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The attractive interactions between aromatic rings, also known as π-π interactions, have been widely used for decades. However, the origin of π-π interactions remains controversial due to the difficulties in experimentally measuring the weak interactions between π-systems. Here, we construct an elaborate system to accurately compare the strength of the π-π interactions between phenylalanine derivatives via molecular exchange processes inside a protein nanopore. Based on quantitative comparison of binding strength, we find that in most cases, the π-π interaction is primarily driven by dispersive attraction, with the electrostatic interaction playing a secondary role and tending to be repulsive. However, in cases where electronic effects are particularly strong, electrostatic induction may exceed dispersion forces to become the primary driving force for interactions between π-systems. The results of this study not only deepen our understanding of π-stacking but also have potential implications in areas where π-π interactions play a crucial role.
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Correction for 'Polydopamine-capped AgNPs as a novel matrix overcoming the ion suppression of phosphatidylcholine for MALDI MS comprehensive imaging of glycerophospholipids and sphingolipids in impact-induced injured brain' by Chao Han et al., Analyst, 2019, 144, 6304-6312, https://doi.org/10.1039/C9AN01361J.
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Pyridostatin (PDS) is a well-known G-quadruplex (G4) inducer and stabilizer, yet its target genes have remained unclear. Herein, applying MS proteomics strategy, we revealed PDS significantly downregulated 22 proteins but upregulated 16 proteins in HeLa cancer cells, of which the genes both contain a number of G4 potential sequences, implying that PDS regulation on gene expression is far more complicated than inducing/stabilizing G4 structures. The PDS-downregulated proteins consequently upregulated 6 proteins to activate cyclin and cell cycle regulation, suggesting that PDS itself is not a potential anticancer agent, at least toward HeLa cancer cells. Importantly, SUB1, which encodes human positive cofactor and DNA lesion sensor PC4, was downregulated by 4.76-fold. Further studies demonstrated that the downregulation of PC4 dramatically promoted the cytotoxicity of trans-[PtCl2(NH3)(thiazole)] (trans-PtTz) toward HeLa cells to a similar level of cisplatin, contributable to retarding the repair of 1,3-trans-PtTz crosslinked DNA lesion mediated by PC4. These findings not only provide new insights into better understanding on the biological functions of PDS but also implicate a strategy for the rational design of novel multi-targeting platinum anticancer drugs via conjugation of PDS as a ligand to the coordination scaffold of transplatin for battling drug resistance to cisplatin.
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Antineoplásicos , G-Cuádruplex , Aminoquinolinas , Antineoplásicos/química , Antineoplásicos/farmacología , Cisplatino/química , Cisplatino/farmacología , ADN/química , Células HeLa , Humanos , Ácidos PicolínicosRESUMEN
Ellagic acid, known for its various biological activities, is widely used. Ellagic acid from pomegranate peels is safe for consumption, while that from gallnuts is only suitable for external use. However, there is currently no effective method to confirm the source of ellagic acid. Therefore, this study establishes an analysis method using ultra-high-performance liquid chromatography-electrospray ionization-high-resolution mass spectrometry (UHPLC-ESI-HR-MS) to identify the components of crude ellagic acid extracts from pomegranate peels and gallnuts. The analysis revealed that there was a mix of components in the crude extracts, such as ellagic acid, palmitic acid, oleic acid, stearic acid, and 9(10)-EpODE. Furthermore, it could be observed that ellagic acid extracted from gallnuts contained toxic substances such as anacardic acid and ginkgolic acid (15:1). These components could be used to effectively distinguish the origin of ellagic acid from pomegranate peels or gallnuts. Additionally, a rapid quantitative analysis method using UHPLC-ESI-MS with multiple reaction monitoring (MRM) mode was developed for the quality control of ellagic acid products, by quantifying anacardic acid and ginkgolic acid (15:1). It was found that one of three ellagic acid health care products contained ginkgolic acid (C15:1) and anacardic acid at more than 1 ppm.
