Indole, Phenyl, and Phenol Groups: The Role of the Comonomer on Gene Delivery in Guanidinium Containing Methacrylamide Terpolymers
| Autor: | Juliana Hülsmann, Franz J. Hack, Sebastian Städter, Kalina Peneva, Dagmar Fischer, Ceren Cokca |
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| Rok vydání: | 2020 |
| Předmět: |
Indoles
Polymers and Plastics Phenylalanine 02 engineering and technology 010402 general chemistry Transfection 01 natural sciences chemistry.chemical_compound Polymer chemistry Materials Chemistry Aromatic amino acids Side chain Methacrylamide Guanidine Acrylamides Phenol Comonomer Organic Chemistry Gene Transfer Techniques Chain transfer 021001 nanoscience & nanotechnology 0104 chemical sciences Monomer chemistry Polymerization 0210 nano-technology |
| Zdroj: | Macromolecular rapid communications. 42(8) |
| ISSN: | 1521-3927 |
| Popis: | This report highlights the importance of hydrophobic groups mimicking the side chains of aromatic amino acids, which are tryptophan, phenylalanine, and tyrosine, in guanidinium bearing poly(methacrylamide)s for the design of non-viral gene delivery agents. Guanidinium containing methacrylamide terpolymers are prepared by aqueous reversible addition-fragmentation chain transfer (aRAFT) polymerization with different hydrophobic monomers, N-(2-indolethyl)methacrylamide (IEMA), N-phenethylmethacrylamide (PhEMA), or N-(4-hydroxyphenethyl)methacrylamide (PhOHEMA) by aiming similar contents. The well-defined polymers are obtained with a molar mass of ≈15 000 g mol-1 and ≈1.1 dispersity. All terpolymers demonstrate almost comparable in vitro cell viability and hemocompatibility profiles independent of the type of side chain. Although they all form positively charged, enzymatically stable polyplexes with plasmid DNA smaller than 200 nm, the incorporation of the IEMA monomer improve these parameters by demonstrating a higher DNA binding affinity and forming nanoassemblies of about 100 nm. These physicochemical characteristics are correlated with increased transfection rates in CHO-K1 cells dependent on the type of the monomer and the nitrogen to phosphate (N/P) ratio of the polyplexes, as determined by luciferase reporter gene assays. |
| Databáze: | OpenAIRE |
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