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Literature DB >> 28440074

Applications of Synthetic Organic Tetrasulfides as H₂S Donors.

Matthew M Cerda¹, Matthew D Hammers¹, Mary S Earp¹, Lev N Zakharov¹, Michael D Pluth¹.

Abstract

In an effort to expand the availability of simple polysulfides for H2S donation, we report here the synthesis and H2S release profiles of bis(aryl) and bis(alkyl) tetrasulfides. The tetrasulfide donors release H2S in a first-order dependence on reduced glutathione (GSH) and release more H2S than the commonly used trisulfide DATS.

Entities: Chemical Disease Species

Year: 2017 PMID： 28440074 PMCID： PMC6022400 DOI： 10.1021/acs.orglett.7b00858

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

23 in total

Review 1. Hydrogen sulfide-based therapeutics: exploiting a unique but ubiquitous gasotransmitter.

Authors: John L Wallace; Rui Wang
Journal: Nat Rev Drug Discov Date: 2015-04-07 Impact factor: 84.694

2. Two's company, three's a crowd: can H2S be the third endogenous gaseous transmitter?

Authors: Rui Wang
Journal: FASEB J Date: 2002-11 Impact factor: 5.191

3. Controllable hydrogen sulfide donors and their activity against myocardial ischemia-reperfusion injury.

Authors: Yu Zhao; Shashi Bhushan; Chuntao Yang; Hiroyuki Otsuka; Jason D Stein; Armando Pacheco; Bo Peng; Nelmi O Devarie-Baez; Hector C Aguilar; David J Lefer; Ming Xian
Journal: ACS Chem Biol Date: 2013-04-16 Impact factor: 5.100

Review 4. Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies.

Authors: Y Y Yeh; L Liu
Journal: J Nutr Date: 2001-03 Impact factor: 4.798

5. Hydrogen sulfide-linked sulfhydration of NF-κB mediates its antiapoptotic actions.

Authors: Nilkantha Sen; Bindu D Paul; Moataz M Gadalla; Asif K Mustafa; Tanusree Sen; Risheng Xu; Seyun Kim; Solomon H Snyder
Journal: Mol Cell Date: 2012-01-13 Impact factor: 17.970

6. Passive loss of hydrogen sulfide in biological experiments.

Authors: Eric R DeLeon; Gilbrian F Stoy; Kenneth R Olson
Journal: Anal Biochem Date: 2011-10-15 Impact factor: 3.365

7. Slow generation of hydrogen sulfide from sulfane sulfurs and NADH models.

Authors: Bo Peng; Chunrong Liu; Zhen Li; Jacob J Day; Yun Lu; David J Lefer; Ming Xian
Journal: Bioorg Med Chem Lett Date: 2016-12-09 Impact factor: 2.823

8. Optimization of the synthesis of symmetric aromatic tri- and tetrasulfides.

Authors: Eli Zysman-Colman; David N Harpp
Journal: J Org Chem Date: 2003-03-21 Impact factor: 4.354

9. A Synthetic Supramolecular Receptor for the Hydrosulfide Anion.

Authors: Matthew D Hartle; Ryan J Hansen; Blakely W Tresca; Samuel S Prakel; Lev N Zakharov; Michael M Haley; Michael D Pluth; Darren W Johnson
Journal: Angew Chem Int Ed Engl Date: 2016-08-11 Impact factor: 15.336

Review 10. Biological properties of garlic and garlic-derived organosulfur compounds.

Authors: Małgorzata Iciek; Inga Kwiecień; Lidia Włodek
Journal: Environ Mol Mutagen Date: 2009-04 Impact factor: 3.216

17 in total

1. Effects of sulfane sulfur content in benzyl polysulfides on thiol-triggered H₂S release and cell proliferation.

Authors: Sarah G Bolton; Matthew M Cerda; Annie K Gilbert; Michael D Pluth
Journal: Free Radic Biol Med Date: 2018-12-21 Impact factor: 7.376

2. Thionoesters: A Native Chemical Ligation-Inspired Approach to Cysteine-Triggered H₂S Donors.

Authors: Matthew M Cerda; Yu Zhao; Michael D Pluth
Journal: J Am Chem Soc Date: 2018-09-19 Impact factor: 15.419

Review 3. A review of hydrogen sulfide (H₂S) donors: Chemistry and potential therapeutic applications.

