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RESEARCH PRODUCT

A Chemosensor Bearing Sulfonyl Azide Moieties for Selective Chromo-Fluorogenic Hydrogen Sulfide Recognition in Aqueous Media and in Living Cells

Félix SancenónAna M. CosteroAna M. CosteroSameh El SayedLuis E. Santos-figueroaSalvador GilSalvador GilCristina De LatorreMargarita ParraMargarita ParraRamón Martínez-máñez

subject

HEPESSulfonylchemistry.chemical_classificationHydrogen sulfideOrganic Chemistrychemistry.chemical_elementPhotochemistryFluorescenceSulfurchemistry.chemical_compoundchemistryAzideNaked eyePhysical and Theoretical ChemistryAcetonitrile

description

A simple chemodosimeter based on a sulfonyl azide dye (1-Az), which displayed a highly selective response toward hydrogen sulfide anion in mixed aqueous media, was synthesised and characterised. Addition of hydrogen sulfide to acetonitrile/HEPES 1:1 solutions of 1-Az induced a clear colour change from red-orange to yellow, which was easily detected by the naked eye, and by an enhancement in the emission intensity. Other common anions, thiol-containing biomolecules and oxidants did not induce any noticeable colour or fluorescence modulation in the probe. The chemodosimeter also showed a good sensitivity, with limits of detection of 11.91 and 0.63 μM by using UV/Vis or fluorescence measurements, respectively. Moreover, 1-Az could be used for real-time fluorescence imaging of intracellular HS– at micromolar concentrations.

https://doi.org/10.1002/ejoc.201301514