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Volume 26
Issue 15
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Molecules, Volume 26, Issue 15 (August-1 2021) – 318 articles

Cover Story (view full-size image): Cyclic trinuclear complexes (CTCs) represent some of the simplest polynuclear metal clusters and have various applications, e.g., exploiting intermolecular M(I)–M(I) interactions, π-acidity and basicity or luminescence. The simplest imidazolate-based scaffold—Au3(Methylimidazolate)3—was first synthesized in 1989 but had not been structurally determined until very recently in 2020. When reinvestigating the synthesis, a new solvatomorph was serendipitously discovered and is reported here. The new solid-state phase comprises metallophilic interactions, which are in general related to emission properties. A combined photophysical, structural, and DFT study is presented to investigate the photophysically active phase and highlights the importance of phase analysis also in the context of molecular compounds. View this paper.
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24 pages, 3878 KiB  
Article
Formulation of Environmentally Safe Graffiti Remover Containing Esterified Plant Oils and Sugar Surfactant
by Marcin Bartman, Sebastian Balicki and Kazimiera A. Wilk
Molecules 2021, 26(15), 4706; https://doi.org/10.3390/molecules26154706 - 3 Aug 2021
Cited by 8 | Viewed by 3614
Abstract
The removal of graffiti or over-painting requires special attention in order to not induce the surface destruction but to also address all of the important eco-compatibility concerns. Because of the necessity to avoid the use of volatile and toxic petroleum-based solvents that are [...] Read more.
The removal of graffiti or over-painting requires special attention in order to not induce the surface destruction but to also address all of the important eco-compatibility concerns. Because of the necessity to avoid the use of volatile and toxic petroleum-based solvents that are common in cleaning formulations, much attention has recently been paid to the design of a variety of sustainable formulations that are based on biodegradable raw materials. In the present contribution we propose a new approach to graffiti cleaning formulations that are composed of newly synthesized green solvents such as esterified plant oils, i.e., rapeseed oil (RO), sunflower oil (SO), or used cooking oil (UCO), ethyl lactate (EL), and alkylpolyglucosides (APGs) as surfactants. Oil PEG-8 ester solvents were synthesized through the direct esterification/transesterification of these oils using monobutyltin(IV) tris(2-ethylhexanoate) and titanium(IV) butoxide catalysts under mild process conditions. The most efficient formulations, determined by optimization through the response surface methodology (RSM) was more effective in comparison to the reference solvents such as the so-called Nitro solvent (denoting a mixture of toluene and acetone) and petroleum ether. Additionally, the optimal product was found to be effective in removing graffiti from glass, metal, or sandstone surfaces under open-field conditions in the city of Wrocław. The performed studies could be an invaluable tool for developing future green formulations for graffiti removal. Full article
(This article belongs to the Special Issue Multicomponent Surfactant Systems: Properties, Trends and Applications)
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17 pages, 2007 KiB  
Article
Quadruple Hydrogen Bond-Containing A-AB-A Triblock Copolymers: Probing the Influence of Hydrogen Bonding in the Central Block
by Boer Liu, Xi Chen, Glenn A. Spiering, Robert B. Moore and Timothy E. Long
Molecules 2021, 26(15), 4705; https://doi.org/10.3390/molecules26154705 - 3 Aug 2021
Cited by 7 | Viewed by 3500
Abstract
This work reveals the influence of pendant hydrogen bonding strength and distribution on self-assembly and the resulting thermomechanical properties of A-AB-A triblock copolymers. Reversible addition-fragmentation chain transfer polymerization afforded a library of A-AB-A acrylic triblock copolymers, wherein the A unit contained cytosine acrylate [...] Read more.
This work reveals the influence of pendant hydrogen bonding strength and distribution on self-assembly and the resulting thermomechanical properties of A-AB-A triblock copolymers. Reversible addition-fragmentation chain transfer polymerization afforded a library of A-AB-A acrylic triblock copolymers, wherein the A unit contained cytosine acrylate (CyA) or post-functionalized ureido cytosine acrylate (UCyA) and the B unit consisted of n-butyl acrylate (nBA). Differential scanning calorimetry revealed two glass transition temperatures, suggesting microphase-separation in the A-AB-A triblock copolymers. Thermomechanical and morphological analysis revealed the effects of hydrogen bonding distribution and strength on the self-assembly and microphase-separated morphology. Dynamic mechanical analysis showed multiple tan delta (δ) transitions that correlated to chain relaxation and hydrogen bonding dissociation, further confirming the microphase-separated structure. In addition, UCyA triblock copolymers possessed an extended modulus plateau versus temperature compared to the CyA analogs due to the stronger association of quadruple hydrogen bonding. CyA triblock copolymers exhibited a cylindrical microphase-separated morphology according to small-angle X-ray scattering. In contrast, UCyA triblock copolymers lacked long-range ordering due to hydrogen bonding induced phase mixing. The incorporation of UCyA into the soft central block resulted in improved tensile strength, extensibility, and toughness compared to the AB random copolymer and A-B-A triblock copolymer comparisons. This study provides insight into the structure-property relationships of A-AB-A supramolecular triblock copolymers that result from tunable association strengths. Full article
(This article belongs to the Special Issue A Fascinating Story of Supramolecular Chemistry: A Themed Issue in Honor of Prof. Harry W. Gibson)
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9 pages, 3341 KiB  
Article
π-Stacking Stopper-Macrocycle Stabilized Dynamically Interlocked [2]Rotaxanes
by Sing-Ming Chan, Fung-Kit Tang, Ching-Yau Lam, Chak-Shing Kwan, Sam C. K. Hau and Ken Cham-Fai Leung
Molecules 2021, 26(15), 4704; https://doi.org/10.3390/molecules26154704 - 3 Aug 2021
Cited by 2 | Viewed by 3518
Abstract
The synthesis of mechanically interlocked molecules is valuable due to their unique topologies. With π-stacking intercomponent interaction, e.g., phenanthroline and anthracene, novel [2]rotaxanes have been synthesized by dynamic imine clipping reaction. Their X-ray crystal structures indicate the π-stackings between the anthracene moiety (stopper) [...] Read more.
The synthesis of mechanically interlocked molecules is valuable due to their unique topologies. With π-stacking intercomponent interaction, e.g., phenanthroline and anthracene, novel [2]rotaxanes have been synthesized by dynamic imine clipping reaction. Their X-ray crystal structures indicate the π-stackings between the anthracene moiety (stopper) on the thread and the (hetero)aromatic rings at the macrocycle of the rotaxanes. Moreover, the length of glycol chains affects the extra π-stacking intercomponent interactions between the phenyl groups and the dimethoxy phenyl groups on the thread. Dynamic combinatorial library has shown at best 84% distribution of anthracene-threaded phenanthroline-based rotaxane, coinciding with the crystallography in that the additional π-stacking intercomponent interactions could increase the thermodynamic stability and selectivity of the rotaxanes. Full article
(This article belongs to the Special Issue Synthesis and Properties of Macrocyclic Compound)
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25 pages, 5692 KiB  
Review
Modeling Chemical Reactivity at the Interfaces of Emulsions: Effects of Partitioning and Temperature
by Marlene Costa, Fátima Paiva-Martins, Sonia Losada-Barreiro and Carlos Bravo-Díaz
Molecules 2021, 26(15), 4703; https://doi.org/10.3390/molecules26154703 - 3 Aug 2021
Cited by 13 | Viewed by 2839
Abstract
Bulk phase chemistry is hardly ever a reasonable approximation to interpret chemical reactivity in compartmentalized systems, because multiphasic systems may alter the course of chemical reactions by modifying the local concentrations and orientations of reactants and by modifying their physical properties (acid-base equilibria, [...] Read more.
