Micelles assembled from amphiphilic copolymers have garnered interest for their potential application in targeted drug delivery. To probe the effects of chirality on the micelle stability, chiral amino acids were incorporated into either the hydrophobic or hydrophilic block of an amphiphilic copolymer that was polymerized using controlled radical techniques. For a hydrophilic monomer, Boc-amino acids were functionalized at the C-terminus with a methacrylate handle. Polymerization with MMA and deprotection of the Boc group afforded the cationic copolymer. Polymers exhibited either no or enhanced chirality depending on the side chain identity, as analyzed by optical rotation and circular dichroism. As the basis for a hydrophobic monomer, amino acids were functionalized with alkyl groups at the C-terminus and with an acrylamide handle at the N-terminus (see figure 1). After polymerization and deprotection, the copolymer was anionic and readily self-assembled to micelles ~65 nm in diameter (DLS). These copolymers were thermally stable at pH 7.4.

Amino acid-based amphiphilic copolymers: Synthesis and self-assembly

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.