Data di Pubblicazione:
2016
Citazione:
MediaChrom: exploring a new family of pyrimidoindolone-based polarity-sensitive dyes / M. Dell'Acqua, G. Abbiati, L. Ronda, R. Piano, S. Pellegrino, E. Rossi, F. Clerici, A. Mozzarelli, M.L. Gelmi. ((Intervento presentato al 12. convegno Congress of the Interdivisional Group of Organometallic Chemistry tenutosi a Genova nel 2016.
Abstract:
The modern biological research asks for a continuous development of new fluorescent dyes characterized by improved performances and suitable to be used as markers or probes [1]. A particular class of dyes, called polarity-sensitive dyes have the unique features to display a different emission maximum as a function of the polarity of their molecular environment (media). This peculiarity makes polarity-sensitive dyes the ideal probes to monitor the local properties of particular cell districts as well as different type of biomolecular interactions [2]. Since many years, we have been interested in the development of new strategies for the synthesis and the functionalization of indoles and polycyclic indole-based heterocycles. In this context, we reported a domino approach to pyrimidoindolones [3] that displayed interesting fluorescence properties. Starting from these findings, a small library of original polarity-sensitive fluorescent dyes, nicknamed MediaChrom, has been prepared [4]. They are characterized by a pyrimidoindolone core fitted out with a conjugated push-pull system, and a linker for an easy coupling with biomolecules. The synthetic strategy involves a highly chemo- and regioselective gold catalyzed cycloisomerization as key step. The photophysical properties of MediaChrom dyes have been evaluated, and some potential biological applications have been spottily investigated. [1] Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed.; Springer: New York, 2006.
[2] Klymchenko, A. S.; Mely, Y. In: Progress in Molecular Biology and Translational Science, Morris, M.C. Editor(s), Academic Press, 2013, Vol. 113, Cap. 2, 35.
[3] Facoetti, D.; Abbiati, G.; d’Avolio, L.; Ackermann, L.; Rossi, E. Synlett 2009, 2273.
[4] Dell'Acqua, M.; Ronda, L.; Piano, R.; Pellegrino, S.; Clerici, F.; Rossi, E.; Mozzarelli, A.; Gelmi, M. L.; Abbiati, G. J. Org. Chem. 2015, 21, 10939.
This work has been supported by Fondazione Cariplo, Grant No. 2012-0907.
Tipologia IRIS:
14 - Intervento a convegno non pubblicato
Keywords:
pyrimidoindolone; polarity-sensitive dyes
Elenco autori:
M. Dell'Acqua, G. Abbiati, L. Ronda, R. Piano, S. Pellegrino, E. Rossi, F. Clerici, A. Mozzarelli, M.L. Gelmi
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