An Examination of Chemical Tools for Hydrogen Selenide Donation and Detection

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2024 Aug 29

PMID 39202942

Authors

Rynne A Hankins

John C Lukesh

Affiliations

Soon will be listed here.

Abstract

Hydrogen selenide (HSe) is an emerging biomolecule of interest with similar properties to that of other gaseous signaling molecules (i.e., gasotransmitters that include nitric oxide, carbon monoxide, and hydrogen sulfide). HSe is enzymatically generated in humans where it serves as a key metabolic intermediate in the production of selenoproteins and other selenium-containing biomolecules. However, beyond its participation in biosynthetic pathways, its involvement in cellular signaling or other biological mechanisms remains unclear. To uncover its true biological significance, HSe-specific chemical tools capable of functioning under physiological conditions are required but lacking in comparison to those that exist for other gasotransmitters. Recently, researchers have begun to fill this unmet need by developing new HSe-releasing compounds, along with pioneering methods for selenide detection and quantification. In combination, the chemical tools highlighted in this review have the potential to spark groundbreaking explorations into the chemical biology of HSe, which may lead to its branding as the fourth official gasotransmitter.

References

Kieliszek M, Blazejak S . Current Knowledge on the Importance of Selenium in Food for Living Organisms: A Review. Molecules. 2016; 21(5). PMC: 6274134. DOI: 10.3390/molecules21050609. View

Szabo C . Gaseotransmitters: new frontiers for translational science. Sci Transl Med. 2010; 2(59):59ps54. PMC: 3038605. DOI: 10.1126/scitranslmed.3000721. View

Iwata A, Morrison M, Blackwood J, Roth M . Selenide Targets to Reperfusing Tissue and Protects It From Injury. Crit Care Med. 2015; 43(7):1361-7. DOI: 10.1097/CCM.0000000000000971. View

Tarze A, Dauplais M, Grigoras I, Lazard M, Ha-Duong N, Barbier F . Extracellular production of hydrogen selenide accounts for thiol-assisted toxicity of selenite against Saccharomyces cerevisiae. J Biol Chem. 2007; 282(12):8759-67. DOI: 10.1074/jbc.M610078200. View

Murphy B, Bhattacharya R, Mukherjee P . Hydrogen sulfide signaling in mitochondria and disease. FASEB J. 2019; 33(12):13098-13125. PMC: 6894098. DOI: 10.1096/fj.201901304R. View

Zhao Y, Pluth M . Hydrogen Sulfide Donors Activated by Reactive Oxygen Species. Angew Chem Int Ed Engl. 2016; 55(47):14638-14642. PMC: 5175466. DOI: 10.1002/anie.201608052. View

Kang X, Huang H, Jiang C, Cheng L, Sang Y, Cai X . Cysteine-Activated Small-Molecule HSe Donors Inspired by Synthetic HS Donors. J Am Chem Soc. 2022; 144(9):3957-3967. DOI: 10.1021/jacs.1c12006. View

Choi N, Lee J, Park E, Lee J, Lee J . Recent Advances in Organelle-Targeted Fluorescent Probes. Molecules. 2021; 26(1). PMC: 7795030. DOI: 10.3390/molecules26010217. View

Chen J . An original discovery: selenium deficiency and Keshan disease (an endemic heart disease). Asia Pac J Clin Nutr. 2012; 21(3):320-6. View

10.

Sayehmiri K, Azami M, Mohammadi Y, Soleymani A, Tardeh Z . The association between Selenium and Prostate Cancer: a Systematic Review and Meta-Analysis. Asian Pac J Cancer Prev. 2018; 19(6):1431-1437. PMC: 6103565. DOI: 10.22034/APJCP.2018.19.6.1431. View

11.

Newton T, Li K, Sharma J, Champagne P, Pluth M . Direct hydrogen selenide (HSe) release from activatable selenocarbamates. Chem Sci. 2023; 14(27):7581-7588. PMC: 10337719. DOI: 10.1039/d3sc01936e. View

12.

Barceloux D . Selenium. J Toxicol Clin Toxicol. 1999; 37(2):145-72. DOI: 10.1081/clt-100102417. View

13.

Steiger A, Zhao Y, Pluth M . Emerging Roles of Carbonyl Sulfide in Chemical Biology: Sulfide Transporter or Gasotransmitter?. Antioxid Redox Signal. 2017; 28(16):1516-1532. PMC: 5930797. DOI: 10.1089/ars.2017.7119. View

14.

Xu S, Hamsath A, Neill D, Wang Y, Yang C, Xian M . Strategies for the Design of Donors and Precursors of Reactive Sulfur Species. Chemistry. 2018; 25(16):4005-4016. DOI: 10.1002/chem.201804895. View

15.

Kong F, Zhao Y, Liang Z, Liu X, Pan X, Luan D . Highly Selective Fluorescent Probe for Imaging HSe in Living Cells and in Vivo Based on the Disulfide Bond. Anal Chem. 2016; 89(1):688-693. DOI: 10.1021/acs.analchem.6b03136. View

16.

Newton T, Pluth M . Development of a hydrolysis-based small-molecule hydrogen selenide (HSe) donor. Chem Sci. 2020; 10(46):10723-10727. PMC: 7006510. DOI: 10.1039/c9sc04616j. View

17.

Asfar P, Radermacher P . Drug-Induced "Suspended Animation": Can a Dream Become True?. Crit Care Med. 2015; 43(7):1528-30. DOI: 10.1097/CCM.0000000000000985. View

18.

Zhao Y, Henthorn H, Pluth M . Kinetic Insights into Hydrogen Sulfide Delivery from Caged-Carbonyl Sulfide Isomeric Donor Platforms. J Am Chem Soc. 2017; 139(45):16365-16376. PMC: 6022369. DOI: 10.1021/jacs.7b09527. View

19.

Filipovic M, Zivanovic J, Alvarez B, Banerjee R . Chemical Biology of HS Signaling through Persulfidation. Chem Rev. 2017; 118(3):1253-1337. PMC: 6029264. DOI: 10.1021/acs.chemrev.7b00205. View

20.

Gilbert A, Zhao Y, Otteson C, Pluth M . Development of Acid-Mediated HS/COS Donors That Respond to a Specific pH Window. J Org Chem. 2019; 84(22):14469-14475. PMC: 7024054. DOI: 10.1021/acs.joc.9b01873. View