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

被引：20

作者：

Dell'Acqua, Monica ^{[1
]}

Ronda, Luca ^{[2
]}

Piano, Riccardo ^{[2
]}

Pellegrino, Sara ^{[1
]}

Clerici, Francesca ^{[1
]}

Rossi, Elisabetta ^{[1
]}

Mozzarelli, Andrea ^{[3
,4
]}

Gelmi, Maria Luisa ^{[1
]}

Abbiati, Giorgio ^{[1
]}

机构：

[1] Univ Milan, Sez Chim Gen & Organ A Marchesini, Dipartimento Sci Farmaceut, I-20133 Milan, Italy

[2] Univ Parma, Dipartifnento Neurosci, I-43124 Parma, Italy

[3] Univ Parma, Dipartimento Farm, I-43124 Parma, Italy

[4] CNR, Ist Biofis, I-56124 Pisa, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 21期

关键词：

2-PHOTON FLUORESCENCE MICROSCOPY; STATE DIPOLE-MOMENTS; SOLVATOCHROMIC FLUOROPHORES; INTRAMOLECULAR CYCLIZATION; PHOTOPHYSICAL PROPERTIES; SPECTRAL PROPERTIES; PROTON-TRANSFER; LIVE-CELL; PRODAN; PROBES;

D O I：

10.1021/acs.joc.5b02066

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

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 trifluormethyl 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.

引用

页码：10939 / 10954

页数：16

共 82 条

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