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. 2021 Apr 12;60(16):8766-8771.
doi: 10.1002/anie.202016764. Epub 2021 Mar 17.

GlycoBODIPYs: Sugars Serving as a Natural Stock for Water-soluble Fluorescent Probes of Complex Chiral Morphology

Lukas J Patalag  1 , Somayeh Ahadi  1 , Olesia Lashchuk  2 , Peter G Jones  3 , Simon Ebbinghaus  2 , Daniel B Werz  1
Affiliations

GlycoBODIPYs: Sugars Serving as a Natural Stock for Water-soluble Fluorescent Probes of Complex Chiral Morphology

Lukas J Patalag et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: carbohydrates; cell imaging; dyes; fluorophores; water solubility.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Previous studies on water‐soluble BODIPY scaffolds and our approach, which involves naturally abundant sugar substrates.
Scheme 2
Scheme 2
Synthetic strategy to a range of GlycoBODIPYs.
Scheme 3
Scheme 3
Investigated postfunctionalizations of GlycoBODIPYs and their precursors. [a] 40 % of the starting material was recovered.
Figure 1
Figure 1
Absorption and normalized emission spectra of 5Lac/Me (H2O) and its styryl‐equipped congeners 8Lac/Me and 9Lac/Me in MeOH at RT together with a short overview of spectroscopic data recorded in MeOH and H2O (bold). Lines: absorptions, filled areas: corresponding emissions. [a] Stokes shift. [b] Attenuation coefficient at the main absorption band λ abs. [c] Absolute quantum yield of fluorescence. [d] Fluorescence lifetime. Insert: Juxtaposition of the absorption spectra of 5Glc and 5Gal (MeOH). [e] 20 % MeOH was used as cosolvent because of an incipient aggregation process. See the Supporting Information for the full data set.
Figure 2
Figure 2
Molecular structure of 5LFuc and selected bond lengths and distances obtained by X‐ray diffraction analysis. The synthetic formula is shown for comparison and to illustrate the position of stereocenters.
Figure 3
Figure 3
Confocal microscopy images of HeLa cells incubated with A) l‐fucose‐derived GlycoBODIPYs 5LFuc and B) and l‐rhamnose‐derived 5LRha. C) Corresponding staining result with usual BODIPY species lacking a glycan moiety. D–F) Colocalization study with cellobiose‐derived GlycoBODIPY 5Cel (D) and MitoTracker™ Deep Red FM (MT) (E). F) Merged images; insert: correlation plot (heatmap) for visualization of the colocalization quality, R is the Pearson correlation coefficient (see the Supporting Information for the full data set).
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