The design, synthesis, properties, and cell imaging applications of a series of pyridine-disulfide based fluorescent probes (WSP1, WSP2, WSP3, WSP4 and WSP5) for hydrogen sulfide detection are reported. The strategy is based on the dual-nucleophilicity of hydrogen sulfide. A hydrogen sulfide mediated tandem nucleophilic substitution-cyclization reaction is used to release the fluorophores and turn on the fluorescence. The probes showed high sensitivity and selectivity for hydrogen sulfide over other reactive sulfur species including cysteine and glutathione.
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. While H2Sn are drawing increasing attention, their exact mechanisms of actions are still poorly understood. A major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. In this work we report a H2Sn-mediated benzodithiolone formation under mild conditions. This reaction takes advantage of the unique dual-reactivity of H2Sn as both a nucleophile and an electrophile. It opens a door for better understanding H2Sn's chemical biology. Based on this reaction, three fluorescent probes (PSP-1~3) were synthesized and evaluated. Among the probes prepared, PSP-3 showed a desirable off-on fluorescence response to H2Sn and high specificity. It was successfully applied in visualizing intracellular H2Sn.
A hydrogen polysulfide mediated aziridine
ring-opening reaction
was discovered. Based on this reaction, a novel H2Sn-specific chemosensor (AP) was
developed. AP showed high sensitivity and selectivity
for H2Sn. Notably, the fluorescent
turn-on product (1) exhibited excellent two-photon photophysical
properties, a large Stokes shift, and high solid state luminescent
efficiency.
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.
Highlights d Convergent UMP biosynthetic pathways interchangeably sustain cancer cell proliferation d Phenotypic screens can identify selective modulators of convergent metabolic networks d Multiple protein kinase inhibitors possess secondary targets within UMP metabolism
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