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Ácidos Anacárdicos , Granada (Fruta) , Salicilatos , Espectrometría de Masa por Ionización de Electrospray/métodos , Extractos Vegetales/química , Ácido Elágico/química , Cromatografía Líquida de Alta Presión/métodosRESUMEN
In contrast to edge-on and face-on orientations, end-on uniaxial conjugated polymers have the theoretical possibility of providing a macroscopic crystalline film. However, their fabrication is insurmountable due to sluggishly thermodynamic equilibrium states. Herein, we report the programmatic pathway to fabricate nanoarchitectonics on end-on uniaxial conjugated metallopolymers by surface-initiated simultaneous electrosynthesis and assembly. Self-assembled monolayer (SAM) with bottom-up oriented electroactive molecules as a temple allows orientation, stacking, and reactive addition of monomers triggered by switching alternative redox reactions as well as crystallization of small molecules. Repeating the same reaction can repair the unreactive site on the SAM and dynamically and statistically ensure maximum iterative coverage with ideal linear coefficients between optical or electrical responses and iterative times. The resulting nanoarchitectonics on uniaxially assembled end-on polymers over centimeter-sized areas have a subnanometer-uniform morphology and exhibit ultrahigh modulus as well as an inorganic indium tin oxides and the highest conductance among conjugated molecular monolayers. Their memristive devices provide quantitative electrical and optical responses as a function of molecular length, bias, and iterative junctions. Precise processing of nanoarchitectonics as an electrically assisted assembly or printing technique can present sophisticated optoelectric functions and dimensional batch-to-batch consistency for micro-sized organic materials and electronics.
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The synthesis of crystalline polymer with a well-defined orientated state and a two-dimensional crystalline size beyond a micrometer will be essential to achieve the highest physical feature of polymer material but remain challenging. Herein, we show the synthesis of the crystalline unipolymer monolayer with an unusual ultrahigh modulus that is higher than the ITO substrate and high conductance by simultaneous electrosynthesis and manipulation. We find that the polymer monolayer has fully extended in the vertical and unidirectional orientation, which is proposed to approach their theoretically highest density, modulus, and conductivity among all aggregation formations of the current polymer. The modulus and current density can reach 40 and 1000â times higher than their amorphous counterpart. It is also found that these monolayers exhibit the bias- and length-dependent multiple charge states and asymmetrically negative differential resistance (NDR) effect, indicating that this unique molecular tailoring and ordering design is promising for multilevel resistive memory devices. Our work demonstrates the creation of a crystalline polymer monolayer for approaching the physical limit of polymer electronic materials and also provides an opportunity to challenge the synthetically iterative limit of an isolated ultra-long polymer.
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Every year vast quantities of silver are lost in various waste streams; this, combined with its limited, diminishing supply and rising demand, makes silver recovery of increasing importance. Thus, herein, we report a controllable, green process to produce a host of highly porous metal-organic framework (MOF)/oligomer composites using supercritical carbon dioxide (ScCO2 ) as a medium. One resulting composite, referred to as MIL-127/Poly-o-phenylenediamine (PoPD), has an excellent Ag+ adsorption capacity, removal efficiency (>99 %) and provides rapid Ag+ extraction in as little as 5â min from complex liquid matrices. Notably, the composite can also reduce sliver concentrations below the levels (<0.1â ppm) established by the United States Environmental Protection Agency. Using theoretical simulations, we find that there are spatially ordered polymeric units inside the MOF that promote the complexation of Ag+ over other common competing ions. Moreover, the oligomer is able to reduce silver to its metallic state, also providing antibacterial properties.
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Covalent organic frameworks (COFs) with porphyrins as structural units are a new kind of porous organic polymers, which have a regular and ordered structure, abundant porosity, and good stability. In the past, the construction of porphyrin COFs was generally synthesized by routes such as a Schiff base reaction. Here, we report a new COF structure by linking the porphyrin with the triazine ring. Using a cyano group-terminated porphyrin as a structural unit precursor, a new triazine-porphyrin hyperconjugated COF (TA-Por-sp2-COF) was constructed through the cyano group's self-polymerization. The extension of porphyrin units in two directions that stemmed from the cyano group at para-positions accounts for the establishment of a highly ordered two-dimensional topological structure. Attributing to the collaboration of electron-donating and withdrawing blocks for photo-induced carrier separation and adequate porosity for mass diffusion, this hyperconjugated system showed high photocatalytic performance in organic reactions such as the aerobic coupling reaction of benzylamine and thioanisole selective oxidation.
