MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes
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- 作者：Monica Dell鈥橝cqua ; Luca Ronda ; Riccardo Piano ; Sara Pellegrino ; Francesca Clerici ; Elisabetta Rossi ; Andrea Mozzarelli ; Maria Luisa Gelmi ; Giorgio Abbiati
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：November 6, 2015
- 年：2015
- 卷：80
- 期：21
- 页码：10939-10954
- 全文大小：751K
- ISSN：1520-6904
文摘
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鈥損ull 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.