Abstract
Hydrogen sulfide (H2S) is an important biomolecule that plays key signaling and protective roles in different physiological processes. With goals of advancing both the available research tools and the associated therapeutic potential of H2S, researchers have developed different methods to deliver H2S on demand in different biological contexts. A recent approach to develop such donors has been to design compounds that release carbonyl sulfide (COS), which is quickly converted to H2S in biological systems by the ubiquitous enzyme carbonic anhydrase (CA). Although highly diversifiable, many approaches using this general platform release quinone methides or related electrophiles after donor activation. Many such electrophiles are likely scavenged by water, but recent efforts have also expanded alternative approaches that minimize the formation of electrophilic byproducts generated after COS release. This mini-review focuses specifically on recent examples of COS-based H2S donors that do no generate quinone methide byproducts after donor activation.
Keywords: Hydrogen sulfide, Carbonyl sulfide, Donors, Self-immolation, Engineered release, Reactive sulfur species.
Current Topics in Medicinal Chemistry
Title:Moving Past Quinone-Methides: Recent Advances Toward Minimizing Electrophilic Byproducts from COS/H2S Donors
Volume: 21 Issue: 32
Author(s): Michael D. Pluth*
Affiliation:
- Department of Chemistry and Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, Institute of Molecular Biology. University of Oregon. Eugene, OR,United States
Keywords: Hydrogen sulfide, Carbonyl sulfide, Donors, Self-immolation, Engineered release, Reactive sulfur species.
Abstract: Hydrogen sulfide (H2S) is an important biomolecule that plays key signaling and protective roles in different physiological processes. With goals of advancing both the available research tools and the associated therapeutic potential of H2S, researchers have developed different methods to deliver H2S on demand in different biological contexts. A recent approach to develop such donors has been to design compounds that release carbonyl sulfide (COS), which is quickly converted to H2S in biological systems by the ubiquitous enzyme carbonic anhydrase (CA). Although highly diversifiable, many approaches using this general platform release quinone methides or related electrophiles after donor activation. Many such electrophiles are likely scavenged by water, but recent efforts have also expanded alternative approaches that minimize the formation of electrophilic byproducts generated after COS release. This mini-review focuses specifically on recent examples of COS-based H2S donors that do no generate quinone methide byproducts after donor activation.
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Cite this article as:
Pluth D. Michael*, Moving Past Quinone-Methides: Recent Advances Toward Minimizing Electrophilic Byproducts from COS/H2S Donors, Current Topics in Medicinal Chemistry 2021; 21 (32) . https://dx.doi.org/10.2174/1568026621666210622130002
DOI https://dx.doi.org/10.2174/1568026621666210622130002 |
Print ISSN 1568-0266 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-4294 |
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