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Keywords = quinizarin

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17 pages, 3170 KiB  
Article
Photodynamic Therapy as a Novel Therapeutic Modality Applying Quinizarin-Loaded Nanocapsules and 3D Bioprinting Skin Permeation for Inflammation Treatment
by Stéphanie R. do Amaral, Camila F. Amantino, Aleksandar Atanasov, Stefanie Oliveira Sousa, Richard Moakes, Sonia Maria Oliani, Liam M. Grover and Fernando L. Primo
Pharmaceuticals 2024, 17(9), 1169; https://doi.org/10.3390/ph17091169 - 4 Sep 2024
Cited by 2 | Viewed by 1347
Abstract
Skin inflammation associated with chronic diseases involves a direct role of keratinocytes in its immunopathogenesis, triggering a cascade of immune responses. Despite this, highly targeted treatments remain elusive, highlighting the need for more specific therapeutic strategies. In this study, nanocapsules containing quinizarin (QZ/NC) [...] Read more.
Skin inflammation associated with chronic diseases involves a direct role of keratinocytes in its immunopathogenesis, triggering a cascade of immune responses. Despite this, highly targeted treatments remain elusive, highlighting the need for more specific therapeutic strategies. In this study, nanocapsules containing quinizarin (QZ/NC) were developed and evaluated in an in vitro model of keratinocyte-mediated inflammation, incorporating the action of photodynamic therapy (PDT) and analyzing permeation in a 3D skin model. Comprehensive physicochemical, stability, cytotoxicity, and permeation analyses of the nanomaterials were conducted. The nanocapsules demonstrated desirable physicochemical properties, remained stable throughout the analysis period, and exhibited no spectroscopic alterations. Cytotoxicity tests revealed no toxicity at the lowest concentrations of QZ/NC. Permeation and cellular uptake studies confirmed QZ/NC permeation in 3D skin models, along with intracellular incorporation and internalization of the drug, thereby enhancing its efficacy in drug delivery. The developed model for inducing the inflammatory process in vitro yielded promising results, particularly when the synthesized nanomaterial was combined with PDT, showing a reduction in cytokine levels. These findings suggest a potential new therapeutic approach for treating inflammatory skin diseases. Full article
(This article belongs to the Special Issue Photosensitizers and Drug Delivery Systems for Photodynamic Therapy)
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15 pages, 11760 KiB  
Article
Anthraquinone-Quinizarin Copolymer as a Promising Electrode Material for High-Performance Lithium and Potassium Batteries
by Elena V. Shchurik, Olga A. Kraevaya, Sergey G. Vasil’ev, Ivan S. Zhidkov, Ernst Z. Kurmaev, Alexander F. Shestakov and Pavel A. Troshin
Molecules 2023, 28(14), 5351; https://doi.org/10.3390/molecules28145351 - 12 Jul 2023
Cited by 3 | Viewed by 2703
Abstract
The growing demand for cheap, safe, recyclable, and environmentally friendly batteries highlights the importance of the development of organic electrode materials. Here, we present a novel redox-active polymer comprising a polyaniline-type conjugated backbone and quinizarin and anthraquinone units. The synthesized polymer was explored [...] Read more.
