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

Titelangaben

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

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.

Weitere Angaben

Publikationsform: Artikel in einer Zeitschrift
Begutachteter Beitrag: Ja
Institutionen der Universität: Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie
Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Juniorprofessur Nachhaltige und funktionale Polymersysteme > Juniorprofessur Nachhaltige und funktionale Polymersysteme - Juniorprof. Dr. Meike Leiske
Titel an der UBT entstanden: Ja
Themengebiete aus DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Eingestellt am: 02 Apr 2024 09:11
Letzte Änderung: 02 Apr 2024 09:11
URI: https://eref.uni-bayreuth.de/id/eprint/89101