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 | |
dc.relation.references | Mounce, B.C., Cesaro, T., Carrau, L., Vallet, T., Vignuzzi, M., Curcumin inhibits Zika and chikungunya virus infection by inhibiting cell binding (2017) Antiviral Res., 142, pp. 148-157 | |
dc.relation.references | Sardi, O., Polaquini, C.R., Freires, I.A., Livia, C., Antibacterial activity of diacetylcurcumin against Staphylococcus aureus results in decreased biofilm and cellular adhesion (2017) J. Med. Microbiol., 66, pp. 816-824 | |
dc.relation.references | Esatbeyoglu, T., Huebbe, P., Ernst, I.M.A., Chin, D., Wagner, A.E., Rimbach, G., Curcumin-from molecule to biological function (2012) Angew. Chemie Int. Ed., 51, pp. 5308-5332 | |
dc.relation.references | Gopi, S., Jacob, J., Mathur, K.Y., Acute and subchronic oral toxicity studies of hydrogenated curcuminoid formulation ‘CuroWhite’ in rats (2016) Toxicol. Reports., 3, pp. 817-825 | |
dc.relation.references | Gao, F., Chen, M., Yu, J., Xu, L., Yu, L., Jiang, H., Gu, Z., Tetrahydrocurcumin protects against nonalcoholic fatty liver disease by improving lipid metabolism and redox homeostasis (2022) J. Funct. Foods., p. 89 | |
dc.relation.references | Truong, T.H., Alcantara, K.P., Bulatao, B.P.I., Sorasitthiyanukarn, F.N., Muangnoi, C., Nalinratana, N., Vajragupta, O., Rojsitthisak, P., Chitosan-coated nanostructured lipid carriers for transdermal delivery of tetrahydrocurcumin for breast cancer therapy (2022) Carbohydr. Polym., 288 | |
dc.relation.references | Lai, C.S., Ho, C.T., Pan, M.H., The cancer chemopreventive and therapeutic potential of tetrahydrocurcumin (2020) Biomolecules, 10 | |
dc.relation.references | Liu, B., Xia, M., Ji, X., Xu, L., Dong, J., Synthesis and antiproliferative effect of novel curcumin analogues (2013) Chem. Pharm. Bull., 61, pp. 757-763 | |
dc.relation.references | Vallribera, A., Marquet, J., Moreno-Mañas, M., Cayón, E., Mechanistic studies on the alkylation of pentane-2,4-dione through its Co(II) complex (1993) Tetrahedron, 49, pp. 6437-6450 | |
dc.relation.references | Christoffers, J., Facile nBu4NF mediated benzylation of congested 1,3-diketones (1999) Synth. Commun., 29, pp. 117-122 | |
dc.relation.references | Boonroeng, S., Srikulkit, K., Xin, J.H., He, L., (2015), https://doi.org/10.1007/s12221-015-4585-6, Preparation of a novel cationic curcumin and its properties evaluation on cotton fabric, Fibers Polym. 16 2426–2431 | |
dc.relation.references | Meza-Morales, W., Machado-Rodriguez, J., Alvarez-Ricardo, Y., Obregón-Mendoza, M., Nieto-Camacho, A., Toscano, R., Soriano-García, M., Enríquez, R., A new family of homoleptic copper complexes of curcuminoids: synthesis, characterization and biological properties (2019) Molecules, 24, p. 910 | |
dc.relation.references | Girija, C.R., Begum, N.S., Syed, A.A., Thiruvenkatam, V., Hydrogen-bonding and C-H⋯π interactions in 1,7-bis(4-hydroxy-3- methoxyphenyl)heptane-3,5-dione (tetrahydrocurcumin) (2004) Acta Crystallogr. Sect. C Cryst. Struct. Commun., 60, pp. 611-613 | |
dc.relation.references | Sanphui, P., Goud, N.R., Khandavilli, U.B.R., Nangia, A., Fast dissolving curcumin cocrystals (2011) Cryst. Growth Des., 11, pp. 4135-4145 | |
dc.relation.references | Kong, X., Brinkmann, A., Terskikh, V., Wasylishen, R.E., Bernard, G.M., Duan, Z., Wu, Q., Wu, G., Proton probability distribution in the O⋯H⋯O low-barrier hydrogen bond: a combined solid-state NMR and quantum chemical computational study of dibenzoylmethane and curcumin (2016) J. Phys. Chem. B., 120, pp. 11692-11704 | |
dc.relation.references | Gilli, G., Bellucci, F., Ferretti, V., Bertolasi, V., Evidence for Resonance-Assisted Hydrogen Bonding from Crystal-Structure Correlations on the Enol Form of the β-Diketone Fragment (1989) J. Am. Chem. Soc., 111, pp. 1023-1028 | |
dc.relation.references | McKenzie, R.H., Bekker, C., Athokpam, B., Ramesh, S.G., Effect of quantum nuclear motion on hydrogen bonding (2014) J. Chem. Phys., p. 140 | |
dc.relation.references | MacRae, C.F., Sovago, I., Cottrell, S.J., Galek, P.T.A., McCabe, P., Pidcock, E., Platings, M., Wood, P.A., Mercury 4.0: from visualization to analysis, design and prediction (2020) J. Appl. Crystallogr., 53, pp. 226-235 | |
