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Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin
UiT The Arctic University of Norway, Norway.
UiT The Arctic University of Norway, Norway.
UiT The Arctic University of Norway, Norway.
UiT The Arctic University of Norway, Norway.
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2019 (English)In: Bioorganic chemistry (Print), ISSN 0045-2068, Vol. 84, p. 106-114Article in journal (Refereed) Published
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.

Place, publisher, year, edition, pages
2019. Vol. 84, p. 106-114
Keywords [en]
2, 5-Diketopiperazine, Barettin, CLPAA, Heterocycle, Marine natural products, Structure–activity relationship
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:ri:diva-36590DOI: 10.1016/j.bioorg.2018.11.024Scopus ID: 2-s2.0-85057210847OAI: oai:DiVA.org:ri-36590DiVA, id: diva2:1268773
Note

 Funding details: VINNOVA, 2014-01435; Funding details: Norges Forskningsråd, ES508288;

Available from: 2018-12-06 Created: 2018-12-06 Last updated: 2018-12-06Bibliographically approved

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Svenson, Johan

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