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BACKGROUND: Cisplatin, the alkylating agent of platinum(II) (Pt(II)), is the most common antitumor drug in clinic; however, it has many side effects, therefore it is higly desired to develop low toxicity platinum(IV) (Pt(IV)) drugs. Multi-omics analysis, as a powerful tool, has been frequently employed for the mechanism study of a certain therapy at the molecular level, which might be helpful for elucidating the mechanism of platinum drugs and facilitating their clinical application. METHODS: Strating form cisplatin, a hydrophobic Pt(IV) prodrug (CisPt(IV)) with two hydrophobic aliphatic chains was synthesized, and further encapsulated with a drug carrier, human serum albumin (HSA), to form nanoparticles, namely AbPlatin(IV). The anticancer effect of AbPlatin(IV) was investigated in vitro and in vivo. Moreover, transcriptomics, metabolomics and lipidomics were performed to explore the mechanism of AbPlatin(IV). RESULTS: Compared with cisplatin, Abplatin(IV) exhibited better tumor-targeting effect and greater tumor inhibition rate. Lipidomics study showed that Abplatin(IV) might induce the changes of BEL-7404 cell membrane, and cause the disorder of glycerophospholipids and sphingolipids. In addition, transcriptomics and metabolomics study showed that Abplatin(IV) significantly disturbed the purine metabolism pathway. CONCLUSIONS: This research highlighted the development of Abplatin(IV) and the use of multi-omics for the mechanism elucidation of prodrug, which is the key to the clinical translation of prodrug.
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Antineoplásicos , Carcinoma Hepatocelular , Neoplasias Hepáticas , Profármacos , Antineoplásicos/química , Antineoplásicos/farmacología , Antineoplásicos/uso terapéutico , Carcinoma Hepatocelular/tratamiento farmacológico , Línea Celular Tumoral , Cisplatino/química , Cisplatino/farmacología , Cisplatino/uso terapéutico , Humanos , Neoplasias Hepáticas/tratamiento farmacológico , Platino (Metal)/química , Profármacos/química , Profármacos/farmacologíaRESUMEN
Hydrophilic fullerene derivatives get notable performance in various biological applications, especially in cancer therapy and antioxidation. The biological behaviors of functional fullerenes are much dependent on their surface physicochemical properties. The excellent reactive oxygen species-scavenging capabilities of functional fullerenes promote their outstanding performances in inhibiting pathological symptoms associated with oxidative stress, including neurodegenerative diseases, cardiovascular diseases, acute and chronic kidney disease, and diabetes. Herein, fullerene derivatives with reversed surface charges in aqueous solutions are prepared: cationic C60-EDA and anionic C60-(EDA-EA). Under the driving force of membrane potential (negative inside) in the cell and mitochondria, C60-EDA is much rapidly taken in by cells and transported into mitochondria compared with C60-(EDA-EA) that is enriched in lysosomes. With high cellular uptake and mitochondrial enrichment, C60-EDA exhibits stronger antioxidation capabilities in vitro than C60-(EDA-EA), indicating its better performance in the therapy of oxidation-induced diseases. It is revealed that the cellular uptake rate, subcellular location, and intracellular antioxidation behavior of fullerene derivatives are primarily mediated by their surface charges, providing new strategies for the design of fullerene drugs and their biological applications.
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Fulerenos , Antioxidantes/farmacología , Orgánulos , Estrés Oxidativo , Especies Reactivas de OxígenoRESUMEN
Piperidine and δ-Lactam chemicals have wide application, which are currently produced from fossil resource in industry. Production of this kind of chemicals from lignocellulosic biomass is of great importance, but is challenging and the reported routes give low yield. Herein, we demonstrate the strategy to synthesize 2-methyl piperidine (MP) and 6-methylpiperidin-2-one (MPO) from biomass-derived triacetic acid lactone (TAL) that is produced microbially from glucose. In this route, TAL was firstly converted into 4-hydroxy-6-methylpyridin-2(1H)-one (HMPO) through facile aminolysis, subsequently HMPO was selectively transformed into MP or MPO over Ru catalysts supported on beta zeolite (Ru/BEA-X, X is the molar ratio of Si to Al) via the tandem reaction. It was found that the yield of MP could reach 76.5 % over Ru/BEA-60 in t-BuOH, and the yield of MPO could be 78.5 % in dioxane. Systematic studies reveal that the excellent catalytic performance of Ru/BEA-60 was closely correlated with the cooperative effects between active metal and acidic zeolite with large pore geometries. The related reaction pathway was studied on the basis of control experiments.
