Publicaciones 2011-2020

@article{RN390,
title = {Blue-Fluorescent Probes for Lipid Droplets Based on Dihydrochromeno-Fused Pyrazolo- and Pyrrolopyridines},
author = { M. Becerra-Ruiz and V. Vargas and P. Jara and C. Tirapegui and C. Carrasco and M. Nunez and N. Lezana and A. Gald\'{a}mez and M. Vilches-Herrera},
url = {/brokenurl#<Go to ISI>://WOS:000444540900018},
doi = {10.1002/ejoc.201701633},
issn = {1434-193x},
year = {2018},
date = {2018-01-01},
journal = {European Journal of Organic Chemistry},
volume = {10.1002/ejoc.201701633},
number = {34},
pages = {4795-4801},
abstract = {Lipid droplets (LDs) have been recognized as highly dynamic cellular organelles involved in important biological functions for the survival of organisms such as supplying food or energy. Nevertheless, lipid storage must be tightly controlled, because both its excess and the inability to store lipids can be detrimental to the organism, resulting in metabolic diseases or multifaceted systemic problems. Visualization and the monitoring of the concentration of LDs is essential to understanding these processes. Commercially available LD dyes, such as Nile Red and boron-dipyrromethene (BODIPY), offer several advantageous characteristics, but can be limiting in multicolor imaging because most ready-made fluorescent reporter constructs fluoresce in the green-to-red region of the visible spectrum. Nile Red emits between green and red, and BODIPY can be photoconverted from green to red fluorescence, limiting its ability to be utilized for time-lapse imaging of living cells. Here, we report the design and synthesis, the photophysical characterization, and biological testing of two easily prepared series of new blue-fluorescing dyes as markers for LDs. Confocal fluorescence microscopy results showed an interesting correlation between the chemical structures of these fluorescent probes and their specific staining patterns. The pyrazole-based compound 11c was found to be a specific dye for LDs, whereas the pyrrole-based compound 10d led to prominent staining of the membranous cell organelles.},
keywords = {derivatives, design, diels-alder dyes, fluorescent fused-ring heterocycles, lipids, nitrogen photophysics, probes, prodrugs, reactions, red solvent, systems},
pubstate = {published},
tppubtype = {article}
}

@article{RN364,
title = {Development of an Iron-Selective Antioxidant Probe with Protective Effects on Neuronal Function},
author = { O. Garcia-Beltran and N.P. Mena and P. Aguirre and G. Barriga-Gonz\'{a}lez and A. Gald\'{a}mez and E. Nagles and T. Adasme and C. Hidalgo and M. Nunez},
url = {/brokenurl#<Go to ISI>://WOS:000417648600030},
doi = {10.1371/journal.pone.0189043},
issn = {1932-6203},
year = {2017},
date = {2017-01-01},
journal = {Plos One},
volume = {12},
number = {12},
abstract = {Iron accumulation, oxidative stress and calcium signaling dysregulation are common pathognomonic signs of several neurodegenerative diseases, including Parkinson's and Alzheimer's diseases, Friedreich ataxia and Huntington's disease. Given their therapeutic potential, the identification of multifunctional compounds that suppress these damaging features is highly desirable. Here, we report the synthesis and characterization of N-(1,3-dihydroxy- 2-(hydroxymethyl) propan-2-yl)-2-(7-hydroxy-2-oxo-2H-chromen-4-yl) acetamide, named CT51, which exhibited potent free radical neutralizing activity both in vitro and in cells. CT51 bound Fe2+ with high selectivity and Fe3+ with somewhat lower affinity. Cyclic voltammetric analysis revealed irreversible binding of Fe3+ to CT51, an important finding since stopping Fe2+/Fe3+ cycling in cells should prevent hydroxyl radical production resulting from the Fenton-Haber-Weiss cycle. When added to human neuroblastoma cells, CT51 freely permeated the cell membrane and distributed to both mitochondria and cytoplasm. Intracellularly, CT51 bound iron reversibly and protected against lipid peroxidation. Treatment of primary hippocampal neurons with CT51 reduced the sustained calcium release induced by an agonist of ryanodine receptor-calcium channels. These protective properties of CT51 on cellular function highlight its possible therapeutic use in diseases with significant oxidative, iron and calcium dysregulation.},
keywords = {calcium cells, coumarins, deficiency, fluorescence fluorescence, fragmentation, iron, labile mitochondrial on oxidative parkinsons-disease, probes, sh-sy5y stress},
pubstate = {published},
tppubtype = {article}
}

@article{RN194,
title = {Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(Ii) and Iron(Iii) Ions and Their Application in Bio-Imaging},
author = { O. Garcia-Beltran and B.K. Cassels and C. Perez and N. Mena and M. Nunez and N.P. Martinez and P. Pavez and M.E. Aliaga},
url = {/brokenurl#<Go to ISI>://WOS:000336039100075},
doi = {10.3390/s140101358},
issn = {1424-8220},
year = {2014},
date = {2014-01-01},
journal = {Sensors},
volume = {14},
number = {1},
pages = {1358-1371},
abstract = {Two new coumarin-based "turn-off" fluorescent probes, (E)-3-((3,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS1) and (E)-3-((2,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show that both compounds are highly selective for Cu2+ and Fe3+ ions over other metal ions. However, BS2 is detected directly, while detection of BS1 involves a hydrolysis reaction to regenerate 3-amino-7-hydroxycoumarin (3) and 3,4-dihydroxybenzaldehyde, of which 3 is able to react with copper(II) or iron(III) ions. The interaction between the tested compounds and copper or iron ions is associated with a large fluorescence decrease, showing detection limits of ca. 10(-5) M. Preliminary studies employing epifluorescence microscopy demonstrate that Cu2+ and Fe3+ ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes.},
keywords = {bio-imaging, chemosensor, coumarin-based cu2+ cu2+, design, fe3+ fluorescence ion, probes, sensor sensors, turn-off},
pubstate = {published},
tppubtype = {article}
}

