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Leishmaniasis and Human African trypanosomiasis pose significant public health threats in resource-limited regions, accentuated by the drawbacks of the current antiprotozoal treatments and the lack of approved vaccines. Considering the demand for novel therapeutic drugs, a series of BODIPY derivatives with several functionalizations at the meso, 2 and/or 6 positions of the core were synthesized and characterized. The in vitro activity against Trypanosoma brucei and Leishmania major parasites was carried out alongside a human healthy cell line (MRC-5) to establish selectivity indices (SIs). Notably, the meso-substituted BODIPY, with 1-dimethylaminonaphthalene (1b) and anthracene moiety (1c), were the most active against L. major, displaying IC50 = 4.84 and 5.41 µM, with a 16 and 18-fold selectivity over MRC-5 cells, respectively. In contrast, the mono-formylated analogues 2b and 2c exhibited the highest toxicity (IC50 = 2.84 and 6.17 µM, respectively) and selectivity (SI = 24 and 11, respectively) against T. brucei. Further insights on the activity of these compounds were gathered from molecular docking studies. The results suggest that these BODIPYs act as competitive inhibitors targeting the NADPH/NADP+ linkage site of the pteridine reductase (PR) enzyme. Additionally, these findings unveil a range of quasi-degenerate binding complexes formed between the PRs and the investigated BODIPY derivatives. These results suggest a potential correlation between the anti-parasitic activity and the presence of multiple configurations that block the same site of the enzyme.
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Antiprotozoarios , Compuestos de Boro , Leishmania major , Simulación del Acoplamiento Molecular , Trypanosoma brucei brucei , Compuestos de Boro/química , Compuestos de Boro/farmacología , Compuestos de Boro/síntesis química , Trypanosoma brucei brucei/efectos de los fármacos , Humanos , Antiprotozoarios/farmacología , Antiprotozoarios/química , Antiprotozoarios/síntesis química , Leishmania major/efectos de los fármacos , Diseño de Fármacos , Relación Estructura-Actividad , Línea Celular , Estructura Molecular , Tripanocidas/farmacología , Tripanocidas/química , Tripanocidas/síntesis química , OxidorreductasasRESUMEN
Optical chemosensors are a practical tool for the detection and quantification of important analytes in biological and environmental fields, such as Cu2+ and Fe3+. To the best of our knowledge, a BODIPY derivative capable of detecting Cu2+ and Fe3+ simultaneously through a colorimetric response has not yet been described in the literature. In this work, a meso-triphenylamine-BODIPY derivative is reported for the highly selective detection of Cu2+ and Fe3+. In the preliminary chemosensing study, this compound showed a significant color change from yellow to blue-green in the presence of Cu2+ and Fe3+. With only one equivalent of cation, a change in the absorption band of the compound and the appearance of a new band around 700 nm were observed. Furthermore, only 10 equivalents of Cu2+/Fe3+ were needed to reach the absorption plateau in the UV-visible titrations. Compound 1 showed excellent sensitivity toward Cu2+ and Fe3+ detection, with LODs of 0.63 µM and 1.06 µM, respectively. The binding constant calculation indicated a strong complexation between compound 1 and Cu2+/Fe3+ ions. The 1H and 19F NMR titrations showed that an increasing concentration of cations induced a broadening and shifting of the aromatic region peaks, as well as the disappearance of the original fluorine peaks of the BODIPY core, which suggests that the ligand-metal (1:2) interaction may occur through the triphenylamino group and the BODIPY core.
