Hydrophilic block azidation of PCL-b-PEO block copolymers from epichlorohydrin.
Amphiphilic diblock copolymers poly(ϵ-caprolactone)-b-poly(ethylene oxide) (PCL-b-PEO) with well-controlled pendant azido groups along the hydrophilic PEO block, that is, poly(ϵ-caprolactone)-b-poly(ethylene oxide-co-glycidyl azide) (PCL-b-P(EO-co-GA)), are synthesized from poly(ϵ-caprolactone)-b-poly(ethylene oxide-co-epichlorohydrin) (PCL-b-P(EO-co-ECH)). The further conversion of those azido groups along the hydrophilic block of copolymers into amino or carboxyl groups via click chemistry is studied. The micelles self-assembled from PCL-b-P(EO-co-GA) with azido groups on the shell are crosslinked by the dialkynyl-PEO. The micelles with crosslinked shell show better stability, higher drug loading capacities, subsequent faster drug release rate, and higher cytotoxicity to cancer cells. The introduction of azido groups into PCL-b-PEO amphiphilic diblock copolymers from epichlorohydrin in PEO hydrophilic block in this work provides a new method for biofunctionalization of micelles via mild click chemistry.
CAS Key Laboratory of Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing, 100190, China; University of Chinese Academy of Sciences, Beijing, 100039, China.
Junjie
J
Liu
Zhihua
Z
Gan
D001386:Azides / Q000737:chemistry*; D057930:Click Chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D016503:Drug Delivery Systems / Q000379:methods*; D004811:Epichlorohydrin / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D008823:Micelles; D008958:Models, Molecular; D015394:Molecular Structure; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry; D011092:Polyethylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D003432:Cross-Linking Reagents; D008823:Micelles; D011091:Polyesters; D004811:Epichlorohydrin; C016240:polycaprolactone; D011092:Polyethylene Glycols
block copolymers; crosslinking; drug delivery systems; polymer functionalization polymers; self-assembly