Synthesis, characterization, structures and GPx mimicking activity of pyridyl and pyrimidyl based organoselenium compounds

Pyridyl and pyrimidyl based organoselenium compounds have been synthesized and characterized by analytical and spectroscopic techniques. Molecular structures of 2,2'-dipyrimidyl diselenide (1b), 2,2'-dipyrimidyl selenide (2b) and 2-pyrimidyl seleno ethanoic acid (3d) have been determined by single crystal X-ray diffraction analyses. The 3d is associated in the solid state through hydrogen bonding between carboxylic acid proton and N2 of the pyrimidyl ring of an adjacent molecule. The in vitro GPx-like catalytic activity for these compounds was evaluated by H-1 NMR and HPLC methods where H2O2 was reduced by dithiothreitol (DTTred) and glutathione (GSH) as a thiol cofactor, respectively, in the presence of catalytic amounts of organoselenium compounds. The electron density around selenium atom (-SeSe- or -Se-) which is reflected by Se-77{H-1} NMR chemical shifts, has been found to be one of the crucial factors in influencing their overall GPx like activity. (C) 2012 Elsevier B.V. All rights reserved.