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Structural Elucidation of 2-(6-(Diethylamino)benzofuran-2-yl)-3-hydroxy-4 H -chromen-4-one and Labelling of Mycobacterium aurum Cells.

Authors :
Richter, Adrian
Goddard, Richard
Siersleben, Fabienne
Mann, Lea
Seidel, Rüdiger W.
Source :
Molbank; Jun2023, Vol. 2023 Issue 2, pM1647, 11p
Publication Year :
2023

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<superscript>−1</superscript> 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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14228599
Volume :
2023
Issue :
2
Database :
Complementary Index
Journal :
Molbank
Publication Type :
Academic Journal
Accession number :
164684154
Full Text :
https://doi.org/10.3390/M1647