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1.
Sci Rep ; 14(1): 12878, 2024 06 05.
Artículo en Inglés | MEDLINE | ID: mdl-38834651

RESUMEN

In this study, eleven novel chromene sulfonamide hybrids were synthesized by a convenient method in accordance with green chemistry. At first, chromene derivatives (1-9a) were prepared through the multi-component reaction between aryl aldehydes, malononitrile, and 3-aminophenol. Then, synthesized chromenes were reacted with appropriate sulfonyl chlorides by grinding method to give the corresponding chromene sulfonamide hybrids (1-11b). Synthesized hybrids were obtained in good to high yield and characterized by IR, 1HNMR, 13CNMR, CHN and melting point techniques. In addition, the broth microdilution assay was used to determine the minimal inhibitory concentration of newly synthesized chromene-sulfonamide hybrids. The MTT test was used to determine the cytotoxicity and apoptotic activity of the newly synthesized compounds against fibroblast L929 cells. The 3D­QSAR analysis confirmed the experimental assays, demonstrating that our predictive model is useful for developing new antibacterial inhibitors. Consequently, molecular docking studies were performed to validate the findings of the 3D-QSAR analysis, confirming the potential binding interactions of the synthesized chromene-sulfonamide hybrids with the target enzymes. Molecular docking studies were employed to support the 3D-QSAR predictions, providing insights into the binding interactions between the newly synthesized chromene-sulfonamide hybrids and their target bacterial enzymes, thereby reinforcing the potential efficacy of these compounds as antibacterial agents. Also, some of the experimental outcomes supported or conflicted with the pharmacokinetic prediction (especially about compound carcinogenicity). The performance of ADMET predictor results was assessed. The work presented here proposes a computationally driven strategy for designing and discovering a new sulfonamide scaffold for bacterial inhibition.


Asunto(s)
Antibacterianos , Apoptosis , Benzopiranos , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Relación Estructura-Actividad Cuantitativa , Sulfonamidas , Sulfonamidas/química , Sulfonamidas/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Benzopiranos/química , Benzopiranos/farmacología , Apoptosis/efectos de los fármacos , Ratones , Animales , Línea Celular
2.
ACS Nano ; 18(24): 15978-15990, 2024 Jun 18.
Artículo en Inglés | MEDLINE | ID: mdl-38847448

RESUMEN

Sulfur-substituted dicyanomethylene-4H-chromene (DCM) derivatives based on the intramolecular charge transfer (ICT) mechanism were designed as near-infrared (NIR) fluorescent dyes. Using the Knoevenagel condensation method, the S-DCM-OH(835) fluorescence dye was synthesized, which had an emission wavelength exceeding 800 nm and 220 nm of a Stokes shift. Compared to commercial ICG, S-DCM-OH(835) was not only synchronized in emission wavelength but also far superior in Stokes shifts. These advantages made the design of S-DCM-NIR(835) based on this dye potentially valuable for biological applications. Based on this chemical structure, a fluorescent S-DCM-NIR(835) nanoprobe with a mean diameter of 17.69 nm was fabricated as the NIR imaging nanoprobe. Results showed that the nanoprobe maintained the high-specificity identification of cysteine (Cys) via the Michael addition reaction, with the detection limitation of 0.11 µM endogenous Cys. More importantly, in an ischemic stroke mouse model, the S-DCM-NIR(835) nanoprobe could monitor the Cys concentration change at stroke lesion due to the disruption of Cys metabolism under the ischemic stroke condition. Such a S-DCM-NIR(835) nanoprobe could not only differentiate the severity of the ischemic stroke using response time but also quantify the concentration of Cys in real-time in vivo.


Asunto(s)
Cisteína , Colorantes Fluorescentes , Rayos Infrarrojos , Accidente Cerebrovascular Isquémico , Colorantes Fluorescentes/química , Animales , Cisteína/química , Ratones , Accidente Cerebrovascular Isquémico/diagnóstico por imagen , Imagen Óptica , Nanopartículas/química , Humanos , Espectroscopía Infrarroja Corta/métodos , Masculino , Benzopiranos/química
3.
J Agric Food Chem ; 72(22): 12300-12318, 2024 Jun 05.
Artículo en Inglés | MEDLINE | ID: mdl-38800848

