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Effect of a Bromo Substituent on the Glutathione Peroxidase Activity of a Pyridoxine-like Diselenide
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
Department of Chemistry, Howard University, USA..
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Tekniska sektionen, Institutionen för teknikvetenskaper, Tillämpad materialvetenskap.
Vise andre og tillknytning
2015 (engelsk)Inngår i: The Journal of Organic Chemistry, Vol. 50, nr 15, s. 7385-7395Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

In search for better mimics of the glutathioneperoxidase enzymes, pyridoxine-like diselenides 6 and 11,carrying a 6-bromo substituent, were prepared. Reaction of2,6-dibromo-3-pyridinol 5 with sodium diselenide provided 6via aromatic nucleophilic substitution of the 2-bromosubstituent. LiAlH4 caused reduction of all four ester groupsand returned 11 after acidic workup. The X-ray structure of 6showed that the dipyridyl diselenide moiety was kept in analmost planar, transoid conformation. According to NBOanalysis,this was due to weak intramolecular Se···O (1.1 kcal/mol) and Se···N-interactions (2.5 kcal/mol). That the 6-bromo substituent increased the positive charge on seleniumwas confirmed by NPA-analysis and seen in calculated andobserved 77Se NMR-shifts. Diselenide 6 showed a more than 3-fold higher reactivity than the corresponding des-bromocompound 3a and ebselen when evaluated in the coupled reductase assay. Experiments followed for longer time (2 h) confirmedthat diselenide 6 is a better GPx-catalyst than 11. On the basis of 77Se-NMR experiments, a catalytic mechanism for diselenide 6was proposed involving selenol, selenosulfide and seleninic acid intermediates. At low concentration (10 μM) where it showedonly minimal toxicity, it could scavenge ROS produced by MNC- and PMNC-cells more efficiently than Trolox.

sted, utgiver, år, opplag, sider
2015. Vol. 50, nr 15, s. 7385-7395
HSV kategori
Forskningsprogram
Kemi med inriktning mot organisk kemi; Teknisk fysik med inriktning mot materialvetenskap
Identifikatorer
URN: urn:nbn:se:uu:diva-259460DOI: 10.1021/acs.joc.5b00797ISI: 000359393500007OAI: oai:DiVA.org:uu-259460DiVA, id: diva2:844254
Forskningsfinansiär
Swedish Research CouncilCarl Tryggers foundation , CTS 13:120 13:346Tilgjengelig fra: 2015-08-04 Laget: 2015-08-04 Sist oppdatert: 2015-09-22bibliografisk kontrollert

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