A DFT Study of the Reaction between Benzopyrene Epoxide and C₆₀ Derivatives as Possible Anticancer Activity

Abstract

Benzo (α) pyrene (Bap) is one of the well-known compounds which forming covalent DNA and leads to carcinogenic activity. The [2 + 2] cycloaddition reaction of the benzopyrene epoxide (BaPe) with fullerene could prohibit the initiation of the mutagenic process. This reaction was theoretically studied using the density functional theory method. The functionalization of the C₆₀ with the chemical groups such as OH, COOH, CONH₂, and CH₂OH caused its activity, solubility, and aromaticity to increase. Both cases of the chemical groups being adjacent to and farthest from the reaction site of the fullerenes and BaPe were considered. The reactions were investigated from the viewpoint of quantum molecular descriptors and thermodynamic quantities of the reaction. The results showed that the reaction between BaPe and C₆₀CONH₂ near to CONH₂ with the energy of −16.35 kcal/mol was the most suitable reaction. It was concluded that it would be possible to produce novel species for bio-medical applications by attaching the selected chemical groups.

Keywords:

• Anticancer
• benzopyrene
• C60
• cycloaddition reaction
• DFT

Additional information

Funding

The authors are grateful to the University of Kashan for supporting this work by Grant No. 682229. H. Behzadi also thanks the Kharazmi University for financial support.