title: MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes.
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.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano , Via Venezian, 21, 20133 Milano, Italy.
authors.forename: Monica
authors.initials: M
authors.lastname: Dell'Acqua
authors.forename: Luca
authors.initials: L
authors.lastname: Ronda
authors.forename: Riccardo
authors.initials: R
authors.lastname: Piano
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano , Via Venezian, 21, 20133 Milano, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Pellegrino
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano , Via Venezian, 21, 20133 Milano, Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Clerici
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano , Via Venezian, 21, 20133 Milano, Italy.
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Rossi
authors.affiliation: Istituto di Biofisica, CNR , 56124 Pisa, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Mozzarelli
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano , Via Venezian, 21, 20133 Milano, Italy.
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Gelmi
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano , Via Venezian, 21, 20133 Milano, Italy.
authors.forename: Giorgio
authors.initials: G
authors.lastname: Abbiati
mesh_terms: D002384:Catalysis; D004563:Electrochemistry / Q000379:methods; D004583:Electrons; D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure; D011744:Pyrimidinones / Q000737:chemistry*; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence
chemical_list: D005456:Fluorescent Dyes; D011744:Pyrimidinones