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Pyridoxine-derived organoselenium compounds with glutathione peroxidase-like and chain-breaking antioxidant activity
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Dpt of Chemistry, Howard University.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
2014 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 39, 12563-12571 p.Article in journal (Refereed) Published
Abstract [en]

One of the vitamin B6 vitamers, pyridoxine, wasmodified to incorporate selenium in various oxidation statesin place of the methyl group in position 2. Such compoundswere conveniently accessed by treatment of bis-4,5-(carbo-ethoxy)-2-iodo-3-pyridinol with disodium diselenide andLiAlH4-reduction. After work-up, selone7was isolated ingood yield as an air-stable crystalline material. Hydrogenbonding to the neighboring hydroxyl group, as revealed bythe short intramolecular Se···H distance in the crystal struc-ture is likely to provide extra stabilization to the compound.Computational studies showed that selone7is more stablethan the corresponding selenol tautomer by 12.2 kcalmol1.Hydrogen peroxide oxidation of the selone7afforded di-selenide12, and, on further oxidation, seleninic acid13.Treatment of the seleninic acid with thiophenol provided anisolable selenosulfide14. The glutathione peroxidase-likeproperties of the pyridoxine-derived compounds were as-sessed by using the coupled reductase method. Seleninicacid13was found to be twofold more active than ebselen.The chain-breaking capacity of the pyridoxine compoundswere studied in a water/chlorobenzene membrane modelcontaining linoleic acid as an oxidizable substrate andN-ace-tylcysteine as a thiol reducing agent. Diselenide15couldmatcha-tocopherol when it comes to reactivity towardsperoxyl radicals and inhibition time.

Place, publisher, year, edition, pages
2014. Vol. 20, no 39, 12563-12571 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-232902DOI: 10.1002/chem.201403229ISI: 000342626200030OAI: oai:DiVA.org:uu-232902DiVA: diva2:750169
Available from: 2014-09-26 Created: 2014-09-26 Last updated: 2017-12-05Bibliographically approved

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Singh, VijayPoon, Jia-feiEngman, Lars

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