Peptide sequences can be selected for drug binding by combinatorial means. The corresponding PEG-peptide conjugates exhibited drug structure specific interactions with the cargo and proved there suitability for drug solubilization and topical delivery applications. The potential immunogenicity of peptides might be detoured by exploiting fully synthetic polymers. Here we report on the direct translation of found peptide-based drug hosting sequences into non-peptidic precision polymers from synthetic monomer alphabets, retaining the function of the parent peptide segment. Functional precision polymers based on monodisperse oligo(N-substituted acrylamide)s and oligo(2-substituted-α-hydroxy acid)s have been synthesized for drug solubilization. The discrete sequences applied for the precision polymers originate from a direct one-by-one mapping of the side-chain functionalities of a peptide. The precise incorporation of monomers in a polymer chain was realized by two different synthetic approaches like single unit monomer insertion (SUMI) reaction and segmer assembly polymerization (SAP) to get access to sequence defined oligo(acrylamides) and oligo(esters). The resulting peptidomimetic formulation additives preserved the drug solubilization and release characteristics of the parent peptide. In some cases, superior properties are obtained, reaching up to 40% higher payloads and 27-times faster initial drug release. The understanding on how sequence and backbone of the polymers can affect drug uptake and releasing rates of the incorporated drug gives possibilities to develop highly purpose adapted transport systems for next generation drug delivery.

Specific drug solubilization by precision polymers: Design guide learned from peptides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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