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

J Control Release. 2007 Oct 8;122(3):279-86. doi: 10.1016/j.jconrel.2007.04.010. Epub 2007 Apr 21.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes / chemistry*
  • Drug Carriers* / chemical synthesis
  • Drug Carriers* / chemistry
  • Esters / chemistry*
  • Molecular Structure
  • Molecular Weight
  • Polymers* / chemical synthesis
  • Polymers* / chemistry

Substances

  • Aldehydes
  • Drug Carriers
  • Esters
  • Polymers