Phototriggered Hydrogen Persulfide Donors via Hydrosulfide Radical Formation Enhancing the Reactive Sulfur Metabolome in Cells

Hydrogen persulfide (H<sub>2</sub>S<sub>2</sub>) is an important sulfur-containing signaling molecule that plays a crucial role in the homeostasis of various organ systems, such as the renal, cardiovascular, liver, and gastrointestinal systems. However, research on H<sub>2</sub>S<sub>2</sub> in biological settings is still challenging due to its instability and high reactivity. Compounds that can controllably release H<sub>2</sub>S<sub>2</sub> (also known as donors) are thus crucial research tools. Currently, available H<sub>2</sub>S<sub>2</sub> donors are still very limited, with most of them relying on modified disulfide templates. These templates possess an unavoidable limitation of being susceptible to cellular disulfide exchange which can compromise their efficacy. In this work, we explored nondisulfide-based and nonoxidation-dependent templates for the design of H<sub>2</sub>S<sub>2</sub> donors. We found that tertiary naphthacyl thiols could undergo phototriggered C-S homolytic cleavage to form H<sub>2</sub>S<sub>2</sub> via hydrosulfide (HS) radicals. In addition, the release of H<sub>2</sub>S<sub>2</sub> was associated with the formation of a product with strong blue fluorescence, which allowed for real-time monitoring of the release process. This reaction was demonstrated to proceed effectively in both buffers and cells, with the ability to enhance intracellular production of persulfides, including GSSH, CysSSH, H<sub>2</sub>S<sub>2</sub>, H<sub>2</sub>S<sub>3</sub>, etc. It provides a unique photocontrolled H<sub>2</sub>S<sub>2</sub> donor system with distinct advantages compared to known H<sub>2</sub>S<sub>2</sub> donors due to its good stability and spatiotemporal control ability.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2024-10-25
DOI
https://doi.org/10.1021/jacs.4c11540
Citations
14
Primary Topic
Sulfur Compounds in Biology
Type
article
Field-Weighted Citation Impact
4.13

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article

Phototriggered Hydrogen Persulfide Donors via Hydrosulfide Radical Formation Enhancing the Reactive Sulfur Metabolome in Cells

Meg Shieh, Minkyung Jung, Ming Xian, Tsuyoshi Takata et al.
14 citations
Journal of the American Chemical Society
Sulfur Compounds in Biology
4.13
article

Phototriggered Hydrogen Persulfide Donors via Hydrosulfide Radical Formation Enhancing the Reactive Sulfur Metabolome in Cells

Meg Shieh, Minkyung Jung, Ming Xian, Tsuyoshi Takata, Eshani Das, Biswajit Roy, Takaaki Akaike, Shi Xu
article en
14 citations

Abstract

Hydrogen persulfide (H<sub>2</sub>S<sub>2</sub>) is an important sulfur-containing signaling molecule that plays a crucial role in the homeostasis of various organ systems, such as the renal, cardiovascular, liver, and gastrointestinal systems. However, research on H<sub>2</sub>S<sub>2</sub> in biological settings is still challenging due to its instability and high reactivity. Compounds that can controllably release H<sub>2</sub>S<sub>2</sub> (also known as donors) are thus crucial research tools. Currently, available H<sub>2</sub>S<sub>2</sub> donors are still very limited, with most of them relying on modified disulfide templates. These templates possess an unavoidable limitation of being susceptible to cellular disulfide exchange which can compromise their efficacy. In this work, we explored nondisulfide-based and nonoxidation-dependent templates for the design of H<sub>2</sub>S<sub>2</sub> donors. We found that tertiary naphthacyl thiols could undergo phototriggered C-S homolytic cleavage to form H<sub>2</sub>S<sub>2</sub> via hydrosulfide (HS) radicals. In addition, the release of H<sub>2</sub>S<sub>2</sub> was associated with the formation of a product with strong blue fluorescence, which allowed for real-time monitoring of the release process. This reaction was demonstrated to proceed effectively in both buffers and cells, with the ability to enhance intracellular production of persulfides, including GSSH, CysSSH, H<sub>2</sub>S<sub>2</sub>, H<sub>2</sub>S<sub>3</sub>, etc. It provides a unique photocontrolled H<sub>2</sub>S<sub>2</sub> donor system with distinct advantages compared to known H<sub>2</sub>S<sub>2</sub> donors due to its good stability and spatiotemporal control ability.

Journal of the American Chemical SocietyVol. 146(44)
John Brown University (US), Tohoku University (JP), Brown University (US), Society of Environmental Toxicology and Chemistry (US)
Japan Agency for Medical Research and Development, National Institutes of Health, Japan Science and Technology Agency
Clean water and sanitation
Openalex Percentile: Top 6%
Sulfur Compounds in Biology
4.13
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