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Effect of a Bromo S...
Effect of a Bromo Substituent on the Glutathione Peroxidase Activity of a Pyridoxine-like Diselenide
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- Singh, Vijay P (author)
- Uppsala universitet,Syntetisk organisk kemi
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- Poon, Jia-fei (author)
- Uppsala universitet,Syntetisk organisk kemi
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- Butcher, Ray J. (author)
- Department of Chemistry, Howard University, USA.
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- Lu, Xi (author)
- Uppsala universitet,Tillämpad materialvetenskap
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- Mestres, Gemma, 1984- (author)
- Uppsala universitet,Tillämpad materialvetenskap
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- Karlsson Ott, Marjam (author)
- Uppsala universitet,Tillämpad materialvetenskap
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- Engman, Lars (author)
- Uppsala universitet,Syntetisk organisk kemi
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(creator_code:org_t)
- 2015-07-15
- 2015
- English.
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In: The Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 50:15, s. 7385-7395
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- Kemi med inriktning mot organisk kemi
- Chemistry with specialization in Organic Chemistry
- Teknisk fysik med inriktning mot materialvetenskap
- Engineering Science with specialization in Materials Science
Publication and Content Type
- ref (subject category)
- art (subject category)
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