2018 |
Becerra-Ruiz, M; Vargas, V; Jara, P; Tirapegui, C; Carrasco, C; Nunez, M; Lezana, N; Galdámez, A; Vilches-Herrera, M Blue-Fluorescent Probes for Lipid Droplets Based on Dihydrochromeno-Fused Pyrazolo- and Pyrrolopyridines Artículo de revista European Journal of Organic Chemistry, 10.1002/ejoc.201701633 (34), pp. 4795-4801, 2018, ISSN: 1434-193x. Resumen | Enlaces | BibTeX | Etiquetas: derivatives, design, diels-alder dyes, fluorescent fused-ring heterocycles, lipids, nitrogen photophysics, probes, prodrugs, reactions, red solvent, systems @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} } 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. |
2016 |
Yempala, T; Cassels, B K Simple and Efficient Synthesis of Various Dibenzofuran Carbaldehydes Artículo de revista Synthetic Communications, 46 (23), pp. 1909-1915, 2016, ISSN: 0039-7911. Resumen | Enlaces | BibTeX | Etiquetas: bond bromo carbaldehydes, cascade, derivatives, design, dibenzofuran efficient evaluation, formation, formylation, furans, methoxy phytoalexins, protocols, stems @article{RN292, title = {Simple and Efficient Synthesis of Various Dibenzofuran Carbaldehydes}, author = { T. Yempala and B.K. Cassels}, url = {/brokenurl#<Go to ISI>://WOS:000388722500006}, doi = {10.1080/00397911.2016.1235201}, issn = {0039-7911}, year = {2016}, date = {2016-01-01}, journal = {Synthetic Communications}, volume = {46}, number = {23}, pages = {1909-1915}, abstract = {We herein report simple and efficient methods for the synthesis of various formyl derivatives of dibenzofuran. The aldehydes reported are prepared in at most three steps and in yields greater than 60% from commercially available dibenzofuran, with one exception where isomers must be separated. The protocols described involve either formylation of previously functionalized dibenzofuran derivatives or the initial introduction of the formyl group and subsequent further functionalization under standard reaction conditions as described. We have also reported an efficient and simple method for the synthesis of keywords methoxydibenzofurans in high yield (65% overall for two steps}, keywords = {bond bromo carbaldehydes, cascade, derivatives, design, dibenzofuran efficient evaluation, formation, formylation, furans, methoxy phytoalexins, protocols, stems}, pubstate = {published}, tppubtype = {article} } We herein report simple and efficient methods for the synthesis of various formyl derivatives of dibenzofuran. The aldehydes reported are prepared in at most three steps and in yields greater than 60% from commercially available dibenzofuran, with one exception where isomers must be separated. The protocols described involve either formylation of previously functionalized dibenzofuran derivatives or the initial introduction of the formyl group and subsequent further functionalization under standard reaction conditions as described. We have also reported an efficient and simple method for the synthesis of keywords methoxydibenzofurans in high yield (65% overall for two steps |
2014 |
Garcia-Beltran, O; Cassels, B K; Perez, C; Mena, N; Nunez, M; Martinez, N P; Pavez, P; Aliaga, M E Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(Ii) and Iron(Iii) Ions and Their Application in Bio-Imaging Artículo de revista Sensors, 14 (1), pp. 1358-1371, 2014, ISSN: 1424-8220. Resumen | Enlaces | BibTeX | Etiquetas: bio-imaging, chemosensor, coumarin-based cu2+ cu2+, design, fe3+ fluorescence ion, probes, sensor sensors, turn-off @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} } 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. |
Garcia-Beltran, O; Cassels, B K; Mena, N; Nunez, M; Yanez, O; Caballero, J A Coumarinylaldoxime as a Specific Sensor for Cu2+ and Its Biological Application Artículo de revista Tetrahedron Letters, 55 (4), pp. 873-876, 2014, ISSN: 0040-4039. Resumen | Enlaces | BibTeX | Etiquetas: bilayer, copper, coumarin cu2+-selectivity, derivative, design, dynamics, fluorescent lipid membranes molecular probe @article{RN193, title = {A Coumarinylaldoxime as a Specific Sensor for Cu2+ and Its Biological Application}, author = { O. Garcia-Beltran and B.K. Cassels and N. Mena and M. Nunez and O. Yanez and J. Caballero}, url = {/brokenurl#<Go to ISI>://WOS:000330604500023}, doi = {10.1016/j.tetlet.2013.12.033}, issn = {0040-4039}, year = {2014}, date = {2014-01-01}, journal = {Tetrahedron Letters}, volume = {55}, number = {4}, pages = {873-876}, publisher = {2013 Elsevier Ltd.}, abstract = {In this Letter we present a new probe, (E)-7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (JB), which can detect Cu2+ ions in HEPES buffer under physiological conditions. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu2+ complex formed is 2:1. Possible interference with other analytes was examined, and the decrease of the fluorescence of JB at 510 nm when it reacts with Cu2+ was shown to be highly selective. This probe accumulates in the plasmalemma of human neuroblastoma SH-SY5Y cells. Molecular dynamics (MD) simulations revealed thatJB interacts with the lipid bilayer at the level of the glycerol moieties.}, keywords = {bilayer, copper, coumarin cu2+-selectivity, derivative, design, dynamics, fluorescent lipid membranes molecular probe}, pubstate = {published}, tppubtype = {article} } In this Letter we present a new probe, (E)-7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (JB), which can detect Cu2+ ions in HEPES buffer under physiological conditions. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu2+ complex formed is 2:1. Possible interference with other analytes was examined, and the decrease of the fluorescence of JB at 510 nm when it reacts with Cu2+ was shown to be highly selective. This probe accumulates in the plasmalemma of human neuroblastoma SH-SY5Y cells. Molecular dynamics (MD) simulations revealed thatJB interacts with the lipid bilayer at the level of the glycerol moieties. |
2018 |
Blue-Fluorescent Probes for Lipid Droplets Based on Dihydrochromeno-Fused Pyrazolo- and Pyrrolopyridines Artículo de revista European Journal of Organic Chemistry, 10.1002/ejoc.201701633 (34), pp. 4795-4801, 2018, ISSN: 1434-193x. |
2016 |
Simple and Efficient Synthesis of Various Dibenzofuran Carbaldehydes Artículo de revista Synthetic Communications, 46 (23), pp. 1909-1915, 2016, ISSN: 0039-7911. |
2014 |
Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(Ii) and Iron(Iii) Ions and Their Application in Bio-Imaging Artículo de revista Sensors, 14 (1), pp. 1358-1371, 2014, ISSN: 1424-8220. |
A Coumarinylaldoxime as a Specific Sensor for Cu2+ and Its Biological Application Artículo de revista Tetrahedron Letters, 55 (4), pp. 873-876, 2014, ISSN: 0040-4039. |