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Eva M. García-Frutos
Instituto de Ciencia de Materiales de Madrid, CSIC, Cantoblanco, 28049 Madrid, Spain

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Research article
Published: 02 April 2021 in ACS Chemical Neuroscience
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Multitarget-directed ligands (MTDLs) are considered a promising therapeutic strategy to address the multifactorial nature of Alzheimer’s disease (AD). Novel MTDLs have been designed as inhibitors of human acetylcholinesterases/butyrylcholinesterases, monoamine oxidase A/B, and glycogen synthase kinase 3β and as calcium channel antagonists via the Biginelli multicomponent reaction. Among these MTDLs, (±)-BIGI-3h was identified as a promising new hit compound showing in vitro balanced activities toward the aforementioned recognized AD targets. Additional in vitro studies demonstrated antioxidant effects and brain penetration, along with the ability to inhibit the aggregation of both τ protein and β-amyloid peptide. The in vivo studies have shown that (±)-BIGI-3h (10 mg/kg intraperitoneally) significantly reduces scopolamine-induced cognitive deficits.

ACS Style

Lhassane Ismaili; Julie Monnin; Adeline Etievant; Raquel L. Arribas; Lucía Viejo; Bernard Refouvelet; Ondrej Soukup; Jana Janockova; Vendula Hepnarova; Jan Korabecny; Tomas Kucera; Daniel Jun; Rudolf Andrys; Kamil Musilek; Aurelie Baguet; Eva M. García-Frutos; Angela De Simone; Vincenza Andrisano; Manuela Bartolini; Cristóbal De Los Ríos; José Marco-Contelles; Emmanuel Haffen. (±)-BIGI-3h: Pentatarget-Directed Ligand combining Cholinesterase, Monoamine Oxidase, and Glycogen Synthase Kinase 3β Inhibition with Calcium Channel Antagonism and Antiaggregating Properties for Alzheimer’s Disease. ACS Chemical Neuroscience 2021, 12, 1328 -1342.

AMA Style

Lhassane Ismaili, Julie Monnin, Adeline Etievant, Raquel L. Arribas, Lucía Viejo, Bernard Refouvelet, Ondrej Soukup, Jana Janockova, Vendula Hepnarova, Jan Korabecny, Tomas Kucera, Daniel Jun, Rudolf Andrys, Kamil Musilek, Aurelie Baguet, Eva M. García-Frutos, Angela De Simone, Vincenza Andrisano, Manuela Bartolini, Cristóbal De Los Ríos, José Marco-Contelles, Emmanuel Haffen. (±)-BIGI-3h: Pentatarget-Directed Ligand combining Cholinesterase, Monoamine Oxidase, and Glycogen Synthase Kinase 3β Inhibition with Calcium Channel Antagonism and Antiaggregating Properties for Alzheimer’s Disease. ACS Chemical Neuroscience. 2021; 12 (8):1328-1342.

Chicago/Turabian Style

Lhassane Ismaili; Julie Monnin; Adeline Etievant; Raquel L. Arribas; Lucía Viejo; Bernard Refouvelet; Ondrej Soukup; Jana Janockova; Vendula Hepnarova; Jan Korabecny; Tomas Kucera; Daniel Jun; Rudolf Andrys; Kamil Musilek; Aurelie Baguet; Eva M. García-Frutos; Angela De Simone; Vincenza Andrisano; Manuela Bartolini; Cristóbal De Los Ríos; José Marco-Contelles; Emmanuel Haffen. 2021. "(±)-BIGI-3h: Pentatarget-Directed Ligand combining Cholinesterase, Monoamine Oxidase, and Glycogen Synthase Kinase 3β Inhibition with Calcium Channel Antagonism and Antiaggregating Properties for Alzheimer’s Disease." ACS Chemical Neuroscience 12, no. 8: 1328-1342.

Rapid communication
Published: 26 February 2021 in Chemical Research in Toxicology
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N-Propargylamines are useful synthetic scaffolds for the synthesis of bioactive molecules, and in addition, they possess important pharmacological activities. We obtained several neuroprotective molecules, chiral 1,2-amino alcohols and 1,2-diamines, able to reduce by almost 70% the rotenone and oligomycin A-induced damage in SH-SY5Y cells. Furthermore, some molecules assessed also counteracted the toxicity evoked by the Ser/Thr phosphatase inhibitor okadaic acid. Before extrapolating these data to preclinical studies, we analyze the molecules through an in silico prediction system to detect carcinogenicity risk or other toxic effects. In light of these promising results, these molecules may be considered as a lead family of neuroprotective and relatively safe compounds.

