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

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

Research output: Contribution to journalArticle

7 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

Keywords

  • cyclodextrins
  • fluorescence spectroscopy
  • host-guest interactions
  • mycotoxin metabolites
  • zearalenols

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: Contribution to journalArticle

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.
@article{f2c1e6e010094387a63bd60fadaedc85,
title = "Interaction of α- and β-zearalenols with β-cyclodextrins",
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.",
keywords = "cyclodextrins, fluorescence spectroscopy, host-guest interactions, mycotoxin metabolites, zearalenols",
author = "Mikl{\'o}s Po{\'o} and Afshin Zand and Lajos Szente and Be{\'a}ta Lemli and S. Kuns{\'a}gi-M{\'a}t{\'e}",
year = "2017",
month = "11",
day = "6",
doi = "10.3390/molecules22111910",
language = "English",
volume = "22",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "11",

}

TY - JOUR

T1 - Interaction of α- and β-zearalenols with β-cyclodextrins

AU - Poó, Miklós

AU - Zand, Afshin

AU - Szente, Lajos

AU - Lemli, Beáta

AU - Kunsági-Máté, S.

PY - 2017/11/6

Y1 - 2017/11/6

N2 - 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.

AB - 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.

KW - cyclodextrins

KW - fluorescence spectroscopy

KW - host-guest interactions

KW - mycotoxin metabolites

KW - zearalenols

UR - http://www.scopus.com/inward/record.url?scp=85049100557&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85049100557&partnerID=8YFLogxK

U2 - 10.3390/molecules22111910

DO - 10.3390/molecules22111910

M3 - Article

VL - 22

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 11

ER -