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Molecules, Volume 26, Issue 20 (October-2 2021) – 235 articles

Cover Story (view full-size image): The new dimeric copper(II) bromide complex [Cu(LOHex)Br(μ-Br)]2 was synthesized and fully characterized in the solid state and in solution. In the crystal structure, the complex is interlinked by two bridging bromide ligands and possesses terminal bromide ligands on each copper atom. The new complex was evaluated as a catalyst in copper-catalyzed C−H oxidation for allylic functionalization through a Kharasch–Sosnovsky reaction without any external reducing agent. The general reaction time was slightly decreased, but a very significant lowering of the alkene:Luperox ratio was reached, obtaining allylic benzoates up to 90% yield. These factors make relevant improvements with respect to the classical Kharasch–Sosnovsky reaction in terms of rate and number of reagents. View this paper.
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8 pages, 777 KiB  
Communication
Validation of a Fast and Simple HPLC-UV Method for the Quantification of Adenosine Phosphates in Human Bronchial Epithelial Cells
by Ana Teresa Juarez-Facio, Violaine Martin de Lagarde, Christelle Monteil, Jean-Marie Vaugeois, Cécile Corbiere and Tiphaine Rogez-Florent
Molecules 2021, 26(20), 6324; https://doi.org/10.3390/molecules26206324 - 19 Oct 2021
Cited by 6 | Viewed by 2797
Abstract
A new HPLC method for the simultaneous quantitative analysis of adenosine triphosphate (ATP), adenosine diphosphate (ADP), and adenosine monophosphate (AMP) was developed and validated. ATP, ADP, and AMP were extracted from human bronchial epithelial cells with a rapid extraction procedure and separated with [...] Read more.
A new HPLC method for the simultaneous quantitative analysis of adenosine triphosphate (ATP), adenosine diphosphate (ADP), and adenosine monophosphate (AMP) was developed and validated. ATP, ADP, and AMP were extracted from human bronchial epithelial cells with a rapid extraction procedure and separated with a C18 column (3 × 150 mm, 2.7 µm) using isocratic elution with a mobile phase consisting of 50 mM of potassium hydrogen phosphate (pH 6.80). The absorbance was monitored at 254 nm. The calibration curves were linear in 0.2 to 10 µM, selective, precise, and accurate. This method allowed us to quantify the nucleotides from two cell models: differentiated NHBE primary cells grown at the air–liquid interface (ALI) and BEAS-2B cell line. Our study highlighted the development of a sensitive, simple, and green analytical method that is faster and less expensive than other existing methods to measure ATP, ADP, and AMP and can be carried out on 2D and 3D cell models. Full article
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39 pages, 9353 KiB  
Review
Prospects for More Efficient Multi-Photon Absorption Photosensitizers Exhibiting Both Reactive Oxygen Species Generation and Luminescence
by Emma Robbins, Stéphanie Leroy-Lhez, Nicolas Villandier, Marek Samoć and Katarzyna Matczyszyn
Molecules 2021, 26(20), 6323; https://doi.org/10.3390/molecules26206323 - 19 Oct 2021
Cited by 12 | Viewed by 3493
Abstract
The use of two-photon absorption (TPA) for such applications as microscopy, imaging, and photodynamic therapy (PDT) offers several advantages over the usual one-photon excitation. This creates a need for photosensitizers that exhibit both strong two-photon absorption and the highly efficient generation of reactive [...] Read more.
The use of two-photon absorption (TPA) for such applications as microscopy, imaging, and photodynamic therapy (PDT) offers several advantages over the usual one-photon excitation. This creates a need for photosensitizers that exhibit both strong two-photon absorption and the highly efficient generation of reactive oxygen species (ROS), as well as, ideally, bright luminescence. This review focuses on different strategies utilized to improve the TPA properties of various multi-photon absorbing species that have the required photophysical properties. Along with well-known families of photosensitizers, including porphyrins, we also describe other promising organic and organometallic structures and more complex systems involving organic and inorganic nanoparticles. We concentrate on the published studies that provide two-photon absorption cross-section values and the singlet oxygen (or other ROS) and luminescence quantum yields, which are crucial for potential use within PDT and diagnostics. We hope that this review will aid in the design and modification of novel TPA photosensitizers, which can help in exploiting the features of nonlinear absorption processes. Full article
(This article belongs to the Special Issue Photodynamic Therapy in Cancer Treatment 2021)
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12 pages, 2303 KiB  
Article
Fractionated Lignosulfonates for Laccase-Catalyzed Oxygen-Scavenging Films and Coatings
by Sandra Winestrand, Lars Järnström and Leif J. Jönsson
Molecules 2021, 26(20), 6322; https://doi.org/10.3390/molecules26206322 - 19 Oct 2021
Cited by 3 | Viewed by 1484
Abstract
Lignin derivatives have potential as antioxidants in advanced packaging materials through their ability to scavenge oxygen in reactions catalyzed by phenol-oxidizing enzymes, such as laccase. The effects of size fractionation of lignosulfonates on laccase-catalyzed reactions were investigated in experiments with aqueous solutions, films, [...] Read more.
Lignin derivatives have potential as antioxidants in advanced packaging materials through their ability to scavenge oxygen in reactions catalyzed by phenol-oxidizing enzymes, such as laccase. The effects of size fractionation of lignosulfonates on laccase-catalyzed reactions were investigated in experiments with aqueous solutions, films, and coated paperboard. Four industrial lignosulfonate preparations were compared: Feed (unfractionated), Prod (5–60 kDa enriched), Conc (≥60 kDa enriched), and Perm (≤60 kDa enriched). Extraction of lignosulfonates from films showed that the enzymic reaction increased the average molecular weight from <10,000 to up to 66,000. The enzymatic reaction resulted in an increase in the water contact angle of the films from the range 25–49° to 56–81°. The four preparations showed relatively small differences with regard to their ability to scavenge oxygen in aqueous solution and in experiments with coated paperboards in sealed chambers. Coatings with lignosulfonates where the contents of low-molecular weight material had been reduced (i.e., Prod and Conc) showed improved water resistance after the enzymic reaction. Thus, in both aqueous and solid media, fractionation of lignosulfonates had little effect on oxygen scavenging, but fractionation was beneficial for other reasons, such as improved cross-linking resulting in higher molecular weight and superior water resistance. Full article
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15 pages, 2644 KiB  
Article
Discovery of a Kojibiose Hydrolase by Analysis of Specificity-Determining Correlated Positions in Glycoside Hydrolase Family 65
by Emma De Beul, Alana Jongbloet, Jorick Franceus and Tom Desmet
Molecules 2021, 26(20), 6321; https://doi.org/10.3390/molecules26206321 - 19 Oct 2021
Cited by 5 | Viewed by 3053
Abstract
The Glycoside Hydrolase Family 65 (GH65) is an enzyme family of inverting α-glucoside phosphorylases and hydrolases that currently contains 10 characterized enzyme specificities. However, its sequence diversity has never been studied in detail. Here, an in-silico analysis of correlated mutations was performed, revealing [...] Read more.
