Nitrile-Functionalized Poly(2-oxazoline)s as a Versatile Platform for the Development of Polymer Therapeutics
Autor: | Kristian Kempe, Baptiste Schelle, Zihnil Adha Islamy Mazrad, Joseph A. Nicolazzo, Meike N. Leiske |
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Rok vydání: | 2021 |
Předmět: |
Polymers and Plastics
Nitrile Polymers Bioengineering 02 engineering and technology Oxazoline 010402 general chemistry Ferric Compounds 01 natural sciences Biomaterials chemistry.chemical_compound Nitriles Amphiphile Materials Chemistry Copolymer Oxazoles chemistry.chemical_classification Cationic polymerization Polymer 021001 nanoscience & nanotechnology Combinatorial chemistry 0104 chemical sciences Monomer chemistry Polymerization 0210 nano-technology |
Zdroj: | Biomacromolecules. 22:4618-4632 |
ISSN: | 1526-4602 1525-7797 |
DOI: | 10.1021/acs.biomac.1c00923 |
Popis: | In recent years, polymers bearing reactive groups have received significant interest for biomedical applications. Numerous functional polymer platforms have been introduced, which allow for the preparation of materials with tailored properties via post-polymerization modifications. However, because of their reactivity, many functional groups are not compatible with the initial polymerization. The nitrile group is a highly interesting and relatively inert functionality that has mainly received attention in radical polymerizations. In this Article, a nitrile-functionalized 2-oxazoline monomer (2-(4-nitrile-butyl)-2-oxazoline, BuNiOx) is introduced, and its compatibility with the cationic ring-opening polymerization is demonstrated. Subsequently, the versatility of nitrile-functionalized poly(2-oxazoline)s (POx) is presented. To this end, diverse (co)polymers are synthesized and characterized by nuclear resonance spectroscopy, size-exclusion chromatography, and mass spectrometry. Amphiphilic block copolymers are shown to efficiently encapsulate the hydrophobic drug curcumin (CUR) in aqueous solution, and the anti-inflammatory effect of the CUR-containing nanostructures is presented in BV-2 microglia. Furthermore, the availability of the BuNiOx repeating units for post-polymerization modifications with hydroxylamine to yield amidoxime (AO)-functionalized POx is demonstrated. These AO-containing POx were successfully applied for the complexation of Fe(III) in a quantitative manner. In addition, AO-functionalized POx were shown to release nitric oxide intracellularly in BV-2 microglia. Thus nitrile-functionalized POx represent a promising and robust platform for the design of polymer therapeutics for a wide range of applications. |
Databáze: | OpenAIRE |
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