Bulk phase chemistry is hardly ever a reasonable approximation to interpret chemical reactivity in compartmentalized systems, because multiphasic systems may alter the course of chemical reactions by modifying the local concentrations and orientations of reactants and by modifying their physical properties (acid-base equilibria, redox potentials, etc.), making them—or inducing them—to react in a selective manner. Exploiting multiphasic systems as beneficial reaction media requires an understanding of their effects on chemical reactivity. Chemical reactions in multiphasic systems follow the same laws as in bulk solution, and the measured or observed rate constant of bimolecular reactions can be expressed, under dynamic equilibrium conditions, in terms of the product of the rate constant and of the concentrations of reactants. In emulsions, reactants distribute between the oil, water, and interfacial regions according to their polarity. However, determining the distributions of reactive components in intact emulsions is arduous because it is physically impossible to separate the interfacial region from the oil and aqueous ones without disrupting the existing equilibria and, therefore, need to be determined in the intact emulsions. The challenge is, thus, to develop models to correctly interpret chemical reactivity. Here, we will review the application of the pseudophase kinetic model to emulsions, which allows us to model chemical reactivity under a variety of experimental conditions and, by carrying out an appropriate kinetic analysis, will provide important kineticparameters. Full article
(This article belongs to the Special Issue Interfacial Chemistry)
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14 pages, 926 KiB  
Article
The Changes in Antioxidant Activity of Selected Flavonoids and Caffeine Depending on the Dosage and Form of Thiamine
by Justyna Piechocka, Anna Gramza-Michałowska and Krystyna Szymandera-Buszka
Molecules 2021, 26(15), 4702; https://doi.org/10.3390/molecules26154702 - 3 Aug 2021
Cited by 7 | Viewed by 2583
Abstract
Phenolic compounds and thiamine may serve as therapies against oxidative stress-related neurodegenerative diseases. However, it is important to note that these components show high instability under changing conditions. The study’s aim was to determine the impact of the thiamine concentration (hydrochloride—TH and pyrophosphate—TP; [...] Read more.
Phenolic compounds and thiamine may serve as therapies against oxidative stress-related neurodegenerative diseases. However, it is important to note that these components show high instability under changing conditions. The study’s aim was to determine the impact of the thiamine concentration (hydrochloride—TH and pyrophosphate—TP; in the range 0.02 to 20 mg/100 g on the indices of the chelating properties and reducing power, and free radicals scavenging indices of EGCG, EGC, ECG and caffeine added from 0.04 to 6.0 mg/100 g. Our research confirmed that higher concentrations of TH and TP can exhibit significant activity against the test antioxidant indices of all components. When above 5.0 mg/100 g of thiamine was used, the radical scavenging abilities of the compound decreased in the following order: EGCG > ECG > EGC > caffeine. The highest correlation was found for the concentration of thiamine pyrophosphate to 20.0 mg/100 g and EGCG. Knowledge of the impact of factors associated with the concentration of both EGCG, EGC, ECG or caffeine and thiamine on their activity could carry weight in regulating the quality supplemented foods, especially of nutrition support for people of all ages were oral, enteral tube feeding and parenteral nutrition). Full article
(This article belongs to the Special Issue Flavonoids from Plants to Foods: From Green Extraction to Healthy Food Ingredient)
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8 pages, 262 KiB  
Editorial
Are Ancestral Medical Practices the Future Solution to Today’s Medical Problems?
by José A. Lupiáñez, Eva E. Rufino-Palomares and Amalia Pérez-Jiménez
Molecules 2021, 26(15), 4701; https://doi.org/10.3390/molecules26154701 - 3 Aug 2021
Cited by 1 | Viewed by 2228
Abstract
Our cells and organs are threatened and, in most cases, constantly subjected to the aggression of numerous situations, both endogenous, characterized by unfavorable genetics, and exogenous, by deficient or inadequate nutrition, and even by a hostile environment; in most cases, they ultimately cause [...] Read more.
Our cells and organs are threatened and, in most cases, constantly subjected to the aggression of numerous situations, both endogenous, characterized by unfavorable genetics, and exogenous, by deficient or inadequate nutrition, and even by a hostile environment; in most cases, they ultimately cause a cascade of degenerative and cardiovascular diseases, cancer, and infections, as well as those related to the metabolic syndrome, all of which eventually generate irreversible damage to the organism and, consequently, a significant deterioration in its survival [...] Full article
(This article belongs to the Special Issue Anticancer Properties of Natural and Derivative Products)
13 pages, 965 KiB  
Review
The Therapeutic Potential of Celastrol in Central Nervous System Disorders: Highlights from In Vitro and In Vivo Approaches
by Stefania Schiavone, Maria Grazia Morgese, Paolo Tucci and Luigia Trabace
Molecules 2021, 26(15), 4700; https://doi.org/10.3390/molecules26154700 - 3 Aug 2021
Cited by 15 | Viewed by 4039
Abstract
Celastrol, the most abundant compound derived from the root of Tripterygium wilfordii, largely used in traditional Chinese medicine, has shown preclinical and clinical efficacy for a broad range of disorders, acting via numerous mechanisms, including the induction of the expression of several neuroprotective [...] Read more.
Celastrol, the most abundant compound derived from the root of Tripterygium wilfordii, largely used in traditional Chinese medicine, has shown preclinical and clinical efficacy for a broad range of disorders, acting via numerous mechanisms, including the induction of the expression of several neuroprotective factors, the inhibition of cellular apoptosis, and the decrease of reactive oxygen species (ROS). Given the crucial implication of these pathways in the pathogenesis of Central Nervous System disorders, both in vitro and in vivo studies have focused their attention on the possible use of this compound in these diseases. However, although most of the available studies have reported significant neuroprotective effects of celastrol in cellular and animal models of these pathological conditions, some of these data could not be replicated. This review aims to discuss current in vitro and in vivo lines of evidence on the therapeutic potential of celastrol in neurodegenerative diseases, including Alzheimer’s and Parkinson’s diseases, amyotrophic lateral sclerosis, Huntington’s disease, multiple sclerosis, and cadmium-induced neurodegeneration, as well as in psychiatric disorders, such as psychosis and depression. In vitro and in vivo studies focused on celastrol effects in cerebral ischemia, ischemic stroke, traumatic brain injury, and epilepsy are also described. Full article
(This article belongs to the Special Issue The Therapeutic Potential of Naturally Occurring Compounds in Counteracting Oxidative Stress and Inflammation: From Basic Science to Therapy)
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13 pages, 1460 KiB  
Review
N-Terminomics Strategies for Protease Substrates Profiling
by Mubashir Mintoo, Amritangshu Chakravarty and Ronak Tilvawala
Molecules 2021, 26(15), 4699; https://doi.org/10.3390/molecules26154699 - 3 Aug 2021
Cited by 13 | Viewed by 4403
Abstract
Proteases play a central role in various biochemical pathways catalyzing and regulating key biological events. Proteases catalyze an irreversible post-translational modification called proteolysis by hydrolyzing peptide bonds in proteins. Given the destructive potential of proteolysis, protease activity is tightly regulated. Dysregulation of protease [...] Read more.