RESUMEN

Scaffold structures, new mechanisms of action, and targets present enormous challenges in the discovery of novel pesticides. The discovery of new scaffolds is the basis for the continuous development of modern agrochemicals. Identification of a good scaffold such as triazole, carbamate, methoxy acrylate, pyrazolamide, pyrido-pyrimidinone mesoionic, and bisamide often leads to the development of a new series of pesticides. In addition, pesticides with the same target, including the inhibitors of succinate dehydrogenase (SDH), oxysterol-binding-protein, and p-hydroxyphenyl pyruvate dioxygenase (HPPD), may have the same or similar scaffold structure. Recent years have witnessed significant progress in the discovery of new pesticides using natural products as scaffolds or bridges. In recent years, there have been increasing reports on the application of natural benzopyran compounds in the discovery of new pesticides, especially osthole and coumarin. A systematic and comprehensive review of benzopyran active compounds in the discovery of new agricultural chemicals is helpful to promote the discussion and development of benzopyran active compounds. Therefore, this work systematically reviewed the research and application of benzopyran derivatives in the discovery of agricultural chemicals, summarized the antiviral, herbicidal, antibacterial, fungicidal, insecticidal, nematicidal and acaricidal activities of benzopyran active compounds, and discussed the structural-activity relationship and mechanism of action. In addition, some active fragments were recommended to further optimize the chemical structure of benzopyran active compounds based on reference information.


Asunto(s)
Agroquímicos , Benzopiranos , Descubrimiento de Drogas , Plaguicidas , Benzopiranos/química , Benzopiranos/farmacología , Plaguicidas/química , Plaguicidas/farmacología , Agroquímicos/química , Agroquímicos/farmacología , Animales , Relación Estructura-Actividad , Estructura Molecular
4.
Bioorg Chem ; 148: 107434, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38744168

RESUMEN

Azaphilones represent a particular group of fascinating pigments from fungal source, with easier industrialization and lower cost than the traditional plant-derived pigments, and they also display a wide range of pharmacological activities. Herein, 28 azaphilone analogs, including 12 new ones, were obtained from the fermentation culture of a marine fungus Penicillium sclerotium UJNMF 0503. Their structures were elucidated by MS, NMR and ECD analyses, together with NMR and ECD calculations and biogenetic considerations. Among them, compounds 1 and 2 feature an unusual natural benzo[d][1,3]dioxepine ring embedded with an orthoformate unit, while 3 and 4 represent the first azaphilone examples incorporating a novel rearranged 5/6 bicyclic core and a tetrahydropyran ring on the side chain, respectively. Our bioassays revealed that half of the isolates exhibited neuroprotective potential against H2O2-induced injury on RSC96 cells, while compound 13 displayed the best rescuing capacity toward the cell viability by blocking cellular apoptosis, which was likely achieved by upregulating the PI3K/Akt signaling pathway.


Asunto(s)
Apoptosis , Benzopiranos , Relación Dosis-Respuesta a Droga , Peróxido de Hidrógeno , Fármacos Neuroprotectores , Penicillium , Fosfatidilinositol 3-Quinasas , Pigmentos Biológicos , Proteínas Proto-Oncogénicas c-akt , Apoptosis/efectos de los fármacos , Penicillium/química , Fármacos Neuroprotectores/farmacología , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Proteínas Proto-Oncogénicas c-akt/metabolismo , Proteínas Proto-Oncogénicas c-akt/antagonistas & inhibidores , Fosfatidilinositol 3-Quinasas/metabolismo , Pigmentos Biológicos/farmacología , Pigmentos Biológicos/química , Pigmentos Biológicos/aislamiento & purificación , Peróxido de Hidrógeno/farmacología , Peróxido de Hidrógeno/antagonistas & inhibidores , Estructura Molecular , Benzopiranos/farmacología , Benzopiranos/química , Benzopiranos/aislamiento & purificación , Relación Estructura-Actividad , Animales , Supervivencia Celular/efectos de los fármacos , Ratas , Transducción de Señal/efectos de los fármacos
5.
J Hazard Mater ; 473: 134595, 2024 Jul 15.
Artículo en Inglés | MEDLINE | ID: mdl-38761769

RESUMEN

A biocatalytic system comprising fungal laccase and mediators can generate phenol radicals and efficiently eliminate various triarylmethane dyes. This study systematically explores the kinetic impact of dissolved organic matter (DOM), represented by humic substance (HS consisting of 90% fulvic acid, from lignite), on the decolorization of seven typical triarylmethane dyes by Trametes versicolor laccase and twenty natural mediators. Among these, 4-hydroxybenzyl alcohol (4-HA) and methyl violet (MV) undergo in-depth investigation regarding degradation products, pathways, and reaction mechanisms. In instances where HS hampers laccase-alone decolorization, such as malachite green, Coomassie brilliant blue, bromophenol blue, and acid magenta, this inhibition may persist despite mediator introduction. Conversely, in cases where HS facilitates decolorization, such as crystalline violet and ethyl violet, most laccase-mediator systems (LMSs) can still benefit. For MV decolorization by laccase and 4-HA, HS's kinetic effect is controlled by concentration and reaction time. A 5 mg/L HS increased the decolorization rate from 50% to 67% within the first hour, whereas 10 mg/L HS only achieved 45%. After 16 h of reaction, HS's impact on decolorization rate diminishes. Furthermore, the addition of HS enhances precipitation production, probably due to its involvement in polymerization with MV and mediator. Computational simulations and spectral monitoring reveal that low HS concentrations accelerate laccase-mediated demethylation by disrupting the chromophores bound to MV, thus promoting the decolorization of MV. Conversely, inhibition by high HS concentrations stems from the competitive binding of the enzyme pocket to the mediator, and the reduction of phenol free radicals in the system. Molecular docking and kinetic simulations revealed that laccase forms complexes with both the mediator and MV. Interestingly, the decolorization of MV occurred through a non-radical mechanism in the presence of HS. This work provided a reference for screening of high catalytic performance mediators to remove triarylmethane dyes in the actual water environment.


