Activity-based detection of hydrogen sulfide in live cells can expand our understanding of its reactivity and complex physiological effects. We have discovered a highly efficient method for fluorescent probe activation, which is driven by HS-triggered 1,6-elimination of an α-CF-benzyl to release resorufin. In detecting intracellular HS, 4-azido-(α-CF)-benzyl resorufin offers significantly faster signal generation and improved sensitivity compared to 4-azidobenzyl resorufin. Computed free energy profiles for the 1,6-elimination process support the hypothesis that a benzylic CF group can reduce the activation energy barrier toward probe activation. This novel probe design allows for near-real-time detection of HS in HeLa cells under stimulation conditions.
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| http://dx.doi.org/10.1101/2024.05.30.596105 | DOI Listing |
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