Authors: Chadwick R Powell; Kearsley M Dillon; John B Matson
Journal: Biochem Pharmacol Date: 2017-11-23 Impact factor: 5.858

Review 4. Activatable Small-Molecule Hydrogen Sulfide Donors.

Authors: Carolyn M Levinn; Matthew M Cerda; Michael D Pluth
Journal: Antioxid Redox Signal Date: 2019-10-29 Impact factor: 8.401

5. Cyclic Sulfenyl Thiocarbamates Release Carbonyl Sulfide and Hydrogen Sulfide Independently in Thiol-Promoted Pathways.

Authors: Yu Zhao; Andrea K Steiger; Michael D Pluth
Journal: J Am Chem Soc Date: 2019-08-14 Impact factor: 15.419

6. A Persulfide Donor Responsive to Reactive Oxygen Species: Insights into Reactivity and Therapeutic Potential.

Authors: Chadwick R Powell; Kearsley M Dillon; Yin Wang; Ryan J Carrazzone; John B Matson
Journal: Angew Chem Int Ed Engl Date: 2018-04-26 Impact factor: 15.336

Review 7. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H₂S Levels: H₂S Donors and H₂S Biosynthesis Inhibitors.

Authors: Csaba Szabo; Andreas Papapetropoulos
Journal: Pharmacol Rev Date: 2017-10 Impact factor: 25.468

Applications of Synthetic Organic Tetrasulfides as H₂S Donors.

Review 1. Hydrogen sulfide-based therapeutics: exploiting a unique but ubiquitous gasotransmitter.

2. Two's company, three's a crowd: can H2S be the third endogenous gaseous transmitter?

3. Controllable hydrogen sulfide donors and their activity against myocardial ischemia-reperfusion injury.

Review 4. Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies.

5. Hydrogen sulfide-linked sulfhydration of NF-κB mediates its antiapoptotic actions.

6. Passive loss of hydrogen sulfide in biological experiments.

7. Slow generation of hydrogen sulfide from sulfane sulfurs and NADH models.

8. Optimization of the synthesis of symmetric aromatic tri- and tetrasulfides.

9. A Synthetic Supramolecular Receptor for the Hydrosulfide Anion.

Review 10. Biological properties of garlic and garlic-derived organosulfur compounds.

1. Effects of sulfane sulfur content in benzyl polysulfides on thiol-triggered H₂S release and cell proliferation.

2. Thionoesters: A Native Chemical Ligation-Inspired Approach to Cysteine-Triggered H₂S Donors.

Review 3. A review of hydrogen sulfide (H₂S) donors: Chemistry and potential therapeutic applications.

Review 4. Activatable Small-Molecule Hydrogen Sulfide Donors.

5. Cyclic Sulfenyl Thiocarbamates Release Carbonyl Sulfide and Hydrogen Sulfide Independently in Thiol-Promoted Pathways.

6. A Persulfide Donor Responsive to Reactive Oxygen Species: Insights into Reactivity and Therapeutic Potential.

Review 7. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H₂S Levels: H₂S Donors and H₂S Biosynthesis Inhibitors.

8. SG1002 and Catenated Divalent Organic Sulfur Compounds as Promising Hydrogen Sulfide Prodrugs.

9. Synthesis and Hydrogen Sulfide Releasing Properties of Diaminodisulfides and Dialkoxydisulfides.

10. A Dinuclear Persulfide-Bridged Ruthenium Compound is a Hypoxia-Selective Hydrogen Sulfide (H₂ S) Donor.

Review 1. Hydrogen sulfide-based therapeutics: exploiting a unique but ubiquitous gasotransmitter.

Review 4. Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies.

Review 10. Biological properties of garlic and garlic-derived organosulfur compounds.

Review 3. A review of hydrogen sulfide (H2S) donors: Chemistry and potential therapeutic applications.

Review 4. Activatable Small-Molecule Hydrogen Sulfide Donors.

Review 7. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H2S Levels: H2S Donors and H2S Biosynthesis Inhibitors.

Review 3. A review of hydrogen sulfide (H₂S) donors: Chemistry and potential therapeutic applications.

Review 7. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H₂S Levels: H₂S Donors and H₂S Biosynthesis Inhibitors.