Proteases play a central role in various biochemical pathways catalyzing and regulating key biological events. Proteases catalyze an irreversible post-translational modification called proteolysis by hydrolyzing peptide bonds in proteins. Given the destructive potential of proteolysis, protease activity is tightly regulated. Dysregulation of protease activity has been reported in numerous disease conditions, including cancers, neurodegenerative diseases, inflammatory conditions, cardiovascular diseases, and viral infections. The proteolytic profile of a cell, tissue, or organ is governed by protease activation, activity, and substrate specificity. Thus, identifying protease substrates and proteolytic events under physiological conditions can provide crucial information about how the change in protease regulation can alter the cellular proteolytic landscape. In recent years, mass spectrometry-based techniques called N-terminomics have become instrumental in identifying protease substrates from complex biological mixtures. N-terminomics employs the labeling and enrichment of native and neo-N-termini peptides, generated upon proteolysis followed by mass spectrometry analysis allowing protease substrate profiling directly from biological samples. In this review, we provide a brief overview of N-terminomics techniques, focusing on their strengths, weaknesses, limitations, and providing specific examples where they were successfully employed to identify protease substrates in vivo and under physiological conditions. In addition, we explore the current trends in the protease field and the potential for future developments. Full article
(This article belongs to the Special Issue Small Molecule Inhibitors and Probes of Therapeutically-Relevant Enzymes)
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21 pages, 5130 KiB  
Article
Effect of Sample Preparation on the Detection and Quantification of Selected Nuts Allergenic Proteins by LC-MS/MS
by Sorel Tchewonpi Sagu, Gerd Huschek, Thomas Homann and Harshadrai M. Rawel
Molecules 2021, 26(15), 4698; https://doi.org/10.3390/molecules26154698 - 3 Aug 2021
Cited by 14 | Viewed by 4576
Abstract
The detection and quantification of nut allergens remains a major challenge. The liquid chroma-tography tandem mass spectrometry (LC-MS/MS) is emerging as one of the most widely used methods, but sample preparation prior to the analysis is still a key issue. The objective of [...] Read more.
The detection and quantification of nut allergens remains a major challenge. The liquid chroma-tography tandem mass spectrometry (LC-MS/MS) is emerging as one of the most widely used methods, but sample preparation prior to the analysis is still a key issue. The objective of this work was to establish optimized protocols for extraction, tryptic digestion and LC-MS analysis of almond, cashew, hazelnut, peanut, pistachio and walnut samples. Ammonium bicar-bonate/urea extraction (Ambi/urea), SDS buffer extraction (SDS), polyvinylpolypyrroli-done (PVPP) extraction, trichloroacetic acid/acetone extraction (TCA/acetone) and chloro-form/methanol/sodium chloride precipitation (CM/NaCl) as well as the performances of con-ventional tryptic digestion and microwave-assisted breakdown were investigated. Overall, the protein extraction yields ranged from 14.9 ± 0.5 (almond extract from CM/NaCl) to 76.5 ± 1.3% (hazelnut extract from Ambi/urea). Electrophoretic profiling showed that the SDS extraction method clearly presented a high amount of extracted proteins in the range of 0–15 kDa, 15–35 kDa, 35–70 kDa and 70–250 kDa compared to the other methods. The linearity of the LC-MS methods in the range of 0 to 0.4 µg equivalent defatted nut flour was assessed and recovery of internal standards GWGG and DPLNV(d8)LKPR ranged from 80 to 120%. The identified bi-omarkers peptides were used to relatively quantifier selected allergenic protein form the inves-tigated nut samples. Considering the overall results, it can be concluded that SDS buffer allows a better protein extraction from almond, peanut and walnut samples while PVPP buffer is more appropriate for cashew, pistachio and hazelnut samples. It was also found that conventional overnight digestion is indicated for cashew, pistachio and hazelnut samples, while microwave assisted tryptic digestion is recommended for almond, hazelnut and peanut extracts. Full article
(This article belongs to the Special Issue Method Development of Sampling Preparation Techniques)
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20 pages, 1713 KiB  
Review
Recent Advances in Biopolymer-Based Dye Removal Technologies
by Rohan S. Dassanayake, Sanjit Acharya and Noureddine Abidi
Molecules 2021, 26(15), 4697; https://doi.org/10.3390/molecules26154697 - 3 Aug 2021
Cited by 69 | Viewed by 6535
Abstract
Synthetic dyes have become an integral part of many industries such as textiles, tannin and even food and pharmaceuticals. Industrial dye effluents from various dye utilizing industries are considered harmful to the environment and human health due to their intense color, toxicity and [...] Read more.
Synthetic dyes have become an integral part of many industries such as textiles, tannin and even food and pharmaceuticals. Industrial dye effluents from various dye utilizing industries are considered harmful to the environment and human health due to their intense color, toxicity and carcinogenic nature. To mitigate environmental and public health related issues, different techniques of dye remediation have been widely investigated. However, efficient and cost-effective methods of dye removal have not been fully established yet. This paper highlights and presents a review of recent literature on the utilization of the most widely available biopolymers, specifically, cellulose, chitin and chitosan-based products for dye removal. The focus has been limited to the three most widely explored technologies: adsorption, advanced oxidation processes and membrane filtration. Due to their high efficiency in dye removal coupled with environmental benignity, scalability, low cost and non-toxicity, biopolymer-based dye removal technologies have the potential to become sustainable alternatives for the remediation of industrial dye effluents as well as contaminated water bodies. Full article
(This article belongs to the Special Issue Recent Advances in Dyes Removal Technologies)
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12 pages, 1667 KiB  
Article
Biogenic Silver Nanoparticles from Iris tuberosa as Potential Preservative in Cosmetic Products
by Maria Mondéjar-López, Alberto José López-Jiménez, Minerva Abad-Jordá, Angela Rubio-Moraga, Oussama Ahrazem, Loudes Gómez-Gómez and Enrique Niza
Molecules 2021, 26(15), 4696; https://doi.org/10.3390/molecules26154696 - 3 Aug 2021
Cited by 16 | Viewed by 3492
Abstract
Biogenic-silver nanoparticles emerge as new nanosilver platforms that allow us to obtain silver nanoparticles via “green chemistry”. In our study, biogenic-silver nanoparticles were obtained from Iris tuberosa leaf extract. Nanoparticles were characterized by a UV-vis spectroscopy, dynamical light scattering technique. The transmission electron [...] Read more.