ACS Style

Eva Ramos; Rocío Lajarín-Cuesta; Raquel L. Arribas; Eva M. García-Frutos; Laura González-Lafuente; Javier Egea; Cristóbal De Los Ríos; Alejandro Romero. In Silico Prediction of the Toxic Potential of Neuroprotective Bifunctional Molecules Based on Chiral N-Propargyl-1,2-amino Alcohol Derivatives. Chemical Research in Toxicology 2021, 34, 1245 -1249.

AMA Style

Eva Ramos, Rocío Lajarín-Cuesta, Raquel L. Arribas, Eva M. García-Frutos, Laura González-Lafuente, Javier Egea, Cristóbal De Los Ríos, Alejandro Romero. In Silico Prediction of the Toxic Potential of Neuroprotective Bifunctional Molecules Based on Chiral N-Propargyl-1,2-amino Alcohol Derivatives. Chemical Research in Toxicology. 2021; 34 (5):1245-1249.

Chicago/Turabian Style

Eva Ramos; Rocío Lajarín-Cuesta; Raquel L. Arribas; Eva M. García-Frutos; Laura González-Lafuente; Javier Egea; Cristóbal De Los Ríos; Alejandro Romero. 2021. "In Silico Prediction of the Toxic Potential of Neuroprotective Bifunctional Molecules Based on Chiral N-Propargyl-1,2-amino Alcohol Derivatives." Chemical Research in Toxicology 34, no. 5: 1245-1249.

Review
Published: 11 February 2021 in Molecules
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Organic semiconductor micro/nanocrystals (OSMCs) have attracted great attention due to their numerous advantages such us free grain boundaries, minimal defects and traps, molecular diversity, low cost, flexibility and solution processability. Due to all these characteristics, they are strong candidates for the next generation of electronic and optoelectronic devices. In this review, we present a comprehensive overview of these OSMCs, discussing molecular packing, the methods to control crystallization and their applications to the area of organic solid-state lasers. Special emphasis is given to OSMC lasers which self-assemble into geometrically defined optical resonators owing to their attractive prospects for tuning/control of light emission properties through geometrical resonator design. The most recent developments together with novel strategies for light emission tuning and effective light extraction are presented.

ACS Style

Javier Álvarez-Conde; Eva García-Frutos; Juan Cabanillas-Gonzalez. Organic Semiconductor Micro/Nanocrystals for Laser Applications. Molecules 2021, 26, 958 .

AMA Style

Javier Álvarez-Conde, Eva García-Frutos, Juan Cabanillas-Gonzalez. Organic Semiconductor Micro/Nanocrystals for Laser Applications. Molecules. 2021; 26 (4):958.

Chicago/Turabian Style

Javier Álvarez-Conde; Eva García-Frutos; Juan Cabanillas-Gonzalez. 2021. "Organic Semiconductor Micro/Nanocrystals for Laser Applications." Molecules 26, no. 4: 958.

Paper
Published: 18 November 2020 in RSC Advances
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We report the synthesis, characterization, photophysical properties, and theoretical calculations of a novel indigo derivative, N-octyl-7,7′-diazaindigo.

ACS Style

Gustavo de Miguel; Andrés Garzón-Ruiz; Amparo Navarro; Eva M. García-Frutos. Synthesis and photophysical studies of an indigo derivative: N-octyl-7,7′-diazaindigo. RSC Advances 2020, 10, 42014 -42020.

AMA Style

Gustavo de Miguel, Andrés Garzón-Ruiz, Amparo Navarro, Eva M. García-Frutos. Synthesis and photophysical studies of an indigo derivative: N-octyl-7,7′-diazaindigo. RSC Advances. 2020; 10 (69):42014-42020.

Chicago/Turabian Style

Gustavo de Miguel; Andrés Garzón-Ruiz; Amparo Navarro; Eva M. García-Frutos. 2020. "Synthesis and photophysical studies of an indigo derivative: N-octyl-7,7′-diazaindigo." RSC Advances 10, no. 69: 42014-42020.

