Person: Illescas Martínez, Beatriz María
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First Name
Beatriz María
Last Name
Illescas Martínez
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Ciencias Químicas
Department
Química Orgánica
Area
Química Orgánica
Identifiers
17 results
Search Results
Now showing 1 - 10 of 17
Item Nanocarbon-Based Glycoconjugates as Multivalent Inhibitors of Ebola Virus Infection(Journal of the American Chemical Society, 2018) Rodríguez Pérez, Laura; Ramos-Soriano, Javier; Pérez Sánchez, Alfonso; Illescas Martínez, Beatriz María; Muñoz, Antonio; Luczkowiak, Joanna; Lasala, Fátima; Rojo, Javier; Delgado Vázquez, Rafael; Martín León, NazarioSWCNTs, MWCNTs, and SWCNHs have been employed as virus-mimicking nanocarbon platforms for the multivalent presentation of carbohydrates in an artificial Ebola virus infection model assay. These carbon nanoforms have been chemically modified by the covalent attachment of glycodendrons and glycofullerenes using the CuAAC “click chemistry” approach. This modification dramatically increases the water solubility of these structurally different nanocarbons. Their efficiency in blocking DC-SIGN-mediated viral infection by an artificial Ebola virus has been tested in a cellular experimental assay, finding that glycoconjugates based on MWCNTs functionalized with glycofullerenes are potent inhibitors of viral infection.Item Enhanced Thermoelectricity in Metal–[60]Fullerene–Graphene Molecular Junctions(Nano Letters, 2023) Svatek, Simon; Sacchetti, Valentina; Rodríguez Pérez, Laura; Illescas Martínez, Beatriz María; Rincón-García, Laura; Rubio-Bollinger, Gabino; González, Maria Teresa; Bailey, Steven; Lambert, Colin; Martín León, Nazario; Agraït, NicolasThe thermoelectric properties of molecular junctions consisting of a metal Pt electrode contacting [60]fullerene derivatives covalently bound to a graphene electrode have been studied by using a conducting-probe atomic force microscope (c-AFM). The [60]fullerene derivatives are covalently linked to the graphene via two meta-connected phenyl rings, two para-connected phenyl rings, or a single phenyl ring.We find that the magnitude of the Seebeck coefficient is up to nine times larger than that of Au−C60−Pt molecular junctions.Moreover,the sign of the thermopower can be either positiveor negative depending on the details of the binding geometry and on the local value of the Fermi energy. Our results demonstrate the potential of using graphene electrodes for controlling and enhancing the thermoelectric properties of molecular junctions and confirm the outstanding performance of [60]fullerene derivatives.Item Hexakis [60]Fullerene Adduct-Mediated Covalent Assembly of Ruthenium Nanoparticles and Their Catalytic Properties(Chemistry: a european journal, 2017) Leng, Faqiang; Gerber, Iann C.; Lecante, Pierre; Bentaleb, Ahmed; Muñoz, Antonio; Illescas Martínez, Beatriz María; Martín León, Nazario; Melinte, Georgian; Ersen, Ovidiu; Martínez, Hervé; Axet, Rosa; Serp, PhilippeThe C66(COOH)12 hexa-adduct has been successfully used as a building block to construct via carboxylate bridges 3D networks with very homogeneous sub-1.8 nm ruthenium nanoparticles. The obtained nanostructures are active in nitrobenzene selective hydrogenation.Item Supramolecular Complexation of Carbon Nanostructures by Crown Ethers(Journal of organic chemistry, 2017) Moreira, Luis; Illescas Martínez, Beatriz María; Martín, NazarioSince their discovery, crown ethers as well as the most recent carbon nanostructures, namely fullerenes, carbon nanotubes, and graphene, have received a lot of attention from the chemical community. Merging these singular chemical structures by noncovalent forces has provided a large number of unprecedented supramolecular assemblies with new geometric and electronic properties whose more representative examples are presented in this Synopsis organized according to the different nature of the carbon nanostructures.Item Synthesis of Highly Efficient Multivalent Disaccharide/[60]Fullerene Nanoballs for Emergent Viruses(Journal of the American Chemical Society, 2019) Ramos Soriano, Javier; Reina, José ; Illescas Martínez, Beatriz María; de la Cruz, Noelia; Rodríguez Pérez, Laura; Lasala, Fátima; Rojo, Javier; Delgado Vázquez, Rafael; Martín León, NazarioAfter the last epidemic of the Zika virus (ZIKV) in Brazil that peaked in 2016, growing evidence has been demonstrated of the link between this teratogenic flavivirus and microcephaly cases. However, no vaccine or antiviral drug has been approved yet. ZIKV and Dengue viruses (DENV) entry to the host cell takes place through several receptors, including dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin (DC-SIGN), so that the blockade of this receptor through multivalent glycoconjugates supposes a promising biological target to inhibit the infection process. In order to get enhanced multivalency in biocompatible systems, tridecafullerenes appended with up to 360 1,2-mannobiosides have been synthesized using a strain-promoted cycloaddition of azides to alkynes (SPAAC) strategy. These systems have been tested against ZIKV and DENV infection, showing an outstanding activity in the picomolar range.Item Hexakis-adducts of [60]fullerene as molecular scaffolds of polynuclear spin-crossover molecules(Chemical Science, 2021) Palacios-Corella, Mario; Ramos-Soriano, Javier; Souto, Manuel; Ananias, Duarte; Calbo, Joaquín; Ortí, Enrique; Illescas Martínez, Beatriz María; Clemente-León, Miguel; Martín León, Nazario; Coronado, EugenioA family of hexakis-substituted [60]fullerene adducts endowed with the well-known tridentate 2,6-bis(pyrazol-1-yl)pyridine (bpp) ligand for spin-crossover (SCO) systems has been designed and synthesized. It has been experimentally and theoretically demonstrated that these molecular scaffolds are able to form polynuclear SCO complexes in solution. UV-vis and fluorescence spectroscopy studies have allowed monitoring of the formation of up to six Fe(II)–bpp SCO complexes. In addition, DFT calculations have been performed to model the different complexation environments and simulate their electronic properties. The complexes retain SCO properties in the solid state exhibiting both thermaland photoinduced spin transitions, as confirmed by temperature-dependent magnetic susceptibility and Raman spectroscopy measurements. The synthesis of these complexes demonstrates that [60]fullerene hexakis-adducts are excellent and versatile platforms to develop polynuclear SCO systems in which a fullerene core is surrounded by a SCO molecular shell.Item Multivalent cationic dendrofullerenes for gene transfer: synthesis and DNA complexation(Journal of Materials Chemistry B, 2020) Illescas Martínez, Beatriz María; Pérez Sánchez, Alfonso; Mallo, Araceli; Martín Doménech, Ángel; Rodríguez Crespo, José Ignacio; Martín León, NazarioNon-viral nucleic acid vectors able to display high transfection efficiencies with low toxicity and overcoming the multiple biological barriers are needed to further develop the clinical applications of gene therapy. The synthesis of hexakis-adducts of [60]fullerene endowed with 12, 24 and 36 positive ammonium groups and a tridecafullerene appended with 120 positive charges has been performed. The delivery of a plasmid containing the green fluorescent protein (EGFP) gene into HEK293 (Human Embryonic Kidney) cells resulting in effective gene expression has demonstrated the efficacy of these compounds to form polyplexes with DNA. Particularly, giant tridecafullerene macromolecules have shown higher efficiency in the complexation and transfection of DNA. Thus, they can be considered as promising non-viral vectors for transfection purposes.Item Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection(Nature Chemistry, 2016) Muñoz, Antonio; Sigwalt, David; Illescas Martínez, Beatriz María; Luczkowiak, Joana; Rodríguez, Laura; Nierengarten, Iwona; Holler, Michel; Remy, Jean Serge; Buffet, Kevin; Vincent, Stéphane P.; Rojo, Javier; Delgado Vázquez, Rafael; Nierengarten, Jean-Françoise; Martín León, NazarioThe inhibition of pathogens entry through the blockade of DC-SIGN (dendritic cell-specific intercelular adhesion molecule-3-grabbing nonintegrin) receptor at early stages of infection is an efficient