The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides

Wei Chen, Ethan W. Rosser, Tetsuro Matsunaga, Armando Pacheco, Takaaki Akaike, Ming Xian

Research output: Contribution to journalArticle

116 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)13961-13965
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number47
DOIs
Publication statusPublished - 2015 Nov 16

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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