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Industrial activity has raised significant concerns regarding the widespread pollution caused by metal ions, contaminating ecosystems and causing adverse effects on human health. Therefore, the development of sensors for selective and sensitive detection of these analytes is extremely important. In this regard, an azo dye, Dabcyl 2, was synthesised and investigated for sensing metal ions with environmental and industrial relevance. The cation binding character of 2 was evaluated by colour changes as seen by the naked eye, UV-Vis and 1H NMR titrations in aqueous mixtures of SDS (0.02 M, pH 6) solution with acetonitrile (99:1, v/v). Out of the several cations tested, chemosensor 2 had a selective response for Pd2+, Sn2+ and Fe3+, showing a remarkable colour change visible to the naked eye and large bathochromic shifts in the UV-Vis spectrum of 2. This compound was very sensitive for Pd2+, Sn2+ and Fe3+, with a detection limit as low as 5.4 × 10-8 M, 1.3 × 10-7 M and 5.2 × 10-8 M, respectively. Moreover, comparative studies revealed that chemosensor 2 had high selectivity towards Pd2+ even in the presence of other metal ions in SDS aqueous mixtures.
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Unnatural amino acids with enhanced properties, such as increased complexing ability and luminescence, are considered to be highly attractive building blocks for bioinspired frameworks, such as probes for biomolecule dynamics, sensitive fluorescent chemosensors, and peptides for molecular imaging, among others. Therefore, a novel series of highly emissive heterocyclic alanines bearing a benzo[d]oxazolyl unit functionalized with different heterocyclic π-spacers and (aza)crown ether moieties was synthesized. The new compounds were completely characterized using the usual spectroscopic techniques and evaluated as fluorimetric chemosensors in acetonitrile and aqueous mixtures in the presence of various alkaline, alkaline-earth, and transition metal ions. The different crown ether binding moieties as well as the electronic nature of the π-bridge allowed for fine tuning of the sensory properties of these unnatural amino acids towards Pd2+ and Fe3+, as seen by spectrofluorimetric titrations.
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Fluorescence-based probes represent a powerful tool for noninvasive imaging of living systems in real time and with a high temporal and spatial resolution. Amongst several known fluorophores, 3-difluoroborodipyrromethene (BODIPY) derivatives have become a cornerstone for innovative fluorescent labelling applications, mainly due to their advantageous features including their facile synthesis, structural versatility and exceptional photophysical properties. In this context, we report a BODIPY-based fluorescent probe for imaging of lysosomes in living cells. The BODIPY derivative displayed a remarkable fluorescence enhancement at low pH values with a pKa* of 3.1. In vitro studies by confocal microscopy in HeLa cells demonstrated that the compound was able to permeate cell membrane and selectively label lysosome whilst remaining innocuous to the cell culture at the maximum concentration tested. Herein, the BODIPY derivative holds the promise of investigating lysosomal dynamics and function in living cells through fluorescence imaging.
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Colorantes Fluorescentes , Lisosomas , Humanos , Colorantes Fluorescentes/química , Células HeLa , Lisosomas/metabolismo , Concentración de Iones de HidrógenoRESUMEN
BACKGROUND AND PURPOSE: Mitochondrial dysfunction has been implicated in the pathogenesis of several neurodegenerative disorders, including Machado-Joseph disease (MJD), an autosomal dominant late-onset polyglutamine ataxia that results from an unstable expansion of a CAG tract in the ATXN3 gene. The size of the CAG tract only partially explains age at onset (AO), highlighting the existence of disease modifiers. Mitochondrial DNA (mtDNA) haplogroups have been associated with clinical presentation in other polyglutamine disorders, constituting potential modifiers of MJD phenotype. METHODS: A cross-sectional study, using 235 unrelated patients from Portugal, Brazil, India and Japan, was performed to investigate if mtDNA haplogroups contribute to AO of MJD. mtDNA haplogroups were obtained after sequencing the mtDNA hypervariable region I. Patients were classified in 15 phylogenetically related haplogroup clusters. RESULTS: The AO was significantly different among populations, implying the existence of other non-CAG factors, which seem to be population specific. In the Portuguese population, patients classified as belonging to haplogroup JT presented the earliest onset (estimated onset 34.6 years of age). Haplogroups W and X seem to have a protective effect, causing a delay in onset (estimated onset 47 years of age). No significant association between haplogroup clusters and AO was detected in the other populations or when all patients were pooled. Although haplogroup JT has already been implicated in other neurodegenerative disorders, no previous reports of an association between haplogroups W and X and disease were found. CONCLUSIONS: These findings suggest that haplogroups JT, W and X modify AO in MJD. Replication studies should be performed in European populations, where the frequency of the candidate modifiers is similar.
