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Two-Photon Absorption and Cell Imaging of Fluorene-Functionalized Epicocconone Analogues |
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| Authors: | Dr Samuel Oger Damien Schapman Dr Romain Mougeot Dr Stéphane Leleu Dr Noëlle Lascoux Dr Patrice Baldeck Dr Magalie Bénard Dr Thibault Gallavardin Dr Ludovic Galas Dr Xavier Franck |
| Institution: | 1. COBRA (UMR 6014 and FR 3038), Normandie Univ, CNRS, INSA Rouen, UNIROUEN, 76000 Rouen, France;2. PRIMACEN, Cell Imaging Platform of Normandy, Institute for Research and Innovation in Biomedicine (IRIB), Normandie Univ, Inserm, UNIROUEN, 76000 Rouen, France;3. Laboratoire de Chimie UMR 5182, Ecole Normale Supérieure de Lyon,CNRS, Université Lyon 1, 46, allée d'Italie, 69364 Lyon Cedex 07, France |
| Abstract: | 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. |
| Keywords: | cell imaging dioxinone epicocconone fluorene two-photon |