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

LAPSE

Living Archive for Process Systems Engineering

LAPSE:2019.0975

Published Article

LAPSE:2019.0975

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

September 5, 2019

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.

Record ID

LAPSE:2019.0975

Keywords

binding energy, computational modeling, drug-delivery system, hydrogel, hydrogen bond, Plasmodium falciparum

Subject

Biosystems

Suggested Citation

Cortes E, Márquez E, Mora JR, Puello E, Rangel N, De Moya A, Trilleras J. 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. (2019). LAPSE:2019.0975

Author Affiliations

Cortes E: Grupo de Investigación en Ciencias Naturales y Exactas, Departamento de Ciencias Naturales y Exactas, Universidad de la Costa, Barranquilla 080002, Colombia
Márquez E: Grupo de Investigación en Química y Biología, Departamento de Química y Biología, Universidad del Norte, Barranquilla 081007, Colombia [ORCID]
Mora JR: Grupo de Química Computacional y Teórica (QCT-USFQ) and Instituto de Simulación Computacional (ISC-USFQ), Colegio Politécnico de Ciencias e Ingeniería, Diego de Robles y Vía Interoceánica, Universidad San Francisco de Quito, Quito 170901, Ecuador [ORCID]
Puello E: Grupo de Investigación en Oxi/Hidrotratamiento Catalítico y Nuevos Materiales, Programa de Química-Ciencias Básicas, Universidad del Atlántico, Puerto Colombia 081001, Colombia
Rangel N: TecNM/Instituto Tecnológico de Aguascalientes-División de Estudios de Posgrado e Investigación, Ave. Adolfo López Mateos #1801Ote. Fracc. Bona Gens, Aguascalientes 20256, México
De Moya A: Grupo de Investigación en Ciencias Naturales y Exactas, Departamento de Ciencias Naturales y Exactas, Universidad de la Costa, Barranquilla 080002, Colombia
Trilleras J: Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, Puerto Colombia 081001, Colombia [ORCID]
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Journal Name

Processes

Volume

7

Issue

7

Article Number

E396

Year

2019

Publication Date

2019-06-26