New Chiral Ebselen Analogues with Antioxidant and Cytotoxic Potential.
New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives was evaluated and compared to the reactivity of a series of N-amino acid benzisoselenazol-3(2H)-ones obtained by a modified procedure involving the improved synthesis and isolation of the diseleno bis(dibenzoic) acid. The most efficient peroxide scavengers, N-bornyl and N-leucine methyl ester benzisoselenazol-3(2H)-ones, were further evaluated as cytotoxic agents on four cancer cell lines (MCF-7, HEP G2, HL 6, and DU 145) and normal cell line PNT1A. The highest antiproliferative potential was evaluated for two compounds bearing a 3-methylbutyl carbon chain, N-leucine methyl ester and N-3-methylbutyl benzisoselenazol-3(2H)-ones.
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland. pacula@doktorant.umk.pl.
Agata J
AJ
Pacuła
Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, Debinki 1, 80-211 Gdansk, Poland. awojt@umk.pl.
Katarzyna B
KB
Kaczor
Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, Debinki 1, 80-211 Gdansk, Poland. katarzyna.kaczor@gumed.edu.pl.|Department of Biochemistry, Gdansk University of Physical Education and Sport, Kazimierza Gorskiego 1, 80-336 Gdansk, Poland. katarzyna.kaczor@gumed.edu.pl.
Jędrzej
J
Antosiewicz
Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland. jant@gumed.edu.pl.
Anna
A
Janecka
Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, 92-215 Lodz, Poland. anna.janecka@umed.lodz.pl.
Angelika
A
Długosz
Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland. angelika.dlugosz@stud.umed.lodz.pl.
Tomasz
T
Janecki
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland. tomasz.janecki@p.lodz.pl.
Andrzej
A
Wojtczak
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Torun, Poland. jsch@chem.umk.pl.
Jacek
J
Ścianowski
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001393:Azoles / Q000737:chemistry; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D054833:Isoindoles; D061986:MCF-7 Cells; D015394:Molecular Structure; D009930:Organic Chemicals; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D000975:Antioxidants; D001393:Azoles; D054833:Isoindoles; D009930:Organic Chemicals; D016566:Organoselenium Compounds; D013844:Thiazoles; C042986:ebselen
antioxidant activity; biological activity; organoselenium compounds; terpenes