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Lactamas/síntesis química , Piperidinas/síntesis química , Pironas/química , Biomasa , Lactamas/química , Estructura Molecular , Piperidinas/químicaRESUMEN
The combination of microdialysis and mass spectrometry (MS) provides the potential for rapidly monitoring diverse metabolites in vivo. Unfortunately, the high concentration of salt in biological microdialysates hindered the sensitive and online detection of these small molecular compounds. In this study, we synthesized Co-incorporated mesoporous carbon material (Co-NC) and developed a Co-NC-assisted laser desorption/ionization (LDI) ion source as an online interface of in vivo microdialysis coupled with MS for the direct analysis of diverse metabolites in microdialysates. The Co-NC could be used as a matrix for surface-assisted laser desorption/ionization mass spectrometry (SALDI MS) analysis of small molecular compounds, even under high concentration salt conditions. The Co-NC possessed the adsorption ability for small molecular compounds, and it was believed that the adsorption ability of Co-NC might separate the analytes from the salt in microdialysates at a microscopic level, which might facilitate the desorption and ionization of the analytes and finally improved the salt-tolerance ability as a matrix. Furthermore, the Co-NC-assisted LDI ion source as a novel interface of in vivo microdialysis coupled with MS has been applied to the online monitoring of liver metabolites from the CCl4-induced liver injury rat model for the first time.
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Carbono/química , Microdiálisis/métodos , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción/métodos , Animales , Hígado/metabolismo , Sistemas en Línea , Porosidad , Ratas , Sales (Química)/químicaRESUMEN
Therapeutic target identification and corresponding drug development is a demanding task for the treatment of lung adenocarcinoma, especially the most malignant proximal-proliferative subtype without druggable protein kinase mutations. Using a cell-SELEX-generated aptamer, we discovered a new tumor driver protein, leucine-rich pentatricopeptide repeat-containing protein (LRPPRC), which is specifically overexpressed in the most lethal subtype of lung adenocarcinoma. Targeted LRPPRC protein knockdown is a promising therapeutic strategy for the undruggable LUAD (lung adenocarcinoma). Nevertheless, LRPPRC is mainly located in mitochondria and degraded by protease. Current protein knockdown approaches, such as proteolysis-targeting chimeras (PROTACs), have limitations in their applications to the proteins degraded through proteasome-independent ways. Here, we designed an aptamer-assisted high-throughput method to screen small molecules that could bind to LRPPRC directly, disrupt the interaction of LRPPRC with its stabilizing chaperon protein, and lead to LRPPRC degradation by mitochondrial protease. The screened compound, gossypolacetic acid (GAA), is an old medicine that can accomplish the new function for targeted LRPPRC knockdown. It showed significant antitumor effects even with the LRPPRC-positive patient-derived tumor xenograft (PDX) model. This work not only extended the application of aptamers to screen small-molecule inhibitors for the undruggable lung cancers, but more importantly provided a new strategy to develop protein knockdown methods beyond the proteasome system.