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ADN Mitocondrial/genética , Haplotipos , Enfermedad de Machado-Joseph/genética , Adulto , Edad de Inicio , Brasil , Estudios Transversales , Femenino , Humanos , India , Japón , Masculino , Persona de Mediana Edad , PortugalRESUMEN
BACKGROUND AND PURPOSE: In spinocerebellar ataxia type 3/Machado-Joseph disease (SCA3/MJD), the length of CAG repeat expansions in ATXN3 shows an inverse correlation with age at onset (AO). Recently, a formula for predicting AO based on CAG expansion was developed for European carriers. We tested this formula in SCA3/MJD carriers from distinct origins and developed population-specific models to predict AO. METHODS: This was a parametric survival modelling study. RESULTS: The European formula (EF) was tested in 739 independent SCA3/MJD carriers from South Brazil, Taiwan and the Portuguese Azorean islands, and it largely underestimated AO in South Brazilian and Taiwanese test cohorts. This finding challenged the universal use of the EF, leading us to develop and validate population-specific models for AO prediction. Using validation cohorts, we showed that Brazilian and Taiwanese formulas largely outperformed the EF in a population-specific manner. Inversely, the EF was more accurate at predicting AO among Portuguese Azorean patients. Hence, specific prediction models were required for each SCA3/MJD ethnic group. CONCLUSIONS: Our data strongly support the existence of as yet unknown factors that modulate AO in SCA3/MJD in a population-dependent manner, independent of CAG expansion length. The generated models are made available to the scientific community as they can be useful for future studies on SCA3/MJD carriers from distinct geographical origins.
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Edad de Inicio , Enfermedad de Machado-Joseph/fisiopatología , Adulto , Algoritmos , Pueblo Asiatico , Brasil , Portador Sano , Estudios de Cohortes , Femenino , Humanos , Enfermedad de Machado-Joseph/genética , Masculino , Persona de Mediana Edad , Población , Portugal , Valor Predictivo de las Pruebas , Taiwán , Adulto JovenRESUMEN
A series of π-conjugated molecules, based on pyridazine and thiophene heterocycles 3aâ»e, were synthesized using commercially, or readily available, coupling components, through a palladium catalyzed Suzuki-Miyaura cross-coupling reaction. The electron-deficient pyridazine heterocycle was functionalized by a thiophene electron-rich heterocycle at position six, and different (hetero)aromatic moieties (phenyl, thienyl, furanyl) were functionalized with electron acceptor groups at position three. Density Functional Theory (DFT) calculations were carried out to obtain information on the conformation, electronic structure, electron distribution, dipolar moment, and molecular nonlinear response of the synthesized push-pull pyridazine derivatives. Hyper-Rayleigh scattering in 1,4-dioxane solutions, using a fundamental wavelength of 1064 nm, was used to evaluate their second-order nonlinear optical properties. The thienylpyridazine functionalized with the cyano-phenyl moiety exhibited the largest first hyperpolarizability (ß = 175 × 10-30 esu, using the T convention) indicating its potential as a second harmonic generation (SHG) chromophore.
