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Multifunctional Antioxidants: Regenerable Radical-Trapping and Hydroperoxide-Decomposing Ebselenols
IISER Bhopal.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC.
Vise andre og tillknytning
2016 (engelsk)Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, nr 11, s. 3729-3733Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Regenerable, multifunctional ebselenol antioxidants were prepared that could quench peroxyl radicals more efficiently than -tocopherol. These compounds act as better mimics of the glutathione peroxidase enzymes than ebselen. Production of reactive oxygen species (ROS) and reactive nitrogen species (RNS) in human mononuclear cells was considerably decreased upon exposure to the organoselenium compounds. At a concentration of 25m, the ebselenol derivatives showed minimal toxicity in pre-osteoblast MC3T3cells.

sted, utgiver, år, opplag, sider
2016. Vol. 55, nr 11, s. 3729-3733
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-280006DOI: 10.1002/anie.201510947ISI: 000371521000034PubMedID: 26879742OAI: oai:DiVA.org:uu-280006DiVA, id: diva2:909435
Forskningsfinansiär
Swedish Research CouncilCarl Tryggers foundation , 13:346, 13:120Tilgjengelig fra: 2016-03-07 Laget: 2016-03-07 Sist oppdatert: 2017-11-30bibliografisk kontrollert
Inngår i avhandling
1. Regenerable Organochalcogen Antioxidants: An Explorative Study
Åpne denne publikasjonen i ny fane eller vindu >>Regenerable Organochalcogen Antioxidants: An Explorative Study
2017 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

Antioxidants are widely used to protect organic materials from damages caused by autoxidation, an oxidation process that occurs under normal aerobic conditions. In this thesis, novel multifunctional organoselenium and organotellurium antioxidants were designed, synthesized, and evaluated in search for compounds with better radical-trapping capacity, regenerability, and hydroperoxide-decomposing ability.

Selenium was incorporated into ebselenols and hydroxy-2,3-dihydrobenzo[b]selenophenes and tellurium into diaryl disulfides and aryltellurophenols. All newly developed antioxidants were evaluated in a chlorobenzene/water two-phase lipid peroxidation system containing suitable co-antioxidants in the aqueous phase. Ebselenol carrying a hydroxyl group (OH) ortho to selenium showed a two-fold longer inhibition time than the reference α-tocopherol in the presence of aqueous-phase ascorbic acid. 2,3-Dihydrobenzo[b]selenophenes carrying a 5- or 7-OH outperformed α-tocopherol both when it comes to radical-trapping capacity and regenerability. Alkyltellurothiophenols, in situ formed from their corresponding disulfides by tris(2-carboxyethyl)phosphine, were also efficient regenerable radical-trapping antioxidants. The consumption of N-acetylcysteine in the water phase was followed and found to be limiting for the duration of the inhibition. The hydroperoxide-decomposing ability of all organoselenium antioxidants was evaluated. Ebselenols were often better glutathione peroxidase mimics than the parent.

In an effort to find out more about antioxidant mechanisms, aryltellurophenols carrying electron donating and electron withdrawing groups in the phenolic or aryltelluro parts were synthesized and OH bond dissociation enthalpies, BDEO-Hs, were calculated. Compounds carrying electron donating groups in the phenolic or aryltelluro part of the molecule showed the best radical-trapping capacity. Deuterium labelling experiments suggested that hydrogen atom transfer could be the rate-limiting step in the antioxidant mechanism.  

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis, 2017. s. 70
Serie
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1556
Emneord
autoxidation, antioxidant, selenium, tellurium, regenerable, multifunctional, radical-trapping, hydroperoxide-decomposing, co-antioxidant
HSV kategori
Forskningsprogram
Kemi med inriktning mot organisk kemi
Identifikatorer
urn:nbn:se:uu:diva-329217 (URN)978-91-513-0068-9 (ISBN)
Disputas
2017-10-27, B7:101a, BMC, Husargatan 3, 751 23, Uppsala, 09:30 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2017-10-05 Laget: 2017-09-10 Sist oppdatert: 2017-10-18

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