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.
Titolo: | MediaChrom : Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes |
Autori: | DELL'ACQUA, MONICA (Primo) GELMI, MARIA LUISA (Penultimo) ABBIATI, GIORGIO (Corresponding) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica Settore CHIM/01 - Chimica Analitica |
Data di pubblicazione: | 6-nov-2015 |
Rivista: | |
Tipologia: | Article (author) |
Data ahead of print / Data di stampa: | ott-2015 |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.joc.5b02066 |
Appare nelle tipologie: | 01 - Articolo su periodico |
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MediaChrom_JOC_2015_10939_reprint.pdf | Reprint dell'articolo originale pubblicato dall'editore | Publisher's version/PDF | Administrator Richiedi una copia | |
Abbiati_MediaChrom_text_R1.pdf | Versione post print pubblicata temporaneamente sul sito dell'editore come "just accepted" | Post-print, accepted manuscript ecc. (versione accettata dall'editore) | Open Access Visualizza/Apri | |
Abbiati_Mediachrom_Supp_Info_R2.pdf | Supporting Iinformation dell'articolo principale | Altro | Open Access Visualizza/Apri |