Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin.

Abstract:

: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.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Labrière C,Andersen JH,Albrigtsen M,Hansen JH,Svenson J

doi

10.1016/j.bioorg.2018.11.024

subject

Has Abstract

pub_date

2019-03-01 00:00:00

pages

106-114

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(18)31087-3

journal_volume

84

pub_type

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