Asunto(s)
Colorantes , Lacasa , Lacasa/metabolismo , Lacasa/química , Colorantes/química , Sustancias Húmicas , Cinética , Contaminantes Químicos del Agua/química , Benzopiranos/química , Simulación del Acoplamiento Molecular , Polyporaceae/enzimología
6.
Carbohydr Res ; 541: 109164, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38815342

RESUMEN

Stereoselective synthesis is essential for propelling mainstream academia toward a relentless pursuit of novel and cutting-edge strategies for constructing molecules with unparalleled precision. Naturally derived benzopyrans, benzopyrones, and flavonoids are an essentially prominent group of oxa-heterocycles, highly significant targets in medicinal chemistry owing to their extensive abundance in biologically active natural products and pharmaceuticals. The molecular complexity and stereoselectivity induced by heterocycles embedded with C-glycosides have attracted considerable interest and emerged as a fascinating area of research for synthetic organic chemists. This present article emphasizes the existing growths in the strategies involving the diastereoselective synthesis of C-glycosylated benzopyrans, benzopyrones, and flavonoids using naturally acquired glycones as chiral synthons.


Asunto(s)
Benzopiranos , Productos Biológicos , Flavonoides , Glicósidos , Flavonoides/química , Flavonoides/síntesis química , Estereoisomerismo , Benzopiranos/química , Benzopiranos/síntesis química , Productos Biológicos/síntesis química , Productos Biológicos/química , Glicósidos/química , Glicósidos/síntesis química , Pironas/química , Pironas/síntesis química , Glicosilación , Estructura Molecular
7.
Talanta ; 276: 126227, 2024 Aug 15.
Artículo en Inglés | MEDLINE | ID: mdl-38733935

RESUMEN

Fatty liver disease affects at least 25 percent of the population worldwide and is a severe metabolic syndrome. Viscosity is closely related to fatty liver disease, so it is urgent to develop an effective tool for monitoring viscosity. Herein, a NIR fluorescent probe called MBC-V is developed for imaging viscosity, consisting of dimethylaniline and malonitrile-benzopyran. MBC-V is non-fluorescent in low viscosity solutions due to intramolecular rotation. In high viscosity solution, the intramolecular rotation of MBC-V is suppressed and the fluorescence is triggered. MBC-V has long emission wavelength at 720 nm and large Stokes shift about 160 nm. Moreover, MBC-V can detect changes in cell viscosity in fatty liver cells, and can image the therapeutic effects of drug in fatty liver cells. By taking advantage of NIR emission, MBC-V can be used as an imaging tool for fatty liver disease and a way to evaluate the therapeutic effect of drug for fatty liver disease.


Asunto(s)
Compuestos de Anilina , Hígado Graso , Colorantes Fluorescentes , Colorantes Fluorescentes/química , Colorantes Fluorescentes/síntesis química , Animales , Viscosidad , Ratones , Hígado Graso/diagnóstico por imagen , Hígado Graso/tratamiento farmacológico , Compuestos de Anilina/química , Imagen Óptica , Humanos , Benzopiranos/química , Benzopiranos/síntesis química , Nitrilos/química
8.
Org Biomol Chem ; 22(22): 4521-4527, 2024 06 05.
Artículo en Inglés | MEDLINE | ID: mdl-38752482

RESUMEN

Ten azaphilones including one pair of new epimers and three new ones, penineulones A-E (1-5) with the same structural core of angular deflectin, were obtained from a deep-sea derived Penicillium sp. SCSIO41030 fermented on a liquid medium. Their structures including absolute configurations were elucidated using chiral-phase HPLC analysis, extensive NMR spectroscopic and HRESIMS data, ECD and NMR calculations, and by comparing NMR data with literature data. Biological assays showed that the azaphilones possessed no antitumor and anti-viral (HSV-1/2) activities at concentrations of 5.0 µM and 20 µM, respectively. In addition, azaphilones 8 and 9 showed neuroprotective effects against Aß25-35-induced neurotoxicity in primary cultured cortical neurons at a concentration of 10 µM. Azaphilones 8 and 9 dramatically promoted axonal regrowth against Aß25-35-induced axonal atrophy. Our study indicated that azaphilones could be promising lead compounds for neuroprotection.