The Glycoside Hydrolase Family 65 (GH65) is an enzyme family of inverting α-glucoside phosphorylases and hydrolases that currently contains 10 characterized enzyme specificities. However, its sequence diversity has never been studied in detail. Here, an in-silico analysis of correlated mutations was performed, revealing specificity-determining positions that facilitate annotation of the family’s phylogenetic tree. By searching these positions for amino acid motifs that do not match those found in previously characterized enzymes from GH65, several clades that may harbor new functions could be identified. Three enzymes from across these regions were expressed in E. coli and their substrate profile was mapped. One of those enzymes, originating from the bacterium Mucilaginibacter mallensis, was found to hydrolyze kojibiose and α-1,2-oligoglucans with high specificity. We propose kojibiose glucohydrolase as the systematic name and kojibiose hydrolase or kojibiase as the short name for this new enzyme. This work illustrates a convenient strategy for mapping the natural diversity of enzyme families and smartly mining the ever-growing number of available sequences in the quest for novel specificities. Full article
(This article belongs to the Special Issue Recent Advances in Carbohydrate-Active Enzymes)
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4 pages, 213 KiB  
Editorial
Coumarin and Its Derivatives—Editorial
by Maria João Matos
Molecules 2021, 26(20), 6320; https://doi.org/10.3390/molecules26206320 - 19 Oct 2021
Cited by 6 | Viewed by 2257
Abstract
Coumarins are widely distributed in nature and can be found in a large number of naturally occurring and synthetic bioactive molecules [...] Full article
(This article belongs to the Special Issue Coumarin and Its Derivatives)
3 pages, 183 KiB  
Editorial
Intramolecular Hydrogen Bonding 2021
by Mirosław Jabłoński
Molecules 2021, 26(20), 6319; https://doi.org/10.3390/molecules26206319 - 19 Oct 2021
Cited by 4 | Viewed by 1967
Abstract
Undoubtedly, hydrogen bonds occupy a leading place in the rich world of intermolecular interactions [...] Full article
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding 2021)
19 pages, 5440 KiB  
Article
Characterisation and Classification of Foodborne Bacteria Using Reflectance FTIR Microscopic Imaging
by Jun-Li Xu, Ana Herrero-Langreo, Sakshi Lamba, Mariateresa Ferone, Amalia G. M. Scannell, Vicky Caponigro and Aoife A. Gowen
Molecules 2021, 26(20), 6318; https://doi.org/10.3390/molecules26206318 - 19 Oct 2021
Cited by 5 | Viewed by 2294
Abstract
This work investigates the application of reflectance Fourier transform infrared (FTIR) microscopic imaging for rapid, and non-invasive detection and classification between Bacillus subtilis and Escherichia coli cell suspensions dried onto metallic substrates (stainless steel (STS) and aluminium (Al) slides) in the optical density [...] Read more.
This work investigates the application of reflectance Fourier transform infrared (FTIR) microscopic imaging for rapid, and non-invasive detection and classification between Bacillus subtilis and Escherichia coli cell suspensions dried onto metallic substrates (stainless steel (STS) and aluminium (Al) slides) in the optical density (OD) concentration range of 0.001 to 10. Results showed that reflectance FTIR of samples with OD lower than 0.1 did not present an acceptable spectral signal to enable classification. Two modelling strategies were devised to evaluate model performance, transferability and consistency among concentration levels. Modelling strategy 1 involves training the model with half of the sample set, consisting of all concentrations, and applying it to the remaining half. Using this approach, for the STS substrate, the best model was achieved using support vector machine (SVM) classification, providing an accuracy of 96% and Matthews correlation coefficient (MCC) of 0.93 for the independent test set. For the Al substrate, the best SVM model produced an accuracy and MCC of 91% and 0.82, respectively. Furthermore, the aforementioned best model built from one substrate was transferred to predict the bacterial samples deposited on the other substrate. Results revealed an acceptable predictive ability when transferring the STS model to samples on Al (accuracy = 82%). However, the Al model could not be adapted to bacterial samples deposited on STS (accuracy = 57%). For modelling strategy 2, models were developed using one concentration level and tested on the other concentrations for each substrate. Results proved that models built from samples with moderate (1 OD) concentration can be adapted to other concentrations with good model generalization. Prediction maps revealed the heterogeneous distribution of biomolecules due to the coffee ring effect. This work demonstrated the feasibility of applying FTIR to characterise spectroscopic fingerprints of dry bacterial cells on substrates of relevance for food processing. Full article
(This article belongs to the Special Issue New Insights into Vibrational Spectroscopy and Imaging)
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15 pages, 2425 KiB  
Article
Fractionation of Regenerated Silk Fibroin and Characterization of the Fractions
by Masaaki Aoki, Yu Masuda, Kota Ishikawa and Yasushi Tamada
Molecules 2021, 26(20), 6317; https://doi.org/10.3390/molecules26206317 - 19 Oct 2021
Cited by 2 | Viewed by 2498
Abstract
The molecular weight (MW) of regenerated silk fibroin (RSF) decreases during degumming and dissolving processes. Although MW and the MW distribution generally affect polymer material processability and properties, few reports have described studies examining the influences of MW and the distribution on silk [...] Read more.
The molecular weight (MW) of regenerated silk fibroin (RSF) decreases during degumming and dissolving processes. Although MW and the MW distribution generally affect polymer material processability and properties, few reports have described studies examining the influences of MW and the distribution on silk fibroin (SF) material. To prepare different MW SF fractions, the appropriate conditions for fractionation of RSF by ammonium sulfate (AS) precipitation process were investigated. The MW and the distribution of each fraction were found using gel permeation chromatography (GPC) and SDS-polyacrylamide electrophoresis (SDS-PAGE). After films of the fractionated SFs formed, the secondary structure, surface properties, and cell proliferation of films were evaluated. Nanofiber nonwoven mats and 3D porous sponges were fabricated using the fractionated SF aqueous solution. Then, their structures and mechanical properties were analyzed. The results showed AS precipitation using a dialysis membrane at low temperature to be a suitable fractionation method for RSF. Moreover, MW affects the nanofiber and sponge morphology and mechanical properties, although no influence of MW was observed on the secondary structure or crystallinity of the fabricated materials. Full article
(This article belongs to the Special Issue Silk Fibroin Materials 2.0)
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11 pages, 1531 KiB  
Article
Rapid Structure Determination of Bioactive 4″-Tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC-SPE/Cryo NMR and MS
by Iva Habinovec, Ivana Mikulandra, Lucia Ema Sekula, Jana Gašperov, Saša Kazazić and Predrag Novak
Molecules 2021, 26(20), 6316; https://doi.org/10.3390/molecules26206316 - 19 Oct 2021
Cited by 1 | Viewed by 1790
Abstract
LC-SPE/cryo NMR and MS methodologies have been developed and employed for a rapid structure determination of 4″-tetrahydrofurfuryl macrozone reaction mixture components. Macrozones, novel conjugates of azithromycin, and thiosemicarbazones have shown very good in vitro antibacterial activities against susceptible and some resistant bacterial strains [...] Read more.
