Synthetic boronolectins for selective recognition of saccharides in aqueous media by spectrometric methods

CECILIA SAMANIEGO LÓPEZ; NATALIA COSENZA; MARÍA LAURA UHRIG; CARLA CECILIA SPAGNUOLO

Villa General Belgrano, Córdoba

Simposio; 2nd Argentinean Symposium of Glycobiology; 2016

Moving forward to the development of new probes with higher selectivity toward saccharides present on the membrane surface, we synthesized and studied the sensing performance of derivatives of benzoxaborole, a boronic hemiester with good affinity for pyranoses over furanoses and much less explored as recognition unit for carbohydrates than common boronic acids. As proof of principle, we investigated the sensitivity of benzoxaborole analogs and a new divalent receptor combining benzoxaborole and benzeneboronic acid. By direct inspection of the changes in absorbance and fluorescence emission of the receptor unit upon binding of model carbohydrates and glycoproteins, such as glucose, mannose, N-acetylglucosamine, sialic acid, fucose, we could establish trends in binding affinity. Typically, the fluorescence emission of the benzoxaborole unit decreases with sugar binding. Interestingly, the divalent host is able to recognize sialic acid in an orthogonal manner due to the increase in the fluorescence emission observed while the other sugars caused depletion of the fluorescence intensity. In this work we present also binding studies through indicator displacement assays, and the prospect in construction of multivalent receptors derived from dendrimers and silica nanoparticles in order to achieve sensor platforms with enhanced sensitivity.