Asunto(s)
Benzopiranos , Fármacos Neuroprotectores , Penicillium , Penicillium/química , Fármacos Neuroprotectores/farmacología , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Benzopiranos/farmacología , Benzopiranos/química , Benzopiranos/aislamiento & purificación , Animales , Péptidos beta-Amiloides/antagonistas & inhibidores , Péptidos beta-Amiloides/metabolismo , Péptidos beta-Amiloides/farmacología , Pigmentos Biológicos/farmacología , Pigmentos Biológicos/química , Pigmentos Biológicos/aislamiento & purificación , Humanos , Neuronas/efectos de los fármacos , Fragmentos de Péptidos/farmacología , Fragmentos de Péptidos/química , Estructura Molecular
9.
Comput Biol Chem ; 111: 108097, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38772048

RESUMEN

A new series of 2H-chromene-based sulfonamide derivatives 3-12 has been synthesized and characterized using different spectroscopic techniques. The synthesized 2H-chromenes were synthesized by reacting activated methylene with 5-(piperidin-1-ylsulfonyl)salicylaldehyde through one-step condensation followed by intramolecular cyclization. Virtual screening of the designed molecules on α-glucosidase enzymes (PDB: 3W37 and 3A4A) exhibited good binding affinity suggesting that these derivatives may be potential α-glucosidase inhibitors. In-vitro α-glucosidase activity was conducted firstly at 100 µg/mL, and the results demonstrated good inhibitory potency with values ranging from 90.6% to 96.3% compared to IP = 95.8% for Acarbose. Furthermore, the IC50 values were determined, and the designed derivatives exhibited inhibitory potency less than 11 µg/mL. Surprisingly, two chromene derivatives 6 and 10 showed the highest potency with IC50 values of 0.975 ± 0.04 and 0.584 ± 0.02 µg/mL, respectively, compared to Acarbose (IC50 = 0.805 ± 0.03 µg/mL). Moreover, our work was extended to evaluate the in-vitro α-amylase and PPAR-γ activity as additional targets for diabetic activity. The results exhibited moderate activity on α-amylase and potency as PPAR-γ agonist making it a multiplet antidiabetic target. The most active 2H-chromenes 6 and 10 exhibited significant activity to PPAR-γ with IC50 values of 3.453 ± 0.14 and 4.653 ± 0.04 µg/mL compared to Pioglitazone (IC50 = 4.884±0.29 µg/mL) indicating that these derivatives improve insulin sensitivity by stimulating the production of small insulin-sensitive adipocytes. In-silico ADME profile analysis indicated compliance with Lipinski's and Veber's rules with excellent oral bioavailability properties. Finally, the docking simulation was conducted to explain the expected binding mode and binding affinity.


Asunto(s)
Benzopiranos , Diabetes Mellitus Tipo 2 , Diseño de Fármacos , Inhibidores de Glicósido Hidrolasas , Hipoglucemiantes , PPAR gamma , alfa-Amilasas , alfa-Glucosidasas , PPAR gamma/metabolismo , PPAR gamma/antagonistas & inhibidores , Benzopiranos/química , Benzopiranos/farmacología , Benzopiranos/síntesis química , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Hipoglucemiantes/síntesis química , alfa-Glucosidasas/metabolismo , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Diabetes Mellitus Tipo 2/metabolismo , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/síntesis química , alfa-Amilasas/antagonistas & inhibidores , alfa-Amilasas/metabolismo , Humanos , Relación Estructura-Actividad , Estructura Molecular , Simulación del Acoplamiento Molecular , Evaluación Preclínica de Medicamentos , Descubrimiento de Drogas , Relación Dosis-Respuesta a Droga
10.
Molecules ; 29(10)2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38792180

RESUMEN

The goal of this study was directed to synthesize a novel class of annulated compounds containing difuro[3,2-c:3',2'-g]chromene. Friedländer condensation of o-aminoacetyl derivative 3 was performed with some active methylene ketones, namely, 1,3-cyclohexanediones, pyrazolones, 1,3-thiazolidinones and barbituric acids, furnished furochromenofuroquinolines (4,5), furochromenofuropyrazolopyridines (6-8), furochromenofurothiazolopyridines (9,10) and furochromenofuropyridopyrimidines (11, 12), respectively. Also, condensation of substrate 3 with 5-amine-3-methyl-1H-pyrazole and 6-amino-1,3-dimethyluracil, as cyclic enamines, resulted in polyfused systems 13 and 14, respectively. In vitro antimicrobial efficiency of the prepared heterocycles against microbial strains exhibited variable inhibition action, where compound 3 was the most effective against all kinds of microorganisms. A significant cytotoxic activity was seen upon the annulation of the starting compound with thiazolopyridine (9 and 10) as well as pyridopyrimidine moieties (11, 12 and 14). The spectroscopic and analytical results were used to infer the structures of the novel synthesized compounds.