LC-SPE/cryo NMR and MS methodologies have been developed and employed for a rapid structure determination of 4″-tetrahydrofurfuryl macrozone reaction mixture components. Macrozones, novel conjugates of azithromycin, and thiosemicarbazones have shown very good in vitro antibacterial activities against susceptible and some resistant bacterial strains and are promising agents for further development. The post-column multiple trapping of the chromatographically separated reaction mixture components on the SPE cartridges increased the sensitivity and together with cryogenically cooled NMR probe made it possible to identify and structurally characterize main 4″-tetrahydrofurfuryl macrozone reaction mixture compounds including those present at very low concentration level. This approach has several advantages over a classical off-line procedure, efficiency and low solvent consumption being the two most important ones. All identified components were process-related. It has been demonstrated that two different kinds of compounds with respect to structure were identified, i.e., macrolide-related and thiosemicarbazone-related ones. This methodology can serve as a platform for reliable and effective macrolides reaction components structure profiling, serving as both isolation and identification tools. Full article
(This article belongs to the Special Issue Spectroscopic and Spectrometric Techniques for Structural Analysis)
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18 pages, 2799 KiB  
Review
The Application of Chitosan Nanostructures in Stomatology
by Shunli Chu, Jue Wang and Fengxiang Gao
Molecules 2021, 26(20), 6315; https://doi.org/10.3390/molecules26206315 - 19 Oct 2021
Cited by 2 | Viewed by 3086
Abstract
Chitosan (CS) is a natural polymer with a positive charge, a deacetylated derivative of chitin. Chitosan nanostructures (nano-CS) have received increasing interest due to their potential applications and remarkable properties. They offer advantages in stomatology due to their excellent biocompatibility, their antibacterial properties, [...] Read more.
Chitosan (CS) is a natural polymer with a positive charge, a deacetylated derivative of chitin. Chitosan nanostructures (nano-CS) have received increasing interest due to their potential applications and remarkable properties. They offer advantages in stomatology due to their excellent biocompatibility, their antibacterial properties, and their biodegradability. Nano-CSs can be applied as drug carriers for soft tissue diseases, bone tissue engineering and dental hard tissue remineralization; furthermore, they have been used in endodontics due to their antibacterial properties; and, finally, nano-CS can improve the adhesion and mechanical properties of dental-restorative materials due to their physical blend and chemical combinations. In this review, recent developments in the application of nano-CS for stomatology are summarized, with an emphasis on nano-CS’s performance characteristics in different application fields. Moreover, the challenges posed by and the future trends in its application are assessed. Full article
(This article belongs to the Special Issue Biomedical Applications of Nanomaterials 2021)
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33 pages, 12753 KiB  
Article
Deprotometalation-Iodolysis and Direct Iodination of 1-Arylated 7-Azaindoles: Reactivity Studies and Molecule Properties
by Mohamed Yacine Ameur Messaoud, Ghenia Bentabed-Ababsa, Ziad Fajloun, Monzer Hamze, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Thierry Roisnel, Vincent Dorcet and Florence Mongin
Molecules 2021, 26(20), 6314; https://doi.org/10.3390/molecules26206314 - 19 Oct 2021
Cited by 1 | Viewed by 1859
Abstract
Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The [...] Read more.
Five protocols were first compared for the copper-catalyzed C-N bond formation between 7-azaindole and aryl/heteroaryl iodides/bromides. The 1-arylated 7-azaindoles thus obtained were subjected to deprotometalation-iodolysis sequences using lithium 2,2,6,6-tetramethylpiperidide as the base and the corresponding zinc diamide as an in situ trap. The reactivity of the substrate was discussed in light of the calculated atomic charges and the pKa values. The behavior of the 1-arylated 7-azaindoles in direct iodination was then studied, and the results explained by considering the HOMO orbital coefficients and the atomic charges. Finally, some of the iodides generated, generally original, were involved in the N-arylation of indole. While crystallographic data were collected for fifteen of the synthesized compounds, biological properties (antimicrobial, antifungal and antioxidant activity) were evaluated for others. Full article
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26 pages, 6528 KiB  
Review
Cannabinoids and Neurogenesis: The Promised Solution for Neurodegeneration?
by Andrea Valeri and Emanuela Mazzon
Molecules 2021, 26(20), 6313; https://doi.org/10.3390/molecules26206313 - 19 Oct 2021
Cited by 8 | Viewed by 4020
Abstract
The concept of neurons as irreplaceable cells does not hold true today. Experiments and evidence of neurogenesis, also, in the adult brain give hope that some compounds or drugs can enhance this process, helping to reverse the outcomes of diseases or traumas that [...] Read more.
The concept of neurons as irreplaceable cells does not hold true today. Experiments and evidence of neurogenesis, also, in the adult brain give hope that some compounds or drugs can enhance this process, helping to reverse the outcomes of diseases or traumas that once were thought to be everlasting. Cannabinoids, both from natural and artificial origins, already proved to have several beneficial effects (e.g., anti-inflammatory, anti-oxidants and analgesic action), but also capacity to increase neuronal population, by replacing the cells that were lost and/or regenerate a damaged nerve cell. Neurogenesis is a process which is not highly represented in literature as neuroprotection, though it is as important as prevention of nervous system damage, because it can represent a possible solution when neuronal death is already present, such as in neurodegenerative diseases. The aim of this review is to resume the experimental evidence of phyto- and synthetic cannabinoids effects on neurogenesis, both in vitro and in vivo, in order to elucidate if they possess also neurogenetic and neurorepairing properties. Full article
(This article belongs to the Special Issue Cannabinoids in Health and Disease)
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10 pages, 1315 KiB  
Article
Diaryl Sulfide Derivatives as Potential Iron Corrosion Inhibitors: A Computational Study
by Morad M. El-Hendawy, Asmaa M. Kamel, Mahmoud M. A. Mohamed, Rabah Boukherroub, Jacek Ryl and Mohammed A. Amin
Molecules 2021, 26(20), 6312; https://doi.org/10.3390/molecules26206312 - 19 Oct 2021
Cited by 4 | Viewed by 1698
Abstract
The present work aimed to assess six diaryl sulfide derivatives as potential corrosion inhibitors. These derivatives were compared with dapsone (4,4′-diaminodiphenyl sulfone), a common leprosy antibiotic that has been shown to resist the corrosion of mild steel in acidic media with a corrosion [...] Read more.
