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.

Recent Developments in the Design of New Water-Soluble Boron Dipyrromethenes and Their Applications: An Updated Review

“…The constructed glycoconjugates, regardless of the incorporated sugar moiety, exhibit generally solvent-independent fluorescence effectiveness, which preserves all of the spectroscopic benefits of the BODIPY motif. Confocal imaging research revealed a variety of glyco-BODIPYs’ applications for cellular studies and illustrated their powerful chiral activity for particular cellular applications …”

“…Confocal imaging research revealed a variety of glyco-BODIPYs' applications for cellular studies and illustrated their powerful chiral activity for particular cellular applications. 36 2.6. Metal Ion Detection.…”

Recent developments in design of novel water-soluble BODIPYs and their applications: an updated review

“…The two carborane polymers (35,36) exhibit great biocompatibility was immediately and precisely detected, according to the results of cell imaging. It offers a fresh concept for BNCT research and design.…”

“…Confocal imaging research revealed a variety of GlycoBODIPYs' applications for cellular studies and illustrated their powerful chiral activity for particular cellular applications. 36 Fig. 25 Glyco-BODIPY complexes.…”

A new amino acid, hybrid peptides and BODIPY analogs: synthesis and evaluation of 2-aminotroponyl-l-alanine (ATA) derivatives

“…24 However, dipyrromethene is a versatile N,N-ligand of boron, and has been used for the synthesis of various fluorescent BODIPY molecules. [25][26][27] The non-dipyrromethene scaffold has also been used for the synthesis of BODIPY type fluorescent molecules, and BODIPY analogues, by N,N-/N,Ochelation. [28][29][30] Previously, aminotropone derivatives have also been explored for preparing novel fluorescent molecules, BODIPY analogs, by complexing with BF 2 through N,N-/N,O chelation (Fig.…”