Prediction of the Anticancer Activity of the Fullerene Nanostructure’s Derivatives: DFT Calculations

In this work, the [2 + 2] cycloaddition of fullerenes with the carcinogen BaPe was examined using the DFT method, with the aim of inhibiting the carcinogenic process of the latter. The increase in the electrophilic character of the reagents by the functionalization with electron-withdrawing groups was shown. By the functionalization of C₆₀, an increase in the dipole moment and consequently in the solubility of these reagents was shown. Also, a significant improvement in this solubility for these reagents by the [2 + 2] cycloaddition with BaPe increasing the dipole moment was noted. The most favored electrophilic-nucleophilic interaction between C2 and C3 has been rationalized. In the gaseous phase, very asynchronous concerted mechanisms by functionalization were demonstrated for this type of fullerene cycloaddition. In addition, an insufficiency of the calculations for the prediction of the inhibition of the mutagenic process by forming the C₆₀CONH₂–2.5BaPe complex (the major product) was noted and therefore the inclusion of the effects of biological solvent (water) was mandatory. In the presence of water, a significant decrease in the activation barriers and reaction energies compared to those of the gaseous phase was shown, therefore, a kinetic and thermodynamic preference of the C₆₀CONH₂–2.5BaPe complex from this cycloaddition, is deduced.