Fluorescence enhancement of the aflatoxin B1 by forming inclusion complexes with some cyclodextrins and molecular modeling study

The interaction between the aflatoxin B1 (AFB1) and three cyclodextrins, α-cyclodextrin (α-CD), β-cyclodextrin (β-CD) and heptakis-2,6-dimethyl-o-β-cyclodextrin (ome-CD), was studied by spectrofluorescence technique. It was found that the inclusion association behavior occurs for the complexes of cyclodextrins with AFB1. The fluorescence of AFB1 is generally enhanced in the complexes with cyclodextrins in aqueous solutions. The inclusion complex constants of the three types of cyclodextrins at different temperatures were evaluated from Benesi–Hildebrand plot and also by non-linear regression analysis. These cyclodextrins can only form the 1:1 (host:guest) inclusion complex in the studied temperature range of 20–50 °C. The enthalpy (ΔH°) and entropy (ΔS°) changes of complexation were extracted from the temperature dependency of complex formation constants (K). Temperature-dependent measurements showed that the association step is controlled by enthalpy–entropy compensation effect. The use of ome-CD generally resulted in the greatest fluorescence intensity. On the other hand, the discrepancy between the exhibited enhanced fluorescence and thermodynamic parameters (ΔG°) is proposed to be different only by the orientation of the AFB1 within the cyclodextrin cavity. To find the most favorable structure, the geometry of complex was investigated by molecular modeling approach employing the semiemperical HF–SCF calculations.