Jingquan Liu1, Ronald C Li2, Gregory J Sand2, Volga Bulmus3, Thomas P Davis3, Heather D Maynard2. 1. Department of Chemistry and Biochemistry & California Nanosystems Institute, University of California, Los Angeles, CA 90095-1569, USA ; Centre for Advanced Macromolecular Design, School of Chemical Sciences and Engineering, The University of New South Wales NSW 2052. 2. Department of Chemistry and Biochemistry & California Nanosystems Institute, University of California, Los Angeles, CA 90095-1569, USA. 3. Centre for Advanced Macromolecular Design, School of Chemical Sciences and Engineering, The University of New South Wales NSW 2052.
Abstract
A new methacrylate monomer with a reactive ketone side-chain, 2-(4-oxo-pentanoate) ethyl methacrylate (PAEMA), was synthesized and subsequently polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to give a polymer with a narrow molecular weight distribution (PDI = 1.25). The polymer was chain extended with poly(ethylene glycol methyl ether acrylate) (PEGMA) to yield a block copolymer. Aminooxy containing small molecules and oligoethylene glycol were conjugated to the ketone functionality of the side chain in high yields. Cytotoxicity of the oxime-linked tetra(ethylene glycol) polymer to mouse fibroblast cells was investigated; the polymer was found to be non-cytotoxic up to 1 mg/mL. The ease with which this polymer is functionalized, suggests that it may be useful in forming tailored polymeric medicines.
A new methacrylate monomer with a reactive n class="Chemical">ketone side-chain, 2-(4-oxo-pentanoate) ethyl methacrylate (PAEMA), was synthesized and subsequently polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to give a polymer with a narrow molecular weight distribution (PDI = 1.25). The polymer was chain extended with poly(ethylene glycol methyl ether acrylate) (PEGMA) to yield a block copolymer. Aminooxy containing small molecules and oligoethylene glycol were conjugated to the ketone functionality of the side chain in high yields. Cytotoxicity of the oxime-linked tetra(ethylene glycol) polymer to mouse fibroblast cells was investigated; the polymer was found to be non-cytotoxic up to 1 mg/mL. The ease with which this polymer is functionalized, suggests that it may be useful in forming tailored polymeric medicines.
Authors: Michael Malkoch; Raymond J Thibault; Eric Drockenmuller; Martin Messerschmidt; Brigitte Voit; Thomas P Russell; Craig J Hawker Journal: J Am Chem Soc Date: 2005-10-26 Impact factor: 15.419
Authors: Vincent Ladmiral; Giuseppe Mantovani; Guy J Clarkson; Solene Cauet; Jacob L Irwin; David M Haddleton Journal: J Am Chem Soc Date: 2006-04-12 Impact factor: 15.419