Please use this identifier to cite or link to this item: doi:10.22028/D291-39222
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Title: β-Boronic Acid-Substituted Bodipy Dyes for Fluorescence Anisotropy Analysis of Carbohydrate Binding
Author(s): Hoffmann, Caroline
Jourdain, Matthias
Grandjean, Alexander
Titz, Alexander
Jung, Gregor
Language: English
Title: Analytical Chemistry
Volume: 94
Issue: 16
Pages: 6112-6119
Publisher/Platform: American Chemical Society
Year of Publication: 2022
Free key words: Carbohydrates
Magnetic properties
Organic compounds
DDC notations: 500 Science
Publikation type: Journal Article
Abstract: Boronic acids are widely used for labeling catechols and carbohydrates in analytical (bio)chemistry due to their high binding affinities for diols. Here, we present two asymmetrically substituted Bodipy dyes with a boronic acid at the β-position (BBB). We present a green-emitting BBB, gBBB, and, by expanding the conjugated system of the Bodipy core at α-position, a redemitting rBBB. Especially, gBBB shows a bathochromic shift of the electronic spectra upon binding to saccharides and polyols, whereas the fluorescence lifetime of rBBB is more sensitive to hydroxy-ligand binding. Moreover, gBBB constantly shows higher binding affinities than rBBB, reaching Kb ≈ 103 M−1 at pH 8.5 for fructose. Finally, time-resolved fluorescence anisotropy allows to distinguish the number of saccharide units of oligosaccharides as the bond along the transition dipole moment ensures that the fluorescence anisotropy only decays due to the rotational diffusion of labeled carbohydrates. β-substituted BODIPY dyes are, thus, foreseen as fluorescence anisotropy labels for macromolecule sizing, where conventional fluorophores fail to discriminate due to the chemical similarity of recognition sites.
DOI of the first publication: 10.1021/acs.analchem.1c04654
URL of the first publication:
Link to this record: urn:nbn:de:bsz:291--ds-392229
ISSN: 1520-6882
Date of registration: 6-Mar-2023
Description of the related object: Supporting Information
Related object:
Faculty: NT - Naturwissenschaftlich- Technische Fakultät
Department: NT - Chemie
Professorship: NT - Prof. Dr. Gregor Jung
NT - Univ.-Prof. Dr. phil. Alexander Titz
Collections:SciDok - Der Wissenschaftsserver der Universität des Saarlandes

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