Synthesis of Polymers Containing Potassium Acyltrifluoroborates (KATs) and Post-polymerization Ligation and Conjugation |
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| Authors: | Dominik Schauenburg Dr. Mohammad Divandari Dr. Kevin Neumann Christoph A. Spiegel Thomas Hackett Yi-Chung Dzeng Prof. Dr. Nicholas D. Spencer Prof. Dr. Jeffrey W. Bode |
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| Affiliation: | 1. Laboratorium für Organische Chemie, Department of Chemistry and Applied biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland;2. Laboratory for Surface Science and Technology, Department of Materials, ETH Zurich, Vladimir-Prelog-Weg 5, 8093 Zürich, Switzerland |
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| Abstract: | We report the synthesis of monomers for atom-transfer radical polymerization (ATRP) and a reversible addition-fragmentation chain transfer (RAFT) agent bearing trifluoroborate iminiums (TIMs), which are quantitatively converted into potassium acyltrifluoroborates (KATs) after polymerization. The resulting KAT-containing polymers are suitable for rapid amide-forming ligations for both post-polymerization modification and polymer conjugation. The polymer conjugation occurs rapidly, even under dilute (micromolar) aqueous conditions at ambient temperatures, thereby enabling the synthesis of a variety of linear and star-shaped block copolymers. In addition, we applied post-polymerization modification to the covalent linking of a photocaged cyclic antibiotic (gramicidin S) to the side chains of the KAT-containing copolymer. Cellular assays revealed that the polymer–antibiotic conjugate is biocompatible and provides efficient light-controlled release of the antibiotic on demand. |
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| Keywords: | antibiotics ATRP KAT ligation post-polymerization modification RAFT |
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