Biogenic-silver nanoparticles emerge as new nanosilver platforms that allow us to obtain silver nanoparticles via “green chemistry”. In our study, biogenic-silver nanoparticles were obtained from Iris tuberosa leaf extract. Nanoparticles were characterized by a UV-vis spectroscopy, dynamical light scattering technique. The transmission electron microscope revealed spheric and irregular nanoparticles with 5 to 50 nm in diameter. Antimicrobial properties were evaluated against typical microbial contaminants found in cosmetic products, showing high antimicrobial properties. Furthermore, natural moisturizing cream was formulated with biogenic-silver nanoparticles to evaluate the preservative efficiency through a challenge test, indicating its promising use as preservative in cosmetics. Full article
(This article belongs to the Special Issue Last Advances in Cosmetics and Personal Care Products Analysis)
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14 pages, 1220 KiB  
Essay
A Critical Look at Linus Pauling’s Influence on the Understanding of Chemical Bonding
by Sudip Pan and Gernot Frenking
Molecules 2021, 26(15), 4695; https://doi.org/10.3390/molecules26154695 - 3 Aug 2021
Cited by 11 | Viewed by 4980
Abstract
The influence of Linus Pauling on the understanding of chemical bonding is critically examined. Pauling deserves credit for presenting a connection between the quantum theoretical description of chemical bonding and Gilbert Lewis’s classical bonding model of localized electron pair bonds for a wide [...] Read more.
The influence of Linus Pauling on the understanding of chemical bonding is critically examined. Pauling deserves credit for presenting a connection between the quantum theoretical description of chemical bonding and Gilbert Lewis’s classical bonding model of localized electron pair bonds for a wide range of chemistry. Using the concept of resonance that he introduced, he was able to present a consistent description of chemical bonding for molecules, metals, and ionic crystals which was used by many chemists and subsequently found its way into chemistry textbooks. However, his one-sided restriction to the valence bond method and his rejection of the molecular orbital approach hindered further development of chemical bonding theory for a while and his close association of the heuristic Lewis binding model with the quantum chemical VB approach led to misleading ideas until today. Full article
(This article belongs to the Special Issue Chemical Bonding: A Commemorative Special Issue Honoring Professor Linus Pauling)
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17 pages, 1370 KiB  
Article
Essential Oils Extracted from Organic Propolis Residues: An Exploratory Analysis of Their Antibacterial and Antioxidant Properties and Volatile Profile
by Natália Y. Ikeda, Carmen M. S. Ambrosio, Alberto Claudio Miano, Pedro L. Rosalen, Eduardo M. Gloria and Severino M. Alencar
Molecules 2021, 26(15), 4694; https://doi.org/10.3390/molecules26154694 - 3 Aug 2021
Cited by 11 | Viewed by 2834
Abstract
The industrial processing of crude propolis generates residues. Essential oils (EOs) from propolis residues could be a potential source of natural bioactive compounds to replace antibiotics and synthetic antioxidants in pig production. In this study, we determined the antibacterial/antioxidant activity of EOs from [...] Read more.
The industrial processing of crude propolis generates residues. Essential oils (EOs) from propolis residues could be a potential source of natural bioactive compounds to replace antibiotics and synthetic antioxidants in pig production. In this study, we determined the antibacterial/antioxidant activity of EOs from crude organic propolis (EOP) and from propolis residues, moist residue (EOMR), and dried residue (EODR), and further elucidated their chemical composition. The EOs were extracted by hydrodistillation, and their volatile profile was tentatively identified by GC-MS. All EOs had an antibacterial effect on Escherichia coli and Lactobacillus plantarum as they caused disturbances on the growth kinetics of both bacteria. However, EODR had more selective antibacterial activity, as it caused a higher reduction in the maximal culture density (D) of E. coli (86.7%) than L. plantarum (46.9%). EODR exhibited mild antioxidant activity, whereas EOMR showed the highest antioxidant activity (ABTS = 0.90 μmol TE/mg, FRAP = 463.97 μmol Fe2+/mg) and phenolic content (58.41 mg GAE/g). Each EO had a different chemical composition, but α-pinene and β-pinene were the major compounds detected in the samples. Interestingly, specific minor compounds were detected in a higher relative amount in EOMR and EODR as compared to EOP. Therefore, these minor compounds are most likely responsible for the biological properties of EODR and EOMR. Collectively, our findings suggest that the EOs from propolis residues could be resourcefully used as natural antibacterial/antioxidant additives in pig production. Full article
(This article belongs to the Special Issue Chemical Composition and Biological Activity of Essential Oils and Other Extracts: From Extraction to Application)
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10 pages, 2259 KiB  
Article
Development of a Novel Acoustic Spectroscopy Method for Detection of Eggshell Cracks
by István Kertész, Viktória Zsom-Muha, Rebeka András, Ferenc Horváth, Csaba Németh and József Felföldi
Molecules 2021, 26(15), 4693; https://doi.org/10.3390/molecules26154693 - 3 Aug 2021
Cited by 16 | Viewed by 2637
Abstract
Non-destructive testing (NDT) for eggshell faults is highly important for the egg industry, as cracked eggs account for around 3% of total production. The most commonly used method at present, candling, is labor intensive, while computer vision systems are expensive and complicated. In [...] Read more.
Non-destructive testing (NDT) for eggshell faults is highly important for the egg industry, as cracked eggs account for around 3% of total production. The most commonly used method at present, candling, is labor intensive, while computer vision systems are expensive and complicated. In this paper, we present a simple, yet efficient, novel method for eggshell crack detection by acoustic spectroscopy. Altogether, 693 sound recordings were evaluated by different classification methods. The results show a cross-validated 2.1% total classification error, with only 0.87% false positive rate, which is the crucial metric for fresh eggs. Adapting the developed method to an industrial setting may lead to a reliable, fast and cost-effective detection method. Full article
(This article belongs to the Special Issue Application of Qualitative Spectroscopy and Chemometrics in Food Traceability and Authenticity)
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14 pages, 22601 KiB  
Article
Magnetless Optical Circulator Based on an Iron Garnet with Reduced Magnetization Saturation
by Gianni Portela, Miguel Levy and Hugo E. Hernandez-Figueroa
Molecules 2021, 26(15), 4692; https://doi.org/10.3390/molecules26154692 - 3 Aug 2021
Cited by 2 | Viewed by 2508
Abstract
A three-port circulator for optical communication systems comprising a photonic crystal slab made of a magneto-optical material in which an magnetizing element is not required to keep its magnetic domains aligned is suggested for the first time. By maximizing the incorporation of europium [...] Read more.