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Modelos Teóricos , Acoplamiento Oxidativo , Piridazinas/síntesis química , Piridazinas/química , Piridazinas/farmacología , Análisis EspectralRESUMEN
Novel thienyl and bithienyl amino acids with different substituents were obtained by a multicomponent Ugi reaction between a heterocyclic aldehyde, an amine, an acid and an isocyanide. Due to the presence of the sulphur heterocycle at the side chain, these unnatural amino acids are highly emissive and bear extra electron donating atoms so they were tested for their ability to act as fluorescent probes and chemosensors in the recognition of biomedically relevant ions in acetonitrile and acetonitrile/water solutions. The results obtained from spectrophotometric/spectrofluorimetric titrations in the presence of organic and inorganic anions, and alkaline; alkaline-earth and transition metal cations indicated that the bithienyl amino acid bearing a methoxy group is a selective colorimetric chemosensor for Cu2+, while the other (bi)thienyl amino acids act as fluorimetric chemosensors with high sensitivity towards Fe3+ and Cu2+ in a metal-ligand complex with 1:2 stoichiometry. The photophysical and ion sensing properties of these amino acids confirm their potential as fluorescent probes suitable for incorporation into peptidic frameworks with chemosensory ability.
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Aminoácidos/síntesis química , Materiales Biomiméticos/síntesis química , Cobre/análisis , Colorantes Fluorescentes/síntesis química , Hierro/análisis , Aldehídos/química , Aminas/química , Aminoácidos/química , Materiales Biomiméticos/química , Cationes , Complejos de Coordinación/química , Cianuros/química , Colorantes Fluorescentes/química , Compuestos Heterocíclicos/química , Sensibilidad y Especificidad , Soluciones , Espectrometría de Fluorescencia/métodos , Tiofenos/químicaRESUMEN
Four imidazoanthraquinone derivatives (2a-d) were synthesized and characterized and their coordination behavior against selected anions and cations tested. Acetonitrile solutions of probes showed charge-transfer absorptions in the 407-465 nm range. The four probes emitted in the 533-571 nm interval. The recognition ability of 2a-d was evaluated in the presence of F(-), Cl(-), Br(-), I(-), OCN(-), BzO(-), ClO4(-), AcO(-), HSO4(-), H2PO4(-), and CN(-). Only F(-), AcO(-), and H2PO4(-) induced a new red-shifted absorption band that was attributed to a deprotonation process involving the amine moiety of the imidazole ring. Moreover, upon increasing quantities of F(-), AcO(-), and H2PO4(-), moderate quenching was induced in the emission of 2a-d together with the appearance of a new red-shifted band. The UV-visible and emission behavior of the four probes in the presence of Cu(2+), Co(2+), Mg(2+), Fe(3+), Ba(2+), Fe(2+), Ni(2+), Ca(2+), Zn(2+), Pb(2+), Cd(2+), Cr(3+), Al(3+), K(+), and Li(+) was also assessed. Only addition of Fe(3+), Cr(3+), and Al(3+) caused a new blue-shifted band in 2a-d that was ascribed to a preferential coordination with the acceptor part of the probes. Moreover, an important quenching of the emission was observed which was ascribed to the interaction between these trivalent cations and 2a-d.
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Aniones/química , Antraquinonas/química , Antraquinonas/síntesis química , Cationes/química , Metales/química , Acetonitrilos/química , Estructura Molecular , Espectrometría de FluorescenciaRESUMEN
The demand for dyes with solvatochromic properties has increased in the last few years, mainly due to their wide range of applications in the analytical and industrial fields, such as in the textile industry. The phenomenon of solvatochromism is associated with the differential solvation of the ground and excited states of the solvatochromic compounds, leading to an important tool for the study of the nature of solute-solvent interactions. In this paper we report the synthesis of new bis(indolyl)methane derivatives bearing arylthiophene spacers (2a-d) functionalized with electron-donating and electron-withdrawing groups, and the photophysical studies in different solvents, such as ethanol, acetonitrile, dichloromethane, trichloromethane, dimethylsulfoxide, diethylether and 1,4-dioxane. Aiming to explore their solvatochromic behaviour in the ground and excited states, all solvents employed have different hydrogen-bond donor abilities. The largest colour modifications were visualized for compound 2b, the solution colours of which are orange in DMSO, blue in trichloromethane, green in dichloromethane and purple in 1,4-dioxane. A negative solvatochromism was observed in 2b and a positive one in 2a, 2c and 2d.
