- Carbohydrate coatings via aryldiazonium chemistry for surface biomimicry
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Carbohydrates are extremely important biomolecules and their immobilization onto solid surfaces is of interest for the development of new biomimetic materials and of new methods for understanding processes in glycobiology. We have developed an efficient surface modification methodology for the functionalization of a range of materials with biologically active carbohydrates based on aryldiazonium chemistry. We describe the synthesis and characterization of carbohydrate reagents, which were subsequently employed for the one-step, solution-based modification of carbon, metals, and alloys with monosaccharides. We used a combination of spectroscopic and nanogravimetric methods to characterize the structure of the carbohydrate layers; we report an average surface coverage of 7.8 × 10-10 mol cm-2 under our experimental conditions. Concanavalin A, a mannose-binding lectin, and Peanut Agglutinin, a galactose-binding lectin, were found to bind from solution to their respective monosaccharide binding partners immobilized at the surface. This result suggests that the spontaneous chemisorption of aryldiazonium monosaccharide precursors leads to the formation of monosaccharide layers that retain the biological recognition specificity of the parent carbohydrate molecule. Finally, we carried out measurements using fluorescently labeled Bovine Serum Albumin (BSA) and found that these carbohydrate coatings reduce unspecific adsorption of this protein at carbon surfaces. These results suggest that aryldiazonium-derived carbohydrate coatings may offer a promising strategy for preventing undesirable protein accumulation onto surfaces.
- Jayasundara, Dilushan R.,Duff, Thomas,Angione, M. Daniela,Bourke, Jean,Murphy, Deirdre M.,Scanlan, Eoin M.,Colavita, Paula E.
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- CARBOHYDRATE FUNCTIONALISED SURFACES
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Carbohydrates are biomolecules that are involved in a range of biological processes and play key roles in, for instance, host immune response and cellular adhesion. Accordingly, functionalisation of medical devices such as stents, valves, catheters, prostheses and other devices for in vivoimplantation with carbohydrates is an area in which considerable interest is developing. Disclosed herein are surfaces having carbohydrates immobilised thereon. The carbohydrate has a linker moiety covalently bound thereto and the linker moiety has a carbon atom that forms a covalent bond with an atom on the target surface. The carbon based bond is a strong, non-hydrolysable covalent bond. Diazonium salts are utilised to produce the functionalised surfaces and they are particularly advantageous as they result in non-toxic readily escapable by-products
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Paragraph 0200; 0208-0209
(2014/09/29)
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- Sugar-modified cytostatics
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The invention relates to cytostatics which, by modification with sugar, are tumor-specific. Suitable spacers ensure serum stability and at the same time an intracellular action.
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