Ability of B12N12 fullerene like nano‐cage for sensing and improving the antioxidant activity of juglone and its derivative: Density functional theory investigation

• Published in: International Journal of Quantum Chemistry 2022-02, Vol.122 (4), p.n/a
• Main Authors: Zoua, Vincent de Paul, Tamafo Fouegue, Aymard Didier, Mama, Désiré Bikélé, Ghogomu, Julius Numbonui, Abdoul Ntieche, Rahman
• Format: Article
• Language: English
• Subjects: antioxidant; Antioxidants; B12N12; Cages; Carbonyl groups; Carbonyls; Charge transfer; Chemistry; Density functional theory; drug delivery; Fullerenes; fullerene‐like nanocage; Gibbs free energy; juglone; Oxygen atoms; Physical chemistry; Quantum physics; Quantum theory; Radicals; Scavenging; Vapor phases
• ISSN: 0020-7608; 1097-461X
• DOI: 10.1002/qua.26843

Theoretical chemistry calculations were used to investigate the ability of the B12N12 fullerene like nano‐cage for sensing juglone (Jug) and one of its derivative (JugOH) in gas phase, pentyl ethanoate (PE) and water. Results obtained at DFT/M05‐2X‐D3/6‐311+G(d,p) level of theory showed that B12N12 is able to adsorbed Jug preferentially by binding to one of the O‐atom of its carbonyl groups. Based on natural bond orbital analysis, a charge transfer from the oxygen atoms of Jug and JugOH to the anti‐bonding orbital of B was revealed. Quantum theory of atoms in molecule analysis showed that the B12N12Jug and B12N12JugOH complexes are stabilized by a partially covalent BO bond in addition to attractive non covalent interactions. The ability of Jug, JugOH as well as their complexes A and AOH to scavenge HO● radical has been investigated via the usual hydrogen atom transfer mechanism in the three media of study previously stated. Theoretical evaluation of pH effect on this radical scavenging activity revealed that in water, the anionic forms of JugOH (86%) and AOH (96%) are dominant and mainly transfer their remaining H‐atom to HO● via a spontaneously reaction, the complex presenting the lowest Gibbs free energy. These results provide fundamental knowledge for the development of new antioxidant delivery careers. DFT/M05‐2X‐D3/6‐311+G(d,p) method revealed that juglone and one of its derivative can be adsorbed at the external surface of the B12N12 fullerene like nano‐cage. Moreover, this adsorption leads to an improvement in the free radical scavenging ability of these organic molecules in aqueous medium.