Light induced functionalization of PCL-PEG block copolymers for the covalent immobilization of biomolecules.
Functionalized poly-epsilon-caprolactone-block-polyethyleneglycol (PCL-PEG) amphiphilic copolymers were prepared to be constituents of nanocarriers used for the targeting of specific cells. Hence, we conceived a smooth and simple photografting methodology on these copolymers using a bifunctional molecular clip (O-succinimidyl-4-(p-azido-phenyl)butanoate). We prepared PCL-PEGs with pendent N-hydroxysuccinimide esters and studied the grafting with 3H-lysine, which radioactivity was counted by LSC. Several parameters were investigated, such as behavior of homopolymers, initial concentrations, irradiation, and incubation durations. Evidences of a "PEG directed photografting" are discussed and this selectivity could be improved by a selective solvent technique. The photografting on different PCL-PEGs revealed a dependency of the rates to the crystallinity of the copolymers. Several controls by SEC, DLS, and TEM of the treated copolymers were realized. Lastly, the coupling of alpha-D-mannopyranoside ligand was performed, reaching amounts of 5400 nmol/g of PCL-PEG. This derivatized PCL-PEG enters in the preparation of nanocarriers used for the targeting of antigen presenting cells.
Pourcelle
Vincent
V
Université catholique de Louvain, Unité de Chimie Organique et Médicinale, B-1348 Louvain-la-Neuve, Belgium.
Freichels
Hélène
H
Stoffelbach
François
F
Auzély-Velty
Rachel
R
Jérôme
Christine
C
Marchand-Brynaert
Jacqueline
J
D001672:Biocompatible Materials; D002152:Calorimetry, Differential Scanning; D004337:Drug Carriers; D005027:Ethylene Oxide / Q000737:chemistry* / Q000378:metabolism*; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism*; D008239:Lysine / Q000737:chemistry / Q000378:metabolism; D008422:Materials Testing; D008823:Micelles; D008855:Microscopy, Electron, Scanning; D011108:Polymers / Q000737:chemistry* / Q000378:metabolism*; D013388:Succinimides / Q000737:chemistry; D014316:Tritium
D001672:Biocompatible Materials; D004337:Drug Carriers; D007783:Lactones; D008823:Micelles; C400421:PLC(20)-b-PEO(44); D011108:Polymers; D013388:Succinimides; D014316:Tritium; D005027:Ethylene Oxide; D008239:Lysine; C001426:N-hydroxysuccinimide