A solvatofluorochromic silicon-substituted xanthene dye useful in bioimaging

In this work, we have performed an in-depth study of the photophysics and solvatofluorochromism of a red-emitting Si-xanthene dye, an analog of Tokyo Magenta (TM) historically developed by Egawa et al. (Chem. Commun.2011, 47, 4162–4164). The results show a strong dependency of the emission propertie...

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Bibliographic Details
Published in:	Dyes and pigments Vol. 168; pp. 264 - 272
Main Authors:	Espinar-Barranco, Laura, Luque-Navarro, Pilar, Strnad, Maja A., Herrero-Foncubierta, Pilar, Crovetto, Luis, Miguel, Delia, Giron, Maria D., Orte, Angel, Cuerva, Juan M., Salto, Rafael, Alvarez-Pez, Jose M., Paredes, Jose M.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 01-09-2019
Subjects:	Biosensors Fluorescent dyes Hetero-xanthene dyes Photophysics Solvatofluorochromism Fluorescent dyes Solvatofluorochromism Biosensors Photophysics Hetero-xanthene dyes
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Summary:	In this work, we have performed an in-depth study of the photophysics and solvatofluorochromism of a red-emitting Si-xanthene dye, an analog of Tokyo Magenta (TM) historically developed by Egawa et al. (Chem. Commun.2011, 47, 4162–4164). The results show a strong dependency of the emission properties of 2-Me-4-OMe-TM on the polarity of the solvent. For instance, the dye exhibited an increase in its fluorescence lifetime with the decrease in solvent polarity. Therefore, in this work, this spectral behavior has been used as a new approach for determining the intracellular microenvironment polarity through the measurement of its fluorescence lifetime by Fluorescence Lifetime Imaging Microscopy (FLIM). Our experiments confirmed the ability of the dye to detect changes in polarity between different intracellular compartments. [Display omitted] •A silicon-substituted xanthene dye was synthesized and its photophysics studied.•The dye shows a strong solvatochromic behavior involving two emission bands.•A strong dependency on the solvent’s acidity was observed in the red-shifted band.•The dye works as an intracellular polarity fluorescence lifetime sensor.
ISSN:	0143-7208 1873-3743
DOI:	10.1016/j.dyepig.2019.04.024