Elucidating the Ordering in Self-Assembled Glycocalyx Mimicking Supramolecular Copolymers in Water
| Autor: | Tim P Hogervorst, Jeroen D. C. Codée, Xianwen Lou, E. W. Meijer, Gijsbert A. van der Marel, René P. M. Lafleur, Simone I. S. Hendrikse, Lu Su |
|---|---|
| Přispěvatelé: | Protein Engineering, Macro-Organic Chemistry, Macromolecular and Organic Chemistry, Self-Organizing Soft Matter |
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Supramolecular chemistry General Chemistry Polymer 010402 general chemistry 01 natural sciences Biochemistry Micelle Catalysis Article 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry Monomer chemistry Chemical engineering Polymerization Self-healing hydrogels Copolymer Ethylene glycol |
| Zdroj: | Journal of the American Chemical Society Journal of the American Chemical Society, 141(35), 13877-13886 Journal of the American Chemical Society, 141(35), 13877-13886. American Chemical Society |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | Polysaccharides present in the glycocalyx and extracellular matrix are highly important for a multitude of functions. Oligo- and polysaccharides-based biomaterials are being developed to mimic the glycocalyx, but the spatial functionalization of these polysaccharides represents a major challenge. In this paper, a series of benzene-1,3,5-tricarboxamide (BTA) based supramolecular monomers is designed and synthesized with mono- (BTA-β-d-glucose; BTA-Glc and BTA-α-d-mannose; BTA-Man) or disaccharides (BTA-β-d-cellobiose; BTA-Cel) at their periphery or a monosaccharide (BTA-OEG4-α-d-mannose; BTA-OEG4-Man) at the end of a tetraethylene glycol linker. These glycosylated BTAs have been used to generate supramolecular assemblies and it is shown that the nature of the carbohydrate appendage is crucial for the supramolecular (co)polymerization behavior. BTA-Glc and BTA-Man are shown to assemble into micrometers long 1D (bundled) fibers with opposite helicities, whereas BTA-Cel and BTA-OEG4-Man formed small spherical micelles. The latter two monomers are used in a copolymerization approach with BTA-Glc, BTA-Man, or ethylene glycol BTA (BTA-OEG4) to give 1D fibers with BTA-Cel or BTA-OEG4-Man incorporated. Consequently, the carbohydrate appendage influences both the assembly behavior and the internal order. Using this approach it is possible to create 1D-fibers with adjustable saccharide densities exhibiting tailored dynamic exchange profiles. Furthermore, hydrogels with tunable mechanical properties can be achieved, opening up possibilities for the development of multicomponent functional biomaterials. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|