Asunto(s)
Antiinfecciosos , Antineoplásicos , Benzopiranos , Pruebas de Sensibilidad Microbiana , Humanos , Antineoplásicos/farmacología , Antineoplásicos/síntesis química , Antineoplásicos/química , Benzopiranos/farmacología , Benzopiranos/química , Benzopiranos/síntesis química , Antiinfecciosos/farmacología , Antiinfecciosos/química , Antiinfecciosos/síntesis química , Línea Celular Tumoral , Estructura Molecular , Relación Estructura-Actividad , Bacterias/efectos de los fármacos
11.
Chem Pharm Bull (Tokyo) ; 72(5): 498-506, 2024 May 25.
Artículo en Inglés | MEDLINE | ID: mdl-38735699

RESUMEN

Using (S)-decursinol isolated from root of Angelica gigas Nakai (AGN), we semi-synthesized and evaluated a series of both enantiomerically pure decursin derivatives for their antiproliferative activities against A549 human lung cancer cells. All synthesized compounds showed a broad spectrum of inhibitory activities against the growth of A549 cells. Especially, compound (S)-2d with (E)-(furan-3-yl)acryloyl group showed the most potent activity (IC50: 14.03 µM) against A549 cancer cells as compared with the reference compound, decursin (IC50: 43.55 µM) and its enantiomer, (R)-2d (IC50: 151.59 µM). Western blotting assays indicated that (S)-2d more strongly inhibited Janus kinase 1 (JAK1) and signal transducer and activator of transcription activation 3 (STAT3) phosphorylation than decursin in a dose-dependent manner, while having no effect on CXCR7 overexpression and total STAT3 level. In addition, (S)-2d induced cell cycle arrest at G1 phase and subsequent apoptotic cell death in A549 cancer cells. Our combined analysis of molecular docking studies and biological data suggests that the inhibition of JAK1 with (S)-2d resulted in loss of STAT3 phosphorylation and inhibition of cell growth in A549 cancer cells. These overall results strongly suggest that (S)-2d (MRC-D-004) as a novel JAK1 inhibitor may have therapeutic potential in the treatment of A549 human lung cancers by targeting the JAK1/STAT3 signaling pathway.


Asunto(s)
Apoptosis , Benzopiranos , Butiratos , Proliferación Celular , Ensayos de Selección de Medicamentos Antitumorales , Simulación del Acoplamiento Molecular , Factor de Transcripción STAT3 , Humanos , Proliferación Celular/efectos de los fármacos , Factor de Transcripción STAT3/antagonistas & inhibidores , Factor de Transcripción STAT3/metabolismo , Benzopiranos/farmacología , Benzopiranos/química , Benzopiranos/síntesis química , Butiratos/farmacología , Butiratos/química , Butiratos/síntesis química , Apoptosis/efectos de los fármacos , Células A549 , Estereoisomerismo , Relación Dosis-Respuesta a Droga , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Relación Estructura-Actividad , Janus Quinasa 1/antagonistas & inhibidores , Janus Quinasa 1/metabolismo , Estructura Molecular , Angelica/química , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/síntesis química , Antineoplásicos Fitogénicos/química
12.
Bioorg Chem ; 147: 107419, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38703440

RESUMEN

We formerly reported that EZH2 inhibitors sensitized HIF-1 inhibitor-resistant cells and inhibited HIF-1α to promote SUZ12 transcription, leading to enhanced EZH2 enzyme activity and elevated H3K27me3 levels, and conversely, inhibition of EZH2 promoted HIF-1α transcription. HIF-1α and EZH2 interacted to form a negative feedback loop that reinforced each other's activity. In this paper, a series of 2,2- dimethylbenzopyran derivatives containing pyridone structural fragments were designed and synthesized with DYB-03, a HIF-1α inhibitor previously reported by our group, and Tazemetostat, an EZH2 inhibitor approved by FDA, as lead compounds. Among these compounds, D-01 had significant inhibitory activities on HIF-1α and EZH2. In vitro experiments showed that D-01 significantly inhibited the migration of A549 cells, clone, invasion and angiogenesis. Moreover, D-01 had good pharmacokinetic profiles. All the results about compound D-01 could lay a foundation for the research and development of HIF-1α and EZH2 dual-targeting compounds.


