Effects of Cyclodextrin Analogs on Psychosine Cytotoxicity

The xenoestrogenic mycotoxin zearalenone is a common food contaminant produced by Fusarium strains. The modified mycotoxin zearalenone-14-sulfate (Z14S) is formed in both fungi and mammals during the biotransformation of zearalenone. Cyclodextrins (CD) are cyclic oligosaccharides which can form host-guest type complexes with some mycotoxins, including zearalenone, zearalenols, and zearalenone-14-glucoside. As a result of the complex formation, the fluorescence signal of these mycotoxins strongly increases. Furthermore, CD polymers seem to be suitable for the extraction of some mycotoxins from aqueous solutions and beverages. In this study, the interaction of Z14S with CDs and soluble CD polymers was examined with fluorescence spectroscopy and molecular modeling. Furthermore, the removal of Z14S from aqueous solution by β-CD bead polymer (BBP) was also tested. Our results demonstrate the formation of stable Z14S-CD complexes (K = 0.1 to 5.0 × 104 L/mol). Dimethyl-β-CD (DIMEB) produced the most stable complexes with Z14S at pH 5.0 and 7.4. At pH 10.0, the binding constant of Z14S-DIMEB complex decreased and quaternary ammonium-β-CD showed similar affinity toward the mycotoxin than DIMEB. In addition, Z14S was successfully removed from aqueous solutions by BBP. Considering the above-listed observations, besides the parent mycotoxins, some of their modified/masked derivatives can also interact with CDs.