Literature DB >> 27774732

Hydrogen Sulfide Donors Activated by Reactive Oxygen Species.

Yu Zhao1, Michael D Pluth1.   

Abstract

Hydrogen sulfide (H2 S) exhibits promising protective effects in many (patho)physiological processes, as evidenced by recent reports using synthetic H2 S donors in different biological models. Herein, we report the design and evaluation of compounds denoted PeroxyTCM, which are the first class of reactive oxygen species (ROS)-triggered H2 S donors. These donors are engineered to release carbonyl sulfide (COS) upon activation, which is quickly hydrolyzed to H2 S by the ubiquitous enzyme carbonic anhydrase (CA). The donors are stable in aqueous solution and do not release H2 S until triggered by ROS, such as hydrogen peroxide (H2 O2 ), superoxide (O2- ), and peroxynitrite (ONOO- ). We demonstrate ROS-triggered H2 S donation in live cells and also demonstrate that PeroxyTCM-1 provides protection against H2 O2 -induced oxidative damage, suggesting potential future applications of PeroxyTCM and similar scaffolds in H2 S-related therapies.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbonyl sulfide; hydrogen sulfide; oxidative stress; reactive oxygen species; thiocarbamate

Mesh:

Substances:

Year:  2016        PMID: 27774732      PMCID: PMC5175466          DOI: 10.1002/anie.201608052

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  40 in total

1.  Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells.

Authors:  Leticia A Montoya; Michael D Pluth
Journal:  Chem Commun (Camb)       Date:  2012-04-04       Impact factor: 6.222

2.  Synthesis of a photocontrollable hydrogen sulfide donor using ketoprofenate photocages.

Authors:  Naoki Fukushima; Naoya Ieda; Kiyoshi Sasakura; Tetsuo Nagano; Kenjiro Hanaoka; Takayoshi Suzuki; Naoki Miyata; Hidehiko Nakagawa
Journal:  Chem Commun (Camb)       Date:  2013-11-26       Impact factor: 6.222

Review 3.  Emergence of hydrogen sulfide as an endogenous gaseous signaling molecule in cardiovascular disease.

Authors:  David J Polhemus; David J Lefer
Journal:  Circ Res       Date:  2014-02-14       Impact factor: 17.367

Review 4.  Novel insights into hydrogen sulfide--mediated cytoprotection.

Authors:  John W Calvert; William A Coetzee; David J Lefer
Journal:  Antioxid Redox Signal       Date:  2010-05-15       Impact factor: 8.401

5.  Endogenous hydrogen sulfide regulation of myocardial injury induced by isoproterenol.

Authors:  Bin Geng; Lin Chang; Chunshui Pan; Yongfen Qi; Jing Zhao; Yongzheng Pang; Junbao Du; Chaoshu Tang
Journal:  Biochem Biophys Res Commun       Date:  2004-06-04       Impact factor: 3.575

Review 6.  Enzymology of H2S biogenesis, decay and signaling.

Authors:  Omer Kabil; Ruma Banerjee
Journal:  Antioxid Redox Signal       Date:  2013-06-07       Impact factor: 8.401

7.  Esterase-Sensitive Prodrugs with Tunable Release Rates and Direct Generation of Hydrogen Sulfide.

Authors:  Yueqin Zheng; Bingchen Yu; Kaili Ji; Zhixiang Pan; Vayou Chittavong; Binghe Wang
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-28       Impact factor: 15.336

8.  Design, Synthesis, and Cardioprotective Effects of N-Mercapto-Based Hydrogen Sulfide Donors.

Authors:  Yu Zhao; Chuntao Yang; Chelsea Organ; Zhen Li; Shashi Bhushan; Hiro Otsuka; Armando Pacheco; Jianming Kang; Hector C Aguilar; David J Lefer; Ming Xian
Journal:  J Med Chem       Date:  2015-09-04       Impact factor: 7.446

9.  Hydrogen peroxide-activatable antioxidant prodrug as a targeted therapeutic agent for ischemia-reperfusion injury.

Authors:  Dongwon Lee; Seunggyu Park; Soochan Bae; Dahee Jeong; Minhyung Park; Changsun Kang; Wooyoung Yoo; Mohammed A Samad; Qingen Ke; Gilson Khang; Peter M Kang
Journal:  Sci Rep       Date:  2015-11-13       Impact factor: 4.379

10.  Self-Immolative Thiocarbamates Provide Access to Triggered H2S Donors and Analyte Replacement Fluorescent Probes.

Authors:  Andrea K Steiger; Sibile Pardue; Christopher G Kevil; Michael D Pluth
Journal:  J Am Chem Soc       Date:  2016-06-03       Impact factor: 15.419

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  41 in total

1.  Alleviating Cellular Oxidative Stress through Treatment with Superoxide-Triggered Persulfide Prodrugs.

Authors:  Yin Wang; Kearsley M Dillon; Zhao Li; Ethan W Winckler; John B Matson
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-23       Impact factor: 15.336

2.  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

3.  Inhibition of Mitochondrial Bioenergetics by Esterase-Triggered COS/H2S Donors.

Authors:  Andrea K Steiger; Michela Marcatti; Csaba Szabo; Bartosz Szczesny; Michael D Pluth
Journal:  ACS Chem Biol       Date:  2017-06-30       Impact factor: 5.100

4.  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

5.  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

Review 6.  Emerging Roles of Carbonyl Sulfide in Chemical Biology: Sulfide Transporter or Gasotransmitter?

Authors:  Andrea K Steiger; Yu Zhao; Michael D Pluth
Journal:  Antioxid Redox Signal       Date:  2017-05-18       Impact factor: 8.401

Review 7.  Hydrogen sulfide-mediated regulation of cell death signaling ameliorates adverse cardiac remodeling and diabetic cardiomyopathy.

Authors:  Sumit Kar; Tyler N Kambis; Paras K Mishra
Journal:  Am J Physiol Heart Circ Physiol       Date:  2019-03-29       Impact factor: 4.733

8.  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

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

Review 10.  Chemical Biology of H2S Signaling through Persulfidation.

Authors:  Milos R Filipovic; Jasmina Zivanovic; Beatriz Alvarez; Ruma Banerjee
Journal:  Chem Rev       Date:  2017-11-07       Impact factor: 60.622

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