dc.relation.references | Bernstein, J., Davis, R.E., Shimoni, L., Chang, N.-L., Patterns in hydrogen bonding: functionality and graph set analysis in crystals (1995) Angew. Chemie Int. Ed. eng, 34, pp. 1555-1573 | |
dc.relation.references | Spackman, P.R., Turner, M.J., McKinnon, J.J., Wolff, S.K., Grimwood, D.J., Jayatilaka, D., Spackman, M.A., CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals (2021) J. Appl. Crystallogr., 54, pp. 1006-1011 | |
dc.relation.references | McKinnon, J.J., Jayatilaka, D., Spackman, M.A., Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces (2007) Chem. Commun., pp. 3814-3816 | |
dc.relation.references | Portes, E., Gardrat, C., Castellan, A., A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids (2007) Tetrahedron, 63, pp. 9092-9099 | |
dc.relation.references | Galano, A., Raúl Alvarez-Idaboy, J., Computational strategies for predicting free radical scavengers’ protection against oxidative stress: where are we and what might follow? (2019) Int. J. Quantum Chem., 119, pp. 1-23 | |
dc.relation.references | Alisi, I.O., Uzairu, A., Abechi, S.E., Molecular design of curcumin analogues with potent antioxidant properties and thermodynamic evaluation of their mechanism of free radical scavenge (2020) Bull. Natl. Res. Cent., p. 44 | |
dc.relation.references | Kelly, C.P., Cramer, C.J., Truhlar, D.G., Aqueous solvation free energies of ions and ion-water clusters based on an accurate value for the absolute aqueous solvation free energy of the proton (2006) J. Phys. Chem. B., 110, pp. 16066-16081 | |
dc.relation.references | Alí-Torres, J., Rodríguez-Santiago, L., Sodupe, M., Computational calculations of pKa values of imidazole in Cu(ii) complexes of biological relevance (2011) Phys. Chem. Chem. Phys., 13, pp. 7852-7861 | |
dc.relation.references | Aggarwal, B.B., Deb, L., Prasad, S., Curcumin differs from tetrahydrocurcumin for molecular targets, signaling pathways and cellular responses (2015) Molecules, 20, pp. 185-205 | |
dc.relation.references | Nishio, M., CH/π hydrogen bonds in crystals (2004) CrystEngComm, 6, pp. 130-158 | |
dc.relation.references | Alí-Torres, J., Rimola, A., Rodríguez-Rodríguez, C., Rodríguez-Santiago, L., Sodupe, M., Insights on the binding of thioflavin derivative markers to amyloid-like fibril models from quantum chemical calculations (2013) J. Phys. Chem. B., 117, pp. 6674-6680 | |
dc.relation.references | Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Hratchian, H.P., (2016), D.J.F.J.V., Gaussian 16 | |
dc.relation.references | Rassolov, V.A., Ratner, M.A., Pople, J.A., Redfern, P.C., Curtiss, L.A., 6-31G | |
dc.relation.references | basis set for third-row atoms (2001) J. Comput. Chem., 22, pp. 976-984 | |
dc.relation.references | Hariharan, P.C., Pople, J.A., The influence of polarization functions on molecular orbital hydrogenation energies (1973) Theor. Chim. Acta., 28, pp. 213-222 | |
dc.relation.references | Hehre, W.J., Ditchfield, K., Pople, J.A., Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules (1972) J. Chem. Phys., 56, pp. 2257-2261 | |
dc.relation.references | Becke, A.D., Density-functional thermochemistry. III. The role of exact exchange (1993) J. Chem. Phys., 98, pp. 5648-5652 | |
dc.relation.references | Lee, C., Yang, W., Parr, G.R., Maintainng a heathy rhythm (1998) Phys. Rev. B., 37, pp. 785-789 | |
dc.relation.references | Stephens, P.J., Devlin, F.J., Chabalowski, C.F., Frisch, M.J., Ab Initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields (1994) J. Phys. Chem., 98, pp. 11623-11627 | |
dc.relation.references | Zhao, Y., Truhlar, D.G., The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other function (2008) Theor. Chem. Acc., 120, pp. 215-241 | |
dc.relation.references | Chai, J.D., Head-Gordon, M., Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections (2008) Phys. Chem. Chem. Phys., 10, pp. 6615-6620 | |
dc.relation.references | Zych, D., Slodek, A., Acceptor-π-Acceptor-Acceptor/Donor systems containing dicyanovinyl acceptor group with substituted 1,2,3-triazole motif – synthesis, photophysical and theoretical studies (2020) J. Mol. Struct., 1204 | |
