Examinando por Autor "Soto-Delgado, Jorge"
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Ítem 2D-QSAR and 3D-QSAR/CoMSIA studies on a series of (R)-2-((2-(1H-Indol-2-yl)ethyl)amino)-1-phenylethan-1-ol with human β3-adrenergic activity(MDPI AG, 2017-03) Apablaza, Gastón; Montoya, Luisa; Morales-Verdejo, Cesar; Mellado, Marco; Cuellar, Mauricio; Lagos, Carlos F.; Soto-Delgado, Jorge; Chung, Hery; Pessoa-Mahana, Carlos David; Mella, JaimeThe β3 adrenergic receptor is raising as an important drug target for the treatment of pathologies such as diabetes, obesity, depression, and cardiac diseases among others. Several attempts to obtain selective and high affinity ligands have been made. Currently, Mirabegron is the only available drug on the market that targets this receptor approved for the treatment of overactive bladder. However, the FDA (Food and Drug Administration) in USA and the MHRA (Medicines and Healthcare products Regulatory Agency) in UK have made reports of potentially life-threatening side effects associated with the administration of Mirabegron, casting doubts on the continuity of this compound. Therefore, it is of utmost importance to gather information for the rational design and synthesis of new β3 adrenergic ligands. Herein, we present the first combined 2D-QSAR (two-dimensional Quantitative Structure-Activity Relationship) and 3D-QSAR/CoMSIA (three-dimensional Quantitative Structure-Activity Relationship/Comparative Molecular Similarity Index Analysis) study on a series of potent β3 adrenergic agonists of indole-alkylamine structure. We found a series of changes that can be made in the steric, hydrogen-bond donor and acceptor, lipophilicity and molar refractivity properties of the compounds to generate new promising molecules. Finally, based on our analysis, a summary and a regiospecific description of the requirements for improving β3 adrenergic activity is given. © 2017 by the authors.Ítem Examining the compatibility of collagen and a polythiophene derivative for the preparation of bioactive platforms(Royal Society of Chemistry, 2015) Soto-Delgado, Jorge; Torras, Juan; Del Valle, Luis J.; Estrany, Francesc; Alemán, CarlosFundamental characteristics of bioactive platforms based on biocomposites of poly(3,4-ethylenedioxythiophene) (PEDOT) and collagen, named P(EDOT:CLG), have been examined using an experimental-computational approach. The protein affects both the morphology and electrochemical activity of PEDOT. Specifically, P(EDOT:CLG) shows spherical-like nodules that have been attributed to the collagen rod aggregates organized in phases separated from that of PEDOT. This phase separation results in a reduction of the ability to exchange charge reversibly, even though collagen stabilizes the PEDOT matrix from electrochemical degradation. On the other hand, viability assays indicate that the bioactivity of P(EDOT:CLG) is significantly higher than that of PEDOT in terms of cellular adhesion and proliferation. Thus, the biocomposite promotes the formation of 3D biostructures formed by the superposition of cellular monolayers, mimicking the growth of biological tissues. In order to gain microscopic information about the formation of specific interactions between PEDOT and collagen molecules in the biocomposite, quantum mechanical calculations on complexes formed by their building blocks have been performed in different environments (i.e. vacuum, chloroform and aqueous solution). Results evidence the important role played by non-conventional C-H⋯O hydrogen bonds, which is consistent with previous findings on complexes involving DNA and dopamine. The environment affects considerably the binding energy, which decreases with increasing polarity of the environment. However, in all environments the repeating units of PEDOT form stronger interactions with l-hydroxyproline than with l-proline. On the other hand, intermolecular interaction patterns predicted using implicit and explicit solvation models present a remarkable agreement and have been identified by visualizing the reduced electron density gradient. © The Royal Society of Chemistry 2015.Ítem Influence of structural changes on photophysical properties of terpyridine derivates: Experimental studies and theoretical calculations(Elsevier B.V., 2018-02) Toledo, Dominique; Brovelli, Francisco; Soto-Delgado, Jorge; Peña, Octavio; Pivan, Jean-Yves; Moreno, YankoFour terpyridine ligands containing different aryl substituents 4'-(4-quinolinyl)-3,2':6′,3″-terpyridine (3-qtpy), 4'-(4-quinolinyl)-2,2':6′,2″-terpyridine (2-qtpy), 4'-(3-methyl-2-thienyl)-4,2':6′,4″-terpyridine (4-stpy) and 4'-(3-methyl-2-thienyl)-2,2':6′,2″-terpyridine (2-stpy) were synthesized in a one-pot procedure and characterized by elemental analysis, FT-IR and 1H- and 13C NMR spectroscopy. Additionally, the 2-stpy structure was confirmed by single crystal X-ray diffraction analysis. The influence of the N-position in the tpy and aryl substituents on the photophysical properties was systematically investigated by spectroscopic methods and simulated by density functional theory (DFT and TD-DFT) calculations. Thermal stability was observed until about 280 °C, making these kind of ligands interesting candidates for their use as complex ligands, which are obtained by solvothermal synthesis under temperatures of about 180 °C. The electrochemical behavior was also investigated. All molecules show irreversible anodic and cathodic voltammetric peaks in organic medium. © 2017Ítem Structural reassignment of epierythratidine, an alkaloid from erythrinafusca, based on NMR studies and computational methods(Sociedad Chilena de Química, 2012) García-Beltrán, Olimpo; Soto-Delgado, Jorge; Iturriaga-Vásquez, Patricio; Areche, Carlos; Cassels, Bruce K.The diene Erythrina alkaloids erysotrine (1), erysodine (2), erythraline (3), erytharbine (4), and erysotrine N-oxide (5), plus the hydroxylated dihydro derivative of 1, epierythratidine (6) were isolated from seeds of Erythrina fusca Lour., and their 1H and 13C NMR spectra were completely assigned using 2D experiments (H-H COSY, HMQC, HMBC and H-H NOESY). Our assignments for 1-5 agree well with the literature, but the present work shows that the published interpretation of the spectra of 6 must be revised. A combined study based on NMR data and quantum-mechanical calculations using DFT/GIAO indicate that 6 is the correct structure of epierythratidine.