A small library of six polarity-sensitive fluorescent dyes, nicknamed MediaChrom, was prepared. This class of dyes is characterized by a pyrimidoindolone core fitted out with a conjugated push-pull system and a carboxy linker for a conceivable coupling with biomolecules. The optimized eight-step synthetic strategy involves a highly chemo- and regioselective gold-catalyzed cycloisomerization reaction. The photophysical properties of MediaChrom dyes have been evaluated in-depth. In particular, the MediaChrom bearing a diethylamino as an electron-donating group and a trifluoromethyl as an electron-withdrawing group displays the most interesting and advantageous spectroscopic features (e.g., absorption and emission in the visible range and a good quantum yield). Promising results in terms of sensitivity have been obtained in vitro on this dye as a membrane/lipophilic probe and as a peptide fluorescent label.

MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes / Dell'Acqua, Monica; Ronda, Luca; Piano, Riccardo; Pellegrino, Sara; Clerici, Francesca; Rossi, Elisabetta; Mozzarelli, Andrea; Gelmi, Maria Luisa; Abbiati, Giorgio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:21(2015), pp. 10939-10954. [10.1021/acs.joc.5b02066]

MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes

RONDA, Luca;PIANO, Riccardo;MOZZARELLI, Andrea;
2015

Abstract

A small library of six polarity-sensitive fluorescent dyes, nicknamed MediaChrom, was prepared. This class of dyes is characterized by a pyrimidoindolone core fitted out with a conjugated push-pull system and a carboxy linker for a conceivable coupling with biomolecules. The optimized eight-step synthetic strategy involves a highly chemo- and regioselective gold-catalyzed cycloisomerization reaction. The photophysical properties of MediaChrom dyes have been evaluated in-depth. In particular, the MediaChrom bearing a diethylamino as an electron-donating group and a trifluoromethyl as an electron-withdrawing group displays the most interesting and advantageous spectroscopic features (e.g., absorption and emission in the visible range and a good quantum yield). Promising results in terms of sensitivity have been obtained in vitro on this dye as a membrane/lipophilic probe and as a peptide fluorescent label.
MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes / Dell'Acqua, Monica; Ronda, Luca; Piano, Riccardo; Pellegrino, Sara; Clerici, Francesca; Rossi, Elisabetta; Mozzarelli, Andrea; Gelmi, Maria Luisa; Abbiati, Giorgio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:21(2015), pp. 10939-10954. [10.1021/acs.joc.5b02066]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2796907
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