Phenolic esters with potential anticancer activity - the structural variable |
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Authors: | Nelson F. L. Machado Rita Calheiros Sónia M. Fiuza Fernanda Borges Alexandra Gaspar Jorge Garrido Maria P. Marques |
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Affiliation: | (1) Unidade I&D “Química-Física Molecular”, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, 3000 Coimbra, Portugal;(2) Departamento Química Organica, Faculdade de Farmácia, Universidade do Porto, 4050-047 Porto, Portugal;(3) Departamento Engenharia Química, Instituto Superior de Engenharia do Porto, 4200-072 Porto, Portugal;(4) Departamento Bioquímica, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, Apartado 3126, 3001-401 Coimbra, Portugal |
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Abstract: | The conformational preferences of several potential anticancer dihydroxycinnamic esters with a variable length alkyl chain were studied by quantum-mechanical (DFT) calculations (both for the isolated molecule and for aqueous solutions). The orientation of the hydroxyl ring substituents and of the alkyl ester moiety relative to the carbonyl group showed these to be the most determinant factors for the overall stability of this type of phenolic systems, strongly dependent on an effective π-electron delocalization. Compared to the parent caffeic acid (dihydroxycinnamic acid), esterification was found to lead to a higher conformational freedom, and to affect mainly the energy barrier corresponding to the (O=)C-OR internal rotation. No particular differences were verified to occur upon lengthening of the ester alkyl chain, except when this is branched instead of linear. The vibrational spectra of the whole series of compounds were simulated, based on their calculated harmonic vibrational frequencies, and a preliminary assignment was performed. Figure Schematic representation of the dihydroxycinnamic esters studied in the present work and of the main internal rotations affecting the overall stability of the molecules. (R=(CH2)n, n = 0,1,2,3,7,11 for MC, EC, PC, BC, OC and DC, respectively; R=(CHCH3) for IPC. The atom numbering is included, with the exception of the alkyl ester group) |
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Keywords: | Dihydroxycinnamates Anticancer Density functional theory Conformational analysis Theoretical vibrational spectra |
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