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Literature DB >> 29701221

Cysteine-activated hydrogen sulfide (H₂S) delivery through caged carbonyl sulfide (COS) donor motifs.

Yu Zhao¹, Andrea K Steiger, Michael D Pluth.

Abstract

Hydrogen sulfide (H2S) is an important biomolecule, and controllable H2S donors are needed to investigate H2S biological functions. Here we utilize cysteine-mediated addition/cyclization chemistry to unmask an acrylate-functionalized thiocarbamate and release carbonyl sulfide (COS), which is quickly converted to H2S by carbonic anhydrase (CA).

Entities: Chemical Gene Species

Year: 2018 PMID： 29701221 PMCID： PMC5965689 DOI： 10.1039/c8cc02428f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

31 in total

Review 1. Roles of hydrogen sulfide in the pathogenesis of diabetes mellitus and its complications.

Authors: Csaba Szabo
Journal: Antioxid Redox Signal Date: 2012-01-30 Impact factor: 8.401

Review 2. Physiological implications of hydrogen sulfide: a whiff exploration that blossomed.

Authors: Rui Wang
Journal: Physiol Rev Date: 2012-04 Impact factor: 37.312

3. Two 3-hydroxyflavone derivatives as two-photon fluorescence turn-on chemosensors for cysteine and homocysteine in living cells.

Authors: Qianqian Wu; Kangnan Wang; Zian Wang; Yatong Sun; Duxia Cao; Zhiqiang Liu; Ruifang Guan; Songfang Zhao; Xueying Yu
Journal: Talanta Date: 2017-12-22 Impact factor: 6.057

Review 4. Toward Hydrogen Sulfide Based Therapeutics: Critical Drug Delivery and Developability Issues.

Authors: Yueqin Zheng; Bingchen Yu; Ladie Kimberly De La Cruz; Manjusha Roy Choudhury; Abiodun Anifowose; Binghe Wang
Journal: Med Res Rev Date: 2017-02-27 Impact factor: 12.944

5. The synthesis and stereochemistry of substituted 1,4-thiazepines related to the penicillins.

Authors: N J Leonard; R Y Ning
Journal: J Org Chem Date: 1966-12 Impact factor: 4.354

Review 6. Medicinal Chemistry: Insights into the Development of Novel H2S Donors.

Authors: Yu Zhao; Armando Pacheco; Ming Xian
Journal: Handb Exp Pharmacol Date: 2015

7. Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H2O2-dependent H2S production.

Authors: Vivian S Lin; Alexander R Lippert; Christopher J Chang
Journal: Proc Natl Acad Sci U S A Date: 2013-04-15 Impact factor: 11.205

8. Kinetic Insights into Hydrogen Sulfide Delivery from Caged-Carbonyl Sulfide Isomeric Donor Platforms.

Authors: Yu Zhao; Hillary A Henthorn; Michael D Pluth
Journal: J Am Chem Soc Date: 2017-11-02 Impact factor: 15.419

Review 9. 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

10. Therapeutic Delivery of H₂S via COS: Small Molecule and Polymeric Donors with Benign Byproducts.

Authors: Chadwick R Powell; Jeffrey C Foster; Benjamin Okyere; Michelle H Theus; John B Matson
Journal: J Am Chem Soc Date: 2016-10-07 Impact factor: 15.419

13 in total

1. H₂S donors with optical responses.

Authors: Michael D Pluth; Yu Zhao; Matthew M Cerda
Journal: Methods Enzymol Date: 2020-06-15 Impact factor: 1.600

2. Characterization and Biological Activity of a Hydrogen Sulfide-Releasing Red Light-Activated Ruthenium(II) Complex.

Authors: Joshua J Woods; Jian Cao; Alexander R Lippert; Justin J Wilson
Journal: J Am Chem Soc Date: 2018-09-19 Impact factor: 15.419

3. 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 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

Review 5. Development and Application of Carbonyl Sulfide-Based Donors for H₂S Delivery.

Authors: Carolyn M Levinn; Matthew M Cerda; Michael D Pluth
Journal: Acc Chem Res Date: 2019-08-07 Impact factor: 22.384

6. Self-Amplified Depolymerization of Oligo(thiourethanes) for the Release of COS/H₂S.

Authors: Chadwick R Powell; Jeffrey C Foster; Sarah N Swilley; Kuljeet Kaur; Samantha J Scannelli; Diego Troya; John B Matson
Journal: Polym Chem Date: 2019-04-24 Impact factor: 5.582

7. 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

Cysteine-activated hydrogen sulfide (H₂S) delivery through caged carbonyl sulfide (COS) donor motifs.

Review 1. Roles of hydrogen sulfide in the pathogenesis of diabetes mellitus and its complications.

Review 2. Physiological implications of hydrogen sulfide: a whiff exploration that blossomed.

3. Two 3-hydroxyflavone derivatives as two-photon fluorescence turn-on chemosensors for cysteine and homocysteine in living cells.

Review 4. Toward Hydrogen Sulfide Based Therapeutics: Critical Drug Delivery and Developability Issues.

5. The synthesis and stereochemistry of substituted 1,4-thiazepines related to the penicillins.

Review 6. Medicinal Chemistry: Insights into the Development of Novel H2S Donors.

7. Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H2O2-dependent H2S production.

8. Kinetic Insights into Hydrogen Sulfide Delivery from Caged-Carbonyl Sulfide Isomeric Donor Platforms.

Review 9. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H₂S Levels: H₂S Donors and H₂S Biosynthesis Inhibitors.

10. Therapeutic Delivery of H₂S via COS: Small Molecule and Polymeric Donors with Benign Byproducts.

1. H₂S donors with optical responses.

2. Characterization and Biological Activity of a Hydrogen Sulfide-Releasing Red Light-Activated Ruthenium(II) Complex.

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

Review 4. Activatable Small-Molecule Hydrogen Sulfide Donors.

Review 5. Development and Application of Carbonyl Sulfide-Based Donors for H₂S Delivery.

6. Self-Amplified Depolymerization of Oligo(thiourethanes) for the Release of COS/H₂S.

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

8. Use of Dithiasuccinoyl-Caged Amines Enables COS/H₂ S Release Lacking Electrophilic Byproducts.

9. Colorimetric Carbonyl Sulfide (COS)/Hydrogen Sulfide (H₂ S) Donation from γ-Ketothiocarbamate Donor Motifs.

10. N-Methylation of Self-Immolative Thiocarbamates Provides Insights into the Mechanism of Carbonyl Sulfide Release.

Review 1. Roles of hydrogen sulfide in the pathogenesis of diabetes mellitus and its complications.

Review 2. Physiological implications of hydrogen sulfide: a whiff exploration that blossomed.

Review 4. Toward Hydrogen Sulfide Based Therapeutics: Critical Drug Delivery and Developability Issues.

Review 6. Medicinal Chemistry: Insights into the Development of Novel H2S Donors.

Review 9. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H2S Levels: H2S Donors and H2S Biosynthesis Inhibitors.

Review 4. Activatable Small-Molecule Hydrogen Sulfide Donors.

Review 5. Development and Application of Carbonyl Sulfide-Based Donors for H2S Delivery.

Review 9. International Union of Basic and Clinical Pharmacology. CII: Pharmacological Modulation of H₂S Levels: H₂S Donors and H₂S Biosynthesis Inhibitors.

Review 5. Development and Application of Carbonyl Sulfide-Based Donors for H₂S Delivery.