Asunto(s)
Antineoplásicos , Ensayos de Selección de Medicamentos Antitumorales , Proteína Potenciadora del Homólogo Zeste 2 , Subunidad alfa del Factor 1 Inducible por Hipoxia , Neoplasias Pulmonares , Piridonas , Humanos , Proteína Potenciadora del Homólogo Zeste 2/antagonistas & inhibidores , Proteína Potenciadora del Homólogo Zeste 2/metabolismo , Subunidad alfa del Factor 1 Inducible por Hipoxia/antagonistas & inhibidores , Subunidad alfa del Factor 1 Inducible por Hipoxia/metabolismo , Piridonas/química , Piridonas/farmacología , Piridonas/síntesis química , Neoplasias Pulmonares/tratamiento farmacológico , Neoplasias Pulmonares/patología , Neoplasias Pulmonares/metabolismo , Relación Estructura-Actividad , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Estructura Molecular , Relación Dosis-Respuesta a Droga , Proliferación Celular/efectos de los fármacos , Animales , Benzopiranos/química , Benzopiranos/farmacología , Benzopiranos/síntesis química , Movimiento Celular/efectos de los fármacos
13.
Sci Rep ; 14(1): 11206, 2024 05 16.
Artículo en Inglés | MEDLINE | ID: mdl-38755178

RESUMEN

Contamination of soils by Molybdenum (Mo) has raised increasing concern worldwide. Both fulvic acid (FA) and humic acid (HA) possess numerous positive properties, such as large specific surface areas and microporous structure that facilitates the immobilization of the heavy metal in soils. Despite these characteristics, there have been few studies on the microbiology effects of FA and HA. Therefore, this study aimed to assess the Mo immobilization effects of FA and HA, as well as the associated changes in microbial community in Mo-contaminated soils (with application rates of 0%, 0.5% and 1.0%). The result of the incubation demonstrated a decrease in soil pH (from 8.23 ~ 8.94 to 8.05 ~ 8.77). Importantly, both FA and HA reduced the exchangeable fraction and reducible fraction of Mo in the soil, thereby transforming Mo into a more stable form. Furthermore, the application of FA and HA led to an increase in the relative abundance of Actinobacteriota and Firmicutes, resulting in alterations to the microbial community structure. However, it is worth noting that due to the differing structures and properties of FA and HA, these outcomes were not entirely consistent. In summary, the aging of FA and HA in soil enhanced their capacity to immobilization Mo as a soil amendment. This suggests that they have the potential to serve as effective amendments for the remediation of Mo-contaminated soils.


Asunto(s)
Sustancias Húmicas , Metales Pesados , Microbiología del Suelo , Contaminantes del Suelo , Sustancias Húmicas/análisis , Contaminantes del Suelo/química , Benzopiranos/química , Benzopiranos/farmacología , Molibdeno/química , Suelo/química , Concentración de Iones de Hidrógeno , Bacterias/efectos de los fármacos , Microbiota/efectos de los fármacos
14.
Spectrochim Acta A Mol Biomol Spectrosc ; 317: 124404, 2024 Sep 05.
Artículo en Inglés | MEDLINE | ID: mdl-38723465

RESUMEN

Peroxynitrite is one of the important reactive oxygen species in the human body and is closely related to the physiological and pathological processes of many diseases. Therefore, the development of probes to detect peroxynitrite is important for diagnostic and pathologic studies of many diseases. In this work, a ratiometric probe was designed using benzopyran as the recognition site, and the sensitivity and selectivity of the probe were tuned by modification of substituents on benzopyran. Upon reaction with peroxynitrite, the color of the solution changes to the naked eye (from blue to yellow), and the fluorescence changes from red to blue. The probe SJ has the advantages of large Stokes shift (237 nm), fast response (≤10 s), wide linear range, good selectivity, low detection line (21.3 nm), and low cytotoxicity. Probe SJ has been successfully used for bioimaging of endogenous and exogenous peroxynitrite.


Asunto(s)
Colorantes Fluorescentes , Ácido Peroxinitroso , Espectrometría de Fluorescencia , Ácido Peroxinitroso/análisis , Colorantes Fluorescentes/química , Colorantes Fluorescentes/síntesis química , Humanos , Animales , Benzopiranos/química , Ratones , Límite de Detección
15.
Environ Sci Technol ; 58(21): 9040-9050, 2024 May 28.
Artículo en Inglés | MEDLINE | ID: mdl-38743693

RESUMEN

Despite the widespread use of photochemical and optical properties to characterize dissolved organic matter (DOM), a significant gap persists in our understanding of the relationship among these properties. This study infers the molecular basis for the optical and photochemical properties of DOM using a comprehensive framework and known structural moieties within DOM. Utilizing Suwannee River Fulvic Acid (SRFA) as a model DOM, carboxylated aromatics, phenols, and quinones were identified as dominant contributors to the absorbance spectra, and phenols, quinones, aldehydes, and ketones were identified as major contributors to radiative energy pathways. It was estimated that chromophores constitute ∼63% w/w of dissolved organic carbon in SRFA and ∼47% w/w of overall SRFA. Notably, estimations indicate the pool of fluorescent compounds and photosensitizing compounds in SRFA are likely distinct from each other at wavelengths below 400 nm. This perspective offers a practical tool to aid in the identification of probable chemical groups when interpreting optical and photochemical data and challenges the current "black box" thinking. Instead, DOM photochemical and optical properties can be closely estimated by assuming the DOM is composed of a mixture of individual compounds.


