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

Eliceo Cortes, Edgar Márquez, José R. Mora, Esneyder Puello, Norma Rangel, Aldemar De Moya, Jorge Trilleras

Producción científica: Contribución a una revistaArtículorevisión exhaustiva

16 Citas (Scopus)

Resumen

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.

Idioma originalInglés
Número de artículo396
PublicaciónProcesses
Volumen7
N.º7
DOI
EstadoPublicada - 1 jul. 2019

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