The growing demand for cheap, safe, recyclable, and environmentally friendly batteries highlights the importance of the development of organic electrode materials. Here, we present a novel redox-active polymer comprising a polyaniline-type conjugated backbone and quinizarin and anthraquinone units. The synthesized polymer was explored as a cathode material for batteries, and it delivered promising performance characteristics in both lithium and potassium cells. Excellent lithiation efficiency enabled high discharge capacity values of >400 mA g−1 in combination with good stability upon charge–discharge cycling. Similarly, the potassium cells with the polymer-based cathodes demonstrated a high discharge capacity of >200 mAh g−1 at 50 mA g−1 and impressive stability: no capacity deterioration was observed for over 3000 cycles at 11 A g−1, which was among the best results reported for K ion battery cathodes to date. The synthetic availability and low projected cost of the designed material paves a way to its practical implementation in scalable and inexpensive organic batteries, which are emerging as a sustainable energy storage technology. Full article
(This article belongs to the Special Issue Molecular Wires and Organic Materials for Energy Storage)
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10 pages, 2869 KiB  
Communication
Selective Recognition and Reversible “Turn-Off” Fluorescence Sensing of Acetate (CH3COO) Anion at Ppb Level Using a Simple Quinizarin Fluorescent Dye
by Mannanthara Kunhumon Noushija, Ananthu Shanmughan, Binduja Mohan and Sankarasekaran Shanmugaraju
Chemistry 2022, 4(4), 1407-1416; https://doi.org/10.3390/chemistry4040092 - 29 Oct 2022
Cited by 8 | Viewed by 3191
Abstract
A simple and cost-effective optical sensing system based on quinizarin fluorescent dye (QZ) for the selective and reversible sensing of CH3COO anions is reported. The anion binding affinity of QZ towards different anions was monitored using electronic absorption [...] Read more.
A simple and cost-effective optical sensing system based on quinizarin fluorescent dye (QZ) for the selective and reversible sensing of CH3COO anions is reported. The anion binding affinity of QZ towards different anions was monitored using electronic absorption and fluorescence emission titration studies in DMSO. The UV-visible absorption spectrum of QZ showed a decrease in the intensity of the characteristic absorption peaks at λ = 280, 323, and 475 nm, while a new peak appeared at λ = 586 nm after the addition of CH3COO anions. Similarly, the initial strong emission intensity of QZ was attenuated following titration with CH3COO anions. Notably, similar titration using other anions, such as F, Cl, I, NO3, NO2−, and H2PO4-, caused no observable changes in both absorption and emission spectra. The selective sensing of CH3COO anions was also reflected by a sharp visual color change from bright green to faint green under room light. Further, the binding was found to be reversible, and this makes QZ a potential optical and colorimetric sensor for selective, reversible, and ppb-level detection of CH3COO anions in a DMSO medium. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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19 pages, 3177 KiB  
Article
Unravelling the Puzzle of Anthranoid Metabolism in Living Plant Cells Using Spectral Imaging Coupled to Mass Spectrometry
by Quentin Chevalier, Jean-Baptiste Gallé, Nicolas Wasser, Valérie Mazan, Claire Villette, Jérôme Mutterer, Maria Mercedes Elustondo, Nicolas Girard, Mourad Elhabiri, Hubert Schaller, Andréa Hemmerlin and Catherine Vonthron-Sénécheau
Metabolites 2021, 11(9), 571; https://doi.org/10.3390/metabo11090571 - 25 Aug 2021
Cited by 3 | Viewed by 4048
Abstract
Vismione H (VH) is a fluorescent prenylated anthranoid produced by plants from the Hypericaceae family, with antiprotozoal activities against malaria and leishmaniosis. Little is known about its biosynthesis and metabolism in plants or its mode of action against parasites. When VH is isolated [...] Read more.
