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Counteracting in Vitro Toxicity of the Ionophoric Mycotoxin Beauvericin-Synthetic Receptors to the Rescue.

Authors
  • Ornelis, Vincent1
  • Rajkovic, Andreja
  • Decleer, Marlies2
  • Sas, Benedikt
  • De Saeger, Sarah2
  • Madder, Annemieke1
  • 1 Organic and Biomimetic Chemistry Research Group, Department of Organic and Macromolecular Chemistry , Ghent University , Krijgslaan 281 , 9000 Ghent , Belgium. , (Belgium)
  • 2 Department of Bioanalysis, Laboratory of Food Analysis , Ghent University , Ottergemsesteenweg 460 , 9000 Ghent , Belgium. , (Belgium)
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Aug 16, 2019
Volume
84
Issue
16
Pages
10422–10435
Identifiers
DOI: 10.1021/acs.joc.9b01665
PMID: 31393120
Source
Medline
Language
English
License
Unknown

Abstract

Beauvericin (BEA) and enniatins are toxic ionophoric cyclodepsipeptides that mainly occur in grains. As such, their presence in food commodities poses a concern for public health. To date, despite recent European Food Safety Authority emphasis on the need for more data to evaluate long-term toxicity effects, no suitable affinity reagents are available to detect the presence of BEA and derivatives in food samples. We here report on the synthesis of a small library of artificial receptors with varying cavity sizes and different hydrophobic building blocks. Immobilization of one of the receptors on solid support resulted in a strong retention of beauvericin, thus revealing promising properties as solid-phase extraction material for sample pretreatment. Furthermore, treatment of HepG2 cells with the most promising receptor markedly reduced beauvericin-induced cytotoxicity, hinting toward the possibility of using synthetic receptors as antidotes against ionophoric toxins.

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