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Literature DB >> 31180636

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

Chadwick R Powell^1,2,3, Kuljeet Kaur^1,2,3, Kearsley M Dillon^1,2,3, Mingjun Zhou^1,2,3, Mohammed Alaboalirat^1,2,3, John B Matson^1,2,3.

Abstract

We report a synthetic route toward a family of functional COS/H2S-releasing N-substituted N-thiocarboxyanhydrides (NTAs) with functionalities to accommodate popular conjugation reactions, including olefin cross metathesis, thiol-ene, and copper-catalyzed azide-alkyne cycloaddition. The N-substituted NTAs were attached to small molecules, polymers, and a protein to synthesize novel H2S donors convergently. All conjugates showed sustained H2S release kinetics.

Entities: CellLine Chemical Disease Gene Species

Mesh：

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Year: 2019 PMID： 31180636 PMCID： PMC6911359 DOI： 10.1021/acschembio.9b00248

Source DB: PubMed Journal: ACS Chem Biol ISSN： 1554-8929 Impact factor: 5.100

34 in total

1. Hepatic carbonyl sulfide metabolism.

Authors: C P Chengelis; R A Neal
Journal: Biochem Biophys Res Commun Date: 1979-10-12 Impact factor: 3.575

2. A new gaseous signaling molecule emerges: cardioprotective role of hydrogen sulfide.

Authors: David J Lefer
Journal: Proc Natl Acad Sci U S A Date: 2007-11-08 Impact factor: 11.205

3. Cytoprotective effects of hydrogen sulfide-releasing N-methyl-D-aspartate receptor antagonists are mediated by intracellular sulfane sulfur.

Authors: Eizo Marutani; Masahiro Sakaguchi; Wei Chen; Kiyoshi Sasakura; Jifeng Liu; Ming Xian; Kenjiro Hanaoka; Tetsuo Nagano; Fumito Ichinose
Journal: Medchemcomm Date: 2014-10-01 Impact factor: 3.597

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

Authors: Andrea K Steiger; Yang Yang; Maksim Royzen; Michael D Pluth
Journal: Chem Commun (Camb) Date: 2017-01-24 Impact factor: 6.222

5. Hydrogen Sulfide Donors Activated by Reactive Oxygen Species.

Authors: Yu Zhao; Michael D Pluth
Journal: Angew Chem Int Ed Engl Date: 2016-10-24 Impact factor: 15.336

6. NO prodrug-conjugated, self-assembled, pH-responsive and galactose receptor targeted nanoparticles for co-delivery of nitric oxide and doxorubicin.

Authors: Jimin Zhang; Huijuan Song; Shenglu Ji; Xiaomin Wang; Pingsheng Huang; Chuangnian Zhang; Weiwei Wang; Deling Kong
Journal: Nanoscale Date: 2018-03-01 Impact factor: 7.790

7. Thiol-norbornene photo-click hydrogels for tissue engineering applications.

Authors: Chien-Chi Lin; Chang Seok Ki; Han Shih
Journal: J Appl Polym Sci Date: 2015-02-20 Impact factor: 3.125

8. A general model for selectivity in olefin cross metathesis.

Authors: Arnab K Chatterjee; Tae-Lim Choi; Daniel P Sanders; Robert H Grubbs
Journal: J Am Chem Soc Date: 2003-09-17 Impact factor: 15.419

9. The possible role of hydrogen sulfide as an endogenous neuromodulator.

Authors: K Abe; H Kimura
Journal: J Neurosci Date: 1996-02-01 Impact factor: 6.167

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

7 in total

Review 1. 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

2. Linker-Regulated H₂S Release from Aromatic Peptide Amphiphile Hydrogels.

Authors: Kuljeet Kaur; Yin Wang; John B Matson
Journal: Biomacromolecules Date: 2020-02-13 Impact factor: 6.988

3. Electrospun Scaffolds Functionalized with a Hydrogen Sulfide Donor Stimulate Angiogenesis.

Authors: Tianyu Yao; Teun van Nunen; Rebeca Rivero; Chadwick Powell; Ryan Carrazzone; Lilian Kessels; Paul Andrew Wieringa; Shahzad Hafeez; Tim G A M Wolfs; Lorenzo Moroni; John B Matson; Matthew B Baker
Journal: ACS Appl Mater Interfaces Date: 2022-06-17 Impact factor: 10.383

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

1. Hepatic carbonyl sulfide metabolism.

2. A new gaseous signaling molecule emerges: cardioprotective role of hydrogen sulfide.

3. Cytoprotective effects of hydrogen sulfide-releasing N-methyl-D-aspartate receptor antagonists are mediated by intracellular sulfane sulfur.

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

5. Hydrogen Sulfide Donors Activated by Reactive Oxygen Species.

6. NO prodrug-conjugated, self-assembled, pH-responsive and galactose receptor targeted nanoparticles for co-delivery of nitric oxide and doxorubicin.

7. Thiol-norbornene photo-click hydrogels for tissue engineering applications.

8. A general model for selectivity in olefin cross metathesis.

9. The possible role of hydrogen sulfide as an endogenous neuromodulator.

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

Review 1. Activatable Small-Molecule Hydrogen Sulfide Donors.

2. Linker-Regulated H₂S Release from Aromatic Peptide Amphiphile Hydrogels.

3. Electrospun Scaffolds Functionalized with a Hydrogen Sulfide Donor Stimulate Angiogenesis.

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

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

6. Amino acid-based H₂S donors: N-thiocarboxyanhydrides that release H₂S with innocuous byproducts.

Review 7. Moving Past Quinone-Methides: Recent Advances Toward Minimizing Electrophilic Byproducts from COS/H₂S Donors.

Review 1. Activatable Small-Molecule Hydrogen Sulfide Donors.

Review 7. Moving Past Quinone-Methides: Recent Advances Toward Minimizing Electrophilic Byproducts from COS/H2S Donors.

Review 7. Moving Past Quinone-Methides: Recent Advances Toward Minimizing Electrophilic Byproducts from COS/H₂S Donors.