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Bis-pyridinium quadrupolar derivatives. High Stokes shift selective probes for bio-imaging

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Salice P., Versari S., Bradamante S., Meinardi F., Macchi G., Pagani G. A., Beverina L.

Organic Photonics and Photovoltaics

2013

vol. 1

39-55

We describe the design, synthesis and characterization of five high Stokes shift quadrupolar heteroaryl compounds suitable as fluorescent probes in bio-imaging. In particular, we characterize the photophysical properties and the intracellular localization in Human Umbilical Vein Endothelial Cells (HUVEC) and Human Mesenchymal Stem Cells (HMSCs) for each dye. We show that, amongst all of the investigated derivatives, the 2,5-bis[1-(4-N-methylpyridinium)ethen-2-yl)]- N-methylpyrrole salt is the best candidates as selective mitochondrial tracker. Finally, we recorded the full emission spectrum of the most performing - exclusively mitochondrial selective - fluorescent probe directly from HUVEC stained cells. The emission spectrum collected from the stained mitochondria shows a remarkably more pronounced vibronic structure with respect to the emission of the free fluorophore in solution.

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1 Organic Photonics and Photovoltaics

1 2013

1 Beverina L.

1 Bradamante S.

1 Macchi G.

1 Meinardi F.

1 Pagani G. A.

1 Salice P.

1 Versari S.

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Bis-pyridinium quadrupolar derivatives. High Stokes shift selective probes for bio-imaging