Keto-Functionalized Polymer Scaffolds As Versatile Precursors to Polymer Side Chain Conjugates.
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.
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.
Jingquan
J
Liu
Department of Chemistry and Biochemistry & California Nanosystems Institute, University of California, Los Angeles, CA 90095-1569, USA.
Ronald C
RC
Li
Department of Chemistry and Biochemistry & California Nanosystems Institute, University of California, Los Angeles, CA 90095-1569, USA.
Gregory J
GJ
Sand
Centre for Advanced Macromolecular Design, School of Chemical Sciences and Engineering, The University of New South Wales NSW 2052.
Volga
V
Bulmus
Centre for Advanced Macromolecular Design, School of Chemical Sciences and Engineering, The University of New South Wales NSW 2052.
Thomas P
TP
Davis
Department of Chemistry and Biochemistry & California Nanosystems Institute, University of California, Los Angeles, CA 90095-1569, USA.
Heather D
HD
Maynard