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Adenocarcinoma del Pulmón/tratamiento farmacológico , Antineoplásicos/farmacología , Neoplasias Pulmonares/tratamiento farmacológico , Proteínas/metabolismo , Bibliotecas de Moléculas Pequeñas/farmacología , Células A549 , Adenocarcinoma del Pulmón/metabolismo , Animales , Antineoplásicos/química , Antineoplásicos/uso terapéutico , Aptámeros de Nucleótidos/metabolismo , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Proteínas Repetidas Ricas en Leucina , Neoplasias Pulmonares/metabolismo , Ratones Desnudos , Complejo de la Endopetidasa Proteasomal/metabolismo , Mapas de Interacción de Proteínas/efectos de los fármacos , Proteínas/antagonistas & inhibidores , Bibliotecas de Moléculas Pequeñas/química , Bibliotecas de Moléculas Pequeñas/uso terapéuticoRESUMEN
Matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI MSI) is a powerful tool for the characterization and localization of analytes without the need for extraction, purification, separation or labeling of samples. However, in tissue sections the most abundant lipids, phosphatidylcholines (PCs), could suppress the signals of other classes of coexisting lipids. In this work, polydopamine (PDA)-capped AgNPs (AgNPs@PDA) were synthesized as a matrix of MALDI MSI to analyze lipids in both positive and negative ion modes. By adjusting the thickness of the PDA layer, the signal of silver cluster ions of AgNPs@PDA was effectively controlled, and the ability of AgNPs@PDA serving as a matrix was optimized. More interestingly, using AgNPs@PDA as a matrix, the sensitivity of PCs was dramatically decreased, and the PC signals were greatly suppressed, while for other lipids (including PE, HexCer, PS, PI, PIP, and ST), they were just the opposite. The reason, we believe, is related to the positively charged surface of AgNPs@PDA, and the polyhydroxy and amino groups of PDA. Benefitting from the suppression of the signals of PCs and the improvement of detection sensitivity of other lipids, 58 glycerophospholipids and 25 sphingolipids in brain tissue sections could be imaged in one run with AgNPs@PDA as a matrix by MALDI MSI, much better than when using traditional organic matrices 2,5-dihydroxybenzoic acid and 9-aminoacridine.
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Lesiones Traumáticas del Encéfalo/metabolismo , Glicerofosfolípidos/análisis , Indoles/química , Nanopartículas del Metal/química , Polímeros/química , Esfingolípidos/análisis , Animales , Encéfalo/metabolismo , Química Encefálica , Masculino , Ratones Endogámicos C57BL , Plata/química , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción/métodosRESUMEN
During the past decade, increasing attention has been paid to fluorescent carbon dots (CDs) due to their unique photoluminescence (PL) properties. As synthetic methods gradually develop, many post-functionalization strategies have been developed to enhance the PL of CDs. However, in most cases, the PL enhancement was less than 10-fold with multistep modification processes. In this work, a facile and efficient post-functionalization strategy was successfully applied to enhance the PL intensity of CDs dramatically up to 69â times by surfactants at room temperature for the first time. Furthermore, the mechanism of surfactant-induced PL enhancement of CDs was investigated and in vivo bioimaging was performed. The results demonstrated that electrostatic/non-electrostatic interactions between CDs and surfactants could effectively lower the vibration and rotation of CDs, increase radiative decay processes and, thus, enhance the PL of CDs. This finding may provide new insights into the strategies for enhancing the PL of CDs, further broadening their potential applications.
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2-(Trityliminomethyl)-quinolin-8-ol (HL) and its Zn(II) complex were synthesized and characterized by single-crystal X-ray diffraction. HL is an unsymmetrical molecule and coordinated with Zn(II) ion to form ZnL2 in the antiparallel-mode arrangement via Zn-O (hydroxyl group) and Zn-N (quinoline ring) of HL. A high degree of ZnL2 molecules ordering stacking is formed by the coordination bonds and intermolecular π-π interactions, in which head-to-tail arrangement (J-mode stacking) for L- is found. HL is nonfluorescent and ZnL2 is weakly fluorescent in THF. The fluorescence emission of ZnL2 enhances in THF/H2O as H2O% (volume %) is above 60% and aggregates particles with several hundred nanometers are formed, which is confirmed by DLS data and TEM images. The J-aggregates stacking for L- in ZnL2 results in aggregation-induced emission enhancement (AIEE) for ZnL2 in THF/H2O. Theoretical computations based on B3LYP/6-31G(d, p) and TD-B3LYP/6-31G(d, p) methods were carried out. ESIPT is the supposed mechanism for fluorescent silence of HL, and fluorescence emission of ZnL2 is attributed to the restriction of ESIPT process. The oscillator strength of ZnL2 increases from 0.017 for monomer to 0.032 for trimer. It indicates that a high degree of ZnL2 molecules ordering stacking in THF/H2O is of benefit to fluorescence enhancement. HL is an ESIPT-coupled AIEE chemosensor for Zn(II) with high selectivity and sensitivity in aqueous medium. HL can efficiently detect intracellular Zn(II) ions because of ESIPT-coupled AIEE property of ZnL2 in mixed solvent.