The present work aimed to assess six diaryl sulfide derivatives as potential corrosion inhibitors. These derivatives were compared with dapsone (4,4′-diaminodiphenyl sulfone), a common leprosy antibiotic that has been shown to resist the corrosion of mild steel in acidic media with a corrosion efficiency exceeding 90%. Since all the studied compounds possess a common molecular backbone (diphenyl sulfide), dapsone was taken as the reference compound to evaluate the efficiency of the remainder. In this respect, two structural factors were examined, namely, (i) the effect of replacement of the S-atom of diaryl sulfide by SO or SO2 group, (ii) the effect of the introduction of an electron-withdrawing or an electron-donating group in the aryl moiety. Two computational chemical approaches were used to achieve the objectives: the density functional theory (DFT) and the Monto Carlo (MC) simulation. First, B3LYP/6-311+G(d,p) model chemistry was employed to calculate quantum chemical descriptors of the studied molecules and their geometric and electronic structures. Additionally, the mode of adsorption of the tested molecules was investigated using MC simulation. In general, the adsorption process was favorable for molecules with a lower dipole moment. Based on the adsorption energy results, five diaryl sulfide derivatives are expected to act as better corrosion inhibitors than dapsone. Full article
(This article belongs to the Section Molecular Structure)
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17 pages, 798 KiB  
Article
Volatilome and Essential Oil of Ulomoides dermestoides: A Broad-Spectrum Medical Insect
by Paulina J. Cázares-Samaniego, Claudia G. Castillo, Miguel A. Ramos-López and Marco M. González-Chávez
Molecules 2021, 26(20), 6311; https://doi.org/10.3390/molecules26206311 - 19 Oct 2021
Cited by 7 | Viewed by 1918
Abstract
Ulomoides dermestoides are used as a broad-spectrum medical insect in the alternative treatment of various diseases. Preliminary volatilome studies carried out to date have shown, as the main components, methyl-1,4-benzoquinone, ethyl-1,4-benzoquinone, 1-tridecene, 1-pentadecene, and limonene. This work focused on the production of metabolites [...] Read more.
Ulomoides dermestoides are used as a broad-spectrum medical insect in the alternative treatment of various diseases. Preliminary volatilome studies carried out to date have shown, as the main components, methyl-1,4-benzoquinone, ethyl-1,4-benzoquinone, 1-tridecene, 1-pentadecene, and limonene. This work focused on the production of metabolites and their metabolic variations in U. dermestoides under stress conditions to provide additional valuable information to help better understand the broad-spectrum medical uses. To this end, VOCs were characterized by HS-SPME with PEG and CAR/PDMS fibers, and the first reported insect essential oils were obtained. In HS-SMPE, we found 17 terpenes, six quinones, five alkenes, and four aromatic compounds; in the essential oils, 53 terpenes, 54 carboxylic acids and derivatives, three alkynes, 12 alkenes (1-Pentadecene, EOT1: 77.6% and EOT2: 57.9%), 28 alkanes, nine alkyl disulfides, three aromatic compounds, 19 alcohols, three quinones, and 12 aldehydes were identified. Between both study approaches, a total of 171 secondary metabolites were identified with no previous report for U. dermestoides. A considerable number of the identified metabolites showed previous studies of the activity of pharmacological interest. Therefore, considering the wide variety of activities reported for these metabolites, this work allows a broader vision of the therapeutic potential of U. dermestoides in traditional medicine. Full article
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research II)
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12 pages, 2286 KiB  
Article
d-Allulose Ameliorates Skeletal Muscle Insulin Resistance in High-Fat Diet-Fed Rats
by Yang Gou, Bingyang Liu, Mengyao Cheng, Takako Yamada, Tetsuo Iida, Sixian Wang, Ryoichi Banno and Teruhiko Koike
Molecules 2021, 26(20), 6310; https://doi.org/10.3390/molecules26206310 - 19 Oct 2021
Cited by 10 | Viewed by 3011
Abstract
Background: d-Allulose is a rare sugar with antiobesity and antidiabetic activities. However, its direct effect on insulin sensitivity and the underlying mechanism involved are unknown. Objective: This study aimed to investigate the effect of d-allulose on high-fat diet (HFD)-induced insulin resistance [...] Read more.
Background: d-Allulose is a rare sugar with antiobesity and antidiabetic activities. However, its direct effect on insulin sensitivity and the underlying mechanism involved are unknown. Objective: This study aimed to investigate the effect of d-allulose on high-fat diet (HFD)-induced insulin resistance using the hyperinsulinemic–euglycemic (HE)-clamp method and intramuscular signaling analysis. Methods: Wistar rats were randomly divided into three dietary groups: chow diet, HFD with 5% cellulose (HFC), and HFD with 5% d-allulose (HFA). After four weeks of feeding, the insulin tolerance test (ITT), intraperitoneal glucose tolerance test (IPGTT), and HE-clamp study were performed. The levels of plasma leptin, adiponectin, and tumor necrosis factor (TNF)-α were measured using the enzyme-linked immunosorbent assay. We analyzed the levels of cell signaling pathway components in the skeletal muscle using Western blotting. Results: d-allulose alleviated the increase in HFD-induced body weight and visceral fat and reduced the area under the curve as per ITT and IPGTT. d-Allulose increased the glucose infusion rate in the two-step HE-clamp test. Consistently, the insulin-induced phosphorylation of serine 307 in the insulin receptor substrate-1 and Akt and expression of glucose transporter 4 (Glut-4) in the muscle were higher in the HFA group than HFC group. Furthermore, d-allulose decreased plasma TNF-α concentration and insulin-induced phosphorylation of stress-activated protein kinase/Jun N-terminal kinase in the muscle and inhibited adiponectin secretion in HFD-fed rats. Conclusions: d-allulose improved HFD-induced insulin resistance in Wistar rats. The reduction of the proinflammatory cytokine production, amelioration of adiponectin secretion, and increase in insulin signaling and Glut-4 expression in the muscle contributed to this effect. Full article
(This article belongs to the Special Issue Carbohydrate Chemistry 2021)
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14 pages, 2387 KiB  
Article
iTRAQ-BASED Proteomic Analysis of the Mechanism of Fructose on Improving Fengycin Biosynthesis in Bacillus Amyloliquefaciens
by Hedong Lu, Ruili Li, Panping Yang, Weibo Luo, Shunxian Chen, Muhammad Bilal, Hai Xu, Chengyuan Gu, Shuai Liu, Yuping Zhao, Chengxin Geng and Li Zhao
Molecules 2021, 26(20), 6309; https://doi.org/10.3390/molecules26206309 - 19 Oct 2021
Cited by 7 | Viewed by 1968
Abstract
Fengycin, as a lipopeptide produced by Bacillus subtilis, displays potent activity against filamentous fungi, including Aspergillus flavus and Soft-rot fungus, which exhibits a wide range of potential applications in food industries, agriculture, and medicine. To better clarify the regulatory mechanism of [...] Read more.
