiège > Centre d'études et de rech. sur les macromolécules (CERM)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Auzely-Velty, Rachel; Université Joseph Fourier and the Institut de Chimie Moléculaire de Grenoble, France > Centre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS)
Language :
English
Title :
Mannosylated poly(ethylene oxide)-b-Poly(epsilon-caprolactone) diblock copolymers: Synthesis, characterization, and interaction with a bacterial lectin
Publication date :
September 2007
Journal title :
Biomacromolecules
ISSN :
1525-7797
eISSN :
1526-4602
Publisher :
Amer Chemical Soc, Washington, United States - Washington
BELSPO - Service Public Fédéral de Programmation Politique scientifique [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
Funding text :
J.R., C.J., and R.J. are much indebted
to the “Belgian Science Policy” for financial support in the frame
of the “Interuniversity Attraction Poles Programme (IAP-PAI
P6/27): Supramolecular Chemistry and Supramolecular Catalysis”.
J.R. was a recipient of a Marie Curie fellowship. C.J.
is an Research Associate by the “Fonds National de la Recherche
Scientifique” (FNRS). F.S., C.J., and R.J. also thank the FNRS
for a grant to F.S. in the frame of the “SONS-EUROCORES”
program. E.L. gratefully acknowledges the MENRT for her
thesis grant at the CERMAV. Furthermore, the authors are very
grateful to Ge´rard Chambat for technical support.
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