Issue 30, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
13 3 2020
Accepted
02 7 2020
First published
09 7 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 7823-7828

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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