Interaction of α- and β-zearalenols with β-cyclodextrins

Miklós Poó, Afshin Zand, Lajos Szente, Beáta Lemli, S. Kunsági-Máté

Research output: Article

9 Citations (Scopus)

Abstract

Zearalenone (ZEN) is a mycotoxin produced by Fusarium fungi. ZEN primarily contaminates different cereals, and exerts a strong xenoestrogenic effect in animals and humans. ZEN is a fluorescent mycotoxin, although molecular interactions and microenvironmental changes significantly modify its spectral properties. During biotransformation, ZEN is converted into α-zearalenol (α-ZOL) and β-zearalenol (β-ZOL), the toxic metabolites of ZEN, which mimick the effect of estrogen. Cyclodextrins (CDs) are host molecules, and have been studied extensively; they can form stable complexes with several mycotoxins, including ZEN. However, information is limited regarding the interactions of CDs with ZOLs. Therefore, we studied the interactions of α- and β-ZOLs with native and six chemically modified β-CDs by fluorescence spectroscopy. Fluorescence enhancement during complex formation, as well as binding constants, were determined. To understand ZOL-CD interactions better, molecular modeling studies were also carried out. Both mycotoxin derivatives formed the most stable complexes with methylated and sulfobutylated CD-derivatives; however, the CD complexes of α-ZOL were significantly stronger than those of β-ZOL. The data presented here indicate which of the chemically modified β-CDs appear more suitable as fluorescence enhancers or as potential mycotoxin binders.

Original languageEnglish
JournalMolecules (Basel, Switzerland)
Volume22
Issue number11
DOIs
Publication statusPublished - nov. 6 2017

Fingerprint

Zearalenone
Cyclodextrins
Mycotoxins
molecular interactions
fluorescence
estrogens
fungi
metabolites
interactions
animals
Fluorescence
augmentation
Molecular modeling
Molecular interactions
Poisons
Fluorescence Spectrometry
Fluorescence spectroscopy
Fusarium
spectroscopy
Biotransformation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Interaction of α- and β-zearalenols with β-cyclodextrins. / Poó, Miklós; Zand, Afshin; Szente, Lajos; Lemli, Beáta; Kunsági-Máté, S.

In: Molecules (Basel, Switzerland), Vol. 22, No. 11, 06.11.2017.

Research output: Article

Poó, Miklós ; Zand, Afshin ; Szente, Lajos ; Lemli, Beáta ; Kunsági-Máté, S. / Interaction of α- and β-zearalenols with β-cyclodextrins. In: Molecules (Basel, Switzerland). 2017 ; Vol. 22, No. 11.
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