A three-port circulator for optical communication systems comprising a photonic crystal slab made of a magneto-optical material in which an magnetizing element is not required to keep its magnetic domains aligned is suggested for the first time. By maximizing the incorporation of europium to its molecular formula, the magneto-optical material can remain in the saturated magnetic state even in the absence of an external DC magnetic field. Two- and three-dimensional simulations of the device performed with full-wave electromagnetic solvers based on the finite element method demonstrate that, at the 1550 nm wavelength, the insertion loss, isolation, and reflection levels are equal to or better than −1 dB, −14 dB, and −20 dB, respectively. Since its operation does not require an electromagnet or a permanent magnet, the suggested circulator is much more compact, being able to reach footprints in the range of three orders of magnitude smaller, when compared to other circulator designs referred to in the literature and the presented results can be useful for the design of other nonreciprocal devices with reduced dimensions for optical communication systems. Full article
(This article belongs to the Special Issue Advances in Photonic Materials)
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89 pages, 6033 KiB  
Review
Recent Advances on O-Ethoxycarbonyl and O-Acyl Protected Cyanohydrins
by Héctor Manuel Torres Domínguez, Luis Mauricio Hernández Villaverde and Ronan Le Lagadec
Molecules 2021, 26(15), 4691; https://doi.org/10.3390/molecules26154691 - 3 Aug 2021
Cited by 1 | Viewed by 2573
Abstract
Ethoxycarbonyl cyanohydrins and O-acyl cyanohydrins are examples of O-protected cyanohydrins in which the protecting group presents an electrophilic center, contributing to additional reaction pathways. The first section of this review describes recent advances on the synthesis of O-ethoxycarbonyl and O [...] Read more.
Ethoxycarbonyl cyanohydrins and O-acyl cyanohydrins are examples of O-protected cyanohydrins in which the protecting group presents an electrophilic center, contributing to additional reaction pathways. The first section of this review describes recent advances on the synthesis of O-ethoxycarbonyl and O-acyl protected cyanohydrins. Reactions using KCN or alkyl cyanoformates as the cyanide ion source are described, as well as organic and transition metal catalysis used in their preparation, including asymmetric cyanation. In a second part, transformations, and synthetic applications of O-ethoxycarbonyl/acyl cyanohydrins are presented. A variety of structures has been obtained starting from such protected cyanohydrins and, in particular, the synthesis of oxazoles, 1,4-diketones, 1,3-diketones, 2-vinyl-2-cyclopentenones through various methods are discussed. Full article
(This article belongs to the Special Issue Cyanide Chemistry)
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25 pages, 25613 KiB  
Article
Biochemical and Functional Characterization of Kidney Bean Protein Alcalase-Hydrolysates and Their Preservative Action on Stored Chicken Meat
by Ahmed M. Saad, Mahmoud Z. Sitohy, Alshaymaa I. Ahmed, Nourhan A. Rabie, Shimaa A. Amin, Salama M. Aboelenin, Mohamed M. Soliman and Mohamed T. El-Saadony
Molecules 2021, 26(15), 4690; https://doi.org/10.3390/molecules26154690 - 3 Aug 2021
Cited by 69 | Viewed by 4310
Abstract
A new preservation approach is presented in this article to prolong the lifetime of raw chicken meat and enhance its quality at 4 °C via coating with highly soluble kidney bean protein hydrolysate. The hydrolysates of the black, red, and white kidney protein [...] Read more.
A new preservation approach is presented in this article to prolong the lifetime of raw chicken meat and enhance its quality at 4 °C via coating with highly soluble kidney bean protein hydrolysate. The hydrolysates of the black, red, and white kidney protein (BKH, RKH, and WKH) were obtained after 30 min enzymatic hydrolysis with Alcalase (E/S ratio of 1:100, hydrolysis degree 25–29%). The different phaseolin subunits (8S) appeared in SDS-PAGE in 35–45 kD molecular weight range while vicilin appeared in the molecular weight range of 55–75 kD. The kidney bean protein hydrolysates have considerable antioxidant activity as evidenced by the DPPH-scavenging activity and β-carotine-linolenic assay, as well as antimicrobial activity evaluated by disc diffusion assay. BKH followed by RKH (800 µg/mL) significantly (p ≤ 0.05) scavenged 95, 91% of DPPH and inhibited 82–88% of linoleic oxidation. The three studied hydrolysates significantly inhibited the growth of bacteria, yeast, and fungi, where BKH was the most performing. Kidney bean protein hydrolysates could shield the chicken meat because of their amphoteric nature and many functional properties (water and oil-absorbing capacity and foaming stability). The quality of chicken meat was assessed by tracing the fluctuations in the chemical parameters (pH, met-myoglobin, lipid oxidation, and TVBN), bacterial load (total bacterial count, and psychrophilic count), color parameters and sensorial traits during cold preservation (4 °C). The hydrolysates (800 µg/g) significantly p ≤ 0.05 reduced the increment in meat pH and TVBN values, inhibited 59–70% of lipid oxidation as compared to control during 30 days of cold storage via eliminating 50% of bacterial load and maintained secured storage for 30 days. RKH and WKH significantly (p ≤ 0.05) enhanced L*, a* values, thus augmented the meat whiteness and redness, while, BKH increased b* values, declining all color parameters during meat storage. RKH and WKH (800 µg/g) (p ≤ 0.05) maintained 50–71% and 69–75% of meat color and odor, respectively, increased the meat juiciness after 30 days of cold storage. BKH, RKH and WKH can be safely incorporated into novel foods. Full article
(This article belongs to the Section Food Chemistry)
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13 pages, 1355 KiB  
Communication
Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions
by Jan Bojanowski and Anna Albrecht
Molecules 2021, 26(15), 4689; https://doi.org/10.3390/molecules26154689 - 3 Aug 2021
Cited by 4 | Viewed by 2315
Abstract
The doubly decarboxylative Michael–type addition of pyridylacetic acid to chromone-3-carboxylic acids or coumarin-3-carboxylic acids has been developed. This protocol has been realized under Brønsted base catalysis, providing biologically interesting 4-(pyridylmethyl)chroman-2-ones and 2-(pyridylmethyl)chroman-4-ones in good or very good yields. The decarboxylative reaction pathway has [...] Read more.
The doubly decarboxylative Michael–type addition of pyridylacetic acid to chromone-3-carboxylic acids or coumarin-3-carboxylic acids has been developed. This protocol has been realized under Brønsted base catalysis, providing biologically interesting 4-(pyridylmethyl)chroman-2-ones and 2-(pyridylmethyl)chroman-4-ones in good or very good yields. The decarboxylative reaction pathway has been confirmed by mechanistic studies. Moreover, attempts to develop an enantioselective variant of the cascade are also described. Full article
(This article belongs to the Special Issue Advances in Organic Synthesis: A Theme Issue in Honor of Professor Mieczysław Mąkosza)
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20 pages, 690 KiB  
Review
Downstream Processing of Therapeutic Peptides by Means of Preparative Liquid Chromatography
by Chiara De Luca, Giulio Lievore, Desiree Bozza, Alessandro Buratti, Alberto Cavazzini, Antonio Ricci, Marco Macis, Walter Cabri, Simona Felletti and Martina Catani
Molecules 2021, 26(15), 4688; https://doi.org/10.3390/molecules26154688 - 3 Aug 2021
Cited by 32 | Viewed by 6210
Abstract
The market of biomolecules with therapeutic scopes, including peptides, is continuously expanding. The interest towards this class of pharmaceuticals is stimulated by the broad range of bioactivities that peptides can trigger in the human body. The main production methods to obtain peptides are [...] Read more.