Asunto(s)
Benzopiranos , Benzopiranos/química , Compuestos Orgánicos/química , Ríos/química
16.
Eur J Pharm Biopharm ; 200: 114307, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38685438

RESUMEN

Herein, we report the properties of nanostructured lipid carriers (NLCs) prepared with a gradient concentration of Bergenin (BGN) isolated from Pentaclethra macrophylla stem bark powder. A gradient concentration of BGN (BGN 0, 50, 100, 150, and 200 mg) was prepared in a 5 % lipid matrix consisting of Transcutol HP (75 %), Phospholipon 90H (15 %), and Gelucire 43/01 (10 %) to which a surfactant aqueous phase consisting of Tween 80, sorbitol, and sorbic acid was dissolved. The NLCs were evaluated by size, polydispersity index (PDI), zeta potential, Fourier Transform Infrared Spectroscopy (FTIR), Differential Scanning Calorimetry (DSC), encapsulation efficiency, and in vitro drug release. The result shows polydispersed nanoparticles with high drug encapsulation (94.26-99.50 %). The nanoparticles were mostly spherical, but those from the 50 mg BGN batch were more cuboidal than spherical. The drug release was highest from the latter to the tune of 40 % compared to the pure BGN solution, which released about 15 % BGN. The anti-inflammatory activity of the BGN-NLC and total plant extract was studied on lipopolysaccharide (LPS)-inflamed macrophages. The cell study showed that BGN and plant extract had low cytotoxicity on macrophages and exhibited a dose-dependent anti-inflammatory effect on the LPS-induced inflammatory process in macrophages.


Asunto(s)
Antiinflamatorios , Benzopiranos , Portadores de Fármacos , Lípidos , Lipopolisacáridos , Macrófagos , Nanopartículas , Lipopolisacáridos/farmacología , Animales , Ratones , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Antiinflamatorios/farmacología , Antiinflamatorios/administración & dosificación , Antiinflamatorios/química , Portadores de Fármacos/química , Benzopiranos/farmacología , Benzopiranos/administración & dosificación , Benzopiranos/química , Nanopartículas/química , Lípidos/química , Células RAW 264.7 , Liberación de Fármacos , Nanoestructuras/química , Saxifragaceae/química , Tamaño de la Partícula , Inflamación/tratamiento farmacológico , Inflamación/inducido químicamente , Extractos Vegetales/farmacología , Extractos Vegetales/administración & dosificación , Extractos Vegetales/química
17.
J Hazard Mater ; 470: 134304, 2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38615650

RESUMEN

In lightly polluted water containing heavy metals, organic matter, and green microalgae, the molecular weight of organic matter may influence both the growth of green microalgae and the concentration of heavy metals. This study elucidates the effects and mechanisms by which different molecular weight fractions of fulvic acid (FA), a model dissolved organic matter component, facilitate the bioaccumulation of hexavalent chromium (Cr(VI)) in a typical green alga, Chlorella vulgaris. Findings show that the addition of FA fractions with molecular weights greater than 10 kDa significantly enhances the enrichment of total chromium and Cr(VI) in algal cells, reaching 21.58%-31.09 % and 16.17 %-22.63 %, respectively. Conversely, the efficiency of chromium enrichment in algal cells was found to decrease with decreasing molecular weight of FA. FA molecular weight within the range of 0.22 µm-30 kDa facilitated chromium enrichment primarily through the algal organic matter (AOM) pathway, with minor contributions from the algal cell proliferation and extracellular polymeric substances (EPS) pathways. However, with decreasing FA molecular weight, the AOM and EPS pathways become less prominent, whereas the algal cell proliferation pathway becomes dominant. These findings provide new insights into the mechanism of chromium enrichment in green algae enhanced by medium molecular weight FA.


Asunto(s)
Benzopiranos , Chlorella vulgaris , Cromo , Microalgas , Peso Molecular , Contaminantes Químicos del Agua , Cromo/metabolismo , Cromo/química , Chlorella vulgaris/metabolismo , Chlorella vulgaris/crecimiento & desarrollo , Chlorella vulgaris/efectos de los fármacos , Contaminantes Químicos del Agua/metabolismo , Microalgas/metabolismo , Microalgas/efectos de los fármacos , Microalgas/crecimiento & desarrollo , Benzopiranos/química , Benzopiranos/metabolismo
18.
Environ Sci Technol ; 58(16): 7186-7195, 2024 Apr 23.
Artículo en Inglés | MEDLINE | ID: mdl-38598770

