2018 |
Cassels, B K; Saez-Briones, P Dark Classics in Chemical Neuroscience: Mescaline Artículo de revista Acs Chemical Neuroscience, 9 (10), pp. 2448-2458, 2018, ISSN: 1948-7193. Resumen | Enlaces | BibTeX | Etiquetas: analogs, biosynthesis, cancer, derivatives, diethylamide, hallucinogen, hallucinogenic life-threatening lysergic-acid mescaline, metabolism, pedro, peyote, pharmacology, phenethylamine, phenyl-aethylamine, properties, relationships, san serotonin stimulus structure-activity synthesis, wachuma @article{RN389, title = {Dark Classics in Chemical Neuroscience: Mescaline}, author = { B.K. Cassels and P. Saez-Briones}, url = {/brokenurl#<Go to ISI>://WOS:000447954300015}, doi = {10.1021/acschemneuro.8b00215}, issn = {1948-7193}, year = {2018}, date = {2018-01-01}, journal = {Acs Chemical Neuroscience}, volume = {9}, number = {10}, pages = {2448-2458}, abstract = {Archeological studies in the United States, Mexico, and Peru suggest that mescaline, as a cactus constituent, has been used for more than 6000 years. Although it is a widespread cactus alkaloid, it is present in high concentrations in few species, notably the North American peyote (Lophophora williamsii) and the South American wachuma (Trichocereus pachanoi, T. peruvianus, and T. bridgesii). Spanish 16th century chroniclers considered these cacti "diabolic", leading to their prohibition, but their use persisted to our days and has been spreading for the last 150 years. In the late 1800s, peyote attracted scientific attention; mescaline was isolated, and its role in the psychedelic effects of peyote tops or "mescal buttons" was demonstrated. Its structure was established by synthesis in 1929, and alternative routes were developed, providing larger amounts for pharmacological and biosynthetic research. Although its effects are attributed mainly to its action as a 5-HT2A serotonin receptor agonist, mescaline binds in a similar concentration range to 5-HT1A and alpha(2A) receptors. It is largely excreted unchanged in human urine, and its metabolic products are apparently unrelated to its psychedelic properties. Its low potency is probably responsible for its relative neglect by recreational substance users, as the successful search for structure-activity relationships in the hallucinogen field focused largely on finding more potent analogues. Renewed interest in the possible therapeutic applications of psychedelic drugs may hopefully lead to novel insights regarding the commonalities and differences between the actions of individual classic hallucinogens.}, keywords = {analogs, biosynthesis, cancer, derivatives, diethylamide, hallucinogen, hallucinogenic life-threatening lysergic-acid mescaline, metabolism, pedro, peyote, pharmacology, phenethylamine, phenyl-aethylamine, properties, relationships, san serotonin stimulus structure-activity synthesis, wachuma}, pubstate = {published}, tppubtype = {article} } Archeological studies in the United States, Mexico, and Peru suggest that mescaline, as a cactus constituent, has been used for more than 6000 years. Although it is a widespread cactus alkaloid, it is present in high concentrations in few species, notably the North American peyote (Lophophora williamsii) and the South American wachuma (Trichocereus pachanoi, T. peruvianus, and T. bridgesii). Spanish 16th century chroniclers considered these cacti "diabolic", leading to their prohibition, but their use persisted to our days and has been spreading for the last 150 years. In the late 1800s, peyote attracted scientific attention; mescaline was isolated, and its role in the psychedelic effects of peyote tops or "mescal buttons" was demonstrated. Its structure was established by synthesis in 1929, and alternative routes were developed, providing larger amounts for pharmacological and biosynthetic research. Although its effects are attributed mainly to its action as a 5-HT2A serotonin receptor agonist, mescaline binds in a similar concentration range to 5-HT1A and alpha(2A) receptors. It is largely excreted unchanged in human urine, and its metabolic products are apparently unrelated to its psychedelic properties. Its low potency is probably responsible for its relative neglect by recreational substance users, as the successful search for structure-activity relationships in the hallucinogen field focused largely on finding more potent analogues. Renewed interest in the possible therapeutic applications of psychedelic drugs may hopefully lead to novel insights regarding the commonalities and differences between the actions of individual classic hallucinogens. |