Journal article
Published: 08 March 2020 in Applied Clay Science
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Hybrid systems based on clay minerals and 7-azaindole derivatives, which show an interesting neuroprotective profile in several in vitro models of neurodegeneration, were developed in order to facilitate the oral administration of these drugs in the treatment of Alzheimer's disease and provide a controlled release. Two 7-azaindole derivatives with different substitution at position 5 (-OCH3, -H) were synthesized and adsorbed on nanocarriers of different morphology, the lamellar clay montmorillonite (MMT) and the halloysite nanotubes (HNT). The drugs intercalation in MMT was confirmed by X-ray diffraction, obtaining basal spacing values around 1.9–2.0 nm in the hybrids, with a drug loading around 31–36 g per 100 g of MMT, while the HNT-based hybrids show an uptake of 15–21 g per 100 g of HNT. Studies carried out in cultures of human neuroblastoma cells confirmed the lack of toxicity of the hybrids and their neuroprotective effect against okadaic acid (OA), the inhibitor of the protein phosphatase 2A (PP2A), similarly to the non-encapsulated drugs. The release assays carried out in systems that simulate the gastrointestinal tract show a rapid release of the drugs from the hybrid materials, making necessary their encapsulation in a protective biopolymer matrix to slow down the release kinetics. A blend of alginate and zein was chosen for this purpose, exploiting the gelation of alginate with calcium ions to process the material as microbeads and the hydrophobic character of zein to reduce the water uptake of the material. Therefore, these bionanocomposite systems integrating the drug/clay hybrids seem promising for the oral administration of drugs with multitarget activity for the treatment of Alzheimer's disease.

ACS Style

Rocíogarcía- Vázqueza; Ediana P. Rebitski; Lucía Lucíaviejobc; Cristóbalde Los Ríosbc; Margarita Dardera; Eva M. García-Frutos. Clay-based hybrids for controlled release of 7-azaindole derivatives as neuroprotective drugs in the treatment of Alzheimer's disease. Applied Clay Science 2020, 189, 105541 .

AMA Style

Rocíogarcía- Vázqueza, Ediana P. Rebitski, Lucía Lucíaviejobc, Cristóbalde Los Ríosbc, Margarita Dardera, Eva M. García-Frutos. Clay-based hybrids for controlled release of 7-azaindole derivatives as neuroprotective drugs in the treatment of Alzheimer's disease. Applied Clay Science. 2020; 189 ():105541.

Chicago/Turabian Style

Rocíogarcía- Vázqueza; Ediana P. Rebitski; Lucía Lucíaviejobc; Cristóbalde Los Ríosbc; Margarita Dardera; Eva M. García-Frutos. 2020. "Clay-based hybrids for controlled release of 7-azaindole derivatives as neuroprotective drugs in the treatment of Alzheimer's disease." Applied Clay Science 189, no. : 105541.

Journal article
Published: 19 December 2018 in Journal of Materials Chemistry C
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A new D–A bipolar luminescent azaindole demonstrates its potential applicability in non-doped OLEDs.

ACS Style

Cristina Martin; Carlos Borreguero; Koen Kennes; Mark Van Der Auweraer; Johan Hofkens; Gustavo De Miguel; Eva M. García-Frutos. Bipolar luminescent azaindole derivative exhibiting aggregation-induced emission for non-doped organic light-emitting diodes. Journal of Materials Chemistry C 2018, 7, 1222 -1227.

AMA Style

Cristina Martin, Carlos Borreguero, Koen Kennes, Mark Van Der Auweraer, Johan Hofkens, Gustavo De Miguel, Eva M. García-Frutos. Bipolar luminescent azaindole derivative exhibiting aggregation-induced emission for non-doped organic light-emitting diodes. Journal of Materials Chemistry C. 2018; 7 (5):1222-1227.

Chicago/Turabian Style

Cristina Martin; Carlos Borreguero; Koen Kennes; Mark Van Der Auweraer; Johan Hofkens; Gustavo De Miguel; Eva M. García-Frutos. 2018. "Bipolar luminescent azaindole derivative exhibiting aggregation-induced emission for non-doped organic light-emitting diodes." Journal of Materials Chemistry C 7, no. 5: 1222-1227.