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Colorantes/química , Colorantes/síntesis química , Indoles/química , Indoles/síntesis química , Absorción , Acetonitrilos/química , Cloroformo/química , Dimetilsulfóxido/química , Dioxanos/química , Electrones , Etanol/química , Éter/química , Enlace de Hidrógeno , Luz , Cloruro de Metileno/química , Estructura Molecular , Solventes/química , Análisis Espectral , Rayos UltravioletaRESUMEN
OBJECTIVE: The COVID-19 pandemic has caused a variation in the circulation of respiratory pathogens. Our aim was to analyze the epidemiology of severe acute respiratory infections (SARI) in children during 3 years of the COVID-19 pandemic, in comparison with a previous period. METHODS: An observational study was conducted in a tertiary hospital in Spain, which analyzed the frequency and characteristics of patients admitted for SARI in the Pediatric Intensive Care Unit (PICU) during the COVID-19 pandemic (1 March 2020 to 28 February 2023), compared to pre-pandemic period (1 March 2017 to 29 February 2020). RESULTS: A total of 268 patients were included (59.6% males). The median age was 9.6 months (IQR 1.7 - 37). In the pre-pandemic period, there were 126 admissions with an average of 42 admissions/year. During the pandemic, there were 142 admissions, observing a significant reduction in admissions in the first year (12 admissions/year), in contrast to 82 admissions during the third year, which represented an increase of 95% compared to the average of admissions/year in pre-pandemic. In addition, in the last year there was evidence of an increase in viral coinfections in relation to pre-pandemic period (54.9% vs 39.7%; p=0.032). There were no differences in length of hospital stay or PICU stay. CONCLUSIONS: During the last year, coinciding with low rates of hospitalization for COVID in Spain, we observed a notable increase in admissions to the PICU for SARI. Probably, the prolonged period of low exposure to pathogens due to the measures adopted during the pandemic might have caused a decrease in population immunity with a rise in severe respiratory infections.
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COVID-19 , Infecciones del Sistema Respiratorio , Niño , Masculino , Humanos , Lactante , Femenino , COVID-19/epidemiología , Pandemias , Hospitalización , Tiempo de Internación , Infecciones del Sistema Respiratorio/epidemiología , Estudios RetrospectivosRESUMEN
Kinetic study of the α-lithiation of benzyl methyl ether (BME) by nBuLi has revealed that increasing the concentration of the organolithium compound does not necessarily increase the reactivity, and this is a consequence of the reactivities of the different nBuLi aggregates present in solution. We propose a dimer-based mechanism, in which a pre-complexation step is a key process for substrates bearing a donor oxygen atom that can interact with the lithium cation to form mixed dimers. For these studies, we have developed a system based on UV/Vis spectroscopy that allows kinetic measurements to be conducted at -80 °C under argon.
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Electrostatic and hydrophobic interactions govern most of the properties of supramolecular systems, which is the reason determining the degree of ionization of macromolecules has become crucial for many applications. In this paper, we show that high-resolution ultraviolet spectroscopy (VUV) can be used to determine the degree of ionization and its effect on the electronic excitation energies of layer-by-layer (LbL) films of poly(allylamine hydrochloride) (PAH) and poly[1-[4-(3-carboxy-4 hydroxyphenylazo)benzene sulfonamido]-1,2-ethanediyl, sodium salt] (PAZO). A full assignment of the VUV peaks of these polyelectrolytes in solution and in cast or LbL films could be made, with their pH dependence allowing us to determine the pK(a) using the Henderson-Hasselbach equation. The pK(a) for PAZO increased from ca. 6 in solution to ca. 7.3 in LbL films owing to the charge transfer from PAH. Significantly, even using solutions at a fixed pH for PAH, the amount adsorbed on the LbL films still varied with the pH of the PAZO solutions due to these molecular-level interactions. Therefore, the procedure based on a comparison of VUV spectra from solutions and films obtained under distinct conditions is useful to determine the degree of dissociation of macromolecules, in addition to permitting interrogation of interface effects in multilayer films.
