Highly efficient H 2 S scavengers via thiolysis of positively-charged NBD amines

H S is a well-known toxic gas and also a gaseous signaling molecule involved in many biological processes. Advanced chemical tools that can regulate H S levels are useful for understanding H S biology as well as its potential therapeutic effects. To this end, we have developed a series of 7-nitro-1,...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-08, Vol.11 (30), p.7823-7828
Main Authors: Ismail, Ismail, Chen, Zhuoyue, Sun, Lu, Ji, Xiuru, Ye, Haishun, Kang, Xueying, Huang, Haojie, Song, Haibin, Bolton, Sarah G, Xi, Zhen, Pluth, Michael D, Yi, Long
Format: Article
Language:English
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Summary:H S is a well-known toxic gas and also a gaseous signaling molecule involved in many biological processes. Advanced chemical tools that can regulate H S levels are useful for understanding H S biology as well as its potential therapeutic effects. To this end, we have developed a series of 7-nitro-1,2,3-benzoxadiazole (NBD) amines as potential H S scavengers. The kinetic studies of thiolysis reactions revealed that incorporation of positively-charged groups onto the NBD amines greatly increased the rate of the H S-specific thiolysis reaction. We demonstrate that these reactions proceed effectively, with second order rate constants ( ) of >116 M s at 37 °C for . Additionally, we demonstrate that can effectively scavenge enzymatically-produced and endogenous H S in live cells. Furthering the biological significance, we demonstrate mediates scavenging of H S in mice.
ISSN:2041-6520
2041-6539
DOI:10.1039/D0SC01518K