Matches in SemOpenAlex for { <https://semopenalex.org/work/W1616212752> ?p ?o ?g. }
- W1616212752 endingPage "7395" @default.
- W1616212752 startingPage "7385" @default.
- W1616212752 abstract "In search for better mimics of the glutathione peroxidase enzymes, pyridoxine-like diselenides 6 and 11, carrying a 6-bromo substituent, were prepared. Reaction of 2,6-dibromo-3-pyridinol 5 with sodium diselenide provided 6 via aromatic nucleophilic substitution of the 2-bromo substituent. LiAlH4 caused reduction of all four ester groups and returned 11 after acidic workup. The X-ray structure of 6 showed that the dipyridyl diselenide moiety was kept in an almost planar, transoid conformation. According to NBO-analysis, 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 selenium was confirmed by NPA-analysis and seen in calculated and observed 77Se NMR-shifts. Diselenide 6 showed a more than 3-fold higher reactivity than the corresponding des-bromo compound 3a and ebselen when evaluated in the coupled reductase assay. Experiments followed for longer time (2 h) confirmed that diselenide 6 is a better GPx-catalyst than 11. On the basis of 77Se-NMR experiments, a catalytic mechanism for diselenide 6 was proposed involving selenol, selenosulfide and seleninic acid intermediates. At low concentration (10 μM) where it showed only minimal toxicity, it could scavenge ROS produced by MNC- and PMNC-cells more efficiently than Trolox." @default.
- W1616212752 created "2016-06-24" @default.
- W1616212752 creator A5021563239 @default.
- W1616212752 creator A5033473704 @default.
- W1616212752 creator A5043480847 @default.
- W1616212752 creator A5044409094 @default.
- W1616212752 creator A5049024428 @default.
- W1616212752 creator A5080882260 @default.
- W1616212752 creator A5082831941 @default.
- W1616212752 date "2015-07-15" @default.
- W1616212752 modified "2023-10-15" @default.
- W1616212752 title "Effect of a Bromo Substituent on the Glutathione Peroxidase Activity of a Pyridoxine-like Diselenide" @default.
- W1616212752 cites W1569551216 @default.
- W1616212752 cites W1965982516 @default.
- W1616212752 cites W1966653958 @default.
- W1616212752 cites W1972690165 @default.
- W1616212752 cites W1973095330 @default.
- W1616212752 cites W1974339459 @default.
- W1616212752 cites W1975016511 @default.
- W1616212752 cites W1978294989 @default.
- W1616212752 cites W1978557715 @default.
- W1616212752 cites W1978639137 @default.
- W1616212752 cites W1983424979 @default.
- W1616212752 cites W1984239928 @default.
- W1616212752 cites W1987478997 @default.
- W1616212752 cites W1992534676 @default.
- W1616212752 cites W1992622052 @default.
- W1616212752 cites W1994636910 @default.
- W1616212752 cites W1996776316 @default.
- W1616212752 cites W2001245766 @default.
- W1616212752 cites W2012449274 @default.
- W1616212752 cites W2013303326 @default.
- W1616212752 cites W2015381958 @default.
- W1616212752 cites W2019988834 @default.
- W1616212752 cites W2020167441 @default.
- W1616212752 cites W2021440402 @default.
- W1616212752 cites W2023271753 @default.
- W1616212752 cites W2024912014 @default.
- W1616212752 cites W2025865745 @default.
- W1616212752 cites W2029040572 @default.
- W1616212752 cites W2029251110 @default.
- W1616212752 cites W2030841140 @default.
- W1616212752 cites W2032199878 @default.
- W1616212752 cites W2035211173 @default.
- W1616212752 cites W2035430662 @default.
- W1616212752 cites W2035516824 @default.
- W1616212752 cites W2038307493 @default.
- W1616212752 cites W2038767330 @default.
- W1616212752 cites W2039406638 @default.
- W1616212752 cites W2046349588 @default.
- W1616212752 cites W2049217683 @default.
- W1616212752 cites W2056548454 @default.
- W1616212752 cites W2056575495 @default.
- W1616212752 cites W2065573460 @default.
- W1616212752 cites W2067656252 @default.
- W1616212752 cites W2069233463 @default.
- W1616212752 cites W2069506534 @default.
- W1616212752 cites W2071002974 @default.
- W1616212752 cites W2071195046 @default.
- W1616212752 cites W2073243732 @default.
- W1616212752 cites W2077441216 @default.
- W1616212752 cites W2080710606 @default.
- W1616212752 cites W2084950028 @default.
- W1616212752 cites W2109573075 @default.
- W1616212752 cites W2120591546 @default.
- W1616212752 cites W2122853003 @default.
- W1616212752 cites W2124710306 @default.
- W1616212752 cites W2129000161 @default.
- W1616212752 cites W2131350133 @default.
- W1616212752 cites W2143981217 @default.
- W1616212752 cites W2150808290 @default.
- W1616212752 cites W2151349241 @default.
- W1616212752 cites W2163614186 @default.
- W1616212752 cites W2317203661 @default.
- W1616212752 cites W2323689492 @default.
- W1616212752 cites W2329982771 @default.
- W1616212752 cites W2330989517 @default.
- W1616212752 cites W2334964705 @default.
- W1616212752 cites W2472353210 @default.
- W1616212752 cites W4211144669 @default.
- W1616212752 cites W4236048302 @default.
- W1616212752 cites W4238091676 @default.
- W1616212752 cites W4255609509 @default.
- W1616212752 doi "https://doi.org/10.1021/acs.joc.5b00797" @default.
- W1616212752 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/26133764" @default.
- W1616212752 hasPublicationYear "2015" @default.
- W1616212752 type Work @default.
- W1616212752 sameAs 1616212752 @default.
- W1616212752 citedByCount "28" @default.
- W1616212752 countsByYear W16162127522016 @default.
- W1616212752 countsByYear W16162127522017 @default.
- W1616212752 countsByYear W16162127522018 @default.
- W1616212752 countsByYear W16162127522020 @default.
- W1616212752 countsByYear W16162127522021 @default.
- W1616212752 countsByYear W16162127522022 @default.
- W1616212752 countsByYear W16162127522023 @default.
- W1616212752 crossrefType "journal-article" @default.
- W1616212752 hasAuthorship W1616212752A5021563239 @default.