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Alilamina/química , Poliestirenos/química , Ionización del Aire , Electrólitos/química , Concentración de Iones de Hidrógeno , Estructura Molecular , Soluciones/química , Propiedades de Superficie , VacioRESUMEN
The synthesis and comprehensive characterization of the excited states of four novel triphenylamine-benzimidazole derivatives has been undertaken in solution (ethanol and methylcyclohexane) at room temperature. This includes the determination of the absorption, fluorescence, and triplet-triplet absorption spectra, together with quantum yields of fluorescence, internal conversion, intersystem crossing, and singlet oxygen. From the overall data the radiative and radiationless rate constants could be obtained, and it is shown that the compounds are highly emissive with the radiative decay dominating, with more than 70% of the quanta loss through this deactivation channel. The basic structure of the triphenylamine-benzimidazole derivatives (1a) was modified at position 5 of the heterocyclic moiety with electron-donating (OH (1b), OCH3 (1c)) or electron-withdrawing groups (CN, (1d)). It was found that the photophysical properties remain basically unchanged with the different substitutions, although a marked Stokes shift was observed with 1d. The presence and nature of a charge-transfer transition is discussed with the help of theoretical (DFT and TDFT) data. All compounds displayed exceptionally high thermal stability (between 399 and 454 °C) as seen by thermogravimetric analysis.
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Granulomatous meningoencephalitis (GME) and necrotizing encephalitides (NE) are the most common immune-mediated inflammatory diseases of the central nervous system in dogs. Activation of the fibrinolytic system in multiple sclerosis, a similar immune-mediated disease affecting the central nervous system in humans, seems to be related to disease progression. The aim of this study was to identify fibrin/fibrinogen and D-dimer deposition, as well as presence of intravascular thrombosis (IVT) in brains of dogs with a diagnosis of GME or NE. Immunohistochemical studies using antibodies against fibrin/fibrinogen and D-dimers were performed. Statistical analyses were performed to determine whether there were differences in the presence and location of fibrin/fibrinogen, D-dimers deposits, and IVT between GME and NE. Samples from sixty-four dogs were included in the study: 32 with a diagnosis of GME and 32 with a diagnosis of NE. Fibrin/fibrinogen depositions were detected in all samples and d-dimers were detected in 43/64 samples. IVT was present in 29/64 samples, with a significantly higher score in samples from dogs with NE than in samples from dogs with GME (P = 0.001). These data support hemostatic system activation in both diseases, especially NE. This finding might be related to the origin of the necrotic lesions seen in NE, which could represent chronic ischemic lesions. Further studies are needed to investigate the association between vascular lesions and the histopathological differences between GME and NE and the hemostatic system as a potential therapeutic target.
