101 results on '"Fueyo‐González, Francisco"'
Search Results
2. Flour moisture detection with an europium-based luminescent probe
- Author
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Fueyo-González, Francisco, Cenit, Anabel, Villodres, Rocío, Saiz, Ignacio, Micolonghi, Giulia, Talavera, Eva M., Teychené, Sébastien, Rodriguez-Ruiz, Isaac, Herranz, Rosario, Orte, Angel, Garcia-Fernandez, Emilio, and González-Vera, Juan A. more...
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- 2024
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Catalog
3. Small-molecule TIP60 inhibitors enhance regulatory T cell induction through TIP60-P300 acetylation crosstalk
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Fueyo-González, Francisco, Vilanova, Guillermo, Ningoo, Mehek, Marjanovic, Nada, González-Vera, Juan A., Orte, Ángel, and Fribourg, Miguel
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- 2023
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4. Interferon-β acts directly on T cells to prolong allograft survival by enhancing regulatory T cell induction through Foxp3 acetylation
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Fueyo-González, Francisco, McGinty, Mitchell, Ningoo, Mehek, Anderson, Lisa, Cantarelli, Chiara, Andrea Angeletti, Demir, Markus, Llaudó, Inés, Purroy, Carolina, Marjanovic, Nada, Heja, David, Sealfon, Stuart C., Heeger, Peter S., Cravedi, Paolo, and Fribourg, Miguel more...
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- 2022
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5. A FRET pair for quantitative and superresolution imaging of amyloid fibril formation
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Ruiz-Arias, Álvaro, Jurado, Rocío, Fueyo-González, Francisco, Herranz, Rosario, Gálvez, Natividad, González-Vera, Juan A., and Orte, Angel
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- 2022
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6. Synthesis, biological, and photophysical studies of molecular rotor-based fluorescent inhibitors of the trypanosome alternative oxidase
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Cueto-Díaz, Eduardo J., Ebiloma, Godwin U., Alfayez, Ibrahim A., Ungogo, Marzuq A., Lemgruber, Leandro, González-García, M. Carmen, Giron, Maria D., Salto, Rafael, Fueyo-González, Francisco José, Shiba, Tomoo, González-Vera, Juan A., Ruedas Rama, Maria José, Orte, Angel, de Koning, Harry P., and Dardonville, Christophe more...
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- 2021
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7. Quinolimide-based peptide biosensor for probing p25 in vitro and in living cells
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Fueyo-González, Francisco, Herranz, Rosario, Plesselova, Simona, Giron, Maria D., Salto, Rafael, Paredes, Jose Manuel, Orte, Angel, Morris, May C., and González-Vera, Juan A.
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- 2021
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8. Flour moisture detection with an europium-based luminescent probe
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European Commission, Junta de Andalucía, Universidad de Granada, Fueyo-González, Francisco, Cenit, A., Micolonghi, G., Talavera, E. M., Teychené, S., Rodriguez-Ruiz, I., Herranz, Rosario, Orte, A., Garcia-Fernandez, E., González-Vera, Juan A., European Commission, Junta de Andalucía, Universidad de Granada, Fueyo-González, Francisco, Cenit, A., Micolonghi, G., Talavera, E. M., Teychené, S., Rodriguez-Ruiz, I., Herranz, Rosario, Orte, A., Garcia-Fernandez, E., and González-Vera, Juan A. more...
- Abstract
In this work, we describe the application of the self-assembled europium complex 1:Eu(III) (where 1: diethyl 8-methoxy-2-oxo-1,2,4,5-tetrahydro-cyclopenta[de]quinolin-3-yl)phosphonate) for the analysis of water content of wheat flour. The methodology herein described represents a robust and accurate way for the detection of small amounts of water in food, providing comparing results with well-established methods such as thermogravimetry and Karl-Fischer titration. Interestingly, as an advantage over other methods, our luminescence-based approach can be implemented in lab-on-a-chip microfluidic devices for real-time and on-line detection of water content of food samples. Additionally, the remarkably long luminescence lifetime of Eu(III) allows the use of state-of-the-art imaging strategies based on PLIM microscopy for the direct visualization of unique water content maps of wheat flour particles. more...
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- 2024
9. Naphthalimide-based macrophage nucleus imaging probes
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Fueyo-González, Francisco, Fernández-Gutiérrez, Mar, García-Puentes, Diego, Orte, Angel, González-Vera, Juan A., and Herranz, Rosario
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- 2020
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10. Fluorescence mechanism switching from ICT to PET by substituent chemical manipulation: Macrophage cytoplasm imaging probes
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Fueyo-González, Francisco, González-Vera, Juan A., Alkorta, Ibon, Infantes, Lourdes, Jimeno, M. Luisa, Fernández-Gutiérrez, Mar, González-García, M. Carmen, Orte, Angel, and Herranz, Rosario
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- 2020
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11. Multiple Pathways for Lanthanide Sensitization in Self-Assembled Aqueous Complexes
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Navarro, Amparo, primary, Ruiz-Arias, Alvaro, additional, Fueyo-González, Francisco, additional, Izquierdo-García, Carolina, additional, Peña-Ruiz, Tomás, additional, Gutiérrez-Rodríguez, Marta, additional, Herranz, Rosario, additional, Cuerva, Juan M., additional, Gonzalez-Vera, Juan A., additional, and Orte, Angel, additional more...
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- 2024
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12. Exchangeable Self-Assembled Lanthanide Antennas for PLIM Microscopy
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European Commission, Junta de Andalucía, Consejo Superior de Investigaciones Científicas (España), Universidad de Jaén, Universidad de Granada, Ministerio de Educación y Formación Profesional (España), Fueyo-González, Francisco [0000-0003-1889-6792], Izquierdo-García, Carolina [0000-0001-9801-4053], Gutiérrez-Rodríguez, Marta [0000-0001-9855-8341], Herranz, Rosario [0000-0002-0273-2761], González-Vera, Juan A. [0000-0001-8713-5829], Ruiz-Arias, Alvaro, Fueyo-González, Francisco, Izquierdo-García, Carolina, Navarro, Amparo, Gutiérrez-Rodríguez, Marta, Herranz, Rosario, Burgio, Chiara, Reinoso, Antonio, Cuerva, Juan M., Orte, Angel, González-Vera, Juan A., European Commission, Junta de Andalucía, Consejo Superior de Investigaciones Científicas (España), Universidad de Jaén, Universidad de Granada, Ministerio de Educación y Formación Profesional (España), Fueyo-González, Francisco [0000-0003-1889-6792], Izquierdo-García, Carolina [0000-0001-9801-4053], Gutiérrez-Rodríguez, Marta [0000-0001-9855-8341], Herranz, Rosario [0000-0002-0273-2761], González-Vera, Juan A. [0000-0001-8713-5829], Ruiz-Arias, Alvaro, Fueyo-González, Francisco, Izquierdo-García, Carolina, Navarro, Amparo, Gutiérrez-Rodríguez, Marta, Herranz, Rosario, Burgio, Chiara, Reinoso, Antonio, Cuerva, Juan M., Orte, Angel, and González-Vera, Juan A. more...
