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Synthesis, characterization, theoretical studies and antioxidant and cytotoxic evaluation of a series of Tetrahydrocurcumin (THC)-benzylated derivatives
dc.contributor.author | Alvarez-Ricardo Y | |
dc.contributor.author | Meza-Morales W | |
dc.contributor.author | Obregón-Mendoza M.A | |
dc.contributor.author | Toscano R.A | |
dc.contributor.author | Núñez-Zarur F | |
dc.contributor.author | Germán-Acacio J.M | |
dc.contributor.author | Puentes-Díaz N | |
dc.contributor.author | Alí-Torres J | |
dc.contributor.author | Arenaza-Corona A | |
dc.contributor.author | Ramírez-Apan M.T | |
dc.contributor.author | Morales-Morales D | |
dc.contributor.author | Enríquez R.G. | |
dc.date.accessioned | 2023-10-24T19:24:34Z | |
dc.date.available | 2023-10-24T19:24:34Z | |
dc.date.created | 2023 | |
dc.identifier.issn | 222860 | |
dc.identifier.uri | http://hdl.handle.net/11407/7970 | |
dc.description.abstract | 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. © 2022 Elsevier B.V. | eng |
dc.language.iso | eng | |
dc.publisher | Elsevier B.V. | |
dc.relation.isversionof | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85140596298&doi=10.1016%2fj.molstruc.2022.134355&partnerID=40&md5=0fcd20b755d8ec3602b5883e99e21e2c | |
dc.source | J. Mol. Struct. | |
dc.source | Journal of Molecular Structure | eng |
dc.subject | Benzylation | eng |
dc.subject | Curcumin | eng |
dc.subject | Cytotoxicity | eng |
dc.subject | TBARS | eng |
dc.subject | Tetrahydrocurcumin | eng |
dc.title | Synthesis, characterization, theoretical studies and antioxidant and cytotoxic evaluation of a series of Tetrahydrocurcumin (THC)-benzylated derivatives | eng |
dc.type | Article | |
dc.rights.accessrights | info:eu-repo/semantics/restrictedAccess | |
dc.publisher.program | Ciencias Básicas | spa |
dc.type.spa | Artículo | |
dc.identifier.doi | 10.1016/j.molstruc.2022.134355 | |
dc.relation.citationvolume | 1273 | |
dc.publisher.faculty | Facultad de Ciencias Básicas | spa |
dc.affiliation | Alvarez-Ricardo, Y., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Meza-Morales, W., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Obregón-Mendoza, M.A., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Toscano, R.A., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Núñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30-65, Medellín, 050026, Colombia | |
dc.affiliation | Germán-Acacio, J.M., Red de Apoyo a la Investigación, Coordinación de la Investigación Científica-UNAM, Instituto Nacional de Ciencias Médicas y Nutrición SZ, C.P., Ciudad de México, 14000, Mexico | |
dc.affiliation | Puentes-Díaz, N., Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá111321, Colombia | |
dc.affiliation | Alí-Torres, J., Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá111321, Colombia | |
dc.affiliation | Arenaza-Corona, A., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Ramírez-Apan, M.T., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Morales-Morales, D., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
dc.affiliation | Enríquez, R.G., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico | |
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dc.type.version | info:eu-repo/semantics/publishedVersion | |
dc.identifier.reponame | reponame:Repositorio Institucional Universidad de Medellín | |
dc.identifier.repourl | repourl:https://repository.udem.edu.co/ | |
dc.identifier.instname | instname:Universidad de Medellín |
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