Research article
Published: 05 December 2018 in The Journal of Physical Chemistry C
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In the last years, the 7,7’-diazaisoindigo has emerged as a promising building block for semiconductor materials. In this work, we have studied different electronic properties which can be related to the semiconducting character of a family of 7,7’-diazaisoindigo derivatives. Concretely, we have analyzed the role of halogen substituents and different-length side chains on these properties calculated by means of the Density Functional Theory. In total, sixteen halogenated and non-halogenated diazaisoindigo derivatives were investigated. Four of these compounds were also synthetized and their X-ray structures were employed as starting points for the calculation of crystal structure of the rest of the novel compounds. In general, high electron transfer rate constants and electron mobilites were calculated for the studied 7,7’-diazaisoindigo derivatives, especially for bromine derivatives and compounds with long-side chains. The origin of these high rate constants mainly resides in the strong electronic couplings found for diazaisoindigo crystals in the π-stacking direction.

ACS Style

Mónica Moral; Amparo Navarro; Andrés Garzón-Ruiz; Eva M. García-Frutos. Tuning the Crystal Packing and Semiconductor Electronic Properties of 7,7′-Diazaisoindigo by Side-Chain Length and Halogenation. The Journal of Physical Chemistry C 2018, 123, 153 -164.

AMA Style

Mónica Moral, Amparo Navarro, Andrés Garzón-Ruiz, Eva M. García-Frutos. Tuning the Crystal Packing and Semiconductor Electronic Properties of 7,7′-Diazaisoindigo by Side-Chain Length and Halogenation. The Journal of Physical Chemistry C. 2018; 123 (1):153-164.

Chicago/Turabian Style

Mónica Moral; Amparo Navarro; Andrés Garzón-Ruiz; Eva M. García-Frutos. 2018. "Tuning the Crystal Packing and Semiconductor Electronic Properties of 7,7′-Diazaisoindigo by Side-Chain Length and Halogenation." The Journal of Physical Chemistry C 123, no. 1: 153-164.

Research article
Published: 27 November 2017 in The Journal of Physical Chemistry C
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A new kind of low molecular-mass organic gelator (LMOG) π-electron-deficient N,N-octyl-7,7′-diazaisoindigo (1) with aggregation-induced enhanced emission (AIEE) phenomenon is described. This organogel is capable of self-assembling through intermolecular H-bonding and π–π interactions between diazaisoindigo molecules. Its rheological properties, X-ray diffraction pattern, optical properties and theoretical calculations were investigated. The AIEE effect is exhibited in fluorescence during the formation of the supramolecular organogel, which persisted in the xerogel state, and the spectral red-shifts suggest the formation of J-type aggregates during the gelation process via π–π interactions in microbelts or 3D networks. Fluorescence lifetime and quantum yield significantly increase from dilute solution to the aggregate state. From a theoretical perspective, the effect of the aggregation of 1 on the photophysical properties was also studied by means of the density functional theory (DFT). In this sense, the lowest energy electronic transitions were calculated for both the single molecule and different size aggregates in order to predict spectral shifts. In addition, the geometry and molecular properties of the excited state were analyzed in different material states.

ACS Style

Andrés Garzón; Amparo Navarro; Daniel López; Josefina Perles; Eva M. García-Frutos. Aggregation-Induced Enhanced Emission (AIEE) from N,N-Octyl-7,7′-diazaisoindigo-Based Organogel. The Journal of Physical Chemistry C 2017, 121, 27071 -27081.

AMA Style

Andrés Garzón, Amparo Navarro, Daniel López, Josefina Perles, Eva M. García-Frutos. Aggregation-Induced Enhanced Emission (AIEE) from N,N-Octyl-7,7′-diazaisoindigo-Based Organogel. The Journal of Physical Chemistry C. 2017; 121 (48):27071-27081.

Chicago/Turabian Style

Andrés Garzón; Amparo Navarro; Daniel López; Josefina Perles; Eva M. García-Frutos. 2017. "Aggregation-Induced Enhanced Emission (AIEE) from N,N-Octyl-7,7′-diazaisoindigo-Based Organogel." The Journal of Physical Chemistry C 121, no. 48: 27071-27081.

Rapid communication
Published: 30 October 2017 in ACS Energy Letters
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A new luminescent azaindole derivative has been designed and synthesized to be implemented in a light-emitting device. The molecular geometry and frontier orbital energy have been investigated by using density functional theory. This newly synthesized molecule emits strongly both in solution and solid state. The fluorescence emission in THF upon addition of an increasing amount of H2O has been measured also, displaying an increase of the fluorescence signal which is associated with an aggregation-induced emission phenomenon. Double-layer light-emitting devices including an active layer of the novel emissive material were successfully fabricated. The red-shift of the electroluminescence spectra with respect to the photoluminiscence emission was attributed to the presence of different types of complexes in the emissive material (EM) layer, which are preferentially formed between the nearest-neighbor hole–electron pairs of the electron injection and the EM layers (electroplex).