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- 2023
13. Back Cover: Exchangeable Self‐Assembled Lanthanide Antennas for PLIM Microscopy
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Ruiz‐Arias, Alvaro, primary, Fueyo‐González, Francisco, additional, Izquierdo‐García, Carolina, additional, Navarro, Amparo, additional, Gutiérrez‐Rodríguez, Marta, additional, Herranz, Rosario, additional, Burgio, Chiara, additional, Reinoso, Antonio, additional, Cuerva, Juan M., additional, Orte, Angel, additional, and González‐Vera, Juan A., additional more...
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- 2023
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14. Exchangeable Self‐Assembled Lanthanide Antennas for PLIM Microscopy
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Ruiz-Arias, Alvaro, primary, Fueyo-González, Francisco, additional, Izquierdo-García, Carolina, additional, Navarro, Amparo, additional, Gutiérrez-Rodríguez, Marta, additional, Herranz, Rosario, additional, Burgio, Chiara, additional, Reinoso, Antonio, additional, Cuerva, Juan M., additional, Orte, Angel, additional, and González Vera, Juan Antonio, additional more...
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- 2023
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15. Flour moisture detection with an europium-based luminescent probe
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Fueyo-González, Francisco, primary, Cenit, Anabel, additional, Villodres, Rocío, additional, Saiz, Ignacio, additional, Micolonghi, Giulia, additional, Talavera, Eva M., additional, Teychené, Sébastien, additional, Rodriguez-Ruiz, Isaac, additional, Herranz, Rosario, additional, Orte, Angel, additional, Garcia-Fernandez, Emilio, additional, and González-Vera, Juan A., additional more...
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- 2023
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16. Flour moisture detection with an europium-based luminescent sensor
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Fueyo-González, Francisco, primary, Santiago-Cenit, Anabel, additional, Villodres, Rocio, additional, Sainz, Ignacio, additional, Micolonghi, Giulia, additional, Talavera, Eva M., additional, Teychené, Sébastien, additional, Rodriguez-Ruiz, Isaac, additional, Herranza, Rosario, additional, Orte, Angel, additional, Garcia-Fernandez, Emilio, additional, and Gonzalez-Vera, Juan A., additional more...
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- 2023
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17. Exchangeable Self‐Assembled Lanthanide Antennas for PLIM Microscopy.
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Ruiz‐Arias, Alvaro, Fueyo‐González, Francisco, Izquierdo‐García, Carolina, Navarro, Amparo, Gutiérrez‐Rodríguez, Marta, Herranz, Rosario, Burgio, Chiara, Reinoso, Antonio, Cuerva, Juan M., Orte, Angel, and González‐Vera, Juan A. more...
- Abstract
Lanthanides have unique photoluminescence (PL) emission properties, including very long PL lifetimes. This makes them ideal for biological imaging applications, especially using PL lifetime imaging microscopy (PLIM). PLIM is an inherently multidimensional technique with exceptional advantages for quantitative biological imaging. Unfortunately, due to the required prolonged acquisitions times, photobleaching of lanthanide PL emission currently constitutes one of the main drawbacks of PLIM. In this study, we report a small aqueous‐soluble, lanthanide antenna, 8‐methoxy‐2‐oxo‐1,2,4,5‐tetrahydrocyclopenta[de]quinoline‐3‐phosphonic acid, PAnt, specifically designed to dynamically interact with lanthanide ions, serving as exchangeable dye aimed at mitigating photobleaching in PLIM microscopy in cellulo. Thus, self‐assembled lanthanide complexes that may be photobleached during image acquisition are continuously replenished by intact lanthanide antennas from a large reservoir. Remarkably, our self‐assembled lanthanide complex clearly demonstrated a significant reduction of PL photobleaching when compared to well‐established lanthanide cryptates, used for bioimaging. This concept of exchangeable lanthanide antennas opens new possibilities for quantitative PLIM bioimaging. [ABSTRACT FROM AUTHOR] more...
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- 2024
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18. Synthesis, biological, and photophysical studies of molecular rotorbased fluorescent inhibitors of the trypanosome alternative oxidase
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Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Japan Society for the Promotion of Science, Cueto-Díaz, Eduardo J. [0000-0002-3893-3987], Fueyo-González, Francisco José, Dardonville, Christophe [0000-0001-5395-1932], Cueto-Díaz, Eduardo J., Ebiloma, Godwin U., Alfayez, Ibrahim A., Ungogo, Marzuq A., Lemgruber, Leandro, González-García, Carmen, Giron, Maria D., Salto, Rafael, Fueyo-González, Francisco, Shiba, Tomoo, González-Vera, Juan A., Ruedas Rama, Maria José, de Koning, Harry P., Dardonville, Christophe, Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Japan Society for the Promotion of Science, Cueto-Díaz, Eduardo J. [0000-0002-3893-3987], Fueyo-González, Francisco José, Dardonville, Christophe [0000-0001-5395-1932], Cueto-Díaz, Eduardo J., Ebiloma, Godwin U., Alfayez, Ibrahim A., Ungogo, Marzuq A., Lemgruber, Leandro, González-García, Carmen, Giron, Maria D., Salto, Rafael, Fueyo-González, Francisco, Shiba, Tomoo, González-Vera, Juan A., Ruedas Rama, Maria José, de Koning, Harry P., and Dardonville, Christophe more...
- Abstract
We have recently reported on the development and trypanocidal activity of a class of inhibitors of Trypanosome Alternative Oxidase (TAO) that are targeted to the mitochondrial matrix by coupling to lipophilic cations via C14 linkers to enable optimal interaction with the enzyme’s active site. This strategy resulted in a much-enhanced anti-parasite effect, which we ascribed to the greater accumulation of the compound at the location of the target protein, i.e. the mitochondrion, but to date this localization has not been formally established. We therefore synthesized a series of fluorescent analogues to visualize accumulation and distribution within the cell. The fluorophore chosen, julolidine, has the remarkable extra feature of being able to function as a viscosity sensor and might thus additionally act as a probe of the cellular glycerol that is expected to be produced when TAO is inhibited. Two series of fluorescent inhibitor conjugates incorporating a cationic julolidine-based viscosity sensor were synthesized and their photophysical and biological properties were studied. These probes display a red emission, with a high signal-to-noise ratio (SNR), using both single- and two-photon excitation. Upon incubation with T. brucei and mammalian cells, the fluorescent inhibitors 1a and 2a were taken up selectively in the mitochondria as shown by live-cell imaging. Efficient partition of 1a in functional isolated (rat liver) mitochondria was estimated to 66 ± 20% of the total. The compounds inhibited recombinant TAO enzyme in the submicromolar (1a, 2c, 2d) to low nanomolar range (2a) and were effective against WT and multidrug-resistant trypanosome strains (B48, AQP1-3 KO) in the submicromolar range. Good selectivity (SI > 29) over mammalian HEK cells was observed. However, no viscosity-related shift could be detected, presumably because the glycerol was produced cytosolically, and released through aquaglyceroporins, whereas the probe was located, virtually exclusively more...
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- 2021
19. Self-Assembled Lanthanide Antenna Glutathione Sensor for the Study of Immune Cells
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Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Junta de Andalucía, Universidad de Granada, Fueyo-González, Francisco, Espinar-Barranco, Laura, Herranz, Rosario, Alkorta, Ibon, Crovetto, Luis, Fribourg, Miguel, Paredes, Josep M., Orte, Angel, González-Vera, Juan A., Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Junta de Andalucía, Universidad de Granada, Fueyo-González, Francisco, Espinar-Barranco, Laura, Herranz, Rosario, Alkorta, Ibon, Crovetto, Luis, Fribourg, Miguel, Paredes, Josep M., Orte, Angel, and González-Vera, Juan A. more...
