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  • Title: MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes.
    Author: Dell'Acqua M, Ronda L, Piano R, Pellegrino S, Clerici F, Rossi E, Mozzarelli A, Gelmi ML, Abbiati G.
    Journal: J Org Chem; 2015 Nov 06; 80(21):10939-54. PubMed ID: 26473465.
    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.
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