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  • 1.
    Labriere, Christophe
    et al.
    UiT The Arctic University of Norway, Norway.
    Andersen, Jeanette
    UiT The Arctic University of Norway, Norway.
    Albrigtsen, Marte
    UiT The Arctic University of Norway, Norway.
    Hansen, Jörn
    UiT The Arctic University of Norway, Norway.
    Svenson, Johan
    RISE - Research Institutes of Sweden, Bioscience and Materials, Chemistry and Materials. UiT The Arctic University of Norway, Norway.
    Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin2019In: Bioorganic chemistry (Print), ISSN 0045-2068, Vol. 84, p. 106-114Article in journal (Refereed)
    Abstract [en]

    The marine environment remains a rich source for the discovery and development of novel bioactive compounds. The present paper describes the design, synthesis and biological evaluation of a library of small molecule heterocyclic mimetics of the marine 2,5-diketopiperazine barettin which is a powerful natural antioxidant. By mainly focusing on the influence from the brominated indole and heterocyclic core of barettin, a library of 19 compounds was prepared. The compounds comprised a heterocyclic core, either a 2,5 diketopiperazine, an imidazolidinedione or a thioxothiazolidinone, which were mainly monosubstituted with ranging bulky substituents. The prepared compounds were screened for activity in a cellular lipid peroxidation assay using HepG2 cells. Several of the synthetic compounds showed antioxidant properties superior to the positive control barettin. Two of the prepared compounds displayed inhibitory activity similar to commercial antioxidants with significant inhibition at low µg/mL concentrations. The toxicity of the compounds was also investigated against MRC-5 lung fibroblasts and none of the included compounds displayed any toxicity at 50 µg/mL.

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