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Molecules 2017, 22(11), 1910; doi:10.3390/molecules22111910

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

1
Department of Pharmacology, Faculty of Pharmacy, University of Pécs, Szigeti út 12, H-7624 Pécs, Hungary
2
János Szentágothai Research Center, University of Pécs, Ifjúság útja 20, H-7624 Pécs, Hungary
3
CycloLab Cyclodextrin Research & Development Laboratory, Ltd., Illatos út 7, H-1097 Budapest, Hungary
4
Department of General and Physical Chemistry, University of Pécs, Ifjúság útja 6, H-7624 Pécs, Hungary
*
Author to whom correspondence should be addressed.
Received: 27 September 2017 / Revised: 3 November 2017 / Accepted: 3 November 2017 / Published: 6 November 2017
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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. View Full-Text
Keywords: zearalenols; mycotoxin metabolites; cyclodextrins; fluorescence spectroscopy; host-guest interactions zearalenols; mycotoxin metabolites; cyclodextrins; fluorescence spectroscopy; host-guest interactions
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Poór, M.; Zand, A.; Szente, L.; Lemli, B.; Kunsági-Máté, S. Interaction of α- and β-zearalenols with β-cyclodextrins. Molecules 2017, 22, 1910.

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