Developing Chemical Tools to Influence Redox Biology: Selenium-Sulfur Linkages, Bioorthogonal Chemistry, and Electrophilic Thiol-Blocking Reagents.

Hamsath, Akil

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Overview

Year:: 2023
Contributor:: Hamsath, Akil (creator); Xian, Ming (Advisor); Williard, Paul (Reader); Basu, Amit (Reader); Brown University. Department of Chemistry (sponsor)
Genre:: theses
Subject:: Chemistry, Organic; chemical biology
Extent:: 11, 190 p.

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Description

Abstract:: Cellular redox homeostasis regulates metabolism, cell death, differentiation and development, immune responses, circadian rhythm, and overall cell health. This is achieved through a balance of reactive oxygen species (ROS) and reactive sulfur species (RSS). These species are highly dynamic and can respond to changes in redox status on demand by their consumption or regeneration. Thus, ROS and RSS are suitable triggers for chemical biology applications such as imaging, diagnostics, and therapy. In this thesis defense, I will be presenting: 1) an acyl-selenylsulfide scaffold that can be used to release RSS like H 2 S and H 2 S 2 through a thioselenenic acid intermediate (Se-SH), 2) an unusual intra-molecular tetrazine-acryloyl cyclization reaction that has been utilized to consume ROS and release methylselenenic acid (MeSeOH) with a fluorescent byproduct, and 3) preliminary experiments on a thiol SNAr reaction with a highly effective thiol-blocking reagent. The overall focus will be on the organic method development, chemical structure/activity relationships, and mechanistic studies.
Notes:: Thesis (Ph. D.)--Brown University, 2023

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Citation

Hamsath, Akil, "Developing Chemical Tools to Influence Redox Biology: Selenium-Sulfur Linkages, Bioorthogonal Chemistry, and Electrophilic Thiol-Blocking Reagents." (2023). Chemistry Theses and Dissertations. Brown Digital Repository. Brown University Library. https://repository.library.brown.edu/studio/item/bdr:93zx5du9/

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Chemistry Theses and Dissertations

Theses and Dissertations for the Chemistry department.
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