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Functionalized Vesicles Based on Amphiphilic Boronic Acids: A System for Recognizing Biologically Important Polyols

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journal contribution
posted on 12.03.2013 by Oleksandr Savsunenko, Hubert Matondo, Sophie Franceschi-Messant, Emile Perez, Anatoly F. Popov, Isabelle Rico-Lattes, Armand Lattes, Yevgen Karpichev
We report on a new approach for creating water-soluble functionalized vesicles employing N-alkyl-3-boronopyridinium triflates (alkyl = Me, C12H25, C16H33) as sensors for monosaccharides. The nanoaggregate properties were studied by means of DLS, TEM, high-resolution 1H NMR, and the solvatochromic dyes Reichardt’s betaine and Methyl Orange. The vesicles were shown to have 30–200 nm diameters depending on the amphiphile chain length. Diol binding to the vesicles was studied by steady-state fluorescence and UV–vis using Alizarin Red S as a probe in the solution at pH 7.4 in the presence and in the absence of d-glucose and d-fructose. Strong sensing ability of boronic acid functional moieties in the order d-fructose > d-glucose was demonstrated, and apparent binding constants were estimated.