title: Synthesis and biological evaluation of 2-picolylamide-based diselenides with non-bonded interactions.
abstract: In this paper, we report the synthesis and biological evaluation of picolylamide-based diselenides with the aim of developing a new series of diselenides with O···Se non-bonded interactions. The synthesis of diselenides was performed by a simple and efficient synthetic route. All the products were obtained in good yields and their structures were determined by 1H-NMR, 13C-NMR and HRMS. All these new compounds showed promising activities when tested in different antioxidant assays. These amides exhibited strong thiol peroxidase-like (TPx) activity. In fact one of the compounds showed 4.66 times higher potential than the classical standard i.e., diphenyl diselenide. The same compound significantly inhibited iron (Fe)-induced thiobarbituric acid reactive species (TBARS) production in rat's brain homogenate. In addition, the X-ray structure of the most active compound showed non-bonded interaction between the selenium and the oxygen atom that are in close proximity and may be responsible for the increased antioxidant activity. The present study provides evidence about the possible biochemical influence of nonbonding interactions on organochalcogens potency.
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil. jamal.chm@gmail.com.
authors.forename: Jamal
authors.initials: J
authors.lastname: Rafique
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil. sumbal6s@gmail.com.
authors.forename: Sumbal
authors.initials: S
authors.lastname: Saba
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil. rfscanto@gmail.com.
authors.forename: Rômulo Faria Santos
authors.initials: RF
authors.lastname: Canto
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil. tiagofrizon@gmail.com.
authors.forename: Tiago Elias Allievi
authors.initials: TE
authors.lastname: Frizon
authors.affiliation: Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, Brazil. myemail_id11@yahoo.com.|Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, KPK, Pakistan. myemail_id11@yahoo.com.
authors.forename: Waseem
authors.initials: W
authors.lastname: Hassan
authors.affiliation: Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, Brazil. memypw@yahoo.com.br.
authors.forename: Emily Pansera
authors.initials: EP
authors.lastname: Waczuk
authors.affiliation: Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, KPK, Pakistan. myemail_id11@yahoo.com.
authors.forename: Maryam
authors.initials: M
authors.lastname: Jan
authors.affiliation: Departamento de Química, Laboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, UFSM, Santa Maria 97115-900, RS, Brazil. daviback@gmail.com.
authors.forename: Davi Fernando
authors.initials: DF
authors.lastname: Back
authors.affiliation: Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Santa Maria, UFSM, Santa Maria 97105-900, RS, Brazil. jbtrocha@yahoo.com.br.
authors.forename: João Batista Teixeira
authors.initials: JB
authors.lastname: Da Rocha
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, UFSC, Florianopolis 88040-900, SC, Brazil. braga.antonio@ufsc.br.
authors.forename: Antonio Luiz
authors.initials: AL
authors.lastname: Braga
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D001555:Benzene Derivatives / Q000737:chemistry / Q000494:pharmacology; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D045424:Complex Mixtures / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010544:Peroxidases / Q000737:chemistry; D010848:Picolinic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D017208:Rats, Wistar; D017392:Thiobarbituric Acid Reactive Substances / Q000737:chemistry
chemical_list: D000577:Amides; D000975:Antioxidants; D001555:Benzene Derivatives; D045424:Complex Mixtures; D016566:Organoselenium Compounds; D010848:Picolinic Acids; D011725:Pyridines; D017392:Thiobarbituric Acid Reactive Substances; C061132:diphenyldiselenide; D010544:Peroxidases
keywords: 2-picolylamide; TBARS; TPx; diselenides