Two‐Photon Absorption and Cell Imaging of Fluorene‐Functionalized Epicocconone Analogues.

Oger, Samuel; Schapman, Damien; Mougeot, Romain; Leleu, Stéphane; Lascoux, Noëlle; Baldeck, Patrice; Bénard, Magalie; Gallavardin, Thibault; Galas, Ludovic; Franck, Xavier

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.

CELL imaging; ABSORPTION coefficients; ABSORPTION; NATURAL products; CARBONYLATION

Chemistry - A European Journal, 2019, Vol 25, Issue 46, p10954

0947-6539

Academic Journal

10.1002/chem.201902731