- Abstract
The small molecule 8-methoxy-2-oxo-1,2,4,5- tetrahydrocyclopenta[de]quinoline-3-carboxylic acid (2b) behaves as a reactive non-fluorescent Michael acceptor, which after reaction with thiols becomes fluorescent, and an efficient Eu3+ antenna, after self-assembling with this cation in water. This behavior makes 2b a highly selective GSH biosensor, which has demonstrated high potential for studies in murine and human cells of the immune system (CD4+ T, CD8 + T, and B cells) using flow cytometry. GSH can be monitored by the fluorescence of the product of addition to 2b (445 nm) or by the luminescence of Eu3+ (592 nm). 2b was able to capture baseline differences in GSH intracellular levels among murine and human CD4 + T, CD8 + T, and B cells. We also successfully used 2b to monitor intracellular changes in GSH associated with the metabolic variations governing the induction of CD4+ naï ve T cells into regulatory T cells (TREG ). more...
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- 2022
20. Selecting FRET pairs for visualizing amyloid aggregation
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European Commission, Ministerio de Ciencia, Innovación y Universidades (España), Ministerio de Educación y Formación Profesional (España), Ruiz-Arias, Alvaro, Jurado, Rocío, Fueyo-González, Francisco, Herranz, Rosario, Gálvez, N., González-Vera, Juan A., Orte, Angel, European Commission, Ministerio de Ciencia, Innovación y Universidades (España), Ministerio de Educación y Formación Profesional (España), Ruiz-Arias, Alvaro, Jurado, Rocío, Fueyo-González, Francisco, Herranz, Rosario, Gálvez, N., González-Vera, Juan A., and Orte, Angel more...
- Abstract
In a recent work, we reported a methodology for imaging the different stages of amyloid aggregation in quantitative multiparametric dual-color fluorescence lifetime imaging (FLIM) and superresolution microscopy by using a pair of dyes capable of binding aggregates and undergoing subsequent intra-aggregate energy transfer (FRET) (RuizArias et al. Sensors Actuat. B, 2022, 350:130882). In this microarticle we present the optimization process for choosing the best pair of dyes through a screening of different naphthalimides and quinolimides and other known amyloid-binding dyes. more...
- Published
- 2022
21. A FRET pair for quantitative and superresolution imaging of amyloid fibril formation
- Author
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Ministerio de Ciencia e Innovación (España), European Commission, Universidad de Granada, Ministerio de Educación y Formación Profesional (España), Ruiz-Arias, Alvaro, Jurado, R., Fueyo-González, Francisco, Herranz, Rosario, Gálvez, N., González-Vera, Juan A., Orte, Angel, Ministerio de Ciencia e Innovación (España), European Commission, Universidad de Granada, Ministerio de Educación y Formación Profesional (España), Ruiz-Arias, Alvaro, Jurado, R., Fueyo-González, Francisco, Herranz, Rosario, Gálvez, N., González-Vera, Juan A., and Orte, Angel more...
- Abstract
The presence of neuritic plaques and amyloid fibrils arising from the misfolding of certain proteins is the principal molecular indicator of neurodegenerative diseases such as Alzheimer's and Parkinson's disease. Methodologies for studying the early stages of amyloid aggregation are rapidly arising to provide a better understanding of the mechanism of fibrillization and cytotoxicity and to identify potential targets for diagnosis and therapy. The method presented here involves the simultaneous use of two different fluorophores, a quinolimide derivative and Nile Blue A. These are capable of interacting with and reporting on the formation of preamyloid aggregates and fibrils of apoferritin through fluorescence resonance energy transfer (FRET), which occurs between them, thus maximizing the contrast in detection and quantitative information of such amyloid species by using multidimensional fluorescence lifetime imaging microscopy (FLIM). more...
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- 2022
22. 8-metoxy-2-oxo-1,2-dihydrocyclopenta[de]quinoline derivates and use thereof as reagents for labelling lanthanide luminiscence
- Author
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Herranz, Rosario, Fueyo-González, Francisco, Gutiérrez-Rodríguez, Marta, Izquierdo García, Carolina, González Vera, Juan Antonio, Orte, Angel, Garcia-Fernández, Emilio, and Cano Cortés, María Victoria more...
- Subjects
Biosensores ,C07D 215/58 ,Fluorescencia ,G01N 33/52 ,G01N 21/64 ,Lantánidos ,Luminiscencia - Abstract
La presente invención se refiere al diseño y síntesis de nuevos fluoróforos con aplicación en el desarrollo de biosensores de fluorescencia, y particularmente, a derivados de 8- metoxi-2-oxo-1,2-dihidrociclopenta[de]quinolina y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos. [ES], The present invention relates to the design and synthesis of new fluorophores that can be used to develop fluorescence biosensors, and particularly, to 8-methoxy-2-oxo-1,2-dihydrocyclopenta[de]quinoline derivatives and the use thereof as reagents for labelling lanthanide luminescence. [EN], Consejo Superior de Investigaciones Científicas (CSIC), Universidad de Granada, A1 Solicitud de patente con informe sobre el estado de la técnica more...
- Published
- 2022
23. Haloacetamidas derivadas de antenas de lantanidos y su aplicacion como reactivos de marcaje de la luminiscencia de lantánidos
- Author
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Herranz Herranz, María del Rosario, Fueyo González, Francisco, and González Vera, Juan Antonio
- Subjects
Haloacetamidas ,Antenas de lantánidos ,C07D 215/24 ,G01N 33/52 ,G01N 21/64 ,Luminiscencia - Abstract
Número de publicación: 2847240. Número de solicitud: 202030074., La presente invención se refiere a haloacetamidas derivadas de quinolin-2(1 H)-onas de fórmula (1), que sensibilizan la luminiscencia de lantánidos, y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos en diversas biomoléculas, entre otras, en péptidos y proteínas., Universidad de Granada more...
- Published
- 2022
24. Selecting FRET pairs for visualizing amyloid aggregation
- Author
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Ruiz-Arias, Alvaro, Jurado, Rocío, Fueyo-González, Francisco, Herranz, Rosario, Gálvez, N., González-Vera, Juan A., Orte, Angel, European Commission, Ministerio de Ciencia, Innovación y Universidades (España), and Ministerio de Educación y Formación Profesional (España) more...
- Subjects
FLIM ,Chemistry ,STED microscopy ,Solvatochromic dyes ,General Chemistry ,Protein aggregation ,QD1-999 ,Amyloid fibrils ,Biomarkers - Abstract
This work was supported by grant CTQ2017–85658-R funded by MCIN/AEI/10.13039/501100011033/FEDER “Una manera de hacer Europa” and grants PID2019–104366RB-C22 and PID2020–114256RBI00 funded by MCIN/AEI/10.13039/ 501100011033. A.R.-A. thanks the Spanish Ministerio de Educación y Formación Profesional for an FPU Ph.D. studentship., In a recent work, we reported a methodology for imaging the different stages of amyloid aggregation in quantitative multiparametric dual-color fluorescence lifetime imaging (FLIM) and superresolution microscopy by using a pair of dyes capable of binding aggregates and undergoing subsequent intra-aggregate energy transfer (FRET) (RuizArias et al. Sensors Actuat. B, 2022, 350:130882). In this microarticle we present the optimization process for choosing the best pair of dyes through a screening of different naphthalimides and quinolimides and other known amyloid-binding dyes., Spanish Ministerio de Educación y Formación, Grant CTQ2017–85658-R funded by MCIN/AEI/10.13039/501100011033/FEDER “Una manera de hacer Europa”, Grants PID2019–104366RB-C22 and PID2020–114256RBI00 funded by MCIN/AEI/10.13039/ 501100011033 more...
