4.8 Article

The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 47, Pages 13961-13965

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201506887

Keywords

cyclization; fluorescence; fluorescent probes; hydrogen polysulfides; imaging agents

Funding

  1. ACS Teva Scholar Grant
  2. NIH [R01HL116571]
  3. MEXT of Japan
  4. Grants-in-Aid for Scientific Research [15K20857, 26670207] Funding Source: KAKEN

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Endogenous hydrogen polysulfides (H2Sn; n > 1) have been recognized as important regulators in sulfur-related redox biology. H2Sn can activate tumor suppressors, ion channels, and transcription factors with higher potency than H2S. Although H2Sn are drawing increasing attention, their exact mechanisms of action are still poorly understood. A major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. Herein we report a H2Sn-mediated benzodithiolone formation under mild conditions. This method takes advantage of the unique dual reactivity of H2Sn as both a nucleophile and an electrophile. Based on this reaction, three fluorescent probes (PSP-1, PSP-2, and PSP-3) were synthesized and evaluated. Among the probes prepared, PSP-3 showed a desirable off/on fluorescence response to H2Sn and high specificity. The probe was successfully applied in visualizing intracellular H2Sn.

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