Fluorescence mechanism switching from ICT to PET by substituent chemical manipulation: Macrophage cytoplasm imaging probes

The lack of polarity sensing fluorophores with OFF-ON features when increasing the environment polarity has limited the monitoring of biological processes that involve an increase in local hydrophilicity. In this work, replacement of a hydroxyl group by a dimethylamino group transformed solvatochrom...

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Bibliographic Details
Published in:Dyes and pigments 2020-04, Vol.175, p.108172, Article 108172
Main Authors: Fueyo-González, Francisco, González-Vera, Juan A., Alkorta, Ibon, Infantes, Lourdes, Jimeno, M. Luisa, Fernández-Gutiérrez, Mar, González-García, M. Carmen, Orte, Angel, Herranz, Rosario
Format: Article
Language:English
Subjects:
Fluorescence probes
Macrophage dyes
Naphthalimide derivatives
Off-On water sensors
pH sensors
Quinolimide derivatives
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Summary:The lack of polarity sensing fluorophores with OFF-ON features when increasing the environment polarity has limited the monitoring of biological processes that involve an increase in local hydrophilicity. In this work, replacement of a hydroxyl group by a dimethylamino group transformed solvatochromic ICT naphthalimide- and quinolimide-based fluorophores into reversed solvatochromic ones, with higher emission in polar than in apolar environments. Excited-state dynamics studies, TD-DFT calculations, X-ray and NMR support the existence of a folded conformation for the 2-(dimethylamino)ethyl chain upon the imide ring in apolar solvents, where the dimethylamino group would quench the fluorescence by a PET effect, while in polar solvents the chain has an extended conformation, where the PET is hindered. These PET fluorophores have given rise to H2O and pH sensors in organic solvents as well as to bright macrophage cytoplasm imaging probes. OFF-ON polarity sensing PET fluorophores were obtained by simple substituent manipulation of solvatochromic (ICT) fluorophores. This switching led to H2O and pH sensors and cell cytoplasm imaging probes. [Display omitted] •Naphthalimide and quinolimide-based fluorophores have been prepared.•ICT fluorophores are switched to OFF-ON polarity sensing PET fluorophores.•TRES, TD-DFT calculations, X-ray and NMR support a PET fluorescence mechanism.•The dyes behave as OFF-ON H2O and pH fluorescence sensors.•Macrophage cytoplasm fluorescence imaging probes are obtained.
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2019.108172