Two-Photon Absorption and Cell Imaging of Fluorene-Functionalized Epicocconone Analogues.
Samuel OgerDamien SchapmanRomain MougeotStéphane LeleuNoëlle LascouxPatrice BaldeckMagalie BénardThibault GallavardinLudovic GalasXavier FranckPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)
Epicocconone 1 is a natural chromophore isolated from the fungus Epicoccum nigrum that has shown applications in proteomics and fluorescent microscopy thanks to its unique pro-fluorescence properties. The modification of the skeleton of the natural product by replacing the triene side chain by a fluorenyl scaffold can noticeably increase the fluorophore's absorption coefficient. The synthesis of the analogues of the natural product has been made possible by the use of a palladium-catalyzed carbonylation reaction, allowing the construction of the β-keto-dioxinone key intermediate. Two-photon absorption cross-section measurements of the fluorenyl epicocconone analogues show a structure dependency with values ranging from 60 to 280 GM and live cell imaging show intense staining of intracellular vesicle-like structures around the nucleus.
Keyphrases
- high resolution
- living cells
- molecular docking
- single molecule
- label free
- quantum dots
- mass spectrometry
- fluorescent probe
- structure activity relationship
- single cell
- cell therapy
- stem cells
- computed tomography
- photodynamic therapy
- optical coherence tomography
- magnetic resonance
- energy transfer
- simultaneous determination