strategy for testing new antiviral agents. Although a variety of models have been reported, one of the main problems is achieving adequate size and multivalency to mimic natural systems such as viruses or other pathogens. In this regard, hexakis-adducts of [60]fullerene allow a full control of size and multivalency while maintaining a globular shape. For this purpose,tridecafullerenes decorated with 120 peripheral carbohydrate subunits have been efficiently synthesized from hexakis-adducts of [60]fullerene in one synthetic step by using the copper-catalyzed azide–alkyne cycloaddition (CuAAC) click-chemistry methodology. These so-called 'superballs' decorated with 120 mono-saccharides (mannose or galactose) moieties are water soluble, allowing the study of their biological properties. An infection assay has been employed to test the ability of these compounds to inhibit the infection of cells by an artificial Ebola virus. The results obtained in these experiments show that the 'superballs' are potent inhibitors of cell infection by this artificial Ebola virus with IC50s in the sub-nanomolar range. This implies more than a three-orders-of-magnitude increase of activity in comparison to the hexakis-adduct containing just 12 mannoses and only 18-fold less activity than virus-like glycodendrinanoparticles with diameters of roughly 32 nm displaying up to 1620 glycans.Item Multivalent Tryptophan‐ and Tyrosine‐Containing [60]Fullerene Hexa‐Adducts as Dual HIV and Enterovirus A71 Entry Inhibitors(Chemistry – A European Journal, 2021) Ruiz Santaquiteria, Marta; Illescas Martínez, Beatriz María; Abdelnabi, Rana; Boonen, Arnaud; Mills, Alberto; Martí‐Marí, Olaia; Noppen, Sam; Neyts, Johan; Schols, Dominique; Gago, Federico; San‐Félix, Ana; Camarasa, María‐José; Martín, NazarioUnprecedented 3D hexa-adducts of [60]fullerene peripherally decorated with twelve tryptophan (Trp) or tyrosine (Tyr) residues have been synthesized. Studies on the antiviral activity of these novel compounds against HIV and EV71 reveal that they are much more potent against HIV and equally active against EV71 than the previously described dendrimer prototypes AL-385 and AL-463, which possess the same number of Trp/Tyr residues on the periphery but attached to a smaller and more flexible pentaerythritol core. These results demonstrate the relevance of the globular 3D presentation of the peripheral groups (Trp/Tyr) as well as the length of the spacer connecting them to the central core to interact with the viral envelopes, particularly in the case of HIV, and support the hypothesis that [60]fullerene can be an alternative and attractive biocompatible carbon-based scaffold for this type of highly symmetrical dendrimers. In addition, the functionalized fullerenes here described, which display twelve peripheral negatively charged indole moieties on their globular surface, define a new and versatile class of compounds with a promising potential in biomedical applications.Item Antiviral Activity of Self‐Assembled Glycodendro[60]fullerene Monoadducts(Journal of materials chemistry B, 2017) Muñoz, Antonio; Illescas Martínez, Beatriz María; Luczkowiak, Joanna; Lasala, Fátima; Ribeiro Viana, Renato; Rojo, Javier; Delgado Vázquez, Rafael; Martín León, NazarioA series of amphiphilic glycodendro[60]fullerene monoadducts were efficiently synthesized using the CuAAC “click chemistry” approach. These glycodendrofullerenes can self‐assemble in aqueous media, in a process favoured through π‐ π interactions between the [60]fullerene moieties. This aggregation process leads to big and well‐defined compact micelles with a uniform size and spherical‐shape. The supramolecular aggregate was characterized using electronic microscopy (SEM and TEM), light scattering methods (DLS) and X‐ray methodologies (SAXS and XRD). The antiviral efficiency of these aggregates has been tested in an experimental infection assay using Ebola virus glycoprotein (EboGP) pseudotyped viral particles on Jurkat cells overexpressing DC‐SIGN and it is observed an improvement of the IC50 value with respect to other systems endowed with a higher number of carbohydrate ligands.