2017 |
Sierpe, R; Noyong, M; Simon, U; Aguayo, D; Huerta, J; Kogan, M J; Yutronic, N Construction of 6-Thioguanine and 6-Mercaptopurine Carriers Based on Beta Cyclodextrins and Gold Nanoparticles Artículo de revista Carbohydrate Polymers, 177 , pp. 22-31, 2017, ISSN: 0144-8617. Resumen | Enlaces | BibTeX | Etiquetas: anisotropic antineoplastic, applications, cancer, complex, complexes, cytotoxicity delivery, dielectrics, drug drug-delivery, enhanced inclusion ionic-solutions, nanotechnology, permeability, pharmaceutical photothermal solid-state, sputtering, therapy @article{RN352, title = {Construction of 6-Thioguanine and 6-Mercaptopurine Carriers Based on Beta Cyclodextrins and Gold Nanoparticles}, author = { R. Sierpe and M. Noyong and U. Simon and D. Aguayo and J. Huerta and M.J. Kogan and N. Yutronic}, url = {/brokenurl#<Go to ISI>://WOS:000411876200003}, doi = {10.1016/j.carbpol.2017.08.102}, issn = {0144-8617}, year = {2017}, date = {2017-01-01}, journal = {Carbohydrate Polymers}, volume = {177}, pages = {22-31}, abstract = {As a novel strategy to overcome some of the therapeutic disadvantages of 6-thioguanine (TG) and 6-mercaptopurine (MP), we propose the inclusion of these drugs in beta cyclodextrin (beta CD) to form the complexes beta CD-TG and beta CD-MP, followed by subsequent interaction with gold nanoparticles (AuNPs), generating the ternary systems: beta CD-TG-AuNPs and beta CD-MP-AuNPs. This modification increased their solubility and improved their stability, betting by a site-specific transport due to their nanometric dimensions, among other advantages., The formation of the complexes was confirmed using powder X-ray diffraction, thermogravimetric analysis and one and two-dimensional NMR. A theoretical study using DFT and molecular modelling was conducted to obtain the more stable tautomeric species of TG and MP in solution and confirm the proposed inclusion geometries. The deposition of AuNPs onto beta CD-TG and beta CD-MP via sputtering was confirmed by UV-vis spectroscopy. Subsequently, the ternary systems were characterized by TEM, FE-SEM and EDX to directly observe the deposited AuNPs and evaluate their sizes, size dispersion, and composition. Finally, the in vitro permeability of the ternary systems was studied using parallel artificial membrane permeability assay (PAMPA).}, keywords = {anisotropic antineoplastic, applications, cancer, complex, complexes, cytotoxicity delivery, dielectrics, drug drug-delivery, enhanced inclusion ionic-solutions, nanotechnology, permeability, pharmaceutical photothermal solid-state, sputtering, therapy}, pubstate = {published}, tppubtype = {article} } As a novel strategy to overcome some of the therapeutic disadvantages of 6-thioguanine (TG) and 6-mercaptopurine (MP), we propose the inclusion of these drugs in beta cyclodextrin (beta CD) to form the complexes beta CD-TG and beta CD-MP, followed by subsequent interaction with gold nanoparticles (AuNPs), generating the ternary systems: beta CD-TG-AuNPs and beta CD-MP-AuNPs. This modification increased their solubility and improved their stability, betting by a site-specific transport due to their nanometric dimensions, among other advantages., The formation of the complexes was confirmed using powder X-ray diffraction, thermogravimetric analysis and one and two-dimensional NMR. A theoretical study using DFT and molecular modelling was conducted to obtain the more stable tautomeric species of TG and MP in solution and confirm the proposed inclusion geometries. The deposition of AuNPs onto beta CD-TG and beta CD-MP via sputtering was confirmed by UV-vis spectroscopy. Subsequently, the ternary systems were characterized by TEM, FE-SEM and EDX to directly observe the deposited AuNPs and evaluate their sizes, size dispersion, and composition. Finally, the in vitro permeability of the ternary systems was studied using parallel artificial membrane permeability assay (PAMPA). |
