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J Control Release. 2007 Oct 8;122(3):279-86. Epub 2007 Apr 21.

Well-defined polymers with activated ester and protected aldehyde side chains for bio-functionalization.

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  • 1Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569, USA.


Polymers with reactive side chains and narrow molecular weight distributions were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization, and the potential to utilize these polymers to prepare drug carriers was demonstrated. p-Nitrophenyl methacrylate (NPMA) and diethoxypropyl methacrylate (DEPMA) were polymerized utilizing cumyl dithiobenzoate (CDB) as the chain transfer agent and azobisisobutyronitrile (AIBN) as the initiator to high conversions (> or = 86%). The resulting pNPMA and pDEPMA had narrow molecular weight distributions (polydispersity indices < 1.3). The ability to functionalize these polymers was confirmed. For pNPMA, up to 86% of the side chains were substituted with the amino acid, glycine methyl ester. The side chains of pDEPMA were hydrolyzed to aldehydes and reaction with O-benzylhydroxylamine and O-methylhydroxylamine to form stable oxime bond conjugates was demonstrated. The percent substitution depended on the feed ratios. Conjugation of an aminooxy-functionalized RGD peptide was also demonstrated.

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