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

dc.contributor.authorAlvarez-Ricardo Y
dc.contributor.authorMeza-Morales W
dc.contributor.authorObregón-Mendoza M.A
dc.contributor.authorToscano R.A
dc.contributor.authorNúñez-Zarur F
dc.contributor.authorGermán-Acacio J.M
dc.contributor.authorPuentes-Díaz N
dc.contributor.authorAlí-Torres J
dc.contributor.authorArenaza-Corona A
dc.contributor.authorRamírez-Apan M.T
dc.contributor.authorMorales-Morales D
dc.contributor.authorEnríquez R.G.
dc.date.accessioned2023-10-24T19:24:34Z
dc.date.available2023-10-24T19:24:34Z
dc.date.created2023
dc.identifier.issn222860
dc.identifier.urihttp://hdl.handle.net/11407/7970
dc.description.abstractThe 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.isoeng
dc.publisherElsevier B.V.
dc.relation.isversionofhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85140596298&doi=10.1016%2fj.molstruc.2022.134355&partnerID=40&md5=0fcd20b755d8ec3602b5883e99e21e2c
dc.sourceJ. Mol. Struct.
dc.sourceJournal of Molecular Structureeng
dc.subjectBenzylationeng
dc.subjectCurcumineng
dc.subjectCytotoxicityeng
dc.subjectTBARSeng
dc.subjectTetrahydrocurcumineng
dc.titleSynthesis, characterization, theoretical studies and antioxidant and cytotoxic evaluation of a series of Tetrahydrocurcumin (THC)-benzylated derivativeseng
dc.typeArticle
dc.rights.accessrightsinfo:eu-repo/semantics/restrictedAccess
dc.publisher.programCiencias Básicasspa
dc.type.spaArtículo
dc.identifier.doi10.1016/j.molstruc.2022.134355
dc.relation.citationvolume1273
dc.publisher.facultyFacultad de Ciencias Básicasspa
dc.affiliationAlvarez-Ricardo, Y., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationMeza-Morales, W., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationObregón-Mendoza, M.A., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationToscano, R.A., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationNúñez-Zarur, F., Facultad de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30-65, Medellín, 050026, Colombia
dc.affiliationGermán-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.affiliationPuentes-Díaz, N., Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá111321, Colombia
dc.affiliationAlí-Torres, J., Departamento de Química, Universidad Nacional de Colombia-Sede Bogotá111321, Colombia
dc.affiliationArenaza-Corona, A., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationRamírez-Apan, M.T., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationMorales-Morales, D., Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, C.P., Ciudad de México, 04510, Mexico
dc.affiliationEnríquez, 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.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.reponamereponame:Repositorio Institucional Universidad de Medellín
dc.identifier.repourlrepourl:https://repository.udem.edu.co/
dc.identifier.instnameinstname:Universidad de Medellín


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