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 / M. Dell'Acqua, L. Ronda, R. Piano, S. Pellegrino, F. Clerici, E. Rossi, A. Mozzarelli, M.L. Gelmi, G. Abbiati. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:21(2015 Nov 06), pp. 10939-10954.

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

M. Dell'Acqua
Primo
;
S. Pellegrino;F. Clerici;E. Rossi;M.L. Gelmi
Penultimo
;
G. Abbiati
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.
Settore CHIM/06 - Chimica Organica
Settore CHIM/01 - Chimica Analitica
ott-2015
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/335242
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