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Enfermedades de los Perros , Hemostáticos , Meningoencefalitis , Trombosis , Humanos , Perros , Animales , Fibrina/metabolismo , Encéfalo/metabolismo , Encéfalo/patología , Meningoencefalitis/veterinaria , Productos de Degradación de Fibrina-Fibrinógeno/metabolismo , Trombosis/veterinaria , Enfermedades de los Perros/patologíaRESUMEN
As mRNA vaccines have proved to be very successful in battling the coronavirus disease 2019 (COVID-19) pandemic, this new modality has attracted widespread interest for the development of potent vaccines against other infectious diseases and cancer. Cervical cancer caused by persistent human papillomavirus (HPV) infection is a major cause of cancer-related deaths in women, and the development of safe and effective therapeutic strategies is urgently needed. In the present study, we compared the performance of three different mRNA vaccine modalities to target tumors associated with HPV-16 infection in mice. We generated lipid nanoparticle (LNP)-encapsulated self-amplifying mRNA as well as unmodified and nucleoside-modified non-replicating mRNA vaccines encoding a chimeric protein derived from the fusion of the HPV-16 E7 oncoprotein and the herpes simplex virus type 1 glycoprotein D (gDE7). We demonstrated that single low-dose immunizations with any of the three gDE7 mRNA vaccines induced activation of E7-specific CD8+ T cells, generated memory T cell responses capable of preventing tumor relapses, and eradicated subcutaneous tumors at different growth stages. In addition, the gDE7 mRNA-LNP vaccines induced potent tumor protection in two different orthotopic mouse tumor models after administration of a single vaccine dose. Last, comparative studies demonstrated that all three gDE7 mRNA-LNP vaccines proved to be superior to gDE7 DNA and gDE7 recombinant protein vaccines. Collectively, we demonstrated the immunogenicity and therapeutic efficacy of three different mRNA vaccines in extensive comparative experiments. Our data support further evaluation of these mRNA vaccines in clinical trials.
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Vacunas contra el Cáncer , Neoplasias , Infecciones por Papillomavirus , Vacunas contra Papillomavirus , Vacunas de ADN , Animales , Femenino , Ratones , Linfocitos T CD8-positivos , Modelos Animales de Enfermedad , Inmunización , Ratones Endogámicos C57BL , Neoplasias/terapia , Proteínas E7 de Papillomavirus/genética , Infecciones por Papillomavirus/complicaciones , Infecciones por Papillomavirus/prevención & control , Vacunas contra Papillomavirus/genética , Proteínas Recombinantes , ARN Mensajero/genéticaRESUMEN
Photophysical and TPA properties of series of push-pull aryl(bi)thiophene chromophores bearing electron-donating (D) and electron-withdrawing (A) end-groups of increasing strength are presented. All compounds show an intense intramolecular charge transfer (ICT) absorption band in the visible region. Increasing the D and/or A strength as well as the length of the conjugated path induces bathochromic and hyperchromic shifts of the absorption band as reported for analogous push-pull polyenes. Yet, in contrast with corresponding push-pull polyenes, a significant increase in fluorescence is observed. In particular, chromophores built from a phenyl-bithienyl conjugated path and bearing strong D and A end-groups were found to combine very large one and two-photon brightness as well as strong emission in the red/NIR region. These molecules hold promise as biphotonic fluorescent probes for bioimaging.
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A family of heterocyclic thiosemicarbazone dyes (3a-f and 4) containing furyl groups was synthesized in good yields, characterized and their response in acetonitrile in the presence of selected anions was studied. Acetonitrile solutions of 3a-f and 4 showed absorption bands in the 335-396 nm range which are modulated by the electron donor or acceptor strength of the heterocyclic systems appended to the thiosemicarbazone moiety. Fluoride, chloride, bromide, iodide, dihydrogen phosphate, hydrogen sulphate, nitrate, acetate and cyanide anions were used in recognition studies. From these anions, only sensing features were seen for fluoride, cyanide, acetate and dihydrogen phosphate. Two clearly different chromo-fluorogenic behaviours were observed: (i) a small shift of the absorption band due to the coordination of the anions with the thiourea protons and (ii) the appearance of a new red shifted band due to deprotonation. For the latter effect, a change in the colour of solution from pale yellow to purple was observed. Fluorescence studies were also in agreement with the different effects observed in the UV/Vis titrations. In this case, hydrogen bonding interactions were visible through the enhancement of the emission band, whereas deprotonation induced the appearance of a new red-shifted emission. Logarithms of stability constants for the two processes (complex formation + deprotonation) for receptors in the presence of fluoride and acetate anions were determined from spectrophotometric titrations using the HypSpec V1.1.18 program. Semi-empirical calculations to evaluate the hydrogen-donating ability of the receptors and a prospective electrochemical characterization of compound in the presence of fluoride were also performed.