2015 |
Martinez-Cifuentes, M; Weiss-Lopez, B; Santos, L S; Araya-Maturana, R Heterocyclic Curcumin Derivatives of Pharmacological Interest: Recent Progress Artículo de revista Current Topics in Medicinal Chemistry, 15 (17), pp. 1663-1672, 2015, ISSN: 1568-0266. Resumen | Enlaces | BibTeX | Etiquetas: alzheimer, analogs, antibacterial, antiinflammatory antioxidant, antioxidants, apoptosis, bioavailability, cancer, curcumin, cytotoxicity, heterocycles, in-vitro, inhibitors molecular properties, targets @article{RN266, title = {Heterocyclic Curcumin Derivatives of Pharmacological Interest: Recent Progress}, author = { M. Martinez-Cifuentes and B. Weiss-Lopez and L.S. Santos and R. Araya-Maturana}, url = {/brokenurl#<Go to ISI>://WOS:000355570800003}, doi = {10.2174/1568026615666150427111837}, issn = {1568-0266}, year = {2015}, date = {2015-01-01}, journal = {Current Topics in Medicinal Chemistry}, volume = {15}, number = {17}, pages = {1663-1672}, abstract = {Curcumin, a natural yellow polyphenol, is isolated from the herb Curcuma longa L. (turmeric), a member of the ginger family. It has been extensively studied due to their multiple pharmacological properties. Nevertheless, curcumin has disadvantages such as poor water solubility, poor bioavailability and rapid metabolism, which has prompted the search for analogues that overcome these shortcomings while maintaining or improving their good pharmacological properties. Among the main curcumin analogues that have been developed, the heterocyclic curcuminoids show a high interest. In this review, we describe recent progress in the synthesis and pharmacological properties of new heterocyclic curcumin derivatives. The most recent developments in anti-cancer, anti-Alzheimer, anti-bacterial and anti-oxidants heterocyclic curcumin derivatives are covered.}, keywords = {alzheimer, analogs, antibacterial, antiinflammatory antioxidant, antioxidants, apoptosis, bioavailability, cancer, curcumin, cytotoxicity, heterocycles, in-vitro, inhibitors molecular properties, targets}, pubstate = {published}, tppubtype = {article} } Curcumin, a natural yellow polyphenol, is isolated from the herb Curcuma longa L. (turmeric), a member of the ginger family. It has been extensively studied due to their multiple pharmacological properties. Nevertheless, curcumin has disadvantages such as poor water solubility, poor bioavailability and rapid metabolism, which has prompted the search for analogues that overcome these shortcomings while maintaining or improving their good pharmacological properties. Among the main curcumin analogues that have been developed, the heterocyclic curcuminoids show a high interest. In this review, we describe recent progress in the synthesis and pharmacological properties of new heterocyclic curcumin derivatives. The most recent developments in anti-cancer, anti-Alzheimer, anti-bacterial and anti-oxidants heterocyclic curcumin derivatives are covered. |
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. |
2018 |
Dark Classics in Chemical Neuroscience: Mescaline Artículo de revista Acs Chemical Neuroscience, 9 (10), pp. 2448-2458, 2018, ISSN: 1948-7193. |
2017 |
Construction of 6-Thioguanine and 6-Mercaptopurine Carriers Based on Beta Cyclodextrins and Gold Nanoparticles Artículo de revista Carbohydrate Polymers, 177 , pp. 22-31, 2017, ISSN: 0144-8617. |
2015 |
Heterocyclic Curcumin Derivatives of Pharmacological Interest: Recent Progress Artículo de revista Current Topics in Medicinal Chemistry, 15 (17), pp. 1663-1672, 2015, ISSN: 1568-0266. |
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. |