RESUMEN

Remediation of large and dilute plumes of groundwater contaminated by oxidized pollutants such as chromate is a common and difficult challenge. Herein, we show that in situ formation of FeS nanoparticles (using dissolved Fe(II), S(-II), and natural organic matter as a nucleating template) results in uniform coating of aquifer material to create a regenerable reactive zone that mitigates Cr(VI) migration. Flow-through columns packed with quartz sand are amended first with an Fe2+ solution and then with a HS- solution to form a nano-FeS coating on the sand, which does not hinder permeability. This nano-FeS coating effectively reduces and immobilizes Cr(VI), forming Fe(III)-Cr(III) coprecipitates with negligible detachment from the sand grains. Preconditioning the sand with humic or fulvic acid (used as model natural organic matter (NOM)) further enhances Cr(VI) sequestration, as NOM provides additional binding sites of Fe2+ and mediates both nucleation and growth of FeS nanoparticles, as verified with spectroscopic and microscopic evidence. Reactivity can be easily replenished by repeating the procedures used to form the reactive coating. These findings demonstrate that such enhancement of attenuation capacity can be an effective option to mitigate Cr(VI) plume migration and exposure, particularly when tackling contaminant rebound post source remediation.


Asunto(s)
Cromo , Agua Subterránea , Oxidación-Reducción , Contaminantes Químicos del Agua , Agua Subterránea/química , Cromo/química , Contaminantes Químicos del Agua/química , Nanopartículas/química , Restauración y Remediación Ambiental/métodos , Sustancias Húmicas , Compuestos Ferrosos/química , Benzopiranos/química
19.
Nat Commun ; 15(1): 3539, 2024 Apr 26.
Artículo en Inglés | MEDLINE | ID: mdl-38670975

RESUMEN

Bergenin, a rare C-glycoside of 4-O-methyl gallic acid with pharmacological properties of antitussive and expectorant, is widely used in clinics to treat chronic tracheitis in China. However, its low abundance in nature and structural specificity hampers the accessibility through traditional crop-based manufacturing or chemical synthesis. In the present work, we elucidate the biosynthetic pathway of bergenin in Ardisia japonica by identifying the highly regio- and/or stereoselective 2-C-glycosyltransferases and 4-O-methyltransferases. Then, in Escherichia coli, we reconstruct the de novo biosynthetic pathway of 4-O-methyl gallic acid 2-C-ß-D-glycoside, which is the direct precursor of bergenin and is conveniently esterified into bergenin by in situ acid treatment. Moreover, further metabolic engineering improves the production of bergenin to 1.41 g L-1 in a 3-L bioreactor. Our work provides a foundation for sustainable supply of bergenin and alleviates its resource shortage via a synthetic biology approach.


Asunto(s)
Benzopiranos , Vías Biosintéticas , Escherichia coli , Ingeniería Metabólica , Benzopiranos/metabolismo , Benzopiranos/química , Ingeniería Metabólica/métodos , Escherichia coli/metabolismo , Escherichia coli/genética , Glicosiltransferasas/metabolismo , Metiltransferasas/metabolismo , Ácido Gálico/metabolismo , Ácido Gálico/química , Reactores Biológicos , Glicósidos/biosíntesis , Glicósidos/metabolismo , Glicósidos/química
20.
Int J Biol Macromol ; 266(Pt 2): 131360, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38580017

RESUMEN

A humic acid-gelatin (HA-Gel) hydrogel, a gallic acid-xanthan gum (GA-XG) hydrogel, a HA-Gel/GA-XG hydrogel, and superabsorbent polymer (SAP) of HA-Gel/GA-XG/polyacrylamide (PAM) hydrogel were synthesized using electron beam irradiation method. The capability of synthesized hydrogels in loading and controlled release of fulvic acid (FA) was studied. The chemical and physical structure of sorbents was confirmed by various analyses. The effect of irradiation dose on mechanical properties, gel percentage, swelling, and absorbency under load (AUL) of the sorbents was investigated. By changing the hydrogel structures into the SAP form, its swelling capacity was increased from 37 to 320 g/g. Both hybrid hydrogel and SAP were reusable for up to 7 cycles. The maximum fertilizer loading capacities for SAP and hybrid hydrogel were 402.1 and, 175.5 mg g-1, respectively. In comparison to hydrogels, the SAP showed a slower FA-release performance. Thus, in soil media, 86 % of FA was released in 15-20 days from the hybrid hydrogel while with the SAP, 81 % of FA was released in 30-35 days. The significant improvement in the growth of fodder corn treated with FA-loaded SAP in the greenhouse media in comparison to the control groups showed the effective performance of the designed SAP, favoring its practical applications.


Asunto(s)
Benzopiranos , Gelatina , Hidrogeles , Polisacáridos Bacterianos , Zea mays , Hidrogeles/química , Benzopiranos/química , Polisacáridos Bacterianos/química , Gelatina/química , Zea mays/química , Preparaciones de Acción Retardada/química , Electrones , Polímeros/química , Fertilizantes , Ácido Gálico/química , Sustancias Húmicas
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