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

Jungyeon Hwang1, Ronald C Li, Heather D Maynard

  • 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.

Journal of Controlled Release : Official Journal of the Controlled Release Society
|June 30, 2007
PubMed
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Researchers synthesized polymers with reactive side chains using reversible addition-fragmentation chain transfer (RAFT) polymerization. These polymers show promise for developing advanced drug carriers through side-chain functionalization.

Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biomedical Engineering

Background:

  • Controlled polymerization techniques are crucial for developing advanced functional materials.
  • Polymers with well-defined structures and reactive side chains are essential for creating sophisticated drug delivery systems.
  • Reversible Addition-Fragmentation chain Transfer (RAFT) polymerization offers precise control over polymer architecture.

Purpose of the Study:

  • To synthesize polymers with narrow molecular weight distributions and reactive side chains via RAFT polymerization.
  • To demonstrate the functionalization capabilities of these synthesized polymers.
  • To explore the potential of these functionalized polymers as drug carriers.

Main Methods:

  • Synthesis of p-nitrophenyl methacrylate (pNPMA) and diethoxypropyl methacrylate (pDEPMA) using RAFT polymerization with cumyl dithiobenzoate (CDB) and azobisisobutyronitrile (AIBN).

Related Experiment Videos

  • High conversion polymerization (> or = 86%) achieving narrow molecular weight distributions (polydispersity indices < 1.3).
  • Functionalization of polymer side chains through substitution with glycine methyl ester (for pNPMA) and hydrolysis to aldehydes followed by oxime bond formation (for pDEPMA).

    • Main Results:

    • Successfully synthesized pNPMA and pDEPMA with controlled molecular weights and narrow polydispersity.
    • Achieved high substitution rates: up to 86% side chain functionalization with glycine methyl ester on pNPMA.
    • Demonstrated hydrolysis of pDEPMA side chains to aldehydes and subsequent conjugation with hydroxylamines and an RGD peptide via stable oxime bonds.

    Conclusions:

    • RAFT polymerization is an effective method for creating well-defined polymers with reactive side chains.
    • The synthesized polymers offer versatile platforms for post-polymerization modification and conjugation.
    • These functionalized polymers hold significant potential for the development of targeted drug delivery systems and other biomedical applications.