Studies on the Interaction between Derivatives of 9-Aacridinyl Amino Acid as Anticancer Drugs and Functionalized Carbon Nanotubes: ONIOM2-PCM Approach

Recently, the derivatives of 9-acridinyl amino acid have been synthesized and introduced as the anticancer and anti proliferative agents. In this regard, the functionalized single-wall carbon nanotubes (f-SWCNTs) have been employed as a drug delivery system in the nanomedicine applications. The role of the functionalized armchair (5,5) SWCNT in drug delivery of 9-acridinyl amino acid derivatives, as the anticancer agents, was studied by combining quantum mechanics and molecular mechanics methods. Therefore, the present study was conducted to investigate the binding properties of 9-acridinyl amino acid derivatives, as the anticancer agents, with pristine (5,5) single-walled carbon nanotube (SWCNT) and functionalized SWCNT (COOH-SWCNT) by the ONIOM2 (B3LYP/6-311G:UFF) and ONIOM2-PCM methods. The structural and electronic properties, binding energy, highest occupied molecular orbital and lowest unoccupied molecular orbital of the most stable configuration were also analyzed. Our results displayed that the interaction of the nanotubes with the derivatives of 9-acridinyl amino acid was relatively weak; suggesting that the interaction and adsorption of the anticancer agents with SWCNT can be physical in nature. The interaction of the anticancer agents on the f-SWCNT was stronger than that on the pristine SWCNT. In the aqueous solution, the solubility of the f-SWCNT as the carrier was increased.