title: Functionalized vesicles based on amphiphilic boronic acids: a system for recognizing biologically important polyols.
abstract: 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 (1)H 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.
authors: LM Litvinenko Institute of Physical Organic Chemistry & Coal Chemistry, Donetsk, Ukraine.
authors: Oleksandr
authors: O
authors: Savsunenko
authors: Hubert
authors: H
authors: Matondo
authors: Sophie
authors: S
authors: Franceschi-Messant
authors: Emile
authors: E
authors: Perez
authors: Anatoly F
authors: AF
authors: Popov
authors: Isabelle
authors: I
authors: Rico-Lattes
authors: Armand
authors: A
authors: Lattes
authors: Yevgen
authors: Y
authors: Karpichev
mesh_terms: D015374:Biosensing Techniques; D001897:Boronic Acids / Q000737:chemistry*; D005632:Fructose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D009005:Monosaccharides; D011108:Polymers; C024617:polyol; D005632:Fructose; D005947:Glucose