GlycoBODIPYs: Sugars Serving as a Natural Stock for Water-soluble Fluorescent Probes of Complex Chiral Morphology.
Lukas J PatalagSomayeh AhadiOlesia LashchukPeter G JonesSimon EbbinghausDaniel B WerzPublished in: Angewandte Chemie (International ed. in English) (2021)
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.
Keyphrases
- water soluble
- single cell
- living cells
- cell therapy
- drug delivery
- cancer therapy
- high resolution
- magnetic resonance imaging
- healthcare
- stem cells
- capillary electrophoresis
- escherichia coli
- biofilm formation
- mesenchymal stem cells
- computed tomography
- molecular dynamics
- health information
- pseudomonas aeruginosa
- bone marrow
- candida albicans