2013 |
Soto-Delgado, J; Bahamonde-Padilla, V E; Araya-Maturana, R; Weiss-Lopez, B On the Mechanism of Biological Activity of Hydroquinone Derivatives That Inhibit Tumor Cell Respiration. A Theoretical Study Artículo de revista Computational and Theoretical Chemistry, 1013 , pp. 97-101, 2013, ISSN: 2210-271x. Resumen | Enlaces | BibTeX | Etiquetas: alpha-tocopheryl antioxidant, antitumoral calculation, cancer, cell dft drugs, generation, growth, hydroquinone, in-vivo, mechanism, mitochondria, oxidation, pathways respiration, semiquinone, succinate, targeting tumor @article{RN157, title = {On the Mechanism of Biological Activity of Hydroquinone Derivatives That Inhibit Tumor Cell Respiration. A Theoretical Study}, author = { J. Soto-Delgado and V.E. Bahamonde-Padilla and R. Araya-Maturana and B. Weiss-Lopez}, url = {/brokenurl#<Go to ISI>://WOS:000319102800015}, doi = {10.1016/j.comptc.2013.03.007}, issn = {2210-271x}, year = {2013}, date = {2013-01-01}, journal = {Computational and Theoretical Chemistry}, volume = {1013}, pages = {97-101}, publisher = {2013 Elsevier B.V.}, abstract = {A simple mechanism to understand the biological activity of a series of hydroquinone derivatives is proposed. To validate this proposition Gibbs free energies of formation of the different species involved were calculated. The calculations were performed using density functional theory (DFT) at B3LYP/6-31++G(2df,p) level of theory, including solvation effect. The results show that two important variables to examine are the equilibrium phenol-phenoxide and the solvation energy of neutral species, since the balance between both variables affects the capability of the molecules to cross membranes. Once the molecule crossed the membrane, the formation of radical species shows a qualitative correlation with the magnitude of IC50 values. This provides a reasonable criterion to search for more efficient anticancer drug.}, keywords = {alpha-tocopheryl antioxidant, antitumoral calculation, cancer, cell dft drugs, generation, growth, hydroquinone, in-vivo, mechanism, mitochondria, oxidation, pathways respiration, semiquinone, succinate, targeting tumor}, pubstate = {published}, tppubtype = {article} } A simple mechanism to understand the biological activity of a series of hydroquinone derivatives is proposed. To validate this proposition Gibbs free energies of formation of the different species involved were calculated. The calculations were performed using density functional theory (DFT) at B3LYP/6-31++G(2df,p) level of theory, including solvation effect. The results show that two important variables to examine are the equilibrium phenol-phenoxide and the solvation energy of neutral species, since the balance between both variables affects the capability of the molecules to cross membranes. Once the molecule crossed the membrane, the formation of radical species shows a qualitative correlation with the magnitude of IC50 values. This provides a reasonable criterion to search for more efficient anticancer drug. |
2011 |
Dobado, J A; Gomez-Tamayo, J C; Calvo-Flores, F G; Martinez-Garcia, H; Cardona, W; Weiss-Lopez, B; Ramirez-Rodriguez, O; Pessoa-Mahana, H; Araya-Maturana, R Nmr Assignment in Regioisomeric Hydroquinones Artículo de revista Magnetic Resonance in Chemistry, 49 (6), pp. 358-365, 2011, ISSN: 0749-1581. Resumen | Enlaces | BibTeX | Etiquetas: basis-sets, c-13 calculations, chemical-shifts, coupling-constants, derivatives, dft, diels-alder giao, h, h-1 hmbc, hmqc, hydroquinone, nmr, o3lyp, organic-molecules, reaction, respiration, sensitivity, spin theoretical tumor-cell @article{RN34e, title = {Nmr Assignment in Regioisomeric Hydroquinones}, author = { J.A. Dobado and J.C. Gomez-Tamayo and F.G. Calvo-Flores and H. Martinez-Garcia and W. Cardona and B. Weiss-Lopez and O. Ramirez-Rodriguez and H. Pessoa-Mahana and R. Araya-Maturana}, url = {/brokenurl#<Go to ISI>://WOS:000291114500009}, doi = {10.1002/mrc.2745}, issn = {0749-1581}, year = {2011}, date = {2011-01-01}, journal = {Magnetic Resonance in Chemistry}, volume = {49}, number = {6}, pages = {358-365}, publisher = {2011 John Wiley & Sons, Ltd.}, abstract = {A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8dihydroanthracen- 1(4H)-one (1) and other derivatives, were synthesized and their regiochemistry and NMR spectra assigned by using 1H-detected one-bond(C-H) HMQC and long-range C-HHMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a 3 integral H,H coupling constant of methylene protons evidencing the presence of a seven-membered intramolecular hydrogen bonded ring, not observed for the 8-hydroxymethyl isomers.}, keywords = {basis-sets, c-13 calculations, chemical-shifts, coupling-constants, derivatives, dft, diels-alder giao, h, h-1 hmbc, hmqc, hydroquinone, nmr, o3lyp, organic-molecules, reaction, respiration, sensitivity, spin theoretical tumor-cell}, pubstate = {published}, tppubtype = {article} } A set of regioisomeric pairs of tricyclic hydroquinones, analogues of antitumor 9,10-dihydroxy-4,4-dimethyl-5,8dihydroanthracen- 1(4H)-one (1) and other derivatives, were synthesized and their regiochemistry and NMR spectra assigned by using 1H-detected one-bond(C-H) HMQC and long-range C-HHMBC, in good agreement with theoretical O3LYP/Alhrichs-pVTZ calculations. The 5-hydroxymethyl derivatives (11, 15, 19) showed a 3 integral H,H coupling constant of methylene protons evidencing the presence of a seven-membered intramolecular hydrogen bonded ring, not observed for the 8-hydroxymethyl isomers. |
2013 |
On the Mechanism of Biological Activity of Hydroquinone Derivatives That Inhibit Tumor Cell Respiration. A Theoretical Study Artículo de revista Computational and Theoretical Chemistry, 1013 , pp. 97-101, 2013, ISSN: 2210-271x. |
2011 |
Nmr Assignment in Regioisomeric Hydroquinones Artículo de revista Magnetic Resonance in Chemistry, 49 (6), pp. 358-365, 2011, ISSN: 0749-1581. |