title: New glutathione peroxidase mimetics-Insights into antioxidant and cytotoxic activity.
abstract: A series of N-alkyl benzisoselenazol-3(2H)-ones has been obtained and transformed to corresponding diselenides by the reduction with sodium borohydride. Additionally, efficient methodology for the oxidative Se-N bond formation by potassium iodate has been presented, new conversion of diselenide to benzisoselenazolone was observed. The GPx-like activity of all synthetized derivatives has been evaluated by NMR. N-Allyl diselenide was up to five times better antioxidant than ebselen. Anticancer capacity towards MCF7 and DU145 cancer cells has been also tested. The highest antiproliferative activity was obtained for N-cyclohexyl benzisoselenazolone.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland.
authors.forename: Agata J
authors.initials: AJ
authors.lastname: Pacuła
authors.affiliation: Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, 1 Debinki Street, 80-211 Gdansk, Poland.
authors.forename: Katarzyna B
authors.initials: KB
authors.lastname: Kaczor
authors.affiliation: Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, 1 Debinki Street, 80-211 Gdansk, Poland.
authors.forename: Angelika
authors.initials: A
authors.lastname: Wojtowicz
authors.affiliation: Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, 1 Debinki Street, 80-211 Gdansk, Poland.
authors.forename: Jędrzej
authors.initials: J
authors.lastname: Antosiewicz
authors.affiliation: Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Janecka
authors.affiliation: Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland.
authors.forename: Angelika
authors.initials: A
authors.lastname: Długosz
authors.affiliation: Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Janecki
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland. Electronic address: jsch@chem.umk.pl.
authors.forename: Jacek
authors.initials: J
authors.lastname: Ścianowski
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001393:Azoles / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005979:Glutathione Peroxidase / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D054833:Isoindoles; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D001393:Azoles; D054833:Isoindoles; D016566:Organoselenium Compounds; C042986:ebselen; D005979:Glutathione Peroxidase
keywords: Antioxidant activity; Benzisoselenazolones; Cytotoxicity; Diselenides