Literature DB >> 31327894

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

Kearsley M Dillon1,2, Chadwick R Powell1,2, John B Matson1,2.   

Abstract

H2S, persulfides (R-SSH), and related sulfur species have recently received attention due to the pronounced physiological effects they elicit. Delivering sulfur signaling molecules in a controlled manner presents many challenges, as many available donors have short half-lives, lack water solubility, and exhibit poor trigger specificity. Self-immolative prodrugs provide a unique ability to impart stability to H2S precursors and persulfides while allowing for trigger specificity by tuning the functional group installed on the self-immolative linker. This strategy has proven successful in delivering sulfur signaling species under specific conditions and may lead to the further elucidation of persulfide interactions within biological systems, affording effective therapeutics.

Entities:  

Keywords:  gasotransmitter; perthiol; reactive oxygen species; redox; self-immolation

Year:  2019        PMID: 31327894      PMCID: PMC6641548          DOI: 10.1055/s-0037-1611693

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  44 in total

1.  A self-immolative spacer that enables tunable controlled release of phenols under neutral conditions.

Authors:  Kyle M Schmid; Lasse Jensen; Scott T Phillips
Journal:  J Org Chem       Date:  2012-04-17       Impact factor: 4.354

Review 2.  Hydrogen sulfide: an endogenous mediator of resolution of inflammation and injury.

Authors:  John L Wallace; Jose G P Ferraz; Marcelo N Muscara
Journal:  Antioxid Redox Signal       Date:  2011-12-15       Impact factor: 8.401

3.  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

4.  NOSH-aspirin (NBS-1120), a novel nitric oxide- and hydrogen sulfide-releasing hybrid is a potent inhibitor of colon cancer cell growth in vitro and in a xenograft mouse model.

Authors:  Mitali Chattopadhyay; Ravinder Kodela; Kenneth R Olson; Khosrow Kashfi
Journal:  Biochem Biophys Res Commun       Date:  2012-02-16       Impact factor: 3.575

5.  The vasorelaxant effect of H(2)S as a novel endogenous gaseous K(ATP) channel opener.

Authors:  W Zhao; J Zhang; Y Lu; R Wang
Journal:  EMBO J       Date:  2001-11-01       Impact factor: 11.598

6.  Hydrogen sulfide-releasing aspirin suppresses NF-κB signaling in estrogen receptor negative breast cancer cells in vitro and in vivo.

Authors:  Mitali Chattopadhyay; Ravinder Kodela; Niharika Nath; Arpine Barsegian; Daniel Boring; Khosrow Kashfi
Journal:  Biochem Pharmacol       Date:  2011-12-24       Impact factor: 5.858

7.  Cysteine-activated hydrogen sulfide (H2S) donors.

Authors:  Yu Zhao; Hua Wang; Ming Xian
Journal:  J Am Chem Soc       Date:  2010-12-10       Impact factor: 15.419

8.  Hydrogen sulfide attenuates myocardial ischemia-reperfusion injury by preservation of mitochondrial function.

Authors:  John W Elrod; John W Calvert; Joanna Morrison; Jeannette E Doeller; David W Kraus; Ling Tao; Xiangying Jiao; Rosario Scalia; Levente Kiss; Csaba Szabo; Hideo Kimura; Chi-Wing Chow; David J Lefer
Journal:  Proc Natl Acad Sci U S A       Date:  2007-09-18       Impact factor: 11.205

9.  H2S signals through protein S-sulfhydration.

Authors:  Asif K Mustafa; Moataz M Gadalla; Nilkantha Sen; Seyun Kim; Weitong Mu; Sadia K Gazi; Roxanne K Barrow; Guangdong Yang; Rui Wang; Solomon H Snyder
Journal:  Sci Signal       Date:  2009-11-10       Impact factor: 8.192

10.  Self-immolative polymers.

Authors:  Amit Sagi; Roy Weinstain; Naama Karton; Doron Shabat
Journal:  J Am Chem Soc       Date:  2008-04-01       Impact factor: 15.419

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  3 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.  Polymeric persulfide prodrugs: Mitigating oxidative stress through controlled delivery of reactive sulfur species.

Authors:  Kearsley M Dillon; Ryan J Carrazzone; Yin Wang; Chadwick R Powell; John B Matson
Journal:  ACS Macro Lett       Date:  2020-04-07       Impact factor: 6.903

3.  Targeted Delivery of Persulfides to the Gut: Effects on the Microbiome.

Authors:  Kearsley M Dillon; Holly A Morrison; Chadwick R Powell; Ryan J Carrazzone; Veronica M Ringel-Scaia; Ethan W Winckler; R McAlister Council-Troche; Irving C Allen; John B Matson
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-29       Impact factor: 15.336

  3 in total

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