National Institues of Natural Sciences, Okazaki (Japan). National Institute for Physiological Sciences (NIPS) and xploratory Research Center on Life and Living Systems (ExCELLS)
Tohoku Univ., Sendai (Japan)
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
National Institues of Natural Sciences, Okazaki (Japan). National Institute for Physiological Sciences (NIPS) and xploratory Research Center on Life and Living Systems (ExCELLS); Kyushu Univ., Fukuoka (Japan)
Reactive sulfane sulfur species such as persulfides (RSSH) and H2S2 are important redox regulators and closely linked to H2S signaling. However, the study of these species is still challenging due to their instability, high reactivity, and the lack of suitable donors to produce them. Herein we report a unique compound, 2H-thiopyran-2-thione sulfine (TTS), which can specifically convert H2S to HSOH, and then to H2S2 in the presence of excess H2S. Meanwhile, the reaction product 2H-thiopyran-2-thione (TT) can be oxidized to reform TTS by biological oxidants. The reaction mechanism of TTS is studied experimentally and computationally. TTS can be conjugated to proteins to achieve specific delivery, and the combination of TTS and H2S leads to highly efficient protein persulfidation. When TTS is applied in conjunction with established H2S donors, the corresponding donors of H2S2 (or its equivalents) are obtained. Cell-based studies reveal that TTS can effectively increase intracellular sulfane sulfur levels and compensate for certain aspects of sulfide:quinone oxidoreductase (SQR) deficiency. These properties make TTS a conceptually new strategy for the design of donors of reactive sulfane sulfur species.
Cui, Qi, et al. "2<em>H</em>-Thiopyran-2-thione sulfine, a compound for converting H<sub>2</sub>S to HSOH/H<sub>2</sub>S<sub>2</sub> and increasing intracellular sulfane sulfur levels." Nature Communications, vol. 15, no. 1, Mar. 2024. https://doi.org/10.1038/s41467-024-46652-7
Cui, Qi, Shieh, Meg, Pan, Tony W., et al., "2<em>H</em>-Thiopyran-2-thione sulfine, a compound for converting H<sub>2</sub>S to HSOH/H<sub>2</sub>S<sub>2</sub> and increasing intracellular sulfane sulfur levels," Nature Communications 15, no. 1 (2024), https://doi.org/10.1038/s41467-024-46652-7
@article{osti_2417637,
author = {Cui, Qi and Shieh, Meg and Pan, Tony W. and Nishimura, Akiyuki and Matsunaga, Tetsuro and Kelly, Shane S. and Xu, Shi and Jung, Minkyung and Ogata, Seiryo and Morita, Masanobu and others},
title = {2<em>H</em>-Thiopyran-2-thione sulfine, a compound for converting H<sub>2</sub>S to HSOH/H<sub>2</sub>S<sub>2</sub> and increasing intracellular sulfane sulfur levels},
annote = {Reactive sulfane sulfur species such as persulfides (RSSH) and H2S2 are important redox regulators and closely linked to H2S signaling. However, the study of these species is still challenging due to their instability, high reactivity, and the lack of suitable donors to produce them. Herein we report a unique compound, 2H-thiopyran-2-thione sulfine (TTS), which can specifically convert H2S to HSOH, and then to H2S2 in the presence of excess H2S. Meanwhile, the reaction product 2H-thiopyran-2-thione (TT) can be oxidized to reform TTS by biological oxidants. The reaction mechanism of TTS is studied experimentally and computationally. TTS can be conjugated to proteins to achieve specific delivery, and the combination of TTS and H2S leads to highly efficient protein persulfidation. When TTS is applied in conjunction with established H2S donors, the corresponding donors of H2S2 (or its equivalents) are obtained. Cell-based studies reveal that TTS can effectively increase intracellular sulfane sulfur levels and compensate for certain aspects of sulfide:quinone oxidoreductase (SQR) deficiency. These properties make TTS a conceptually new strategy for the design of donors of reactive sulfane sulfur species.},
doi = {10.1038/s41467-024-46652-7},
url = {https://www.osti.gov/biblio/2417637},
journal = {Nature Communications},
issn = {ISSN 2041-1723},
number = {1},
volume = {15},
place = {United States},
publisher = {Nature Publishing Group},
year = {2024},
month = {03}}
