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Issue 30, 2020
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Highly efficient H2S scavengers via thiolysis of positively-charged NBD amines

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Abstract

H2S is a well-known toxic gas and also a gaseous signaling molecule involved in many biological processes. Advanced chemical tools that can regulate H2S levels in vivo are useful for understanding H2S 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 H2S scavengers. The kinetic studies of thiolysis reactions revealed that incorporation of positively-charged groups onto the NBD amines greatly increased the rate of the H2S-specific thiolysis reaction. We demonstrate that these reactions proceed effectively, with second order rate constants (k2) of >116 M−1 s−1 at 37 °C for NBD-S8. Additionally, we demonstrate that NBD-S8 can effectively scavenge enzymatically-produced and endogenous H2S in live cells. Furthering the biological significance, we demonstrate NBD-S8 mediates scavenging of H2S in mice.

Graphical abstract: Highly efficient H2S scavengers via thiolysis of positively-charged NBD amines

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Supplementary files

Article information


Submitted
13 Mar 2020
Accepted
02 Jul 2020
First published
09 Jul 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7823-7828
Article type
Edge Article

Highly efficient H2S scavengers via thiolysis of positively-charged NBD amines

I. Ismail, Z. Chen, L. Sun, X. Ji, H. Ye, X. Kang, H. Huang, H. Song, S. G. Bolton, Z. Xi, M. D. Pluth and L. Yi, Chem. Sci., 2020, 11, 7823
DOI: 10.1039/D0SC01518K

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