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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2012
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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. |
format | Online Article Text |
id | pubmed-6268572 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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