GlycoBODIPYs: Sugars Serving as a Natural Stock for Water-soluble Fluorescent Probes of Complex Chiral Morphology.
A range of unprocessed, reducing sugar substrates (mono-, di-, and trisaccharides) is shown to take part in a straightforward four-step synthetic route to water-soluble, uncharged BODIPY derivatives with unimpaired chiral integrity and high fluorescence efficiency. A wide compatibility with several postfunctionalizations is demonstrated, thus suggesting a universal utility of the multifunctional glycoconjugates, which we call GlycoBODIPYs. Knoevenagel condensations are able to promote a red-shift in the spectra, thereby furnishing strongly fluorescent red and far-red glycoconjugates of high hydrophilicity. The synthetic outcome was studied by X-ray crystallography and by comprehensive photophysical investigations in several solvent systems. Furthermore, cell experiments illustrate efficient cell uptake and demonstrate differential cell targeting as a function of the integrated chiral information.
['Patalag|Lukas J|LJ|', 'Ahadi|Somayeh|S|', 'Lashchuk|Olesia|O|', 'Jones|Peter G|PG|', 'Ebbinghaus|Simon|S|0000-0001-9309-1279', 'Werz|Daniel B|DB|0000-0002-3973-2212']
D001896:Boron Compounds D005456:Fluorescent Dyes D006031:Glycosylation D006367:HeLa Cells D006801:Humans D015394:Molecular Structure D012995:Solubility D000073893:Sugars D014867:Water
carbohydrates cell imaging dyes fluorophores water solubility