Shining a light on SSP4: A comprehensive analysis and biological applications for the detection of sulfane sulfurs

Shieh, Meg; Ni, Xiang; Xu, Shi; Lindahl, Stephen; Yang, Moua; Matsunaga, Tetsuro; Flaumenhaft, Robert; Akaike, Takaaki; Xian, Ming

doi:10.1016/j.redox.2022.102433

Cited by 29 publications

(33 citation statements)

References 32 publications

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“…Next, we measured the ability of 21 to photorelease RSSH within cells using SSP4 (Figure 4b), an established fluorescent probe that has been used to detect intracellular sulfane sulfur levels qualitatively. 47 When MCF-7 cells are pretreated with 21 for 20 min and photolyzed with 420 nm light, we observe a clear increase in SSP4-derived fluorescence (Figure 4a), indicating intracellular RSSH release. Released RSSH in cells may also undergo a disproportionation reaction leading to polysulfide formation, which can also react with SSP4 to give a fluorescence signal.…”

Section: ■ Results and Discussionmentioning

confidence: 90%

“…In addition, photolysis at 420 nm (1500 W, LED lamp) for 45 min has no effect on MCF-7 cell viability (Supporting Information, Figure S48). Next, we measured the ability of 21 to photorelease RSSH within cells using SSP4 (Figure b), an established fluorescent probe that has been used to detect intracellular sulfane sulfur levels qualitatively . When MCF-7 cells are pretreated with 21 for 20 min and photolyzed with 420 nm light, we observe a clear increase in SSP4-derived fluorescence (Figure a), indicating intracellular RSSH release.…”

Section: Resultsmentioning

confidence: 99%

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Photochemical Release of Hydropersulfides

et al. 2022

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Hydropersulfides (RSSH) have received significant interest in the field of redox biology because of their intriguing biochemical properties. However, because RSSH are inherently unstable, their study is challenging, and as a result, the details of their physiological roles remain ill-defined. Herein, we report strategies to release RSSH utilizing photoremovable protecting groups. RSSH protection with the well-established p-hydroxyphenacyl (pHP) photoprotecting group resulted in inefficient RSSH photorelease along with complex chemistry. Therefore, an alternative precursor was examined in which a self-immolative linker was inserted between the pHP group and RSSH, providing nearly quantitative RSSH release following photolysis at 365 nm. Inspired by these results, we also synthesized an analogous precursor derivatized with 7-diethylaminocoumarin (DEACM), a visible light-cleavable photoprotecting group. Photolysis of this precursor at 420 nm led to efficient RSSH release, and in vitro experiments demonstrated intracellular RSSH delivery in breast cancer MCF-7 cells.

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Section: ■ Results and Discussionmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Photochemical Release of Hydropersulfides

et al. 2022

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“…Since HSSNO and its degradation product polysulfide are reactive sulfane sulfur species, their presence can be detected by the fluorescent probe SSP4 . As shown in Figure c, when the solution of Naph-SNO was subjected to UV light together with SSP4, the desired fluorescence increase at 510 nm was noted.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Since HSSNO and its degradation product polysulfide are reactive sulfane sulfur species, their presence can be detected by the fluorescent probe SSP4. 25 As shown in Figure 5c, when the solution of Naph-SNO was subjected to UV light together with SSP4, the desired fluorescence increase at 510 nm was noted. To further explore the possible formation of HSSNO in this process, we carried out spectroscopic studies of the "authentic" HSSNO preparation and compared the spectra with those of Naph-SNO release.…”

Section: Evaluation Of the Stability And Photophysical Property Of Th...mentioning

confidence: 86%

Single-Component Photo-Responsive Template for the Controlled Release of NO and H₂S₂

Roy

Shieh

et al. 2022

J. Am. Chem. Soc.

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Redox signaling molecules include a number of reactive oxygen species (ROS), reactive nitrogen species (RNS), and reactive sulfur species (RSS). These molecules work collectively in the regulation of many physiological processes. Understanding the crosstalk mechanisms in these signaling molecules is important but challenging. The development of donor compounds of ROS/RNS/RSS will aid the advances in this field. While many donors that can release one ROS/RNS/RSS have been developed, dual donors that can release two signaling species and facilitate their crosstalk studies are still very rare. Those limited examples lack the ability to precisely control the timing of two releases. In this work, a 2-methoxy-6-naphthacyl-derived tertiary SNO compound, Naph-SNO, was designed and evaluated as the dual donor for NO and H2S2. The 2-methoxy-6-naphthacyl structure was demonstrated to be a novel photoremovable protecting group that could directly uncage C–S bonds. Under the irradiation of lights with different wavelengths (visible or UV), Naph-SNO could release NO and H2S2 in a stepwise manner, or simultaneously (i.e., likely producing the crosstalk product HSNO/HSSNO). In addition, the release of payloads from the donor also produced an end product with blue fluorescence. Therefore, the release process could be easily monitored in “real time.” This controllable photo-triggered release strategy has the potential to be used in the design of other RNS/RSS dual donors.

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“…In 2013, our lab reported the first fluorescent probes, SSP1 and SSP2, for sulfane sulfurs and have since developed additional probes in the sulfane sulfur probe (SSP) series [ 21 , 22 ]. Our design exploits the electrophilic nature of sulfane sulfurs and their special affinity to thiol-based nucleophiles.…”

Section: Fluorescent Probes For the Detection Of Sulfane Sulfursmentioning

confidence: 99%

Detection of sulfane sulfur species in biological systems

Shieh

Lederberg

et al. 2022

Redox Biology

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Shining a light on SSP4: A comprehensive analysis and biological applications for the detection of sulfane sulfurs

Cited by 29 publications

References 32 publications

Photochemical Release of Hydropersulfides

Photochemical Release of Hydropersulfides

Single-Component Photo-Responsive Template for the Controlled Release of NO and H₂S₂

Detection of sulfane sulfur species in biological systems

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Shining a light on SSP4: A comprehensive analysis and biological applications for the detection of sulfane sulfurs

Cited by 29 publications

References 32 publications

Photochemical Release of Hydropersulfides

Photochemical Release of Hydropersulfides

Single-Component Photo-Responsive Template for the Controlled Release of NO and H2S2

Detection of sulfane sulfur species in biological systems

Contact Info

Product

Resources

About

Single-Component Photo-Responsive Template for the Controlled Release of NO and H₂S₂