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

Chemical Science
Ismail IsmailLong Yi

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 (k 2) 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.

References

Apr 1, 1965·Analytical Biochemistry·L M SIEGEL
Oct 7, 2009·Antioxidants & Redox Signaling·Hideo Kimura
Dec 4, 2009·Proceedings of the National Academy of Sciences of the United States of America·Andreas PapapetropoulosCsaba Szabó
Mar 2, 2010·Amino Acids·Hideo Kimura
Jan 8, 2011·Annual Review of Pharmacology and Toxicology·Ling LiPhilip K Moore
Nov 19, 2011·Science·Konstantin ShatalinEvgeny Nudler
Jan 24, 2013·Nature Communications·Norihiro ShibuyaHideo Kimura
Apr 23, 2013·Antioxidants & Redox Signaling·Omer Kabil, Ruma Banerjee
Jun 6, 2013·The Journal of Organic Chemistry·Leticia A MontoyaMichael D Pluth
Jul 16, 2013·Nitric Oxide : Biology and Chemistry·Gopi K KolluruChristopher G Kevil
Mar 13, 2014·Plant Physiology and Biochemistry : PPB·J T Hancock, M Whiteman
Apr 16, 2014·Antioxidants & Redox Signaling·Mark R HellmichCsaba Szabo
Jul 16, 2014·Chemical Communications : Chem Comm·Yu ZhaoMing Xian
Jul 18, 2014·Chemical Communications : Chem Comm·Fabiao YuLingxin Chen
Nov 6, 2015·Journal of the American Chemical Society·Hillary A Henthorn, Michael D Pluth
Dec 19, 2015·Nature Reviews. Drug Discovery·Csaba Szabo
Apr 21, 2016·Analytical Chemistry·Yen Leng PakJuyoung Yoon
May 12, 2016·Chemical Society Reviews·Matthew D Hartle, Michael D Pluth
Oct 21, 2016·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Katalin MódisRui Wang
Mar 23, 2017·The Journal of Biological Chemistry·Sabine ArndtMichael P Murphy
Jul 13, 2017·Antioxidants & Redox Signaling·Ashley Untereiner, Lingyun Wu
Nov 8, 2017·Chemical Reviews·Milos R FilipovicRuma Banerjee
Nov 28, 2017·Biochemical Pharmacology·Chadwick R PowellJohn B Matson
Dec 31, 2017·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Enrico GugliandoloSalvatore Cuzzocrea
Feb 14, 2018·Current Medicinal Chemistry·Valentina CitiAlma Martelli
Oct 30, 2018·Journal of the American Chemical Society·Yin WangJohn B Matson
Dec 1, 2018·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Fiona Augsburger, Csaba Szabo
Mar 8, 2019·Chemical Science·Matthew M CerdaMichael D Pluth
Apr 28, 2019·Nutrients·Levi M TeigenAlexander Khoruts

❮ Previous
Next ❯

Citations

Jun 25, 2021·Antioxidants & Redox Signaling·Yingying WangMing Xian
Aug 13, 2021·Chemical Communications : Chem Comm·Xiaoqiang TuLong Yi

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

© 2021 Meta ULC. All rights reserved