Synthesis, characterization, theoretical studies and antioxidant and cytotoxic evaluation of a series of Tetrahydrocurcumin (THC)-benzylated derivatives

Yair Alvarez-Ricardo, William Meza-Morales, Marco A. Obregón-Mendoza, Rubén A. Toscano, Francisco Núñez-Zarur, Juan M. Germán-Acacio, Nicolás Puentes-Díaz, Jorge Alí-Torres, Antonino Arenaza-Corona, María Teresa Ramírez-Apan, David Morales-Morales, Raúl G. Enríquez

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

Resumen

The benzylation reaction of curcumin and tetrahydrocurcumin (THC) with benzyl bromide and potassium carbonate in acetone was investigated. It was found that curcumin undergoes O-alkylation first, followed by C-1 substitution. In contrast, THC undergoes these reactions in reverse order, which was further explained by DFT calculations showing a clear energetic preference (19.5 Kcal/mol) for the C-1 versus the O-alkylation reaction of THC. In addition, the antioxidant activities on lipid peroxidation and cytotoxic activities of both benzylated derivatives were studied, showing that the C-dibenzylated curcuminoid (C-DiBn, 2b), exerts a superior activity than both tribenzylated (TriBn, 2c) and tetrabenzylated (TetraBn, 2d) curcuminoid derivatives in both essays. A DFT theoretical study to explain the experimental results and the preferences for the nucleophilic attack between the phenolic oxygen or C-1 anions was conducted. Furthermore, docking calculations on a DNA fragment shed light on the potential factors affecting the biological activity of these benzylated curcuminoids.

Idioma originalInglés
Número de artículo134355
PublicaciónJournal of Molecular Structure
Volumen1273
DOI
EstadoPublicada - 5 feb. 2023

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