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These studies reveal that the antithyroid drugs methimazole (MMI), 6\u2010<jats:italic>n<\/jats:italic>\u2010propyl\u20102\u2010thiouracil (PTU), and 6\u2010methyl\u20102\u2010thiouracil (MTU), which contain thione moieties, significantly reduce the tyrosine nitration of both BSA and cytochrome\u2005c. While MMI exhibits good peroxynitrite (PN) scavenging activity, the thiouracil compounds PTU and MTU are slightly less effective than MMI. The S\u2010 and Se\u2010 methylated compounds show a weak inhibitory effect in the nitration of tyrosine, indicating that the presence of a thione or selone moiety is important for an efficient inhibition. Similarly, the replacement of N\uf8ffH moiety in MMI by <jats:italic>N<\/jats:italic>\u2010methyl or <jats:italic>N<\/jats:italic>\u2010<jats:italic>m<\/jats:italic>\u2010methoxybenzyl substituents dramatically reduces the antioxidant activity of the parent compound. Theoretical studies indicate that the substitution of N\uf8ffH moiety by N\uf8ffMe significantly increases the energy required for the oxidation of sulfur center by PN. However, such substitution in the selenium analogue of MMI increases the activity of parent compound. This is due to the facile oxidation of the selone moiety to the corresponding selenenic and seleninic acids. Unlike <jats:italic>N,N\u2032<\/jats:italic>\u2010disubstituted thiones, the corresponding selones efficiently scavenge PN, as they predominantly exist in their zwitterionic forms in which the selenium atom carries a large negative charge.<\/jats:p>","DOI":"10.1002\/chem.200902145","type":"journal-article","created":{"date-parts":[[2009,12,22]],"date-time":"2009-12-22T03:08:32Z","timestamp":1261451312000},"page":"1175-1185","source":"Crossref","is-referenced-by-count":52,"title":["Antithyroid Drugs and their Analogues Protect Against Peroxynitrite\u2010Mediated Protein Tyrosine Nitration\u2014A Mechanistic Study"],"prefix":"10.1002","volume":"16","author":[{"given":"Krishna\u2005P.","family":"Bhabak","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Govindasamy","family":"Mugesh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2010,1,20]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","first-page":"761","volume":"15","author":"Doerge D. 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