Fengycin, as a lipopeptide produced by Bacillus subtilis, displays potent activity against filamentous fungi, including Aspergillus flavus and Soft-rot fungus, which exhibits a wide range of potential applications in food industries, agriculture, and medicine. To better clarify the regulatory mechanism of fructose on fengycin biosynthesis, the iTRAQ-based proteomic analysis was utilized to investigate the differentially expressed proteins of B. amyloliquefaciens fmb-60 cultivated in ML (without fructose) and MLF (with fructose) medium. The results indicated that a total of 811 proteins, including 248 proteins with differential expression levels (162 which were upregulated (fold > 2) and 86, which were downregulated (fold < 0.5) were detected, and most of the proteins are associated with cellular metabolism, biosynthesis, and biological regulation process. Moreover, the target genes’ relative expression was conducted using quantitative real-time PCR to validate the proteomic analysis results. Based on the results of proteome analysis, the supposed pathways of fructose enhancing fengycin biosynthesis in B. amyloliquefaciens fmb-60 can be summarized as improvement of the metabolic process, including cellular amino acid and amide, fatty acid biosynthesis, peptide and protein, nucleotide and nucleobase-containing compound, drug/toxin, cofactor, and vitamin; reinforcement of peptide/protein translation, modification, biological process, and response to a stimulus. In conclusion, this study represents a comprehensive and systematic investigation of the fructose mechanism on improving fengycin biosynthesis in B. amyloliquefaciens, which will provide a road map to facilitate the potential application of fengycin or its homolog in defending against filamentous fungi. Full article
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17 pages, 4697 KiB  
Review
Research Progress of NMR in Natural Product Quantification
by Zhi-Fan Wang, Yu-Lin You, Fei-Fei Li, Wen-Ru Kong and Shu-Qi Wang
Molecules 2021, 26(20), 6308; https://doi.org/10.3390/molecules26206308 - 19 Oct 2021
Cited by 23 | Viewed by 5236
Abstract
In the fields of medicine and health, traditional high-performance liquid chromatography or UV-visible spectrophotometry is generally used for substance quantification. However, over time, nuclear magnetic resonance spectroscopy (NMR) has gradually become more mature. Nuclear magnetic resonance spectroscopy has certain advantages in the quantitative [...] Read more.
In the fields of medicine and health, traditional high-performance liquid chromatography or UV-visible spectrophotometry is generally used for substance quantification. However, over time, nuclear magnetic resonance spectroscopy (NMR) has gradually become more mature. Nuclear magnetic resonance spectroscopy has certain advantages in the quantitative analysis of substances, such as being nondestructive, having a high flux and short analysis time. Nuclear magnetic resonance spectroscopy has been included in the pharmacopoeiae of various countries. In this paper, the principle of nuclear magnetic resonance spectroscopy and the recent progress in the quantitative study of natural products by NMR are reviewed, and its application in the quantitative study of natural products is proposed. At the same time, the problems of using NMR alone to quantify natural products are summarized and corresponding suggestions are put forward. Full article
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30 pages, 3119 KiB  
Review
Stabilization Techniques of Essential Oils by Incorporation into Biodegradable Polymeric Materials for Food Packaging
by Elena Stoleru and Mihai Brebu
Molecules 2021, 26(20), 6307; https://doi.org/10.3390/molecules26206307 - 19 Oct 2021
Cited by 13 | Viewed by 3048
Abstract
Human health, food spoilage, and plastic waste, which are three great topical concerns, intersect in the field of food packaging. This has created a trend to replace synthetic food preservatives with natural ones, to produce bio-functional food packaging, and to shift towards biodegradable [...] Read more.
Human health, food spoilage, and plastic waste, which are three great topical concerns, intersect in the field of food packaging. This has created a trend to replace synthetic food preservatives with natural ones, to produce bio-functional food packaging, and to shift towards biodegradable polymeric materials. Among the natural bioactive agents, essential oils are gaining more and more attention in food packaging applications due to their various benefits and fewer side-effects. However, their volatility, hydrophobicity, and strong odor and taste limit the direct use in food-related applications. Fixation into polymeric matrices represents a suitable strategy to promote the benefits and reduce the drawbacks. Emulsification and electrospinning are largely used techniques for protection and stabilization of essential oils. These methods offer various advantages in active food packaging, such as controlled release, ensuring long-term performance, decreased amounts of active agents that gain enhanced functionality through increased available surface area in contact with food, and versatility in packaging design. This review focuses on creating correlations between the use of essential oils as natural additives, stabilization methods, and biodegradable polymeric matrices or substrates in developing bioactive food packaging materials. Documentation was performed via the Scopus, ScienceDirect, and PubMed databases, selecting the publications after the year 2018. Particular attention was given to the publications that tested materials on food/food pathogens to evaluate their performances in retarding spoilage. Research gaps were also identified on the topic, materials being tested mainly at short time after preparation without considering the long-term storage that usually occurs in actual practice between production and use, and insufficient research related to upscaling. Full article
(This article belongs to the Special Issue Stabilization of Active Principles in Food Packaging Materials)
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41 pages, 67149 KiB  
Review
Novel Synthetic Approach to Heteroatom Doped Polycyclic Aromatic Hydrocarbons: Optimizing the Bottom-Up Approach to Atomically Precise Doped Nanographenes
by Giacomo Biagiotti, Ilaria Perini, Barbara Richichi and Stefano Cicchi
Molecules 2021, 26(20), 6306; https://doi.org/10.3390/molecules26206306 - 19 Oct 2021
Cited by 11 | Viewed by 5361
Abstract
The success of the rational bottom-up approach to nanostructured carbon materials and the discovery of the importance of their doping with heteroatoms puts under the spotlight all synthetic organic approaches to polycyclic aromatic hydrocarbons. The construction of atomically precise heteroatom doped nanographenes has [...] Read more.
The success of the rational bottom-up approach to nanostructured carbon materials and the discovery of the importance of their doping with heteroatoms puts under the spotlight all synthetic organic approaches to polycyclic aromatic hydrocarbons. The construction of atomically precise heteroatom doped nanographenes has evidenced the importance of controlling its geometry and the position of the doping heteroatoms, since these parameters influence their chemical–physical properties and their applications. The growing interest towards this research topic is testified by the large number of works published in this area, which have transformed a once “fundamental research” into applied research at the cutting edge of technology. This review analyzes the most recent synthetic approaches to this class of compounds. Full article
(This article belongs to the Special Issue Featured Reviews in Applied Chemistry)
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20 pages, 15502 KiB  
Article
Stereoselective Synthesis of the Di-Spirooxindole Analogs Based Oxindole and Cyclohexanone Moieties as Potential Anticancer Agents
by Abdullah Mohammed Al-Majid, M. Ali, Mohammad Shahidul Islam, Saeed Alshahrani, Abdullah Saleh Alamary, Sammer Yousuf, M. Iqbal Choudhary and Assem Barakat
Molecules 2021, 26(20), 6305; https://doi.org/10.3390/molecules26206305 - 19 Oct 2021
Cited by 13 | Viewed by 2205
Abstract
A new series of di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were synthesized. Initially, azomethine ylides were generated via reaction of the substituted isatins 3a–f (isatin, 3a, 6-chloroisatin, 3b, 5-fluoroisatin, 3c, 5-nitroisatin, 3d, 5-methoxyisatin, 3e, and 5-methylisatin, [...] Read more.