Vismione H (VH) is a fluorescent prenylated anthranoid produced by plants from the Hypericaceae family, with antiprotozoal activities against malaria and leishmaniosis. Little is known about its biosynthesis and metabolism in plants or its mode of action against parasites. When VH is isolated from Psorospermum glaberrimum, it is rapidly converted into madagascine anthrone and anthraquinone, which are characterized by markedly different fluorescent properties. To locate the fluorescence of VH in living plant cells and discriminate it from that of the other metabolites, an original strategy combining spectral imaging (SImaging), confocal microscopy, and non-targeted metabolomics using mass spectrometry, was developed. Besides VH, structurally related molecules including madagascine (Mad), emodin (Emo), quinizarin (Qui), as well as lapachol (Lap) and fraxetin (Fra) were analyzed. This strategy readily allowed a spatiotemporal characterization and discrimination of spectral fingerprints from anthranoid-derived metabolites and related complexes with cations and proteins. In addition, our study validates the ability of plant cells to metabolize VH into madagascine anthrone, anthraquinones and unexpected metabolites. These results pave the way for new hypotheses on anthranoid metabolism in plants. Full article
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22 pages, 7800 KiB  
Article
OVAT Analysis and Response Surface Methodology Based on Nutrient Sources for Optimization of Pigment Production in the Marine-Derived Fungus Talaromyces albobiverticillius 30548 Submerged Fermentation
by Mekala Venkatachalam, Alain Shum-Chéong-Sing, Yanis Caro, Laurent Dufossé and Mireille Fouillaud
Mar. Drugs 2021, 19(5), 248; https://doi.org/10.3390/md19050248 - 27 Apr 2021
Cited by 21 | Viewed by 4759
Abstract
Pigment production from filamentous fungi is gaining interest due to the diversity of fungal species, the variety of compounds synthesized, and the possibility of controlled massive productions. The Talaromyces species produce a large panel of metabolites, including Monascus-like azaphilone pigments, with potential use [...] Read more.
Pigment production from filamentous fungi is gaining interest due to the diversity of fungal species, the variety of compounds synthesized, and the possibility of controlled massive productions. The Talaromyces species produce a large panel of metabolites, including Monascus-like azaphilone pigments, with potential use as natural colorants in industrial applications. Optimizing pigment production from fungal strains grown on different carbon and nitrogen sources, using statistical methods, is widespread nowadays. The present work is the first in an attempt to optimize pigments production in a culture of the marine-derived T. albobiverticillius 30548, under the influence of several nutrients sources. Nutrient combinations were screened through the one-variable-at-a-time (OVAT) analysis. Sucrose combined with yeast extract provided a maximum yield of orange pigments (OPY) and red pigments (RPY) (respectively, 1.39 g/L quinizarin equivalent and 2.44 g/L Red Yeast pigment equivalent), as well as higher dry biomass (DBW) (6.60 g/L). Significant medium components (yeast extract, K2HPO4 and MgSO4·7H2O) were also identified from one-variable-at-a-time (OVAT) analysis for pigment and biomass production. A five-level central composite design (CCD) and a response surface methodology (RSM) were applied to evaluate the optimal concentrations and interactive effects between selected nutrients. The experimental results were well fitted with the chosen statistical model. The predicted maximum response for OPY (1.43 g/L), RPY (2.59 g/L), and DBW (15.98 g/L) were obtained at 3 g/L yeast extract, 1 g/L K2HPO4, and 0.2 g/L MgSO4·7H2O. Such optimization is of great significance for the selection of key nutrients and their concentrations in order to increase the pigment production at a pilot or industrial scale. Full article
(This article belongs to the Special Issue Fungal Natural Products: An Ongoing Source for New Drug Leads)
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13 pages, 2027 KiB  
Article
Crosstalk of Cancer Signaling Pathways by Cyclic Hexapeptides and Anthraquinones from Rubia cordifolia
by Premalatha Balachandran, Mohamed Ali Ibrahim, Jin Zhang, Mei Wang, David S. Pasco and Ilias Muhammad
Molecules 2021, 26(3), 735; https://doi.org/10.3390/molecules26030735 - 31 Jan 2021
Cited by 15 | Viewed by 4417
Abstract
The anticancer activities of Rubia cordifolia and its constituents have been reported earlier, but their influence on the crosstalk of complex cancer-related signaling metabolic pathways (i.e., transcription factors; TF) has not yet been fully investigated. In this study, R. cordifolia root extract was [...] Read more.
