Theoretical study of the adsorption process of antimalarial drugs into acrylamide-base hydrogel model using dft methods: the first approach to the rational design of a controlled drug delivery system

The interaction between three widely used antimalarial drugs chloroquine, primaquine and amodiaquine with acrylamide dimer and trimer as a hydrogel model, were studied by means of density functional theory calculation in both vacuum and water environments, using the functional wb97xd with 6-31++G(d,p) basis set and polarizable continuum model (C-PCM) of solvent. According to binding energy, around −3.15 to −11.91 kJ/mol, the interaction between antimalarial compounds and hydrogel model are exothermic in nature. The extent of interaction found is primaquine > amodiaquine > chloroquine. The natural bond orbital (NBO) calculation and application of second-order perturbation theory show strong charge transfer between the antimalarial and hydrogel model. In addition, the results suggest these interactions are polar in nature, where hydrogen bonds play a principal role in stabilization of the complex. Comparing with the gas-phase, the complexes in the water environment are also stable, with suitable values of Log P (Partition coefficient), and dipolar momentum. Consequently, these results encourage to test acrylamide hydrogels as antimalarial delivery systems.

• Autores: Márquez, Edgar; Mora, José R.; Puello, Esneyder; Rangel, Norma; De Moya, Aldemar; Trilleras, Jorge; Cortes, Eliceo
• Tipo de recurso: Article of journal
• Fecha de publicación: 2019
• Institución: Corporación Universidad de la Costa
• Repositorio: REDICUC - Repositorio CUC
• Idioma: eng
• OAI Identifier: oai:repositorio.cuc.edu.co:11323/5301
• Acceso en línea: https://hdl.handle.net/11323/5301; https://repositorio.cuc.edu.co/
• Palabra clave: Plasmodium falciparum; Hydrogen bond; Hydrogel; Computational modeling; Binding energy; Drug-delivery system
• Rights: openAccess
• License: http://creativecommons.org/publicdomain/zero/1.0/