- Published
- 2022
25. Self-Assembled Lanthanide Antenna Glutathione Sensor for the Study of Immune Cells
- Author
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Fueyo-González, Francisco, primary, Espinar-Barranco, Laura, additional, Herranz, Rosario, additional, Alkorta, Ibon, additional, Crovetto, Luis, additional, Fribourg, Miguel, additional, Paredes, Jose Manuel, additional, Orte, Angel, additional, and González-Vera, Juan A., additional more...
- Published
- 2022
- Full Text
- View/download PDF
26. Haloacetamidas derivadas de antenas de lantánidos y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos
- Author
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Herranz, Rosario, Fueyo-González, Francisco, González-Vera, Juan A., Herranz, Rosario, Fueyo-González, Francisco, and González-Vera, Juan A.
- Abstract
[ES] La presente invención se refiere a haloacetamidas derivadas de quinolin-2(1H)-onas de fórmula (I), que sensibilizan la luminiscencia de lantánidos, y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos en diversas biomoléculas, entre otras, en péptidos y proteínas., [EN] The present invention relates to haloacetamides derived from quinolin-2 (1H) -ones of formula (I), which sensitize lanthanide luminescence, and their application as labeling reagents for lanthanide luminescence in various biomolecules, among others, in peptides and proteins. more...
- Published
- 2021
27. Derivados de 8-metoxi-2-oxo-1,2-dihidrociclopenta[de]quinolina y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos
- Author
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Herranz, Rosario, Fueyo-González, Francisco, Gutiérrez-Rodríguez, Marta, Izquierdo García, Carolina, González-Vera, Juan A., Orte, Angel, García-Fernández, Emilio, Cano Cortés, María Victoria, Herranz, Rosario, Fueyo-González, Francisco, Gutiérrez-Rodríguez, Marta, Izquierdo García, Carolina, González-Vera, Juan A., Orte, Angel, García-Fernández, Emilio, and Cano Cortés, María Victoria more...
- Abstract
La presente invención se refiere al diseño y síntesis de nuevos fluoróforos con aplicación en el desarrollo de biosensores de fluorescencia, y particularmente, a derivados de 8- metoxi-2-oxo-1,2-dihidrociclopenta[de]quinolina y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos. [ES], The present invention relates to the design and synthesis of new fluorophores that can be used to develop fluorescence biosensors, and particularly, to 8-methoxy-2-oxo-1,2-dihydrocyclopenta[de]quinoline derivatives and the use thereof as reagents for labelling lanthanide luminescence. [EN] more...
- Published
- 2021
28. Quinolimide-based peptide biosensor for probing p25 in vitro and in living cells
- Author
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Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Agencia Estatal de Investigación (España), Consejo Superior de Investigaciones Científicas (España), Centre National de la Recherche Scientifique (France), Herranz, Rosario [0000-0002-0273-2761], Fueyo-González, Francisco, Herranz, Rosario, Plesselova, Simona, Giron, Maria D., Salto, Rafael, Paredes, Josep M., Orte, Angel, Morris, May C., González-Vera, Juan A., Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Agencia Estatal de Investigación (España), Consejo Superior de Investigaciones Científicas (España), Centre National de la Recherche Scientifique (France), Herranz, Rosario [0000-0002-0273-2761], Fueyo-González, Francisco, Herranz, Rosario, Plesselova, Simona, Giron, Maria D., Salto, Rafael, Paredes, Josep M., Orte, Angel, Morris, May C., and González-Vera, Juan A. more...
- Abstract
CDK5 kinase is activated through interactions with different partners including the p35/p25 regulators. Active CDK5 plays a key role in several neuronal functions and its hyperactivity contributes to a variety of neurodegenerative processes and several human cancers, in particular glioblastomas and neuroblastomas. In order to probe partners that interact with CDK5, we designed and synthesized fluorescent quinolimide-labelled peptides derived from the C-helix of CDK5, which were implemented to probe CDK5 partners in vitro and by in cellulo imaging in U87 glioblastoma and N2a neuroblastoma cells. Ectopic expression of a NIR fluorescent protein miRFP670 fusion with p25 (p25-miRFP670) in N2a cells induced FRET between a quinolimide-labelled peptide biosensor and p25-miRFP670, and fluorescence intensity was proportional to the expression level of p25, thereby demonstrating the potential of the quinolimide-labelled peptide biosensor to report on p25 relative abundance. more...
- Published
- 2021
29. Biosensor luminiscente basado en péptidos para el estudio de la actividad de la quinasa en células T.
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Salto Girón, Carmen, Priego Marín, Angélica, Reinoso Rodríguez, Antonio, Fueyo González, Francisco, Fribourg, Miguel, Orte, Ángel, and González Vera, Juan Antonio
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- 2024
30. Fluorescence mechanism switching from ICT to PET by substituent 1 chemical manipulation: Macrophage cytoplasm imaging probes
- Author
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Fueyo-González, Francisco, González-Vera, Juan A., Alkorta, Ibon, Infantes, L., Jimeno, M. Luisa, Fernández-Gutiérrez, Mar, González-García, M. Carmen, Orte, Angel, Herranz, Rosario, Agencia Estatal de Investigación (España), Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), Consejo Superior de Investigaciones Científicas (España), Comunidad de Madrid, Fueyo-González, Francisco, González-Vera, Juan A., Alkorta, Ibon [0000-0001-6876-6211], Infantes, Lourdes, Jimeno, M. Luisa, Fernández-Gutiérrez, Mar, González-García, M. Carmen, Orte, Angel, Herranz, Rosario, and Alkorta, Ibon more...
- Subjects
Naphthalimide derivatives ,Fluorescence probes ,pH sensors ,Quinolimide derivatives ,Macrophage dyes ,Off-On water sensors - Abstract
The lack of polarity sensing fluorophores with OFF-ON features when increasing the environment polarity has limited the monitoring of biological processes that involve an increase in local hydrophilicity. In this work, replacement of a hydroxyl group by a dimethylamino group transformed solvatochromic ICT naphthalimide- and quinolimide-based fluorophores into reversed solvatochromic ones, with higher emission in polar than in apolar environments. Excited-state dynamics studies, TD-DFT calculations, X-ray and NMR support the existence of a folded conformation for the 2-(dimethylamino)ethyl chain upon the imide ring in apolar solvents, where the dimethylamino group would quench the fluorescence by a PET effect, while in polar solvents the chain has an extended conformation, where the PET is hindered. These PET fluorophores have given rise to H2O and pH sensors in organic solvents as well as to bright macrophage cytoplasm imaging probes., The work was supported by the Spanish Ministerio de Economía y Competividad grants SAF2012-32209, FU2015-67284-R, CTQ2017-85658-R, CTQ2015-63997-C2, the CSIC grant 201580E073, and Comunidad Autónoma de Madrid (S2013/MIT2841, Fotocarbon) more...
