title: Effect of functional groups on antioxidant properties of substituted selenoethers.
abstract: Selenoethers attached to functional groups through propyl chain viz., bis(3-carboxypropyl)selenide (SeBA), bis(3-hydroxypropyl)selenide (SePOH) and bis(3-aminopropyl)selenide dihydrochloride (SePAm), have been examined for their ability to inhibit peroxyl radical mediated DNA damage, peroxyl radical scavenging ability and glutathione peroxidase (GPx) like activity. The DNA damage was monitored by gel electrophoresis, bimolecular rate constants for scavenging of model peroxyl radical were determined by pulse radiolysis and the GPx activity was followed by their ability to reduce hydrogen peroxide in the presence of glutathione utilizing NADPH decay and HPLC analysis. Among these compounds, SeBA showed maximum DNA protecting activity and it was also the most efficient in scavenging peroxyl radicals with the highest GPx mimicking activity. Quantum chemical calculations confirmed that SeBA with the highest energy level of HOMO (highest occupied molecular orbital) is the easiest to undergo oxidation and therefore exhibits better radical scavenging, GPx mimicking and DNA protecting activity than SePOH or SePAm.
authors.affiliation: Chemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, India.
authors.forename: P
authors.initials: P
authors.lastname: Prabhu
authors.forename: P P
authors.initials: PP
authors.lastname: Bag
authors.forename: B G
authors.initials: BG
authors.lastname: Singh
authors.forename: A
authors.initials: A
authors.lastname: Hodage
authors.forename: V K
authors.initials: VK
authors.lastname: Jain
authors.forename: M
authors.initials: M
authors.lastname: Iwaoka
authors.forename: K I
authors.initials: KI
authors.lastname: Priyadarsini
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000378:metabolism*; D002251:Carbon Tetrachloride / Q000031:analogs & derivatives / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D004249:DNA Damage; D004987:Ethers / Q000138:chemical synthesis / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000378:metabolism; D005978:Glutathione / Q000378:metabolism; D005979:Glutathione Peroxidase / Q000378:metabolism*; D018716:Molecular Mimicry; D009249:NADP / Q000378:metabolism; D010084:Oxidation-Reduction; D010957:Plasmids / Q000378:metabolism; D011675:Pulse Radiolysis; D064586:Selenic Acid; D012643:Selenium / Q000737:chemistry / Q000378:metabolism; D018036:Selenium Compounds / Q000737:chemistry*; D012996:Solutions
chemical_list: D000975:Antioxidants; D004987:Ethers; D016166:Free Radical Scavengers; D018036:Selenium Compounds; D012996:Solutions; C025280:trichloromethyl free radical; D009249:NADP; D002251:Carbon Tetrachloride; D005979:Glutathione Peroxidase; D005978:Glutathione; D012643:Selenium; D064586:Selenic Acid