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Open AccessArticle

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.
Molecules 2017, 22(11), 1910; https://doi.org/10.3390/molecules22111910
Received: 27 September 2017 / Revised: 3 November 2017 / Accepted: 3 November 2017 / Published: 6 November 2017
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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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. https://doi.org/10.3390/molecules22111910

AMA Style

Poór M, Zand A, Szente L, Lemli B, Kunsági-Máté S. Interaction of α- and β-zearalenols with β-cyclodextrins. Molecules. 2017; 22(11):1910. https://doi.org/10.3390/molecules22111910

Chicago/Turabian Style

Poór, Miklós; Zand, Afshin; Szente, Lajos; Lemli, Beáta; Kunsági-Máté, Sándor. 2017. "Interaction of α- and β-zearalenols with β-cyclodextrins" Molecules 22, no. 11: 1910. https://doi.org/10.3390/molecules22111910

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