Photoderivatized polymer-coated gold surfaces have been developed following a perfluorophenylazide-based double ligation strategy. Gold-plated quartz crystal microbalance (QCM) crystals were initially covalently functionalized with a monolayer of poly(ethylene glycol) (PEG), using photo-or thermolytic nitrene formation and insertion. The polymer surfaces were subsequently used as substrates for photoinsertion of carbohydrate-derivatized photoprobes, yielding different recognition motifs for selective protein binding. The resulting robust and biocompatible sensor surfaces were applied to a flow-through QCM instrument for monitoring lectin-carbohydrate interactions in real time. The results clearly show the predicted lectin selectivity, demonstrating the applicability of the approach.Selective surface generation and functionalization form the basis for intense research in a number of diverse areas such as chemical sensors, interface engineering, and nanotechnology. A versatile method to covalent derivatization is based on the specific chemistry of arylazides. Upon thermal activation or light irradiation, the azide functionality in these structures becomes converted to a highly reactive nitrene species that readily inserts into CH and NH bonds. 1 Especially perfluorophenylazides (PFPAs), 2 which produce markedly enhanced insertion yields, have thus been used to thermo-and photochemically introduce functional groups in a range of entities, including proteins, nanostructures, and synthetic polymers. [3][4][5][6][7][8][9] The versatility of the PFPA chemistry makes it an attractive choice for surface modification. Surfaces can either be globally modified by the technique, or discrete areas can be addressed by arraying techniques such as photomasking and conventional printing devices. HHS Public Access Author Manuscript Author ManuscriptAuthor Manuscript Author ManuscriptThe surface presentation of recognition motifs based on bioactive compounds is central for many applications in bioanalytical and biomaterials science, and carbohydrates and glycomimetic structures are in this context attracting increasing interest. [10][11][12][13][14] Interactions between cellular glycans and proteins have been found to be of special importance in many biological processes, being involved in cell-cell interactions, cell communication, cell proliferation, and cell death. This emerging significance prompts for new means to analytically study these interactions. To date, various methods have been developed to analyze interactions of carbohydrates and proteins, including biosensors, enzyme-linked lectin assays (ELLAs) and cell assays, nuclear magnetic resonance, calorimetric techniques, and, more recently, microarray technologies. [15][16][17][18][19][20][21][22][23] Among these methods, the quartz crystal microbalance (QCM) biosensor format is being increasingly adopted due to its convenient means of operation coupled with high performance. [24][25][26][27][28][29][30][31][32][33] Measurements can also be performed in real tim...
Sugars in a row. A new strategy for carbohydrate microarrays based on photochemical ligation of perfluorophenylazide‐derivatized carbohydrates to PEO surfaces is presented. It constitutes a controllable and robust method of array fabrication, on the carbohydrate‐chemistry and on the surface‐chemistry levels, and the resulting carbohydrate arrays can be efficiently used to reveal the recognition patterns of carbohydrate‐binding proteins.
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