@article{RN192,
title = {Synthesis of Coumarin Derivatives as Fluorescent Probes for Membrane and Cell Dynamics Studies},
author = { O. Garcia-Beltran and O. Yanez and J. Caballero and A. Gald\'{a}mez and N. Mena and M. Nunez and B.K. Cassels},
url = {/brokenurl#<Go to ISI>://WOS:000335487400009},
doi = {10.1016/j.ejmech.2014.02.016},
issn = {0223-5234},
year = {2014},
date = {2014-01-01},
journal = {European Journal of Medicinal Chemistry},
volume = {76},
pages = {79-86},
publisher = {2014 Elsevier Masson SAS.},
abstract = {Three coumarin-derived fluorescent probes, 3-acetyl-7-[(6-bromohexyl)oxy]-2H-chromen-2-one (FM1), 7-[(6-bromohexyl)oxy]-4-methyl-2H-chromen-2-one (FM2) and ethyl 2-7-[(6-bromohexyl)oxy]-2-oxo-2H-chromen-4-ylacetate (FM3), are described, with their photophysical constants. The compounds were tested in preliminary studies employing epifluorescence microscopy demonstrating that they allow the imaging of human neuroblastoma SH-SY5Y cell membranes. The structure of FM3 was confirmed by X-ray crystallographic analysis. Molecular dynamics (MD) simulations were used to characterize the localization and interactions of the studied compounds with a lipid bilayer model of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC).},
keywords = {biological-membranes, carboxylic-acids, cell coumarins, crystal-structure, decarboxylation depth, dynamics, energy-transfer, hydrogen-bond, membranes, model, molecular molecular-dynamics, probes, proteins, resonance},
pubstate = {published},
tppubtype = {article}
}

@article{RN163,
title = {Hydrogen Bond Contribution to Preferential Solvation in Snar Reactions},
author = { R. Ormazabal-Toledo and J.G. Santos and P. Rios and E.A. Castro and P.R. Campodonico and R. Contreras},
url = {/brokenurl#<Go to ISI>://WOS:000319649800012},
doi = {10.1021/jp4005295},
issn = {1520-6106},
year = {2013},
date = {2013-01-01},
journal = {Journal of Physical Chemistry B},
volume = {117},
number = {19},
pages = {5908-5915},
abstract = {Preferential solvation in aromatic nucleophilic substitution reactions is discussed using a kinetic study complemented with quantum chemical calculations. The model system is the reaction of a series of secondary alicyclic amines toward phenyl 2,4,6-trinitrophenyl ether in aqueous ethanol mixtures of different compositions. From solvent effect studies, it is found that only piperidine is sensitive to solvation effects, a result that may be traced to the polarity of the solvent composition in the ethanol/water mixture, which points to a specific electrophilic solvation in the aqueous phase.},
keywords = {amines aromatic behavior, binary chemical ether, kinetics, mixtures, molecules, nucleophilic-substitution, piperidine, probes, solvent},
pubstate = {published},
tppubtype = {article}
}

@article{RN17e,
title = {The Development of a Fluorescence Turn-on Sensor for Cysteine, Glutathione and Other Biothiols. A Kinetic Study},
author = { O. Garcia-Beltran and N. Mena and E.G. Perez and B.K. Cassels and M. Nunez and F. Werlinger and D. Zavala and M.E. Aliaga and P. Pavez},
url = {/brokenurl#<Go to ISI>://WOS:000297442400022},
doi = {10.1016/j.tetlet.2011.09.137},
issn = {0040-4039},
year = {2011},
date = {2011-01-01},
journal = {Tetrahedron Letters},
volume = {52},
number = {49},
pages = {6606-6609},
publisher = {2011 Elsevier Ltd.},
abstract = {Two fluorescence probes for the detection of cysteine (Cys), glutathione (GSH) and other biothiols, such as homocysteine (Hcy) and cysteinyl-glycine (Cys-Gly), were developed. These molecular probes are coumarin-based derivatives containing a chalcone-like moiety that reacts with biothiols through a Michael addition reaction, leading to strong fluorescence enhancements. The reactivity of the tested biothiols toward both probes (ChC1 and ChC2) follows the order Cys > GSH > Hcy > Cys-Gly, ChC1 being less reactive than ChC2. Possible interference with other amino acids was assessed. ChC1 and ChC2 display a highly selective fluorescence enhancement with thiols, allowing these probes to be used for fluorimetric thiol determination in SH-SY5Y cells.},
keywords = {addition, biothiols, coumarin-based derivatives, disease, fluorescence homocysteine, michael probe, probes, thiols, water},
pubstate = {published},
tppubtype = {article}
}