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The quantitative analysis by matrix-assisted laser desorption ionization mass spectrometry (MALDI MS) is a challenge due to the poor reproducibility originating from the heterogeneity of the matrix-analyte crystals. Polystyrene (PS) colloidal spheres have superior monodispersed property and can self-assemble to form photonic crystals. With the assistance of PS spheres, a uniform matrix-analyte cocrystal was constructed for the quantitative analysis of plasma lysophosphatidylcholines (LPCs). The matrix and the solvent in MALDI MS analysis were optimized, and the reproducibility and the accuracy were investigated in detail. This is the first report about the very simple method of PS spheres-assisted MALDI MS for quantitative analysis, where it is believed that this approach will greatly expand the applications of MALDI MS.
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Adenoma/sangre , Neoplasias Colorrectales/sangre , Lisofosfatidilcolinas/sangre , Poliestirenos/química , Humanos , Espectrometría de Masa por Láser de Matriz Asistida de Ionización DesorciónRESUMEN
Understanding how the charge travels through sequence-controlled molecules has been a formidable challenge because of simultaneous requirements in well-controlled synthesis and well-manipulated orientation. Here, we report electrically driven simultaneous synthesis and crystallization as a general strategy to study the conductance of composition and sequence-controlled unioligomer and unipolymer monolayers. The structural disorder of molecules and conductance variations on random positions can be extremely minimized, by uniform synthesis of monolayers unidirectionally sandwiched between electrodes, as an important prerequisite for the reproducible measurement on the micrometer scale. These monolayers show tunable current density and on/off ratios in four orders of magnitude with controlled multistate and massive negative differential resistance (NDR) effects. The conductance of monolayer mainly depends on the metal species in homo-metal monolayers, while the sequence becomes a matter in hetero-metal monolayers. Our work demonstrates a promising way to release an ultra-rich variety of electrical parameters and optimize the functions and performances of multilevel resistive devices.
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Electricidad , Alimentos , Cristalización , Electrodos , ViajeRESUMEN
Ferroptosis, an iron-dependent regulated cell death process driven by excessive lipid peroxides, can enhance cancer vulnerability to chemotherapy, targeted therapy and immunotherapy. As an essential upstream process for ferroptosis activation, lipid peroxidation of biological membranes is expected to be primarily induced by intrabilayer reactive oxygen species (ROS), indicating a promising strategy to initiate peroxidation by improving the local content of diffusion-limited ROS in the lipid bilayer. Herein, liposomes embedded with PEG-coated 3 nm γ-Fe2O3 nanoparticles in the bilayer (abbreviated as Lp-IO) were constructed to promote the intrabilayer generation of hydroxyl radicals (â¢OH) from hydrogen peroxide (H2O2), and the integration of amphiphilic PEG moieties with liposomal bilayer improved lipid membrane permeability to H2O2 and â¢OH, resulting in efficient initiation of lipid peroxidation and thus ferroptosis in cancer cells. Additionally, Lp-IO enabled traceable magnetic resonance imaging and pH/ROS dual-responsive drug delivery. Synergistic antineoplastic effects of chemotherapy and ferroptosis, and alleviated chemotherapeutic toxicity, were achieved by delivering doxorubicin (capable of xCT and glutathione peroxidase inhibition) with Lp-IO. This work provides an efficient alternative for triggering therapeutic lipid peroxidation and a ferroptosis-activating drug delivery vehicle for combination cancer therapies.
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Electrocatalytic reduction of carbon monoxide into fuels or chemicals with two or more carbons is very attractive due to their high energy density and economic value. Herein we demonstrate the synthesis of a hydrophobic Cu/Cu2O sheet catalyst with hydrophobic n-butylamine layer and its application in CO electroreduction. The CO reduction on this catalyst produces two or more carbon products with a Faradaic efficiency of 93.5% and partial current density of 151 mA cm-2 at the potential of -0.70 V versus a reversible hydrogen electrode. A Faradaic efficiency of 68.8% and partial current density of 111 mA cm-2 for ethanol were reached, which is very high in comparison to all previous reports of CO2/CO electroreduction with a total current density higher than 10 mA cm-2. The as-prepared catalyst also showed impressive stability that the activity and selectivity for two or more carbon products could remain even after 100 operating hours. This work opens a way for efficient electrocatalytic conversion of CO2/CO to liquid fuels.