- Published
- 2019
31. Haloacetamides derived from lanthanide antennas and use thereof as reagents for labelling lanthanide luminiscence
- Author
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Herranz, Rosario, Fueyo-González, Francisco, and González-Vera, Juan A.
- Abstract
[ES] La presente invención se refiere a haloacetamidas derivadas de quinolin-2(1H)-onas de fórmula (I), que sensibilizan la luminiscencia de lantánidos, y su aplicación como reactivos de marcaje de la luminiscencia de lantánidos en diversas biomoléculas, entre otras, en péptidos y proteínas., [EN] The present invention relates to haloacetamides derived from quinolin-2 (1H) -ones of formula (I), which sensitize lanthanide luminescence, and their application as labeling reagents for lanthanide luminescence in various biomolecules, among others, in peptides and proteins., Consejo Superior de Investigaciones Científicas (CSIC), Universidad de Granada, B2 Patente con examen previo more...
- Published
- 2020
32. Naphthalimide-based macrophage nucleus imaging probes
- Author
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Ministerio de Economía y Competitividad (España), Agencia Estatal de Investigación (España), European Commission, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, Fernández-Gutiérrez, Mar, González-Vera, Juan A., García-Puentes, Diego [0000-0002-8093-4334], Herranz, Rosario [0000-0002-0273-2761], Orte, Angel, García-Puentes, Diego, Herranz, Rosario, Ministerio de Economía y Competitividad (España), Agencia Estatal de Investigación (España), European Commission, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, Fernández-Gutiérrez, Mar, González-Vera, Juan A., García-Puentes, Diego [0000-0002-8093-4334], Herranz, Rosario [0000-0002-0273-2761], Orte, Angel, García-Puentes, Diego, and Herranz, Rosario more...
- Abstract
The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues (PET fluorophores) decrease their solvent polarity sensitivity or even reversed them to solvatochromic fluorophores. These fluorophores resulted macrophage nucleus imaging probes, which bind DNA as intercalants and showed low cytotoxicity in human cancer cells more...
- Published
- 2020
33. Smart lanthanide antennas for sensing water
- Author
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Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, Infantes, Lourdes [0000-0001-6932-4212], González-Vera, Juan A., Herranz, Rosario [0000-0002-0273-2761], García-Fernández, Emilio, Martínez, David, Infantes, L., Orte, Angel, Herranz, Rosario, Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, Infantes, Lourdes [0000-0001-6932-4212], González-Vera, Juan A., Herranz, Rosario [0000-0002-0273-2761], García-Fernández, Emilio, Martínez, David, Infantes, L., Orte, Angel, and Herranz, Rosario more...
- Abstract
Two new families of lanthanide antennas are described. 8-Methoxy- 4,5-dihydrocyclopenta[de]quinolin-2(1H)-one phosphonates or carboxylates behave as selective antennas exhibiting Eu3+ luminescence in organic solvents, while quinolin-2(1H)-one analogues selectively sensitize the Tb3+ emission. These emissions are quenched by H2O addition. Based on this behaviour, the new lanthanide antennas can be used as highly sensitive water sensors. more...
- Published
- 2020
34. Environment-Sensitive Probes for Illuminating Amyloid Aggregation In Vitro and in Zebrafish
- Author
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Fueyo-González, Francisco, primary, González-Vera, Juan A., additional, Alkorta, Ibon, additional, Infantes, Lourdes, additional, Jimeno, Maria Luisa, additional, Aranda, Paula, additional, Acuña-Castroviejo, Dario, additional, Ruiz-Arias, Alvaro, additional, Orte, Angel, additional, and Herranz, Rosario, additional more...
- Published
- 2020
- Full Text
- View/download PDF
35. Smart lanthanide antennas for sensing water
- Author
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Fueyo-González, Francisco, primary, Garcia-Fernandez, Emilio, additional, Martínez, David, additional, Infantes, Lourdes, additional, Orte, Angel, additional, González-Vera, Juan A., additional, and Herranz, Rosario, additional more...
- Published
- 2020
- Full Text
- View/download PDF
36. Nuevos fluoróforos con aplicación en el desarrollo de biosensores fluorescentes de proteínas
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Fueyo González, Francisco José, Herranz Herranz, María Rosario, González Vera, Antonio, Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica, and Universidad de Alcalá. Programa de Doctorado en Química Médica more...
- Subjects
Diseño. Síntesis y Estudio Nuevos Fármacos ,Chemistry ,Fluorimetría ,Química ,Química de Los Colorantes - Abstract
Esta tesis se ha realizado en el Instituto de Química Médica del CSIC, en el marco de los proyectos “Búsqueda de moduladores de interacciones proteína-proteína. Nuevas vías hacia fármacos novedosos” (SAF2012-32209) y “Herramientas para el estudio de interacciones proteína-proteína: Aplicación al estudio y validación de la proteína DREAM como diana terapéutica” (BFU2015-67284-R) y se planteó con el objetivo general de desarrollo de sensores de fluorescencia como herramientas para el estudio de interacciones proteína-proteína. Para la consecución de este objetivo se ha diseñado, sintetizado y caracterizado una nueva familia de fluoróforos derivados de quinolimida altamente fluorogénicos y solvatocrómicos, con propiedades fotofísicas superiores a las de fluoróforos análogos conocidos. La manipulación química de los sustituyentes sobre el esqueleto de quinolimida ha permitido modular las propiedades fotofísicas para la obtención de fluoróforos con emisión de fluorescencia por transferencia de carga (ITC), que han resultado muy solvatocrómicos, o por transferencia fotoinducida de electrones (PET), que presentan solvatocromismo inverso. Los fluoróforos solvatocrómicos, sensibles a la polaridad del medio, han mostrado alto potencial como sensores de fluorescencia de interacciones proteína-proteína, tales como la interacción de la quinasa CDK5 con su proteína reguladora p25 o la agregación del péptido -amiloide. Mientras que, los fluoróforos PET han mostrado potencial como sensores de agua y se han obtenido sensores selectivos del citoplasma o del núcleo en macrófagos, donde interaccionan como intercalantes con el ADN. Por otra parte, se han obtenido derivados de dihidrociclopenta[de]quinolin-2-ona portadoras de grupos fosfonato o carboxilato que se coordinan con el catión Eu3+ y, tras su excitación UV, transfieren energía al catión, actuando como antenas de la luminiscencia del lantánido, que, dependiendo de los sustituyentes, han mostrado alto potencial como sensores luminiscentes de agua o biotioles. La simplificación de la estructura de estas dihidrociclopenta[de]quinolin-2-onas para dar lugar a quinolin-2-onas, análogas de carbostirilo, ha conducido a antenas selectivas de la emisión de Tb3+, que también han mostrado aplicación como sensores de agua. En resumen, se ha diseñado, sintetizado y estudiado una nueva familia de fluoróforos y de antenas de lantánidos que han demostrado un alto potencial como herramientas para el desarrollo de novedosos biosensores de fluorescencia. more...
- Published
- 2019
37. Naphthalimide-Based Fluorescence Macrophage Sensors. Localization Selectivity through Substituent Chemical Manipulation
- Author
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Herranz, Rosario, Fueyo-González, Francisco, González-Verdejo, Juan A., Orte, Angel, Fernández-Gutiérrez, Mar, Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), and Consejo Superior de Investigaciones Científicas (España) more...
