Insights into the Mechanism of Thiol-Triggered COS/H 2 S Release from N -Dithiasuccinoyl Amines

The hydrolysis of carbonyl sulfide (COS) to form H S by carbonic anhydrase has been demonstrated to be a viable strategy to deliver H S in a biological system. Herein, we describe -dithiasuccinoyl amines as thiol-triggered COS/H S donors. Notably, thiol species especially GSH and homocysteine can tr...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2020-07, Vol.85 (13), p.8352-8359
Main Authors: Zhou, Shengchao, Mou, Yujie, Liu, Miao, Du, Qian, Ali, Basharat, Ramprasad, Jurupula, Qiao, Chunhua, Hu, Li-Fang, Ji, Xingyue
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The hydrolysis of carbonyl sulfide (COS) to form H S by carbonic anhydrase has been demonstrated to be a viable strategy to deliver H S in a biological system. Herein, we describe -dithiasuccinoyl amines as thiol-triggered COS/H S donors. Notably, thiol species especially GSH and homocysteine can trigger the release of both COS and H S directly from several specific analogues via an unexpected mechanism. Importantly, two representative analogues and show intracellular H S release, and imparts potent anti-inflammatory effects in LPS-challenged microglia cells. In conclusion, -dithiasuccinoyl amine could serve as promising COS/H S donors for either H S biological studies or H S-based therapeutics development.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00559