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Amino-Acid-Derived Anionic Polyacrylamides with Tailored Hydrophobicity : Physicochemical Properties and Cellular Interactions

Title data

De Breuck, Jonas ; Streiber, Michael ; Ringleb, Michael ; Schröder, Dennis ; Herzog, Natascha ; Schubert, Ulrich S. ; Zechel, Stefan ; Traeger, Anja ; Leiske, Meike N.:
Amino-Acid-Derived Anionic Polyacrylamides with Tailored Hydrophobicity : Physicochemical Properties and Cellular Interactions.
In: ACS Polymers Au. (2024) .
ISSN 2694-2453
DOI: https://doi.org/10.1021/acspolymersau.3c00048

Abstract in another language

Polyanions can internalize into cells via endocytosis without any cell disruption and are therefore interesting materials for biomedical applications. In this study, amino-acid-derived polyanions with different alkyl side-chains are synthesized via postpolymerization modification of poly(pentafluorophenyl acrylate), which is synthesized via reversible addition–fragmentation chain-transfer (RAFT) polymerization, to obtain polyanions with tailored hydrophobicity and alkyl branching. The success of the reaction is verified by size-exclusion chromatography, NMR spectroscopy, and infrared spectroscopy. The hydrophobicity, surface charge, and pH dependence are investigated in detail by titrations, high-performance liquid chromatography, and partition coefficient measurements. Remarkably, the determined pKa-values for all synthesized polyanions are very similar to those of poly(acrylic acid) (pKa = 4.5), despite detectable differences in hydrophobicity. Interactions between amino-acid-derived polyanions with L929 fibroblasts reveal very slow cell association as well as accumulation of polymers in the cell membrane. Notably, the more hydrophobic amino-acid-derived polyanions show higher cell association. Our results emphasize the importance of macromolecular engineering toward ideal charge and hydrophobicity for polymer association with cell membranes and internalization. This study further highlights the potential of amino-acid-derived polymers and the diversity they provide for tailoring properties toward drug delivery applications.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Junior Professor Sustainable and Functional Polymer Systems > Junior Professor Sustainable and Functional Polymer Systems - Juniorprof. Dr. Meike Leiske
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 02 Apr 2024 09:11
Last Modified: 02 Apr 2024 09:11
URI: https://eref.uni-bayreuth.de/id/eprint/89101