ACS Style

Cristina Martin; Carlos Borreguero; Koen Kennes; Mark Van der Auweraer; J. Hofkens; Gustavo De Miguel; Eva M. García-Frutos. Simple Donor–Acceptor Luminogen Based on an Azaindole Derivative as Solid-State Emitter for Organic Light-Emitting Devices. ACS Energy Letters 2017, 2, 2653 -2658.

AMA Style

Cristina Martin, Carlos Borreguero, Koen Kennes, Mark Van der Auweraer, J. Hofkens, Gustavo De Miguel, Eva M. García-Frutos. Simple Donor–Acceptor Luminogen Based on an Azaindole Derivative as Solid-State Emitter for Organic Light-Emitting Devices. ACS Energy Letters. 2017; 2 (12):2653-2658.

Chicago/Turabian Style

Cristina Martin; Carlos Borreguero; Koen Kennes; Mark Van der Auweraer; J. Hofkens; Gustavo De Miguel; Eva M. García-Frutos. 2017. "Simple Donor–Acceptor Luminogen Based on an Azaindole Derivative as Solid-State Emitter for Organic Light-Emitting Devices." ACS Energy Letters 2, no. 12: 2653-2658.

Full paper
Published: 04 September 2017 in Advanced Functional Materials
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This study reports on the use of a self‐assembling organogel, 5‐(4‐nonylphenyl)‐7‐azaindole (1), as a new emitter in small‐molecule organic light emitting devices (OLEDs). The theoretical calculations along with the photophysical characterization studies suggest the coexistence of the monomer and dimer species at high concentration of compound 1. The presence of this type of dimer (formed via H‐bonding) is responsible for the increased emission. However, the most notable feature is the 3D network of vastly interconnected fibers formed in the organogel that modifies the photophysical properties. Based on this, several OLED architectures are made in order to understand the mechanism involved in the electroluminescence (EL) behavior of 1. Although the position of the EL spectra differs from that of the photoluminescence (PL) spectra, the trends observed in the device properties perfectly match with dimer formation. In this framework a better device performance is associated to a higher efficiency of dimer formation, which optimizes in the OLED prepared from the organogel. Therefore, these results show that the rational combination of a moiety showing a strong PL intensity increased upon aggregation with organogel properties is an efficient strategy to create alternative emitters for OLED devices.

ACS Style

Cristina Martín; Koen Kennes; Mark Van Der Auweraer; Johan Hofkens; Gustavo De Miguel; Eva M. García-Frutos. Self-Assembling Azaindole Organogel for Organic Light-Emitting Devices (OLEDs). Advanced Functional Materials 2017, 27, 1 .

AMA Style

Cristina Martín, Koen Kennes, Mark Van Der Auweraer, Johan Hofkens, Gustavo De Miguel, Eva M. García-Frutos. Self-Assembling Azaindole Organogel for Organic Light-Emitting Devices (OLEDs). Advanced Functional Materials. 2017; 27 (41):1.

Chicago/Turabian Style

Cristina Martín; Koen Kennes; Mark Van Der Auweraer; Johan Hofkens; Gustavo De Miguel; Eva M. García-Frutos. 2017. "Self-Assembling Azaindole Organogel for Organic Light-Emitting Devices (OLEDs)." Advanced Functional Materials 27, no. 41: 1.

Journals
Published: 05 January 2016 in Journal of Materials Chemistry C
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A new family of 7,7′-diazaisoindigo is presented. Theoretical calculations and photophysical studies demonstrate that it could be a good candidate for organic electronics.

ACS Style

Gustavo de Miguel; Luis Camacho; Eva M. García-Frutos. 7,7′-Diazaisoindigo: a novel building block for organic electronics. Journal of Materials Chemistry C 2016, 4, 1208 -1214.

AMA Style

Gustavo de Miguel, Luis Camacho, Eva M. García-Frutos. 7,7′-Diazaisoindigo: a novel building block for organic electronics. Journal of Materials Chemistry C. 2016; 4 (6):1208-1214.

Chicago/Turabian Style

Gustavo de Miguel; Luis Camacho; Eva M. García-Frutos. 2016. "7,7′-Diazaisoindigo: a novel building block for organic electronics." Journal of Materials Chemistry C 4, no. 6: 1208-1214.