Development of a reversible fluorescent probe for reactive sulfur species, sulfane sulfur, and its biological application

Abstract

We report a reversible off/on fluorescent probe for monitoring concentration changes of sulfane sulfur by utilizing the unique ability of sulfane sulfur to bind reversibly to other sulfur atoms and the intramolecular spirocyclization reaction of xanthene dyes. It reversibly visualized sulfane sulfur in living A549 cells and primary-cultured hippocampal astrocytes.

Polysulfides (H2Sn) produced from the interaction of hydrogen sulfide (H2S) and nitric oxide (NO) activate TRPA1 channels

“…H 2 S 2 and H 2 S 3 generated by the reaction of H 2 S and NO in DRG neurons were also examined using SSip-1, a fluorescence probe that specifically and reversibly binds to sulfane sulfur32 (Supplemental Fig. 2).…”

“…32) were diluted in a HEPES-buffered saline (HBS; in mM: 137 NaCl, 5.4 KCl, 0.8 MgCl 2 , 1.8 CaCl 2 , 10 glucose, 10 HEPES (pH 7.4)). DRG neurons were loaded with 5 μM fluo-4 AM in 0.02% cremophor EL for 45 min at room temperature or with 20 μM SSip-1 DA in 0.02% cremophor EL for 45 min at 37 °C.…”

N-Acetyl Cysteine Functions as a Fast-Acting Antioxidant by Triggering Intracellular H2S and Sulfane Sulfur Production

“…Changes in intracellular sulfane sulfur levels were monitored with the SSip-1 DA probe (Takano et al, 2017). Cells were seeded in black flat-bottomed 96-well imaging plate (BD Falcon 353219) at a density of 166 x 10 3 cells/ml in DMEM.…”

Synthesis of Pyridyl and N‐Methylpyridinium Analogues of Rosamines: Relevance of Solvent and Charge on Their Photophysical Properties

“…In comparison with functionalized rhodamines, rosamines lack the carboxylate functional group in the ortho ‐position of the aryl ring, that is C‐2′ (Figure a), and for this reason they will not form the corresponding spirolactone form. Rosamines also exhibit valuable spectral properties, more precisely a high molar absorptivity and an intense fluorescence spectrum in the visible region, which have enabled its successful use for different optical applications, as bioimaging probes or as fluorescent chemosensors …”

“…Rosaminesa lso exhibit valuable spectral properties, more precisely ah igh molara bsorptivity and an intense fluorescence spectrum in the visible region, which have enabled its successful use for different optical applications, as bioimaging probes [1][2][3][4][5][6] or as fluorescent chemosensors. [7][8][9][10] Regardless of the huge number of studies conducted recently,t he explanation fort he photophysical behavior of rhodaminesa nd analoguesi ss till very controversial. [11][12][13] One of the more consensual theories suggestst hat at wisted intramolecular charge transfer (TICT) state takes place by an electron transfer from the two amino groups, alternating between planar and pyramidal structure, to the xanthene ring ( Figure 1b).…”