title: Charge transfer fluorescent probes using boronic acids for monosaccharide signaling.
abstract: We have developed a new series of glucose sensitive fluorophores that display shifts in emission wavelengths and/or intensity change upon the binding of monosaccharides. Complexation of glucose with the boronic acid moiety changes both its orbital hybridization and its ability to accept and donate electrons. This change results in distinct emission spectra for the fluorophores when free in solution or complexed with monosaccharide. The spectral changes upon saccharide binding can be modified by substitution of electron donor or acceptor group on the fluorophore allowing rational design of the spectral response.
authors.affiliation: University of Maryland, Baltimore, Center for Fluorescence Spectroscopy, Department of Biochemistry and Molecular Biology, 725 W. Lombard St., Baltimore, Maryland, 21201, USA.
authors.forename: Nicolas
authors.initials: N
authors.lastname: DiCesare
authors.forename: Joseph R
authors.initials: JR
authors.lastname: Lakowicz
mesh_terms: D001897:Boronic Acids / Q000737:chemistry; D002599:Chalcone / Q000031:analogs & derivatives / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009005:Monosaccharides / Q000378:metabolism*; D010080:Oxazoles / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry; D015398:Signal Transduction; D013050:Spectrometry, Fluorescence; D013267:Stilbenes / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D005456:Fluorescent Dyes; D009005:Monosaccharides; D010080:Oxazoles; D011090:Polyenes; D013267:Stilbenes; D002599:Chalcone