Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors

Díaz-Rubio, Laura y Hernández-Martínez, Rufina y Estolano-Cobián, Arturo y Chávez-Velasco, Daniel y Salazar-Aranda, Ricardo y Waksman de Torres, Noemí y Rivero, Ignacio y García-González, Víctor y Ramos, Marco y Córdova Guerrero, Iván (2019) Synthesis, Biological Evaluation and Docking Studies of Chalcone and Flavone Analogs as Antioxidants and Acetylcholinesterase Inhibitors. Applied Sciences, 9 (3). pp. 1-20. ISSN 2076-3417

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URL o página oficial: http://doi.org/10.3390/app9030410

Resumen

Several oxidative processes are related to a wide range of human chronic and degenerative diseases, like Alzheimer’s disease, which also has been related to cholinergic processes. Therefore, search for new or improved antioxidant molecules with acetylcholinesterase activity is essential to offer alternative chemotherapeutic agents to support current drug therapies. A series of chalcone (2a–2k) and flavone (3a–3k) analogs were synthesized, characterized, and evaluated as acetylcholinesterase (AChE) inhibitors, and antioxidant agents using 1,1-diphenyl-2-picrylhydrazyl (DPPH•), 2-20-azino-bis-(3-ethylbenzothiazoline-6-sulfonate) (ABTS•), and β-carotene/linoleic acid bleaching assay. Compounds more active were 3j and 2k in DPPH with EC50 of 1 × 10−8 and 5.4 × 10−3 µg/mL, respectively; 2g and 3i in ABTS (1.14 × 10−2 and 1.9 × 10−3 µg/mL); 2e, 2f, 3f, 2j, and 3j exceeded the α-tocopherol control in the β-carotene assay (98–99% of antioxidant activity). At acetylcholinesterase inhibition assay, flavones were more active than chalcones; the best results were compounds 2d and 3d (IC50 21.5 and 26.8 µg/mL, respectively), suggesting that the presence of the nitro group enhances the inhibitory activity. The docking of these two structures were made to understand their interactions with the AChE receptor. Although further in vivo testing must be performed, our results represent an important step towards the identification of improved antioxidants and acetylcholinesterase inhibitors.

Tipo de elemento: Article
Materias: Q Ciencia > QR Microbiología
Divisiones: Medicina
Usuario depositante: Lic. Josimar Pulido
Creadores:
CreadorEmailORCID
Díaz-Rubio, LauraNO ESPECIFICADONO ESPECIFICADO
Hernández-Martínez, RufinaNO ESPECIFICADONO ESPECIFICADO
Estolano-Cobián, ArturoNO ESPECIFICADONO ESPECIFICADO
Chávez-Velasco, DanielNO ESPECIFICADONO ESPECIFICADO
Salazar-Aranda, RicardoNO ESPECIFICADONO ESPECIFICADO
Waksman de Torres, NoemíNO ESPECIFICADONO ESPECIFICADO
Rivero, IgnacioNO ESPECIFICADONO ESPECIFICADO
García-González, VíctorNO ESPECIFICADONO ESPECIFICADO
Ramos, MarcoNO ESPECIFICADONO ESPECIFICADO
Córdova Guerrero, IvánNO ESPECIFICADONO ESPECIFICADO
Fecha del depósito: 22 Jun 2020 16:32
Última modificación: 15 Abr 2021 15:26
URI: http://eprints.uanl.mx/id/eprint/15807

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