The market of biomolecules with therapeutic scopes, including peptides, is continuously expanding. The interest towards this class of pharmaceuticals is stimulated by the broad range of bioactivities that peptides can trigger in the human body. The main production methods to obtain peptides are enzymatic hydrolysis, microbial fermentation, recombinant approach and, especially, chemical synthesis. None of these methods, however, produce exclusively the target product. Other species represent impurities that, for safety and pharmaceutical quality reasons, must be removed. The remarkable production volumes of peptide mixtures have generated a strong interest towards the purification procedures, particularly due to their relevant impact on the manufacturing costs. The purification method of choice is mainly preparative liquid chromatography, because of its flexibility, which allows one to choose case-by-case the experimental conditions that most suitably fit that particular purification problem. Different modes of chromatography that can cover almost every separation case are reviewed in this article. Additionally, an outlook to a very recent continuous chromatographic process (namely Multicolumn Countercurrent Solvent Gradient Purification, MCSGP) and future perspectives regarding purification strategies will be considered at the end of this review. Full article
(This article belongs to the Special Issue Separation and Purification of Peptides)
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15 pages, 11235 KiB  
Article
Noble Metal Nanoparticles Stabilized by Hyper-Cross-Linked Polystyrene as Effective Catalysts in Hydrogenation of Arenes
by Elena S. Bakhvalova, Arina O. Pinyukova, Alexey V. Mikheev, Galina N. Demidenko, Mikhail G. Sulman, Alexey V. Bykov, Linda Z. Nikoshvili and Lioubov Kiwi-Minsker
Molecules 2021, 26(15), 4687; https://doi.org/10.3390/molecules26154687 - 3 Aug 2021
Cited by 4 | Viewed by 2531
Abstract
This work is addressing the arenes’ hydrogenation—the processes of high importance for petrochemical, chemical and pharmaceutical industries. Noble metal (Pd, Pt, Ru) nanoparticles (NPs) stabilized in hyper-cross-linked polystyrene (HPS) were shown to be active and selective catalysts in hydrogenation of a wide range [...] Read more.
This work is addressing the arenes’ hydrogenation—the processes of high importance for petrochemical, chemical and pharmaceutical industries. Noble metal (Pd, Pt, Ru) nanoparticles (NPs) stabilized in hyper-cross-linked polystyrene (HPS) were shown to be active and selective catalysts in hydrogenation of a wide range of arenes (monocyclic, condensed, substituted, etc.) in a batch mode. HPS effectively stabilized metal NPs during hydrogenation in different medium (water, organic solvents) and allowed multiple catalyst reuses. Full article
(This article belongs to the Special Issue Catalysis by Hybrid Materials)
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14 pages, 1829 KiB  
Article
The Properties of Cu Ions in Zeolites CuY Studied by IR Spectroscopy
by Jerzy Podobiński, Mariusz Gackowski, Grzegorz Mordarski, Katarzyna Samson, Michał Śliwa, Dorota Rutkowska-Zbik and Jerzy Datka
Molecules 2021, 26(15), 4686; https://doi.org/10.3390/molecules26154686 - 3 Aug 2021
Cited by 2 | Viewed by 2309
Abstract
The properties of both Cu2+ and Cu+ ions in zeolite CuY were followed with NO and CO as probe molecules. Cu2+ was found to be located in SII, SII*, and SIII sites, whereas Cu+ [...] Read more.
The properties of both Cu2+ and Cu+ ions in zeolite CuY were followed with NO and CO as probe molecules. Cu2+ was found to be located in SII, SII*, and SIII sites, whereas Cu+ was found in SII and SII* sites. The fine analysis of the spectra of Cu2+-NO and Cu+-CO adducts suggests that both in SII and in SII* sites two kinds of Cu cations exist. They differ in the positive charge, which may be related to the varying numbers of AlO4− in close proximity. The experiments of NO and CO adsorption and desorption evidenced that both Cu2+ and Cu+ sites of highest positive charge bind probe molecules most strongly but activate them to a lesser extent than the Cu sites of lowest positive charge. The experiments of reduction with hydrogen evidenced that the Cu ions of higher positive charge are first reduced by hydrogen. On the other hand, Cu sites of the lowest positive charge are first oxidized by oxygen. The experiments with CuNaY zeolites of various Cu contents suggest that the first introduced Cu (at low Cu contents) created Cu+, which was the most neutralized by framework oxygens. Such Cu cations are the most stabilized by framework oxygens. Full article
(This article belongs to the Collection Porous Materials)
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12 pages, 1376 KiB  
Article
Detection of 4a,5-dihydropravastatin as Impurity in the Cholesterol Lowering Drug Pravastatin
by Wibo B. van Scheppingen, Peter P. Lankhorst, Marcus Hans and Marco A. van den Berg
Molecules 2021, 26(15), 4685; https://doi.org/10.3390/molecules26154685 - 3 Aug 2021
Viewed by 2490
Abstract
Dihydro analogues are known byproducts of the fermentative production of statins and cannot be detected with existing pharmacopoeia analysis methods. We detected dihydropravastatin in most commercial formulations of pravastatin with LC-MS, in some cases in levels requiring identification. In fermentation broth samples of [...] Read more.
Dihydro analogues are known byproducts of the fermentative production of statins and cannot be detected with existing pharmacopoeia analysis methods. We detected dihydropravastatin in most commercial formulations of pravastatin with LC-MS, in some cases in levels requiring identification. In fermentation broth samples of the single step production of pravastatin, we detected and identified for the first time 4a,5-dihydropravastatin, and confirmed that after several recrystallization steps this impurity can be fully removed from the pravastatin powder. Full article
(This article belongs to the Special Issue Drug Analysis in Pharmaceutical Development and Drug Manufacturing)
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14 pages, 1550 KiB  
Article
Antiallergic Activity of 6-Deoxy-2-O-methyl-6-(N-hexadecanoyl)amino-l-ascorbic Acid
by Kaori Miura, Hiroaki Matsuno, Yuji Iwaoka, Hideyuki Ito and Akihiro Tai
Molecules 2021, 26(15), 4684; https://doi.org/10.3390/molecules26154684 - 3 Aug 2021
Cited by 1 | Viewed by 3332
Abstract
Allergy is an excessive immune response to a specific antigen. Type I allergies, such as hay fever and food allergies, have increased significantly in recent years and have become a worldwide problem. We previously reported that an ascorbic acid derivative having palmitoyl and [...] Read more.
