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Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols

Diphenyl diselenide has shown interesting biological activities in various free-radical-induced damage models and can be considered as a potential candidate drug against oxidative stress. Apart from its anti-oxidant activity, this compound can oxidize various thiols. However there are no detailed st...

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Autores principales: Hassan, Waseem, Rocha, Joao Batista Teixeira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268572/
https://www.ncbi.nlm.nih.gov/pubmed/23085664
http://dx.doi.org/10.3390/molecules171012287
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author Hassan, Waseem
Rocha, Joao Batista Teixeira
author_facet Hassan, Waseem
Rocha, Joao Batista Teixeira
author_sort Hassan, Waseem
collection PubMed
description Diphenyl diselenide has shown interesting biological activities in various free-radical-induced damage models and can be considered as a potential candidate drug against oxidative stress. Apart from its anti-oxidant activity, this compound can oxidize various thiols. However there are no detailed studies in the literature about the thiol oxidase-like activity of this compound against biologically significant mono and di-thiols with respect to various pH conditions. Keeping in mind the scarcity of data in this area of organochalcogen chemistry, we report for the first time the kinetics of thiol oxidation by diphenyl diselenide, which was carried out in a commonly used phosphate buffer, not only at physiological pH, but also at a number of acidic values. The relative reactivities of the different thiols with diphenyl diselenide were independent of the pKa of the thiol group, such that at pH 7.4, cysteine and dithiothreitol were the most reactive, while 2,3-dimercapto-1-propanesulfonic acid and glutathione were weakly reactive and extremely low reactivity was observed with dimercaptosuccinic acid. Rate of oxidation was dependent on the pH of the incubation medium. The results obtained will help us in the design of rational strategies for the safe pharmacological use of diphenyl diselenide.
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spelling pubmed-62685722018-12-12 Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols Hassan, Waseem Rocha, Joao Batista Teixeira Molecules Article Diphenyl diselenide has shown interesting biological activities in various free-radical-induced damage models and can be considered as a potential candidate drug against oxidative stress. Apart from its anti-oxidant activity, this compound can oxidize various thiols. However there are no detailed studies in the literature about the thiol oxidase-like activity of this compound against biologically significant mono and di-thiols with respect to various pH conditions. Keeping in mind the scarcity of data in this area of organochalcogen chemistry, we report for the first time the kinetics of thiol oxidation by diphenyl diselenide, which was carried out in a commonly used phosphate buffer, not only at physiological pH, but also at a number of acidic values. The relative reactivities of the different thiols with diphenyl diselenide were independent of the pKa of the thiol group, such that at pH 7.4, cysteine and dithiothreitol were the most reactive, while 2,3-dimercapto-1-propanesulfonic acid and glutathione were weakly reactive and extremely low reactivity was observed with dimercaptosuccinic acid. Rate of oxidation was dependent on the pH of the incubation medium. The results obtained will help us in the design of rational strategies for the safe pharmacological use of diphenyl diselenide. MDPI 2012-10-19 /pmc/articles/PMC6268572/ /pubmed/23085664 http://dx.doi.org/10.3390/molecules171012287 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Hassan, Waseem
Rocha, Joao Batista Teixeira
Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols
title Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols
title_full Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols
title_fullStr Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols
title_full_unstemmed Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols
title_short Interaction Profile of Diphenyl Diselenide with Pharmacologically Significant Thiols
title_sort interaction profile of diphenyl diselenide with pharmacologically significant thiols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268572/
https://www.ncbi.nlm.nih.gov/pubmed/23085664
http://dx.doi.org/10.3390/molecules171012287
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