Theoretical insights into the formation, structure, and electronic properties of anticancer oxaliplatin drug and cucurbit[n]urils n = 5 to 8

Geometries, formation and electronic properties of cucurbit[n]uril-oxaliplatin n = 5–8, host-guest complexes are investigated with DFT calculations. The formation of inclusion complexes of CB[n]-oxaliplatin are facile in CB[n] n = 6–8. In the complex, the cyclohexyl group is found to be deep inside the cavity, with the formation of a hydrogen bonding between the portal oxygen atoms and the amine nitrogen of the oxaliplatin guest. NBO analysis shows the transfer of charge from the metal center to the CB[7] unit and the existence of hydrogen bonding between the oxygen portal and amine nitrogen. The HOMO orbital is localized on the carboxylate group and the LUMO orbital are localized on the cucurbituril unit in CB[7]-oxaliplatin complex. The strength of the interaction determined here reflects the ability of CB[n] to act as a host for suitably oxaliplatin guests, even in aqueous solution.