Allergy is an excessive immune response to a specific antigen. Type I allergies, such as hay fever and food allergies, have increased significantly in recent years and have become a worldwide problem. We previously reported that an ascorbic acid derivative having palmitoyl and glucosyl groups, 2-O-α-d-glucopyranosyl-6-O-hexadecanoyl-l-ascorbic acid (6-sPalm-AA-2G), showed inhibitory effects on degranulation in vitro and on the passive cutaneous anaphylaxis (PCA) reaction in mice. In this study, several palmitoyl derivatives of ascorbic acid were synthesized and a structure–activity relationship study was performed to discover more potent ascorbic acid derivatives with degranulation inhibitory activity. 6-Deoxy-2-O-methyl-6-(N-hexadecanoyl)amino-l-ascorbic acid (2-Me-6-N-Palm-AA), in which a methyl group was introduced into the hydroxyl group at the C-2 position of ascorbic acid and in which the hydroxyl group at the C-6 position was substituted with an N-palmitoyl group, exhibited much higher inhibitory activity for degranulation in vitro than did 6-sPalm-AA-2G. 2-Me-6-N-Palm-AA strongly inhibit the PCA reaction in mice at lower doses than those of 6-sPalm-AA-2G. These findings suggest that 2-Me-6-N-Palm-AA may be a promising therapeutic candidate for allergic diseases. Full article
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17 pages, 4734 KiB  
Article
Anti-Cancer Effects of Zotarolimus Combined with 5-Fluorouracil Treatment in HCT-116 Colorectal Cancer-Bearing BALB/c Nude Mice
by Geng-Ruei Chang, Chan-Yen Kuo, Ming-Yang Tsai, Wei-Li Lin, Tzu-Chun Lin, Huei-Jyuan Liao, Chung-Hung Chen and Yu-Chen Wang
Molecules 2021, 26(15), 4683; https://doi.org/10.3390/molecules26154683 - 2 Aug 2021
Cited by 15 | Viewed by 3718
Abstract
Zotarolimus is a semi-synthetic derivative of rapamycin and an inhibitor of mammalian target of rapamycin (mTOR) signaling. Currently, zotarolimus is used to prolong the survival time of organ grafts, but it is also a novel immunosuppressive agent with potent anti-proliferative activity. Here, we [...] Read more.
Zotarolimus is a semi-synthetic derivative of rapamycin and an inhibitor of mammalian target of rapamycin (mTOR) signaling. Currently, zotarolimus is used to prolong the survival time of organ grafts, but it is also a novel immunosuppressive agent with potent anti-proliferative activity. Here, we examine the anti-tumor effect of zotarolimus, alone and in combination with 5-fluorouracil, on HCT-116 colorectal adenocarcinoma cells implanted in BALB/c nude mice. Compared with the control mice, mice treated with zotarolimus or zotarolimus combined with 5-FU showed retarded tumor growth; increased tumor apoptosis through the enhanced expression of cleaved caspase 3 and extracellular signal-regulated kinase (ERK) phosphorylation; reduced inflammation-related factors such as IL-1β, TNF-α, and cyclooxygenase-2 (COX-2) protein; and inhibited metastasis-related factors such as CD44, epidermal growth factor receptor (EGFR), transforming growth factor β (TGF-β), and vascular endothelial growth factor (VEGF). Notably, mice treated with a combination of zotarolimus and 5-FU showed significantly retarded tumor growth, reduced tumor size, and increased tumor inhibition compared with mice treated with 5-FU or zotarolimus alone, indicating a strong synergistic effect. This in vivo study confirms that zotarolimus or zotarolimus combined with 5-FU can be used to retard colorectal adenocarcinoma growth and inhibit tumorigenesis. Our results suggest that zotarolimus may increase the chemo-sensitization of tumor cells. Therefore, zotarolimus alone and zotarolimus combined with 5-FU may be potential anti-tumor agents in the treatment of human colon adenocarcinoma. Future research on zotarolimus may lead to the development of new therapeutic strategies. Full article
(This article belongs to the Special Issue Novel Anticancer Compounds)
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15 pages, 1809 KiB  
Article
Effect of Methyl Jasmonate on the Terpene Trilactones, Flavonoids, and Phenolic Acids in Ginkgo biloba L. Leaves: Relevance to Leaf Senescence
by Marcin Horbowicz, Wiesław Wiczkowski, Justyna Góraj-Koniarska, Kensuke Miyamoto, Junichi Ueda and Marian Saniewski
Molecules 2021, 26(15), 4682; https://doi.org/10.3390/molecules26154682 - 2 Aug 2021
Cited by 22 | Viewed by 3782
Abstract
The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the [...] Read more.
The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the major TTLs, ginkgolides B and C, were significantly higher in the leaf blades of naturally senesced yellow leaves harvested on 20 October compared with green leaves harvested on 9 September. In petioles, a similar effect was found, although the levels of these compounds were almost half as high. These facts indicate the importance of the senescence process on TTL accumulation. Some flavonoids and phenolic acids also showed changes in content related to maturation or senescence. Generally, the application of JA-Me slightly but substantially increased the levels of TTLs in leaf blades irrespective of the difference in its application side on the leaves. Of the flavonoids analyzed, levels of quercetin, rutin, quercetin-4-glucoside, apigenin, and luteolin were dependent on the JA-Me application site, whereas levels of (+) catechin and (−) epicatechin were not. Application of JA-Me increased ferulic acid and p-coumaric acid esters in the petiole but decreased the levels of these compounds in the leaf blade. The content of p-coumaric acid glycosides and caffeic acid esters was only slightly modified by JA-Me. In general, JA-Me application affected leaf senescence by modifying the accumulation of ginkogolides, flavonoids, and phenolic acids. These effects were also found to be different in leaf blades and petioles. Based on JA-Me- and aging-related metabolic changes in endogenous levels of the secondary metabolites in G. biloba leaves, we discussed the results of study in the context of basic research and possible practical application. Full article
(This article belongs to the Special Issue Natural Plant Substances—Structural and Application Aspects: A Theme Issue in Honor of Professor Wieslaw Oleszek)
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40 pages, 1179 KiB  
Review
Application of Experimental Design Methodologies in the Enantioseparation of Pharmaceuticals by Capillary Electrophoresis: A Review
by Gabriel Hancu, Serena Orlandini, Lajos Attila Papp, Adriana Modroiu, Roberto Gotti and Sandra Furlanetto
Molecules 2021, 26(15), 4681; https://doi.org/10.3390/molecules26154681 - 2 Aug 2021
Cited by 20 | Viewed by 3155
Abstract
Chirality is one of the major issues in pharmaceutical research and industry. Capillary electrophoresis (CE) is an interesting alternative to the more frequently used chromatographic techniques in the enantioseparation of pharmaceuticals, and is used for the determination of enantiomeric ratio, enantiomeric purity, and [...] Read more.
