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

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 Xray 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.

A Multifunctional AIE Nanoprobe as a Drug Delivery Bioimaging and Cancer Treatment System

“…Efficient uptake of by in vivo cells was the key to achieving the biological performance of material design ( Patalag et al, 2021 ). To verify the targeting of T7 on LN229 cells, cell uptakes of PLA-PEG/TPE and PLA-PEG-T7/TPE were also compared by flow cytometry as shown in Figure 2A .…”

Bringing Color to Sugars: The Chemical Assembly of Carbohydrates to BODIPY Dyes

“…However, very recently, Patalag, Werz and coworkers, have proved that naturally abundant reducing sugars can be smoothly integrated into highly fluorescent BODIPY derivatives, e. g. 138 (Scheme 30). [92] Their synthetic strategy is based on the condensation of α‐substituted pyrroles (2‐ethyl or 2‐methyl‐pyrrole) with the anomeric hemiacetalic position of unprotected carbohydrates. This transformation was compatible with a large number of sugar substrates, including pentoses, e. g., d ‐xylose, d ‐ribose or d ‐2‐deoxyribose, hexoses, e.g, d ‐glucose, d ‐galactose, d ‐mannose, l ‐fucose or l ‐rhamnose, disaccharides, e. g. d ‐cellobiose, d ‐maltose, d ‐lactose, and even a trisaccharide, d ‐maltotriose.…”

“…However, very recently, Patalag, Werz and coworkers, have proved that naturally abundant reducing sugars can be smoothly integrated into highly fluorescent BODIPY derivatives, e. g. 138 (Scheme 30). [92] Their synthetic strategy is based on the condensation of α-substituted pyrroles (2-ethyl or 2-methyl-pyrrole) with the anomeric hemiacetalic position of unprotected carbohydrates. This transformation was compatible with a large number of sugar substrates, including pentoses, e. g. Thus, the overall synthetic pathway involves an hemiacetal to hydroxy-aldehyde ring opening, followed by condensation of the ensuing formyl group with two units of the substituted pyrrole, to yield dipyrromethane structure 136.…”

Supramolecular J-aggregates of aza-BODIPY by steric and π–π nteractions for NIR-II phototheranostics

“…In the past decade, as a class of classical fluorescent dyes, boron dipyrromethenes (BODIPYs) have received much attention for bioimaging applications such as biological molecule detection, 12–16 bioimaging, 17–20 and photothermal and photodynamic therapies 21–27 on account of their excellent properties including intense absorption, ease of synthesis and modification, and outstanding optical and chemical stability. However, the majority of BODIPY dyes have absorption and emission bands that are only located in the NIR-I region.…”