Please use this identifier to cite or link to this item:
http://dx.doi.org/10.25673/108901
Title: | Structural elucidation of 2-(6-(Diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one and labelling of mycobacterium aurum cells |
Author(s): | Richter, Adrian![]() Goddard, Richard W. ![]() Siersleben, Fabienne Brinkmann, Lea ![]() Seidel, Rüdiger W. ![]() |
Issue Date: | 2023 |
Type: | Article |
Language: | English |
Abstract: | Trehalose conjugates of 3-hydroxychromone (3HC) dyes have previously been utilized as fluorescence labels to detect metabolically active mycobacteria with a view to facilitating point-of-care detection of mycobacterial pathogens, especially Mycobacterium tuberculosis. We subjected the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) to a combined X-ray crystallography and density functional theory (DFT) study, and conducted preliminary fluorescence labelling experiments with the model organism Mycobacterium aurum. In the crystal, 3HC-2 exhibits an s-cis conformation of the chromone and the benzofuran moieties about the central C–C bond. According to DFT calculations, the s-cis conformer is about 1.8 kcal mol−1 lower in energy than the s-trans conformer. The solid-state supramolecular structure features hydrogen-bonded dimers and π…π stacking. Fluorescence microscopy revealed fluorescence of M. aurum cells treated with the dye trehalose conjugate 3HC-2-Tre in the GFP channel. It was concluded that s-cis is the preferred conformation of 3HC-2 and that the generally considered non-pathogenic M. aurum can be labelled with the fluorescence probe 3HC-2-Tre for convenient in vitro drug screening of new antimycobacterial agents. |
URI: | https://opendata.uni-halle.de//handle/1981185920/110856 http://dx.doi.org/10.25673/108901 |
Open Access: | ![]() |
License: | ![]() |
Journal Title: | Molbank |
Publisher: | MDPI |
Publisher Place: | Basel |
Volume: | 2023 |
Issue: | 2 |
Original Publication: | 10.3390/M1647 |
Page Start: | 1 |
Page End: | 11 |
Appears in Collections: | Open Access Publikationen der MLU |
Files in This Item:
File | Description | Size | Format | |
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molbank-2023-M1647.pdf | 4.02 MB | Adobe PDF | ![]() View/Open |