Literature DB >> 28074971

Bio-orthogonal "click-and-release" donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H2S).

Andrea K Steiger1, Yang Yang2, Maksim Royzen2, Michael D Pluth1.   

Abstract

Hydrogen sulfide (H2S) is an important biomolecule with high therapeutic potential. Here we leverage the inverse-electron demand Diels-Alder (IEDDA) click reaction between a thiocarbamate-functionalized trans-cyclooctene and a tetrazine to deliver carbonyl sulfide (COS), which is quickly converted to H2S by the uniquitous enzyme carbonic anhydrase (CA), thus providing a new strategy for bio-orthogonal COS/H2S donation.

Entities:  

Year:  2017        PMID： 28074971     DOI： 10.1039/c6cc09547j

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


  24 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.  Self-Immolative Prodrugs: Effective Tools for the Controlled Release of Sulfur Signaling Species.

Authors:  Kearsley M Dillon; Chadwick R Powell; John B Matson
Journal:  Synlett       Date:  2019-01-09       Impact factor: 2.454

3.  Functional N-Substituted N-Thiocarboxyanhydrides as Modular Tools for Constructing H2S Donor Conjugates.

Authors:  Chadwick R Powell; Kuljeet Kaur; Kearsley M Dillon; Mingjun Zhou; Mohammed Alaboalirat; John B Matson
Journal:  ACS Chem Biol       Date:  2019-06-10       Impact factor: 5.100

4.  Investigations into the carbonic anhydrase inhibition of COS-releasing donor core motifs.

Authors:  Andrea K Steiger; Yu Zhao; Won Jin Choi; Alder Crammond; McKinna R Tillotson; Michael D Pluth
Journal:  Biochem Pharmacol       Date:  2017-11-10       Impact factor: 5.858

Review 5.  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

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

Authors:  Yu Zhao; Andrea K Steiger; Michael D Pluth
Journal:  Chem Commun (Camb)       Date:  2018-05-10       Impact factor: 6.222

Review 7.  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

8.  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

9.  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

10.  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
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