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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| Published in: | Dyes and pigments Vol. 168; pp. 264 - 272 |
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| Main Authors: | , , , , , , , , , , , |
| Format: | Journal Article |
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01-09-2019
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| Abstract | 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.
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•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. |
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| AbstractList | 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. |
| Author | Giron, Maria D. Cuerva, Juan M. Espinar-Barranco, Laura Herrero-Foncubierta, Pilar Paredes, Jose M. Salto, Rafael Strnad, Maja A. Alvarez-Pez, Jose M. Miguel, Delia Luque-Navarro, Pilar Orte, Angel Crovetto, Luis |
| Author_xml | – sequence: 1 givenname: Laura surname: Espinar-Barranco fullname: Espinar-Barranco, Laura organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 2 givenname: Pilar surname: Luque-Navarro fullname: Luque-Navarro, Pilar organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 3 givenname: Maja A. surname: Strnad fullname: Strnad, Maja A. organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 4 givenname: Pilar surname: Herrero-Foncubierta fullname: Herrero-Foncubierta, Pilar organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 5 givenname: Luis surname: Crovetto fullname: Crovetto, Luis organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 6 givenname: Delia surname: Miguel fullname: Miguel, Delia organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 7 givenname: Maria D. surname: Giron fullname: Giron, Maria D. organization: Departamento de Bioquímica y Biología Molecular, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 8 givenname: Angel surname: Orte fullname: Orte, Angel email: angelort@ugr.es organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 9 givenname: Juan M. surname: Cuerva fullname: Cuerva, Juan M. organization: Departamento de Química Orgánica, Facultad de Ciencias, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), C. U. Fuentenueva s/n, 18071, Granada, Spain – sequence: 10 givenname: Rafael surname: Salto fullname: Salto, Rafael organization: Departamento de Bioquímica y Biología Molecular, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 11 givenname: Jose M. surname: Alvarez-Pez fullname: Alvarez-Pez, Jose M. organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain – sequence: 12 givenname: Jose M. surname: Paredes fullname: Paredes, Jose M. email: jmparedes@ugr.es organization: Departamento de Fisicoquimica, Facultad de Farmacia, Unidad de Excelencia en Quimica Aplicada a Biomedicina y Medioambiente (UEQ), Universidad de Granada, Campus Cartuja, 18071, Granada, Spain |
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| Keywords | Fluorescent dyes Solvatofluorochromism Biosensors Photophysics Hetero-xanthene dyes |
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| SubjectTerms | Biosensors Fluorescent dyes Hetero-xanthene dyes Photophysics Solvatofluorochromism |
| Title | A solvatofluorochromic silicon-substituted xanthene dye useful in bioimaging |
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