A new series of di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were synthesized. Initially, azomethine ylides were generated via reaction of the substituted isatins 3a–f (isatin, 3a, 6-chloroisatin, 3b, 5-fluoroisatin, 3c, 5-nitroisatin, 3d, 5-methoxyisatin, 3e, and 5-methylisatin, 3f, and (2S)-octahydro-1H-indole-2-carboxylic acid 2, in situ azomethine ylides reacted with the cyclohexanone based-chalcone 1a–f to afford the target di-spirooxindole compounds 4a–n. This one-pot method provided diverse structurally complex molecules, with biologically relevant spirocycles in a good yields. All synthesized di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were evaluated for their anticancer activity against four cancer cell lines, including prostate PC3, cervical HeLa, and breast (MCF-7, and MDA-MB231) cancer cell lines. The cytotoxicity of these di-spirooxindole analogs was also examined against human fibroblast BJ cell lines, and they appeared to be non-cytotoxic. Compound 4b was identified as the most active member of this series against prostate cancer cell line PC3 (IC50 = 3.7 ± 1.0 µM). The cyclohexanone engrafted di-spirooxindole analogs 4a and 4l (IC50 = 7.1 ± 0.2, and 7.2 ± 0.5 µM, respectively) were active against HeLa cancer cells, whereas NO2 substituted isatin ring and meta-fluoro-substituted (2E,6E)-2,6-dibenzylidenecyclohexanone containing 4i (IC50 = 7.63 ± 0.08 µM) appeared to be a promising agent against the triple negative breast cancer MDA-MB231 cell line. To explore the plausible mechanism of anticancer activity of di-spirooxindole analogs, molecular docking studies were investigated which suggested that spirooxindole analogs potentially inhibit the activity of MDM2. Full article
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15 pages, 3501 KiB  
Article
Effect of the Amount of Polysorbate 80 and Oregano Essential Oil on the Emulsion Stability and Characterization Properties of Sodium Alginate Microcapsules
by Juste Baranauskaite, Mehmet Ali Ockun, Burcu Uner, Cetin Tas and Liudas Ivanauskas
Molecules 2021, 26(20), 6304; https://doi.org/10.3390/molecules26206304 - 19 Oct 2021
Cited by 4 | Viewed by 2997
Abstract
Essential oils have a high volatility that leads to evaporation and loss of their pharmacological effect when exposed to the environment. The objectives of the present work were to prepare microcapsules with oregano essential oil by extrusion using sodium alginate as a shell [...] Read more.
Essential oils have a high volatility that leads to evaporation and loss of their pharmacological effect when exposed to the environment. The objectives of the present work were to prepare microcapsules with oregano essential oil by extrusion using sodium alginate as a shell material and non-ionic surfactant polysorbate 80 as an emulsifier to stabilize the emulsion. The present study was aimed to evaluate the physical parameters of microcapsules and to compare the influence of the amount of emulsifier and the essential oil-to-emulsifier ratio on the capsules’ physical parameters and encapsulation efficiency; to our knowledge, the existing research had not yet revealed whether unstable emulsion affects the encapsulation efficiency of oregano essential oil. This study showed that increasing the emulsifier amount in the formulation significantly influenced encapsulation efficiency and particle size. Moreover, increasing the emulsion stability positively influenced the encapsulation efficiency. The emulsion creaming index depended on the emulsifier amount in the formulation: the highest creaming index (%) was obtained with the highest amount of polysorbate 80. However, the essential oil-to-polysorbate 80 ratio and essential oil amount did not affect the hardness of the microcapsules (p > 0.05). In conclusion, the obtained results could be promising information for production of microcapsules. Despite the fact that microencapsulation of essential oils is a promising and extremely attractive application area for the pharmaceutical industry, further basic research needs to be carried out. Full article
(This article belongs to the Section Natural Products Chemistry)
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9 pages, 561 KiB  
Article
Chemical Composition of Cinnamomum verum Leaf and Flower Essential Oils and Analysis of Their Antibacterial, Insecticidal, and Larvicidal Properties
by Arunaksharan Narayanankutty, Krishnaprasad Kunnath, Ahmed Alfarhan, Rajakrishnan Rajagopal and Varsha Ramesh
Molecules 2021, 26(20), 6303; https://doi.org/10.3390/molecules26206303 - 19 Oct 2021
Cited by 19 | Viewed by 3002
Abstract
Cinnamomum verum is widely used in traditional medicines, and the different parts of the plant, such as bark, leaves, and flowers, are used for essential oil production. The present study compared the chemical composition of the essential oil of C. verum extracted from [...] Read more.
Cinnamomum verum is widely used in traditional medicines, and the different parts of the plant, such as bark, leaves, and flowers, are used for essential oil production. The present study compared the chemical composition of the essential oil of C. verum extracted from the leaves and flowers. In addition, efficacy of these essential oils against the two common pests Sitophilus oryzae and Callosobruchus maculatus was also evaluated. The results indicated the presence of cinnamaldehyde, eugenol, caryophyllene, and linalool in these essential oils, however, at different concentrations. The leaf essential oil was found to be 10–20% more effective as a fumigant against both the pests. Likewise, the leaf essential oil found to repel these pests even at lower concentrations than that of flower essential oil of C. verum. Besides, these essential oils were also effective in controlling the growth of various gram positive and gram negative microbial pathogens and possibly a safeguard for human health. On contrary, both the essential oils were found to be safe for the application on grains, as indicated by their germination potentials. It was also observed that these essential oils do not cause any significant toxicity to guppy fishes, thus confirming their ecological safety for use as a biopesticide. Full article
(This article belongs to the Special Issue Essential Oils: Biological Activities and New Possible Applications)
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9 pages, 722 KiB  
Article
Effects of Curcumin Analogues DMC and EF24 in Combination with the Cytokine TRAIL against Kidney Cancer
by Verónica Ibáñez Gaspar, Jasmin McCaul, Hilary Cassidy, Craig Slattery and Tara McMorrow
Molecules 2021, 26(20), 6302; https://doi.org/10.3390/molecules26206302 - 18 Oct 2021
Cited by 7 | Viewed by 2415
Abstract
The natural compound curcumin has been shown to have therapeutic potential against a wide range of diseases such as cancer. Curcumin reduces cell viability of renal cell carcinoma (RCC) cells when combined with TNF-related apoptosis-inducing ligand (TRAIL), a cytokine that specifically targets cancer [...] Read more.