The anticancer activities of Rubia cordifolia and its constituents have been reported earlier, but their influence on the crosstalk of complex cancer-related signaling metabolic pathways (i.e., transcription factors; TF) has not yet been fully investigated. In this study, R. cordifolia root extract was subjected to the cancer signaling assay based bioactivity-guided fractionation, which yielded the following compounds viz., three anthraquinones, namely alizarin (1), purpurin (2), and emodin (3); two lignans, namely eudesmin (4) and compound 5; and two cyclic hexapeptides, namely deoxybouvardin RA-V (6), and a mixture of 6+9 (RA-XXI). The structures of the isolated compounds were determined by NMR spectroscopy and HRESIMS. The isolated compounds 1, 2, 3, 6, and a mixture of 6+9 were tested against a panel of luciferase reporter genes that assesses the activity of a wide-range of cancer-related signaling pathways. In addition, reference anthraquinones viz., chrysophanol (11), danthron (12), quinizarin (13), aloe-emodin (14), and α-lapachone (15) were also tested. Among the tested compounds, the cyclic hexapeptide 6 was found to be very active against several signaling pathways, notably Wnt, Myc, and Notch with IC50 values of 50, 75, and 93 ng/mL, respectively. Whereas, the anthraquinones exhibited very mild or no inhibition against these signaling pathways. Compound 6 being the most active, we tested it for stability in simulated intestinal (SIF) and gastric fluids (SGF), since the stability in biological fluid is a key short-coming of cyclic hexapeptides. The anticancer activity of 6 was found to remain unchanged before and after the treatment of simulated gastric/intestinal fluids, indicating that RA-V was stable. As a result, it could be bioavailable when orally used in therapeutics and possibly a drug candidate for cancer treatment. The mechanism for the preferential inhibition of these pathways and the possible crosstalk effect with other previously reported signaling pathways has been discussed. Full article
(This article belongs to the Special Issue Antitumoral Properties of Natural Products Ⅱ)
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21 pages, 1990 KiB  
Review
Biophysical Characterization and Anticancer Activities of Photosensitive Phytoanthraquinones Represented by Hypericin and Its Model Compounds
by Valéria Verebová, Jiří Beneš and Jana Staničová
Molecules 2020, 25(23), 5666; https://doi.org/10.3390/molecules25235666 - 1 Dec 2020
Cited by 24 | Viewed by 4208
Abstract
Photosensitive compounds found in herbs have been reported in recent years as having a variety of interesting medicinal and biological activities. In this review, we focus on photosensitizers such as hypericin and its model compounds emodin, quinizarin, and danthron, which have antiviral, antifungal, [...] Read more.
Photosensitive compounds found in herbs have been reported in recent years as having a variety of interesting medicinal and biological activities. In this review, we focus on photosensitizers such as hypericin and its model compounds emodin, quinizarin, and danthron, which have antiviral, antifungal, antineoplastic, and antitumor effects. They can be utilized as potential agents in photodynamic therapy, especially in photodynamic therapy (PDT) for cancer. We aimed to give a comprehensive summary of the physical and chemical properties of these interesting molecules, emphasizing their mechanism of action in relation to their different interactions with biomacromolecules, specifically with DNA. Full article
(This article belongs to the Special Issue Anticancer Properties of Natural and Derivative Products)
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11 pages, 2785 KiB  
Article
Powder and Nanotubes Titania Modified by Dye Sensitization as Photocatalysts for the Organic Pollutants Elimination
by Julie J. Murcia, Elsa G. Ávila-Martínez, Hugo Rojas, Jairo Cubillos, Svetlana Ivanova, Anna Penkova and Oscar H. Laguna
Nanomaterials 2019, 9(4), 517; https://doi.org/10.3390/nano9040517 - 2 Apr 2019
Cited by 18 | Viewed by 3986
Abstract
In this study, titanium dioxide powder obtained by the sol-gel method and TiO2 nanotubes, were prepared. In order to increase the TiO2 photoactivity, the powders and nanotubes obtained were modified by dye sensitization treatment during the oxide synthesis. The sensitizers applied [...] Read more.
