Well-defined polymers with activated ester and protected aldehyde side chains for bio-functionalization.
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.
Hwang
Jungyeon
J
Department 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.
Li
Ronald C
RC
Maynard
Heather D
HD
D000447:Aldehydes / Q000737:chemistry*; D004337:Drug Carriers / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D008970:Molecular Weight; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry
D000447:Aldehydes; D004337:Drug Carriers; D004952:Esters; D011108:Polymers