NDLI: Facile synthesis of thiol-functionalized amphiphilic polylactide

Content Provider	Royal Society of Chemistry (RSC)
Author	Armes, Steven P. Battaglia, Giuseppe Themistou, Efrosyni
Copyright Year	2014
Abstract	Biodegradable amphiphilic diblock copolymers based on an aliphatic ester block and various hydrophilic methacrylic monomers were synthesized using a novel hydroxyl-functionalized trithiocarbonate-based chain transfer agent. One protocol involved the one-pot simultaneous ring-opening polymerization (ROP) of the biodegradable monomer (3S)-cis-3,6-dimethyl-1,4-dioxane-2,5-dione (L-lactide, LA) and reversible addition–fragmentation chain transfer (RAFT) polymerization of 2-(dimethylamino)ethyl methacrylate (DMA) or oligo(ethylene glycol) methacrylate (OEGMA) monomer, with 4-dimethylaminopyridine being used as the ROP catalyst and 2,2′-azobis(isobutyronitrile) as the initiator for the RAFT polymerization. Alternatively, a two-step protocol involving the initial polymerization of LA followed by the polymerization of DMA, glycerol monomethacrylate or 2-(methacryloyloxy)ethyl phosphorylcholine using 4,4′-azobis(4-cyanovaleric acid) as a RAFT initiator was also explored. Using a solvent switch processing step, these amphiphilic diblock copolymers self-assemble in dilute aqueous solution. Their self-assembly provides various copolymer morphologies depending on the block compositions, as judged by transmission electron microscopy and dynamic light scattering. Two novel disulfide-functionalized PLA-branched block copolymers were also synthesized using simultaneous ROP of LA and RAFT copolymerization of OEGMA or DMA with a disulfide-based dimethacrylate. The disulfide bonds were reductively cleaved using tributyl phosphine to generate reactive thiol groups. Thiol–ene chemistry was utilized for further derivatization with thiol-based biologically important molecules and heavy metals for tissue engineering or bioimaging applications, respectively.
Starting Page	1405
Ending Page	1417
Page Count	13
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	5
Issue Number	4
Journal	Polymer Chemistry
DOI	10.1039/c3py01446k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Ring-opening polymerization 4-Dimethylaminopyridine Oligomer Ester Chain transfer Dynamic light scattering Carboxylic acid DMA Hydrophile Dimethylacetamide Copolymer Monomer Solvent Biodegradation Ethylene glycol Thiol Aliphatic compound Phosphine Tissue engineering Polymerization Glycerol Organic chemistry Self-assembly Transmission electron microscopy Disulfide Amphiphile OEGMA 1,4-Dioxane
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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