- Abstract
The 1,8-naphthalimide scaffold is found among the most fruitful structures in the design of fluorophores with application in the development of fluorescence biosensors, due to its favorable photophysical properties, such as strong absorption and emission, large Stokes shifts, and photostability[1]. Considering that introduction of a nitrogen atom into the 1,8-naphtalimide skeleton could red-shift the fluorescence emission and increase water solubility, we have recently studied the design, synthesis and photophysical properties of 8-methoxy-4,5-quinolimides[2]. The photophysical properties of both scaffolds depend on the attached substituents and can be tuned by chemical manipulation. We have synthesized and will communicate new naphthalimide (A) and quinolimide (B) derivatives with a dimethylaminoethyl chain at the imide nitrogen atom, which behave as macrophage fluorescence sensors. Depending on the nature of the R substituent, these fluorophores can be used to imagine either the macrophage cytoplasm or the nucleus. The nucleus sensors bind DNA as intercalants., The work was supported by the Spanish Ministerio de Economía y Competividad grants SAF2012-32209, FU2015-67284-R, CTQ2017-85658-R, and the CSIC grant 201580E07 more...
- Published
- 2019
38. Naphthalimide-Based Fluorescence Macrophage Sensors. Localization Selectivity through Substituent Chemical Manipulation
- Author
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Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), Consejo Superior de Investigaciones Científicas (España), Herranz, Rosario, Fueyo-González, Francisco, González-Verdejo, Juan A., Orte, Angel, Fernández-Gutiérrez, Mar, Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), Consejo Superior de Investigaciones Científicas (España), Herranz, Rosario, Fueyo-González, Francisco, González-Verdejo, Juan A., Orte, Angel, and Fernández-Gutiérrez, Mar more...
- Abstract
The 1,8-naphthalimide scaffold is found among the most fruitful structures in the design of fluorophores with application in the development of fluorescence biosensors, due to its favorable photophysical properties, such as strong absorption and emission, large Stokes shifts, and photostability[1]. Considering that introduction of a nitrogen atom into the 1,8-naphtalimide skeleton could red-shift the fluorescence emission and increase water solubility, we have recently studied the design, synthesis and photophysical properties of 8-methoxy-4,5-quinolimides[2]. The photophysical properties of both scaffolds depend on the attached substituents and can be tuned by chemical manipulation. We have synthesized and will communicate new naphthalimide (A) and quinolimide (B) derivatives with a dimethylaminoethyl chain at the imide nitrogen atom, which behave as macrophage fluorescence sensors. Depending on the nature of the R substituent, these fluorophores can be used to imagine either the macrophage cytoplasm or the nucleus. The nucleus sensors bind DNA as intercalants. more...
- Published
- 2019
39. Fluorescence mechanism switching from ICT to PET by substituent 1 chemical manipulation: Macrophage cytoplasm imaging probes
- Author
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Agencia Estatal de Investigación (España), Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), Consejo Superior de Investigaciones Científicas (España), Comunidad de Madrid, Fueyo-González, Francisco, González-Vera, Juan A., Alkorta, Ibon [0000-0001-6876-6211], Infantes, Lourdes, Jimeno, M. Luisa, Fernández-Gutiérrez, Mar, González-García, M. Carmen, Orte, Angel, Herranz, Rosario, Alkorta, Ibon, Infantes, L., Agencia Estatal de Investigación (España), Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), Consejo Superior de Investigaciones Científicas (España), Comunidad de Madrid, Fueyo-González, Francisco, González-Vera, Juan A., Alkorta, Ibon [0000-0001-6876-6211], Infantes, Lourdes, Jimeno, M. Luisa, Fernández-Gutiérrez, Mar, González-García, M. Carmen, Orte, Angel, Herranz, Rosario, Alkorta, Ibon, and Infantes, L. more...
- Abstract
The lack of polarity sensing fluorophores with OFF-ON features when increasing the environment polarity has limited the monitoring of biological processes that involve an increase in local hydrophilicity. In this work, replacement of a hydroxyl group by a dimethylamino group transformed solvatochromic ICT naphthalimide- and quinolimide-based fluorophores into reversed solvatochromic ones, with higher emission in polar than in apolar environments. Excited-state dynamics studies, TD-DFT calculations, X-ray and NMR support the existence of a folded conformation for the 2-(dimethylamino)ethyl chain upon the imide ring in apolar solvents, where the dimethylamino group would quench the fluorescence by a PET effect, while in polar solvents the chain has an extended conformation, where the PET is hindered. These PET fluorophores have given rise to H2O and pH sensors in organic solvents as well as to bright macrophage cytoplasm imaging probes. more...
- Published
- 2019
40. Conjugates of 2,4-dihydroxybenzoate and salicylhydroxamate and lipocations display potent antiparasite effects by efficiently targeting the Trypanosoma brucei and Trypanosoma congolense mitochondrion
- Author
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Fueyo González, Francisco José, Ebiloma, Godwin U., Izquierdo García, Carolina, Bruggeman, Victor, Sánchez Villamañán, José María, Donachie, Anne, Balogun, Emmanuel Oluwadare, Inaoka, Daniel Ken, Shiba, Tomoo, Harada, Shigeharu, Kita, Kiyoshi, de Koning, Harry P., and Dardonville, Christophe more...
- Abstract
We investigated a chemical strategy to boost the trypanocidal activity of 2,4-dihydroxybenzoic acid (2,4-DHBA)- and salicylhydroxamic acid (SHAM)-based trypanocides with triphenylphosphonium and quinolinium lipophilic cations (LC). Three series of LC conjugates were synthesized that were active in the submicromolar (5a–d and 10d–f) to low nanomolar (6a–f) range against wild-type and multidrug resistant strains of African trypanosomes (Trypanosoma brucei brucei and T. congolense). This represented an improvement in trypanocidal potency of at least 200-fold, and up to >10 000-fold, compared with that of non-LC-coupled parent compounds 2,4-DHBA and SHAM. Selectivity over human cells was >500 and reached >23 000 for 6e. Mechanistic studies showed that 6e did not inhibit the cell cycle but affected parasite respiration in a dose-dependent manner. Inhibition of trypanosome alternative oxidase and the mitochondrial membrane potential was also studied for selected compounds. We conclude that effective mitochondrial targeting greatly potentiated the activity of these series of compounds. more...
- Published
- 2017
41. Back Cover: Exchangeable Self‐Assembled Lanthanide Antennas for PLIM Microscopy (Angew. Chem. Int. Ed. 6/2024).
- Author
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Ruiz‐Arias, Alvaro, Fueyo‐González, Francisco, Izquierdo‐García, Carolina, Navarro, Amparo, Gutiérrez‐Rodríguez, Marta, Herranz, Rosario, Burgio, Chiara, Reinoso, Antonio, Cuerva, Juan M., Orte, Angel, and González‐Vera, Juan A. more...
- Abstract
The article discusses a significant advancement in quantitative PLIM bioimaging called PAnt (phosphonic acid antenna). PAnt is a small water-soluble lanthanide antenna that can self-assemble with lanthanide ions, serving as an exchangeable probe to overcome photobleaching in PLIM microscopy in cellulo. This allows for continuous replenishment of lanthanide complexes that may be photobleached during acquisition, resulting in remarkable photostability compared to traditional lanthanide cryptates. The research was conducted by Angel Orte, Juan A. González-Vera, and their team, and the article includes artwork by M. Eugenio Vázquez from the University of Santiago de Compostela. [Extracted from the article] more...
