Chemoselective Alteration of Fluorophore Scaffolds as a Strategy for the Development of Ratiometric Chemodosimeters

Xinqi Zhou, Lauren Lesiak, Rui Lai, Jon R. Beck, Jia Zhao, Christian G. Elowsky, Hui Li, Clifford I Stains

Research output: Contribution to journalArticle

18 Scopus citations

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 languageEnglish (US)
Pages (from-to)4197-4200
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number15
DOIs
Publication statusPublished - Jan 1 2017

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Keywords

  • bioorthogonal reaction
  • fluorescent probes
  • reactive oxygen species
  • sensors
  • signal transduction

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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