The natural compound curcumin has been shown to have therapeutic potential against a wide range of diseases such as cancer. Curcumin reduces cell viability of renal cell carcinoma (RCC) cells when combined with TNF-related apoptosis-inducing ligand (TRAIL), a cytokine that specifically targets cancer cells, by helping overcome TRAIL resistance. However, the therapeutic effects of curcumin are limited by its low bioavailability. Similar compounds to curcumin with higher bioavailability, such as demethoxycurcumin (DMC) and 3,5-bis(2-fluorobenzylidene)-4-piperidone (EF24), can potentially have similar anticancer effects and show a similar synergy with TRAIL, thus reducing RCC viability. This study aims to show the effects of DMC and EF24 in combination with TRAIL at reducing ACHN cell viability and ACHN cell migration. It also shows the changes in death receptor 4 (DR4) expression after treatment with these compounds individually and in combination with TRAIL, which can play a role in their mechanism of action. Full article
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18 pages, 5812 KiB  
Article
Monascin and Ankaflavin of Monascus purpureus Prevent Alcoholic Liver Disease through Regulating AMPK-Mediated Lipid Metabolism and Enhancing Both Anti-Inflammatory and Anti-Oxidative Systems
by Jhao-Ru Lai, Ya-Wen Hsu, Tzu-Ming Pan and Chun-Lin Lee
Molecules 2021, 26(20), 6301; https://doi.org/10.3390/molecules26206301 - 18 Oct 2021
Cited by 18 | Viewed by 4134
Abstract
Alcohol metabolism causes an excessive accumulation of liver lipids and inflammation, resulting in liver damage. The yellow pigments monascin (MS) and ankaflavin (AK) of Monascus purpureus-fermented rice were proven to regulate ethanol-induced damage in HepG2 cells, but the complete anti-inflammatory and anti-fatty [...] Read more.
Alcohol metabolism causes an excessive accumulation of liver lipids and inflammation, resulting in liver damage. The yellow pigments monascin (MS) and ankaflavin (AK) of Monascus purpureus-fermented rice were proven to regulate ethanol-induced damage in HepG2 cells, but the complete anti-inflammatory and anti-fatty liver mechanisms in the animal model are still unclear. This study explored the roles of MS and AK in improving alcoholic liver injury. MS and AK were simultaneously fed to evaluate their effects and mechanisms in C57BL/6J mice fed the Lieber–DeCarli liquid alcohol diet for 6 weeks. The results indicated that MS and AK significantly reduced the serum aspartate aminotransferase and alanine aminotransferase activity, as well as the total liver cholesterol and triglyceride levels. The histopathological results indicated that MS and AK prevented lipid accumulation in the liver. MS and AK effectively enhanced the activity of antioxidant enzymes and reduced the degree of lipid peroxidation; AK was particularly effective and exhibited a superior preventive effect against alcoholic liver injury and fatty liver. In addition to inhibiting the phosphorylation of the MAPK family, MS and AK directly reduced TNF-α, IL-6, and IL-1β levels, thereby reducing NF-κB and its downstream iNOS and COX-2 expressions, as well as increasing PPAR-γ, Nrf-2, and HO-1 expressions to prevent liver damage. MS and AK also directly reduced TNF-α, IL-6, and IL-1β expression, thereby reducing the production of NF-κB and its downstream iNOS and COX-2, and increasing PPAR-γ, Nrf-2, and HO-1 expressions, preventing alcohol damage to the liver. Full article
(This article belongs to the Special Issue Functional Food and Their Pharmaceutical Properties)
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16 pages, 444 KiB  
Article
Content and Nutritional Evaluation of Zinc in PDO and Traditional Italian Cheeses
by Pamela Manzi, Maria Gabriella Di Costanzo and Mena Ritota
Molecules 2021, 26(20), 6300; https://doi.org/10.3390/molecules26206300 - 18 Oct 2021
Cited by 6 | Viewed by 1854
Abstract
Zinc is an essential mineral which plays a key role in several important biological processes in the human body. The determination of its level in food matrices can contribute to the food quality characterization and to the adequacy of the diet. Animal food [...] Read more.
Zinc is an essential mineral which plays a key role in several important biological processes in the human body. The determination of its level in food matrices can contribute to the food quality characterization and to the adequacy of the diet. Animal food products generally have a higher zinc content compared to vegetables. Among them, dairy products consumption can provide a great contribution to the zinc reference intakes. In this study, different Italian cheeses (38 Protected Denomination of Origin and 9 Traditional) were evaluated for their zinc content. Cow cheeses generally showed the highest zinc content (1.83–7.75 mg/100 g cheese), followed by sheep cheeses (1.34–3.69 mg/100 g), and cheeses from mixed milk (0.39–4.54 mg/100 g). The only cheese from buffalo milk (Mozzarella di Bufala Campana PDO) showed a zinc content of 2.14 mg/100 g. The great variability in the zinc content observed among the samples is the result of the influence of several factors, such as the feeding system, the species (cow, sheep, goat, and buffalo), and the cheese-making. Most of the samples resulted in a great contribution (>10%) to the zinc Daily Reference Intake set by EU (10 mg/day), with only two samples contributing to less than 4%. Full article
(This article belongs to the Special Issue Health Promoting Compounds in Milk and Dairy Products)
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17 pages, 2650 KiB  
Article
Deposition of Polymer Particles with Fibrinogen Corona at Abiotic Surfaces under Flow Conditions
by Paulina Żeliszewska, Monika Wasilewska, Michał Cieśla and Zbigniew Adamczyk
Molecules 2021, 26(20), 6299; https://doi.org/10.3390/molecules26206299 - 18 Oct 2021
Cited by 5 | Viewed by 1552
Abstract
The deposition kinetics of polymer particles with fibrinogen molecule coronas at bare and poly-L-lysine (PLL) modified mica was studied using the microfluid impinging-jet cell. Basic physicochemical characteristics of fibrinogen and the particles were acquired using dynamic light scattering and the electrophoretic mobility methods, [...] Read more.
The deposition kinetics of polymer particles with fibrinogen molecule coronas at bare and poly-L-lysine (PLL) modified mica was studied using the microfluid impinging-jet cell. Basic physicochemical characteristics of fibrinogen and the particles were acquired using dynamic light scattering and the electrophoretic mobility methods, whereas the zeta potential of the substrates was determined using streaming potential measurements. Subsequently, an efficient method for the preparation of the particles with coronas, characterized by a controlled fibrinogen coverage, was developed. This enabled us to carry out measurements, which confirmed that the deposition kinetics of the particles at mica vanished at pH above 5. In contrast, the particle deposition of PLL modified mica was at maximum for pH above 5. It was shown that the deposition kinetics could be adequately analyzed in terms of the mean-field approach, analogously to the ordinary colloid particle behavior. This contrasts the fibrinogen molecule behavior, which efficiently adsorbs at negatively charged substrates for the entire range pHs up to 9.7. These results have practical significance for conducting label-free immunoassays governed by the specific antigen/antibody interactions. Full article
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11 pages, 1442 KiB  
Article
Effect of the Gintonin-Enriched Fraction on Glucagon-Like-Protein-1 Release
by Rami Lee, Sun-Hye Choi, Han-Sung Cho, Hongik Hwang, Hyewhon Rhim, Hyoung-Chun Kim, Sung-Hee Hwang and Seung-Yeol Nah
Molecules 2021, 26(20), 6298; https://doi.org/10.3390/molecules26206298 - 18 Oct 2021
Cited by 1 | Viewed by 1869
Abstract
Ginseng-derived gintonin reportedly contains functional lysophosphatidic acids (LPAs) as LPA receptor ligands. The effect of the gintonin-enriched fraction (GEF) on in vitro and in vivo glucagon-like protein-1 (GLP-1) secretion, which is known to stimulate insulin secretion, via LPA receptor(s) remains unclear. Accordingly, we [...] Read more.