- Published
- 2024
- Full Text
- View/download PDF
42. Rücktitelbild: Exchangeable Self‐Assembled Lanthanide Antennas for PLIM Microscopy (Angew. Chem. 6/2024).
- Author
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Ruiz‐Arias, Alvaro, Fueyo‐González, Francisco, Izquierdo‐García, Carolina, Navarro, Amparo, Gutiérrez‐Rodríguez, Marta, Herranz, Rosario, Burgio, Chiara, Reinoso, Antonio, Cuerva, Juan M., Orte, Angel, and González‐Vera, Juan A. more...
- Subjects
- *
ANTENNAS (Electronics) , *PHOSPHONIC acids , *MICROSCOPY , *IONS - Abstract
The article discusses a significant advancement in quantitative PLIM bioimaging called PAnt (phosphonic acid antenna). PAnt is a small water-soluble lanthanide antenna that can self-assemble with lanthanide ions, serving as an exchangeable probe to overcome photobleaching in PLIM microscopy in cellulo. The use of PAnt allows for continuous replenishment of lanthanide complexes that may be photobleached during acquisition, resulting in remarkable photostability compared to traditional lanthanide cryptates. The research was conducted by Angel Orte, Juan A. González-Vera, and their colleagues. [Extracted from the article] more...
- Published
- 2024
- Full Text
- View/download PDF
43. Conjugates of 2,4-Dihydroxybenzoate and Salicylhydroxamate and Lipocations Display Potent Antiparasite Effects by Efficiently Targeting the Trypanosoma brucei and Trypanosoma congolense Mitochondrion
- Author
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Ministerio de Economía y Competitividad (España), Fueyo-González, Francisco, de Koning, Harry P., Ebiloma, Godwin U., Izquierdo García, Carolina, Bruggeman, V., Sánchez Villamañán, J. M., Donachie, Anne, Balogun, Emmanuel O., Inaoka, D. K., Shiba, T., Harada, S., Dardonville, Christophe, Ministerio de Economía y Competitividad (España), Fueyo-González, Francisco, de Koning, Harry P., Ebiloma, Godwin U., Izquierdo García, Carolina, Bruggeman, V., Sánchez Villamañán, J. M., Donachie, Anne, Balogun, Emmanuel O., Inaoka, D. K., Shiba, T., Harada, S., and Dardonville, Christophe more...
- Abstract
We investigated a chemical strategy to boost the trypanocidal activity of 2,4-dihydroxybenzoic acid (2,4-DHBA)- and salicylhydroxamic acid (SHAM)-based trypanocides with triphenylphosphonium and quinolinium lipophilic cations (LC). Three series of LC conjugates were synthesized that were active in the submicromolar (5a-d and 10d-f) to low nanomolar (6a-f) range against wild-type and multidrug resistant strains of African trypanosomes (Trypanosoma brucei brucei and T. congolense). This represented an improvement in trypanocidal potency of at least 200-fold, and up to >10 000-fold, compared with that of non-LC-coupled parent compounds 2,4-DHBA and SHAM. Selectivity over human cells was >500 and reached >23 000 for 6e. Mechanistic studies showed that 6e did not inhibit the cell cycle but affected parasite respiration in a dose-dependent manner. Inhibition of trypanosome alternative oxidase and the mitochondrial membrane potential was also studied for selected compounds. We conclude that effective mitochondrial targeting greatly potentiated the activity of these series of compounds. more...
- Published
- 2017
44. Targeting the Trypanosome Alternative Oxidase (TAO) as Promising Chemotherapeutic Approach for African Trypanosomiasis
- Author
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Dardonville, Christophe, primary, Fueyo González, Francisco José, additional, Izquierdo García, Carolina, additional, Díaz Ayuga, Teresa, additional, Ebiloma, Godwin, additional, Balogun, Emmanuel, additional, Kita, Kiyoshi, additional, and de Koning, Harry, additional more...
- Published
- 2017
- Full Text
- View/download PDF
45. Mitochondrion targeted trypanosome alternative oxidase inhibitors as chemotherapeutic agents against T. brucei
- Author
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Dardonville, Christophe, Fueyo-González, Francisco, Díaz Ayuga, Teresa, Ebiloma, Godwin U., Izquierdo García, C., Bruggeman, V., Sánchez Villamañán, J. M., Donachie, Anne, Balogun, Emmanuel O., Kita, Kiyoshi, Koning, Harry P. de, Dardonville, Christophe, Fueyo-González, Francisco, Díaz Ayuga, Teresa, Ebiloma, Godwin U., Izquierdo García, C., Bruggeman, V., Sánchez Villamañán, J. M., Donachie, Anne, Balogun, Emmanuel O., Kita, Kiyoshi, and Koning, Harry P. de more...
- Abstract
During their life-cycle, trypanosomes adapt their energy metabolism to the availability of nutrients in their environment. Hence, procyclic forms of T. brucei have a fully functional respiratory chain and synthesize ATP by oxidative phosphorylation in the mitochondrion. In contrast, respiration of bloodstream forms (BSF) of T. brucei (i.e. the human-infective form) relies exclusively on glycolysis for energy production. The trypanosome alternative oxidase (TAO) is the sole terminal oxidase enzyme to re-oxidize NADH accumulated during glycolysis. It is a cyanide-resistant and cytochrome-independent ubiquinol oxidase which is sensitive to the specific inhibitors salicylhydroxamic acid (SHAM) and ascofuranone. This enzyme which is essential to the viability of BSF trypanosomes and has no counterpart in the mammalian host is a potential target for chemotherapy. To boost the activity of TAO inhibitors against T. brucei, we investigated a chemical strategy consisting in the conjugation of the inhibitor with lipophilic cations (LC) that can cross lipid bilayers by non-carrier mediated transport, and thus accumulate specifically into the mitochondrion, driven by the plasma and mitochondrial transmembrane potentials (negative inside). This design afforded several LC¿TAO inhibitor conjugates active in the submicromolar to low nanomolar range against wild type and resistant strains of African trypanosomes (T. b. brucei, T. congolense). Selectivity over human cells was >500. Studies of the effects on purified TAO, parasite respiration, mitochondrial membrane potential (¿m), and cell cycle suggest that TAO is a likely target of the compounds in vivo. more...
- Published
- 2016
46. Highly solvatochromic and tunable fluorophores based on a 4,5-quinolimide scaffold: Novel CDK5 probes
- Author
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Ministerio de Economía y Competitividad (España), Consejo Superior de Investigaciones Científicas (España), European Commission, González-Vera, Juan A., Fueyo-González, Francisco, Alkorta, Ibon, Peyressatre, Marion, Morris, May C., Herranz, Rosario, Ministerio de Economía y Competitividad (España), Consejo Superior de Investigaciones Científicas (España), European Commission, González-Vera, Juan A., Fueyo-González, Francisco, Alkorta, Ibon, Peyressatre, Marion, Morris, May C., and Herranz, Rosario more...
- Abstract
Novel 4,5-quinolimide-based fluorophores are more solvatochromic and red-shifted than known naphthalimide analogues. Conjugation of one of these fluorophores to a peptide derived from CDK5 kinase demonstrated its sensitivity for monitoring the interaction with its regulatory partner p25. Introduction of the quinolimide-labelled peptide into living glioblastoma cells probed the interaction with endogenous p25. more...
