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The glutathione peroxidase (GPx)\u2010like antioxidant activity has been studied by using H<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>, <jats:italic>tert<\/jats:italic>\u2010butyl hydroperoxide (<jats:italic>t<\/jats:italic>BuOOH), and cumene hydroperoxide (Cum\u2010OOH) as substrates, and glutathione (GSH) as a cosubstrate. Although all the peptide\u2010based compounds have a selenazole ring similar to that of ebselen, the GPx activity of these compounds highly depends on the nature of the peptide moiety attached to the nitrogen atom of the selenazole ring. It was observed that the introduction of a phenylalanine (Phe) amino acid residue in the N\u2010terminal reduces the activity in all three peroxide systems. On the other hand, the introduction of aliphatic amino acid residues such as valine (Val) significantly enhances the GPx activity of the ebselen analogues. The difference in the catalytic activity of dipeptide\u2010based ebselen derivatives can be ascribed mainly to the change in the reactivity of these compounds toward GSH and peroxide. Although the presence of the Val\u2010Ala\u2010CO<jats:sub>2<\/jats:sub>Me moiety facilitates the formation of a catalytically active selenol species, the reaction of ebselen analogues that has a Phe\u2010Ile\u2010CO<jats:sub>2<\/jats:sub>Me residue with GSH does not generate the corresponding selenol. To understand the antioxidant activity of the peptide\u2010based ebselen analogues in the absence of GSH, these compounds were studied for their ability to inhibit peroxynitrite (PN)\u2010mediated nitration of bovine serum albumin (BSA) and oxidation of dihydrorhodamine\u2005123. In contrast to the GPx activity, the PN\u2010scavenging activity of the Phe\u2010based peptide analogues was found to be comparable to that of the Val\u2010based compounds. However, the introduction of an additional Phe residue to the ebselen analogue that had a Val\u2010Ala dipeptide significantly reduced the potency of the parent compound in PN\u2010mediated nitration.<\/jats:p>","DOI":"10.1002\/chem.201003417","type":"journal-article","created":{"date-parts":[[2011,3,11]],"date-time":"2011-03-11T08:59:39Z","timestamp":1299833979000},"page":"4849-4857","source":"Crossref","is-referenced-by-count":67,"title":["Synthesis and Antioxidant Activity of Peptide\u2010Based Ebselen Analogues"],"prefix":"10.1002","volume":"17","author":[{"given":"Kandhan","family":"Satheeshkumar","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":[[2011,3,11]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For glutathione peroxidases and their biological functions see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-5793(73)80755-0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.179.4073.588"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1983.tb07429.x"},{"key":"e_1_2_6_5_2","volume-title":"Selenium in Biology and Human Health","year":"1994"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20010401)7:7<1365::AID-CHEM1365>3.0.CO;2-Y"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300573"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300573"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02708441"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/a908114c"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr000426w"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/b308117f"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0406559"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/b716239a"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar100059g"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(84)90083-2"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(84)90084-4"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja963602k"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo000418f"},{"key":"e_1_2_6_21_2","unstructured":"\u00a0"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00197a065"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00085a040"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/a805941a"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja994467p"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/b505299h"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic052033r"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800963"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic8019183"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200800483"},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.3390\/30700164"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1093\/hmg\/11.24.3055"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamcr.2004.10.014"},{"key":"e_1_2_6_35_2","unstructured":"\u00a0"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028030k"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0357588"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200353128"},{"key":"e_1_2_6_38_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200353128"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00119a024"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/b505299h"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460380"},{"key":"e_1_2_6_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460380"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja908080u"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200801258"},{"key":"e_1_2_6_44_2","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2797(92)90121-Z"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/0009-2797(92)90122-2"},{"key":"e_1_2_6_47_2","first-page":"914","volume":"17","author":"Xiao Y. 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