In this study, titanium dioxide powder obtained by the sol-gel method and TiO2 nanotubes, were prepared. In order to increase the TiO2 photoactivity, the powders and nanotubes obtained were modified by dye sensitization treatment during the oxide synthesis. The sensitizers applied were Quinizarin (Q) and Zinc protoporphyrin (P). The materials synthesized were extensively characterized and it was found that the dye sensitization treatment leads to modify the optical and surface properties of Titania. It was also found that the effectiveness of the dye-sensitized catalysts in the phenol and methyl orange (MO) photodegradation strongly depends on the dye sensitizer employed. Thus, the highest degradation rate for MO was obtained over the conventional Q-TiO2 photocatalyst. In the case of the nanotubes series, the most effective photocatalyst in the MO degradation was based on TiO2-nanotubes sensitized with the dye protoporfirin (ZnP). Selected catalysts were also tested in the phenol and MO photodegradation under visible light and it was observed that these samples are also active under this radiation. Full article
(This article belongs to the Special Issue Nano‐Photocatalytic Materials: Possibilities and Challenges)
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20 pages, 3060 KiB  
Review
Fundamental Properties of Packing Materials for Liquid Chromatography
by Toshihiko Hanai
Separations 2019, 6(1), 2; https://doi.org/10.3390/separations6010002 - 5 Jan 2019
Cited by 7 | Viewed by 5717
Abstract
The high performance of chemically-modified silica gel packing materials is based on the utilization of pure silica gels. Earlier silica gels used to be made from inorganic silica; however, nowadays, silica gels are made from organic silanes. The surface smoothness and lack of [...] Read more.
The high performance of chemically-modified silica gel packing materials is based on the utilization of pure silica gels. Earlier silica gels used to be made from inorganic silica; however, nowadays, silica gels are made from organic silanes. The surface smoothness and lack of trace metals of new silica gels permits easy surface modifications (chemical reactions) and improves the reproducibility and stability. Sharpening peak symmetry is based on developing better surface modification methods (silylation). Typical examples can be found in the chromatography of amitriptyline for silanol testing and that of quinizarin for trace metal testing. These test compounds were selected and demonstrated sensitive results in the measurement of trace amounts of either silanol or trace metals. Here, we demonstrate the three-dimensional model chemical structures of bonded-phase silica gels with surface electron density for easy understanding of the molecular interaction sites with analytes. Furthermore, a quantitative explanation of hydrophilic and hydrophobic liquid chromatographies was provided. The synthesis methods of superficially porous silica gels and their modified products were introduced. Full article
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10 pages, 4440 KiB  
Article
Monitoring the Activity of Immobilized Lipase with Quinizarin Diester Fluoro-Chromogenic Probe
by Carolina Aparecida Sabatini, Denis Massucatto dos Santos, Sabrina Matos de Oliveira da Silva and Marcelo Henrique Gehlen
Molecules 2017, 22(12), 2136; https://doi.org/10.3390/molecules22122136 - 4 Dec 2017
Viewed by 4955
Abstract
Quinizarin diester is used as a fluoro-chromogenic substrate of the activity of lipase supported in poly(methylmetacrylate) beads (CALB, Novozym® 435) dispersed in organic solvents. The monoester and diester of quinizarin are both non-fluorescent species contrasting with the enzymatic product quinizarin that shows [...] Read more.
Quinizarin diester is used as a fluoro-chromogenic substrate of the activity of lipase supported in poly(methylmetacrylate) beads (CALB, Novozym® 435) dispersed in organic solvents. The monoester and diester of quinizarin are both non-fluorescent species contrasting with the enzymatic product quinizarin that shows optical absorption in the visible region and strong fluorescence signal. The enzymatic conversion is accomplished by spectroscopic measurements and it follows a sigmoid curve from which the mean reaction time of the enzymatic process can be determined. This parameter indicates the enzyme activity of the immobilized lipase. Its dependency with the amount of lipase allowed the determination of the ratio of the catalytic rate and the Michaelis constant (kc/Km) and the experimental value found was (1.0 ± 0.1) × 10−2 mg−1/min in the case of quinizarin diacetate. Full article
(This article belongs to the Special Issue Lipases and Lipases Modification)
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