Chirality is one of the major issues in pharmaceutical research and industry. Capillary electrophoresis (CE) is an interesting alternative to the more frequently used chromatographic techniques in the enantioseparation of pharmaceuticals, and is used for the determination of enantiomeric ratio, enantiomeric purity, and in pharmacokinetic studies. Traditionally, optimization of CE methods is performed using a univariate one factor at a time (OFAT) approach; however, this strategy does not allow for the evaluation of interactions between experimental factors, which may result in ineffective method development and optimization. In the last two decades, Design of Experiments (DoE) has been frequently employed to better understand the multidimensional effects and interactions of the input factors on the output responses of analytical CE methods. DoE can be divided into two types: screening and optimization designs. Furthermore, using Quality by Design (QbD) methodology to develop CE-based enantioselective techniques is becoming increasingly popular. The review presents the current use of DoE methodologies in CE-based enantioresolution method development and provides an overview of DoE applications in the optimization and validation of CE enantioselective procedures in the last 25 years. Moreover, a critical perspective on how different DoE strategies can aid in the optimization of enantioseparation procedures is presented. Full article
(This article belongs to the Special Issue Enantioselective Synthesis, Enantiomeric Separations and Chiral Recognition II)
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15 pages, 5227 KiB  
Article
Excited States Symmetry Breaking and In-Plane Polarization Cause Chiral Reversal in Diastereomers
by Chenglong Wang, Jingang Wang and Chunyang Wang
Molecules 2021, 26(15), 4680; https://doi.org/10.3390/molecules26154680 - 2 Aug 2021
Cited by 1 | Viewed by 1649
Abstract
In this work, we investigate the electronic transitions and chirality of three isomers of huge conjugated systems: asymmetric diastereomers (MMMM) and two symmetrical diastereomers (PMPM and PPMM). The physical mechanism of flipping has been studied theoretically. The new ribbon-shaped polycyclic aromatic hydrocarbons (PAHs) [...] Read more.
In this work, we investigate the electronic transitions and chirality of three isomers of huge conjugated systems: asymmetric diastereomers (MMMM) and two symmetrical diastereomers (PMPM and PPMM). The physical mechanism of flipping has been studied theoretically. The new ribbon-shaped polycyclic aromatic hydrocarbons (PAHs) molecule is formed by connecting three graphene-like systems with large conjugated π orbitals. By calculating and analyzing electromagnetic interaction decomposition over distance, it can be found that the chirality reversal of different energies is caused by the symmetrical fracture of TMDM in the Z direction. The chirality reversal at the same energy is caused by the in-plane polarization of the TMDM along the Y direction. Full article
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21 pages, 4602 KiB  
Article
Fluorescent Phthalocyanine-Encapsulated Bovine Serum Albumin Nanoparticles: Their Deployment as Therapeutic Agents in the NIR Region
by Raluca Borlan, Daria Stoia, Luiza Gaina, Andreea Campu, Gabriel Marc, Maria Perde-Schrepler, Mihaela Silion, Dana Maniu, Monica Focsan and Simion Astilean
Molecules 2021, 26(15), 4679; https://doi.org/10.3390/molecules26154679 - 2 Aug 2021
Cited by 10 | Viewed by 2670
Abstract
In recent times, researchers have aimed for new strategies to combat cancer by the implementation of nanotechnologies in biomedical applications. This work focuses on developing protein-based nanoparticles loaded with a newly synthesized NIR emitting and absorbing phthalocyanine dye, with photodynamic and photothermal properties. [...] Read more.
In recent times, researchers have aimed for new strategies to combat cancer by the implementation of nanotechnologies in biomedical applications. This work focuses on developing protein-based nanoparticles loaded with a newly synthesized NIR emitting and absorbing phthalocyanine dye, with photodynamic and photothermal properties. More precisely, we synthesized highly reproducible bovine serum albumin-based nanoparticles (75% particle yield) through a two-step protocol and successfully encapsulated the NIR active photosensitizer agent, achieving a good loading efficiency of 91%. Making use of molecular docking simulations, we confirm that the NIR photosensitizer is well protected within the nanoparticles, docked in site I of the albumin molecule. Encouraging results were obtained for our nanoparticles towards biomedical use, thanks to their negatively charged surface (−13.6 ± 0.5 mV) and hydrodynamic diameter (25.06 ± 0.62 nm), favorable for benefitting from the enhanced permeability and retention effect; moreover, the MTT viability assay upholds the good biocompatibility of our NIR active nanoparticles. Finally, upon irradiation with an NIR 785 nm laser, the dual phototherapeutic effect of our NIR fluorescent nanoparticles was highlighted by their excellent light-to-heat conversion performance (photothermal conversion efficiency 20%) and good photothermal and size stability, supporting their further implementation as fluorescent therapeutic agents in biomedical applications. Full article
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20 pages, 3433 KiB  
Article
CYPstrate: A Set of Machine Learning Models for the Accurate Classification of Cytochrome P450 Enzyme Substrates and Non-Substrates
by Malte Holmer, Christina de Bruyn Kops, Conrad Stork and Johannes Kirchmair
Molecules 2021, 26(15), 4678; https://doi.org/10.3390/molecules26154678 - 2 Aug 2021
Cited by 11 | Viewed by 4141
Abstract
The interaction of small organic molecules such as drugs, agrochemicals, and cosmetics with cytochrome P450 enzymes (CYPs) can lead to substantial changes in the bioavailability of active substances and hence consequences with respect to pharmacological efficacy and toxicity. Therefore, efficient means of predicting [...] Read more.
The interaction of small organic molecules such as drugs, agrochemicals, and cosmetics with cytochrome P450 enzymes (CYPs) can lead to substantial changes in the bioavailability of active substances and hence consequences with respect to pharmacological efficacy and toxicity. Therefore, efficient means of predicting the interactions of small organic molecules with CYPs are of high importance to a host of different industries. In this work, we present a new set of machine learning models for the classification of xenobiotics into substrates and non-substrates of nine human CYP isozymes: CYPs 1A2, 2A6, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1, and 3A4. The models are trained on an extended, high-quality collection of known substrates and non-substrates and have been subjected to thorough validation. Our results show that the models yield competitive performance and are favorable for the detection of CYP substrates. In particular, a new consensus model reached high performance, with Matthews correlation coefficients (MCCs) between 0.45 (CYP2C8) and 0.85 (CYP3A4), although at the cost of coverage. The best models presented in this work are accessible free of charge via the “CYPstrate” module of the New E-Resource for Drug Discovery (NERDD). Full article
(This article belongs to the Special Issue Advancing Cheminformatics—A Theme Issue in Honor of Professor Jürgen Bajorath)
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9 pages, 1642 KiB  
Article
Noble Gas in a Ring
by Wei-Te Lin, Ya-Jyun Shih, Tzu-Jeng Hsu and Wei-Ping Hu
Molecules 2021, 26(15), 4677; https://doi.org/10.3390/molecules26154677 - 2 Aug 2021
Cited by 2 | Viewed by 2150
Abstract
We have designed a new type of molecule with a noble gas (Ng = Kr and Xe) atom in a six-membered ring. Their structures and stability have been studied by density functional theory and by correlated electronic structure calculations. The results showed that [...] Read more.
We have designed a new type of molecule with a noble gas (Ng = Kr and Xe) atom in a six-membered ring. Their structures and stability have been studied by density functional theory and by correlated electronic structure calculations. The results showed that the six-membered ring is planar with very short Ng–O and Ng–N polar covalent bonds. The calculated energy barriers for all the unimolecular dissociation pathways are higher than 20 and 35 kcal/mol for Ng = Kr and Xe, respectively. The current study suggests that these molecules and their derivatives might be synthesized and observable at cryogenic conditions. Full article
(This article belongs to the Section Computational and Theoretical Chemistry)
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