Ginseng-derived gintonin reportedly contains functional lysophosphatidic acids (LPAs) as LPA receptor ligands. The effect of the gintonin-enriched fraction (GEF) on in vitro and in vivo glucagon-like protein-1 (GLP-1) secretion, which is known to stimulate insulin secretion, via LPA receptor(s) remains unclear. Accordingly, we examined the effects of GEF on GLP-1 secretion using human enteroendocrine NCI-H716 cells. The expression of several of LPA receptor subtypes in NCI-H716 cells using qPCR and Western blotting was examined. LPA receptor subtype expression was in the following order: LPA6 > LPA2 > LPA4 > LPA5 > LPA1 (qPCR), and LPA6 > LPA4 > LPA2 > LPA1 > LPA3 > LPA5 (Western blotting). GEF-stimulated GLP-1 secretion occurred in a dose- and time-dependent manner, which was suppressed by cAMP-Rp, a cAMP antagonist, but not by U73122, a phospholipase C inhibitor. Furthermore, silencing the human LPA6 receptor attenuated GEF-mediated GLP-1 secretion. In mice, low-dose GEF (50 mg/kg, peroral) increased serum GLP-1 levels; this effect was not blocked by Ki16425 co-treatment. Our findings indicate that GEF-induced GLP-1 secretion could be achieved via LPA6 receptor activation through the cAMP pathway. Hence, GEF-induced GLP secretion via LPA6 receptor regulation might be responsible for its beneficial effects on human endocrine physiology. Full article
(This article belongs to the Special Issue The Functional Applications of Medicinal Plants)
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19 pages, 847 KiB  
Article
Synthesis and Anti-HIV Activity of a Novel Series of Isoquinoline-Based CXCR4 Antagonists
by Mastaneh Safarnejad Shad, Sandra Claes, Eline Goffin, Tom Van Loy, Dominique Schols, Steven De Jonghe and Wim Dehaen
Molecules 2021, 26(20), 6297; https://doi.org/10.3390/molecules26206297 - 18 Oct 2021
Cited by 2 | Viewed by 2246
Abstract
An expansion of the structure–activity relationship study of CXCR4 antagonists led to the synthesis of a series of isoquinolines, bearing a tetrahydroquinoline or a 3-methylpyridinyl moiety as head group. All compounds were investigated for CXCR4 affinity and antagonism in competition binding and calcium [...] Read more.
An expansion of the structure–activity relationship study of CXCR4 antagonists led to the synthesis of a series of isoquinolines, bearing a tetrahydroquinoline or a 3-methylpyridinyl moiety as head group. All compounds were investigated for CXCR4 affinity and antagonism in competition binding and calcium mobilization assays, respectively. In addition, the anti-HIV activity of all analogues was determined. All compounds showed excellent activity, with compound 24c being the most promising one, since it displayed consistently low nanomolar activity in the various assays. Full article
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14 pages, 1994 KiB  
Review
ZNF224 Protein: Multifaceted Functions Based on Its Molecular Partners
by Elena Cesaro, Angelo Lupo, Roberta Rapuano, Arianna Pastore, Michela Grosso and Paola Costanzo
Molecules 2021, 26(20), 6296; https://doi.org/10.3390/molecules26206296 - 18 Oct 2021
Cited by 5 | Viewed by 2159
Abstract
The transcription factor ZNF224 is a Kruppel-like zinc finger protein that consists of 707 amino acids and contains 19 tandemly repeated C2H2 zinc finger domains that mediate DNA binding and protein–protein interactions. ZNF224 was originally identified as a transcriptional repressor [...] Read more.
The transcription factor ZNF224 is a Kruppel-like zinc finger protein that consists of 707 amino acids and contains 19 tandemly repeated C2H2 zinc finger domains that mediate DNA binding and protein–protein interactions. ZNF224 was originally identified as a transcriptional repressor of genes involved in energy metabolism, and it was demonstrated that ZNF224-mediated transcriptional repression needs the interaction of its KRAB repressor domain with the co-repressor KAP1 and its zinc finger domains 1–3 with the arginine methyltransferase PRMT5. Furthermore, the protein ZNF255 was identified as an alternative isoform of ZNF224 that possesses different domain compositions mediating distinctive functional interactions. Subsequent studies showed that ZNF224 is a multifunctional protein able to exert different transcriptional activities depending on the cell context and the variety of its molecular partners. Indeed, it has been shown that ZNF224 can act as a repressor, an activator and a cofactor for other DNA-binding transcription factors in different human cancers. Here, we provide a brief overview of the current knowledge on the multifaceted interactions of ZNF224 and the resulting different roles of this protein in various cellular contexts. Full article
(This article belongs to the Special Issue Protein-Protein Interactions 2021)
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14 pages, 7394 KiB  
Article
Methoxy-Substituted γ-Oxa-ε-Lactones Derived from Flavanones—Comparison of Their Anti-Tumor Activity In Vitro
by Aleksandra Pawlak, Marta Henklewska, Beatriz Hernández-Suárez, Monika Siepka, Witold Gładkowski, Czesław Wawrzeńczyk, Karolina Motykiewicz-Pers and Bożena Obmińska-Mrukowicz
Molecules 2021, 26(20), 6295; https://doi.org/10.3390/molecules26206295 - 18 Oct 2021
Cited by 1 | Viewed by 1417
Abstract
Background: The study investigated four flavanone-derived γ-oxa-ε-lactones: a parent unsubstituted compound and its three derivatives with the methoxy group in positions 2′, 4′ and 8. Our objective was to find out if the introduction of the methoxy group into the aromatic ring affects [...] Read more.
Background: The study investigated four flavanone-derived γ-oxa-ε-lactones: a parent unsubstituted compound and its three derivatives with the methoxy group in positions 2′, 4′ and 8. Our objective was to find out if the introduction of the methoxy group into the aromatic ring affects in vitro anti-tumor potency of the investigated lactones. Methods: Cytotoxic and pro-apoptotic effects were assessed with cytometric tests with propidium iodide, annexin V, and Western blot techniques. We also investigated potential synergistic potency of the tested lactones and glucocorticoids in canine lymphoma/leukemia cell lines. Results: The tested flavanone-derived lactones showed anti-cancer activity in vitro. Depending on its location, the methoxy group either increased or decreased cytotoxicity of the derivatives as compared with the parent compound. The most potent lactone was the one with the methoxy group at position 4′ of the B ring (compound 3), and the weakest activity was observed when the group was located at C-8 in the A ring. A combination of the lactones with glucocorticoids confirmed their synergy in anti-tumor activity in vitro. Conclusions: Methoxy-substituted flavanone-derived lactones effectively kill canine lymphoma/leukemia cells in vitro and, thanks to their synergistic action with glucocorticoids, may potentially be applied in the treatment of hematopoietic cancers. Full article
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