- Published
- 2016
47. Highly solvatochromic and tunable fluorophores based on a 4,5-quinolimide scaffold: novel CDK5 probes
- Author
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González-Vera, Juan A., primary, Fueyo-González, Francisco, additional, Alkorta, Ibon, additional, Peyressatre, Marion, additional, Morris, May C., additional, and Herranz, Rosario, additional
- Published
- 2016
- Full Text
- View/download PDF
48. Smart lanthanide antennas for sensing water
- Author
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Emilio Garcia-Fernandez, Francisco Fueyo-González, David Martínez, Juan A. González-Vera, Lourdes Infantes, Rosario Herranz, Angel Orte, Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, Infantes, Lourdes [0000-0001-6932-4212], González-Vera, Juan A., Herranz, Rosario [0000-0002-0273-2761], Infantes, Lourdes, and Herranz, Rosario more...
- Subjects
Lanthanide ,Materials science ,Materials Chemistry ,Metals and Alloys ,Ceramics and Composites ,General Chemistry ,Luminescence ,Photochemistry ,Catalysis ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,Highly sensitive - Abstract
Two new families of lanthanide antennas are described. 8-Methoxy- 4,5-dihydrocyclopenta[de]quinolin-2(1H)-one phosphonates or carboxylates behave as selective antennas exhibiting Eu3+ luminescence in organic solvents, while quinolin-2(1H)-one analogues selectively sensitize the Tb3+ emission. These emissions are quenched by H2O addition. Based on this behaviour, the new lanthanide antennas can be used as highly sensitive water sensors., Spanish Ministerio de Economia y Competividad SAF2012-32209 FU2015-67284-R, Ministerio de Ciencia e Innovacion/Agencia Estatal de Investigacion/European Regional Development Fund CTQ2017-85658-R CTQ2015-63997-C2, Consejo Superior de Investigaciones Cientificas (CSIC) 201580E073 more...
- Published
- 2020
49. Environment-Sensitive Probes for Illuminating Amyloid Ag-gregation in vitro and in Zebrafish
- Author
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Angel Orte, Paula Aranda, Darío Acuña-Castroviejo, Rosario Herranz, Lourdes Infantes, María Luisa Jimeno, Juan A. González-Vera, Ibon Alkorta, Álvaro Ruiz-Arias, Francisco Fueyo-González, Ministerio de Economía y Competitividad (España), Ministerio de Ciencia, Innovación y Universidades (España), Comunidad de Madrid, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, González-Vera, Juan A, Alkorta, Ibon [0000-0001-6876-6211], Orte, Angel [0000-0003-1905-4183], Jimeno, Maria Luisa [0000-0001-6784-162X], Herranz, Rosario [0000-0002-0273-2761], Alkorta, Ibon, Orte, Angel, Jimeno, Maria Luisa, and Herranz, Rosario more...
- Subjects
Amyloid ,Bioengineering ,Peptide ,02 engineering and technology ,01 natural sciences ,Inclusion bodies ,Protein–protein interaction ,Amyloid disease ,In vivo ,Fluorescence microscope ,Quinolimide derivatives ,Zebrafish imaging ,Instrumentation ,Zebrafish ,Amyloid aggregation ,Fluid Flow and Transfer Processes ,chemistry.chemical_classification ,biology ,Process Chemistry and Technology ,010401 analytical chemistry ,β-amyloid peptide aggregation sensing ,Two-photon excitation imaging ,021001 nanoscience & nanotechnology ,biology.organism_classification ,0104 chemical sciences ,chemistry ,ratiometric Fluorescence lifetime imaging microscopy ,Environment-sensitive probes ,Biophysics ,Fluorescent probes ,0210 nano-technology - Abstract
The aberrant aggregation of certain peptides and proteins, forming extracellular plaques of fibrillar material, is one of the hallmarks of amyloid diseases, such as Alzheimer’s and Parkinson’s. Herein, we have designed a new family of solvatochromic dyes based on the 9-aminoquinolimide moiety capable of reporting during the early stages of amyloid fibrillization. We have rationally improved the photophysical properties of quinolimides by placing diverse amino groups at the 9-position of the quinolimide core, leading to higher solvatochromic and fluorogenic character and higher lifetime dependence on the hydrophobicity of the environment, which represent excellent properties for the sensitive detection of prefibrillar aggregates. Among the different probes prepared, the 9-azetidinylquinolimide derivative showed striking performance in the following β-amyloid peptide (Aβ) aggregation in solution in real time and identifying the formation of different types of early oligomers of Aβ, the most important species linked to cytotoxicity, using novel, multidimensional fluorescence microscopy, with one- or two-photon excitation. Interestingly, the new dye allowed the visualization of proteinaceous inclusion bodies in a zebrafish model with neuronal damage induced by the neurotoxin 1-methyl-4- phenyl-1,2,3,6-tetrahydropyridine. Our results support the potential of the novel fluorophores as powerful tools to follow amyloid aggregation using fluorescence microscopy in vivo, revealing heterogeneous populations of different types of aggregates and, more broadly, to study protein interactions., The work was supported by the Spanish Ministerio de Economía y Competividad grants SAF2012-32209, FU2015-67284-R, CTQ2017-85658-R, Ministerio de Ciencia, Innovación y Univer-sidades grant PGC2018-094644-B-C22, CSIC grant 201580E073, and Comunidad Autónoma de Madrid grant P2018/EMT-4329 AIRTEC-CM. more...
- Published
- 2020
50. Naphthalimide-based macrophage nucleus imaging probes
- Author
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Juan A. González-Vera, Francisco Fueyo-González, Angel Orte, Mar Fernández-Gutiérrez, Rosario Herranz, Diego García-Puentes, Ministerio de Economía y Competitividad (España), Agencia Estatal de Investigación (España), European Commission, Consejo Superior de Investigaciones Científicas (España), Fueyo-González, Francisco, Fernández-Gutiérrez, Mar, González-Vera, Juan A., García-Puentes, Diego [0000-0002-8093-4334], Herranz, Rosario [0000-0002-0273-2761], García-Puentes, Diego, and Herranz, Rosario more...
- Subjects
Azetidine ,Cyclohexylamine ,01 natural sciences ,DNA intercalants ,Structure-Activity Relationship ,03 medical and health sciences ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,medicine ,Quinolimide derivatives ,Humans ,Cytotoxicity ,Fluorescent Dyes ,030304 developmental biology ,Cell Nucleus ,Pharmacology ,0303 health sciences ,010405 organic chemistry ,Macrophages ,Macrophage imaging probes ,Organic Chemistry ,Solvatochromism ,DNA ,General Medicine ,Combinatorial chemistry ,Intercalating Agents ,Molecular Imaging ,0104 chemical sciences ,Naphthalimides ,medicine.anatomical_structure ,Naphthalimide derivatives ,chemistry ,Fluorescence probes ,Ethylamine ,Nucleus ,Human cancer - Abstract
The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues (PET fluorophores) decrease their solvent polarity sensitivity or even reversed them to solvatochromic fluorophores. These fluorophores resulted macrophage nucleus imaging probes, which bind DNA as intercalants and showed low cytotoxicity in human cancer cells, The work was supported by grants SAF2012-32209, FU2015-67284-R, CTQ2017-85658-R form the Spanish Ministerio de Economía y Competividad, Agencia Estatal de Investigación and the European Regional Development Fund; and the CSIC grant 201580E073 more...
- Published
- 2020
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