Abstract
Ratiometric sensors generally couple binding events or chemical reactions at a distal site to changes in the fluorescence of a core fluorophore scaffold. However, such approaches are often hindered by spectral overlap of the product and reactant species. We provide a strategy to design ratiometric sensors that display dramatic spectral shifts by leveraging the chemoselective reactivity of novel functional groups inserted within fluorophore scaffolds. As a proof-of-principle, fluorophores containing a borinate (RF620) or silanediol (SiOH2R) functionality at the bridging position of the xanthene ring system are developed as endogenous H2O2 sensors. Both these fluorophores display far-red to near-infrared excitation and emission prior to reaction. Upon oxidation by H2O2 both sensors are chemically converted to tetramethylrhodamine, producing significant (≥66 nm) blue-shifts in excitation and emission maxima. This work provides a new concept for the development of ratiometric probes.
Original language | English (US) |
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Pages (from-to) | 4197-4200 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 56 |
Issue number | 15 |
DOIs | |
State | Published - Apr 3 2017 |
Keywords
- bioorthogonal reaction
- fluorescent probes
- reactive oxygen species
- sensors
- signal transduction
ASJC Scopus subject areas
- Catalysis
- General Chemistry