dc.relation.references | Zycha, D., Slodek, A., Sensitizers for DSSC containing triazole motif with acceptor/donor substituents–Correlation between theoretical and experimental data in prediction of consistent photophysical parameters (2020) J. Mol. Struct., 1207 | |
dc.relation.references | Grimme, S., Antony, J., Ehrlich, S., Krieg, H., A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu (2010) J. Chem. Phys., p. 132 | |
dc.relation.references | Grimme, S., Ehrlich, S., Goerigk, L., Effect of the damping function in dispersion corrected density functional theory (2011) J. Comput. Chem., 32, pp. 1456-1465 | |
dc.relation.references | Marenich, A.V., Cramer, C.J., Truhlar, D.G., Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions (2009) J. Phys. Chem. B., 113, pp. 6378-6396 | |
dc.relation.references | Domínguez, M., Nieto, A., Marin, J.C., Keck, A.S., Jeffery, E., Céspedes, C.L., Antioxidant activities of extracts from Barkleyanthus salicifolius (Asteraceae) and Penstemon gentianoides (Scrophulariaceae) (2005) J. Agric. Food Chem., 53, pp. 5889-5895 | |
dc.relation.references | Rossato, J.I., Ketzer, L.A., Centurião, F.B., Silva, S.J.N., Lüdtke, D.S., Zeni, G., Braga, A.L., Da Rocha, J.B.T., Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain (2002) Neurochem. Res., 27, pp. 297-303 | |
dc.relation.references | Lowry, O.H., Rosebrough, N.J., Farr, A.L., Randall, R.J., Protein measurement with the Folin phenol reagent (1951) J. Biol. Chem., 193, pp. 265-275 | |
dc.relation.references | Ng, T., Liu, F., Wang, Z., Antioxidative activity of natural products from plants (2000) Life Sci, 66, pp. 709-723 | |
dc.relation.references | Ohkawa, H., Ohishi, N., Yagi, K., Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction (1979) Anal. Biochem., 95, pp. 351-358 | |
dc.relation.references | Esterbauer, H., Cheeseman, K.H., Determination of aldehydic lipid peroxidation products: malonaldehyde and 4-hydroxynonenal (1990) Methods Enzymol, 186, pp. 407-421 | |
dc.relation.references | Chaparro, D., Flores-Gaspar, A., Alí-Torres, J., Computational design of copper ligands with controlled metal chelating, pharmacokinetics, and redox properties for alzheimer's disease (2021) J. Alzheimer's Dis., 82, pp. S179-S193 | |
dc.relation.references | Chaparro, D., Alí-Torres, J., Assessment of the isodesmic method in the calculation of standard reduction potential of copper complexes (2017) J. Mol. Model., p. 23 | |
dc.relation.references | Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Boyd, M., Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines (1991) J. Natl. Cancer Inst., 83, pp. 757-766 | |
dc.relation.references | Sumantran, V.N., Cellular chemosensitivity assays: an overview (2011) Methods Mol. Biol., 731, pp. 219-236 | |
dc.relation.references | Concepción Lozada, M., Soria-Arteche, O., Teresa Ramírez Apan, M., Nieto-Camacho, A., Enríquez, R.G., Izquierdo, T., Jiménez-Corona, A., Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone (2012) Bioorganic Med. Chem., 20, pp. 5077-5084 | |
dc.relation.references | Drew, H.R., Wing, R.M., Takano, T., Broka, C., Tanaka, S., Itakura, K., Dickerson, R.E., Structure of a B-DNA dodecamer: conformation and dynamics (1981) Proc. Natl. Acad. Sci. U. S. A., 78, pp. 2179-2183 | |
dc.relation.references | Backman-Blanco, G., Valdés, H., Ramírez-Apan, M.T., Cano-Sanchez, P., Hernandez-Ortega, S., Orjuela, A.L., Alí-Torres, J., Morales-Morales, D., Synthesis of Pt(II) complexes of the type [Pt(1,10-phenanthroline)(SArFn)2] (SArFn = SC6H3-3,4-F2 | |
dc.relation.references | SC6F4-4-H | |
dc.relation.references | SC6F5). Preliminary evaluation of their in vitro anticancer activity (2020) J. Inorg. Biochem., 211 | |
dc.relation.references | Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., Olson, A.J., AutoDock4 and autodocktools4: automated docking with selective receptor flexibility (2012) J. Comput. Chem., 30, pp. 2785-2791 | |
dc.relation.references | (2021), Schrödinger, Schrödinger Release 2021-4: maestro | |
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 | |