Molecules

15 pages, 1694 KiB

Open AccessArticle

Palladium-Catalyzed Direct (Het)arylation Reactions of Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole and 4,8-Dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole)

by Timofey N. Chmovzh, Timofey A. Kudryashev, Daria A. Alekhina and Oleg A. Rakitin

Molecules 2023, 28(9), 3977; https://doi.org/10.3390/molecules28093977 - 08 May 2023

Cited by 4 | Viewed by 1900

Abstract

Palladium-catalyzed direct (het)arylation reactions of strongly electron-withdrawing tricyclic benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) and its 4,8-dibromo derivative were studied; the conditions for the selective formation of mono- and bis-aryl derivatives were found. The reaction of 4,8-dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) with thiophenes in the presence of palladium acetate as a catalyst [...] Read more.

Palladium-catalyzed direct (het)arylation reactions of strongly electron-withdrawing tricyclic benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) and its 4,8-dibromo derivative were studied; the conditions for the selective formation of mono- and bis-aryl derivatives were found. The reaction of 4,8-dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) with thiophenes in the presence of palladium acetate as a catalyst and potassium pivalate as a base, depending on the conditions used, selectively gave both mono- and bis-thienylated benzo-bis-thiadiazoles in low to moderate yields; arenes were found to be inactive in these reactions. It was discovered that direct C–H arylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with bromo(iodo)arenes and -thiophenes in the presence of Pd(OAc)2 and di-tert-butyl(methyl)phosphonium tetrafluoroborate salt is a powerful tool for the selective formation of 4-mono- and 4,8-di(het)arylated benzo-bis-thiadiazoles. Oxidative double C–H hetarylation of benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole with thiophenes in the presence of Pd(OAc)₂ and silver (I) oxide in DMSO was successfully employed to prepare bis-thienylbenzo-bis-thiadiazoles in moderate yields. Full article

(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)

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12 pages, 2624 KiB

Open AccessArticle

High-Contrast Visualization Chemiluminescence Based on AIE-Active and Base-Sensitive Emitters

by Xiao-Wen Zhang, Xu-Lin Chen and Can-Zhong Lu

Molecules 2023, 28(9), 3976; https://doi.org/10.3390/molecules28093976 - 08 May 2023

Viewed by 1369

Abstract

Peroxyoxalate chemiluminescence (PO-CL) is one of the most popular cold light sources, yet the drawback of aggregation-caused quenching limits their use. Here, we report a new kind of efficient bifunctional emitter derived from salicylic acid, which not only exhibits typical aggregation-induced emission (AIE) [...] Read more.

Peroxyoxalate chemiluminescence (PO-CL) is one of the most popular cold light sources, yet the drawback of aggregation-caused quenching limits their use. Here, we report a new kind of efficient bifunctional emitter derived from salicylic acid, which not only exhibits typical aggregation-induced emission (AIE) character but also has the ability to catalyze the CL process under basic conditions based on base sensitivity. By taking advantage of these unique features, we successfully confine the CL process on the surface of solid bases and provide a high-contrast visualization of CL emission. This method allows most of the common basic salts like sodium carbonate to be invisible encryption information ink and PO-CL solution to be a decryption tool to visualize the hidden information. The current study opens up an appealing way for the development of multifunction CL emitters for information encryption and decryption applications. Full article

(This article belongs to the Topic Advances in Chemistry and Chemical Engineering)

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31 pages, 13612 KiB

Open AccessArticle

Design, Synthesis and Biological Evaluation of Novel Pleuromutilin Derivatives Containing 6-Chloro-1-R-1H-pyrazolo[3,4-d]pyrimidine-4-amino Side Chain

by Jun Wang, Yu-Han Hu, Ke-Xin Zhou, Wei Wang, Fei Li, Ke Li, Guang-Yu Zhang and You-Zhi Tang

Molecules 2023, 28(9), 3975; https://doi.org/10.3390/molecules28093975 - 08 May 2023

Viewed by 1293

Abstract

Two series of pleuromutilin derivatives were designed and synthesized as inhibitors against Staphylococcus aureus (S. aureus). 6-chloro-4-amino-1-R-1H-pyrazolo[3,4-d]pyrimidine or 4-(6-chloro-1-R-1H-pyrazolo[3,4-d]pyrimidine-4-yl)amino-phenylthiol were connected to pleuromutilin. A diverse array of substituents was introduced at the N-1 [...] Read more.

Two series of pleuromutilin derivatives were designed and synthesized as inhibitors against Staphylococcus aureus (S. aureus). 6-chloro-4-amino-1-R-1H-pyrazolo[3,4-d]pyrimidine or 4-(6-chloro-1-R-1H-pyrazolo[3,4-d]pyrimidine-4-yl)amino-phenylthiol were connected to pleuromutilin. A diverse array of substituents was introduced at the N-1 position of the pyrazole ring. The in vitro antibacterial activities of these semisynthetic derivatives were evaluated against two standard strains, Methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, Staphylococcus aureus (S. aureus), ATCC 29213 and two clinical S. aureus strains (144, AD3) using the broth dilution method. Compounds 12c, 19c and 22c (MIC = 0.25 μg/mL) manifested good in vitro antibacterial ability against MRSA which was similar to that of tiamulin (MIC = 0.5 μg/mL). Among them, compound 22c killed MRSA in a time-dependent manner and performed faster bactericidal kinetics than tiamulin in time–kill curves. In addition, compound 22c exhibited longer PAE than tiamulin, and showed no significant inhibition on the cell viability of RAW 264.7, Caco-2 and 16-HBE cells at high doses (≤8 μg/mL). The neutropenic murine thigh infection model study revealed that compound 22c displayed more effective in vivo bactericidal activity than tiamulin in reducing MRSA load. The molecular docking studies indicated that compound 22c was successfully localized inside the binding pocket of 50S ribosomal, and four hydrogen bonds played important roles in the binding of them. Full article

(This article belongs to the Section Bioorganic Chemistry)

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14 pages, 2290 KiB

Open AccessArticle

Erlotinib-Loaded Dendrimer Nanocomposites as a Targeted Lung Cancer Chemotherapy

by Wafa K. Fatani, Fadilah S. Aleanizy, Fulwah Y. Alqahtani, Mohammed M. Alanazi, Abdullah A. Aldossari, Faiyaz Shakeel, Nazrul Haq, Hosam Abdelhady, Hamad M. Alkahtani and Ibrahim A. Alsarra

Molecules 2023, 28(9), 3974; https://doi.org/10.3390/molecules28093974 - 08 May 2023

Cited by 8 | Viewed by 1825

Abstract

Lung cancer is the main cause of cancer-related mortality globally. Erlotinib is a tyrosine kinase inhibitor, affecting both cancerous cell proliferation and survival. The emergence of oncological nanotechnology has provided a novel drug delivery system for erlotinib. The aims of this current investigation [...] Read more.

Lung cancer is the main cause of cancer-related mortality globally. Erlotinib is a tyrosine kinase inhibitor, affecting both cancerous cell proliferation and survival. The emergence of oncological nanotechnology has provided a novel drug delivery system for erlotinib. The aims of this current investigation were to formulate two different polyamidoamine (PAMAM) dendrimer generations—generation 4 (G4) and generation 5 (G5) PAMAM dendrimer—to study the impact of two different PAMAM dendrimer formulations on entrapment by drug loading and encapsulation efficiency tests; to assess various characterizations, including particle size distribution, polydispersity index, and zeta potential; and to evaluate in vitro drug release along with assessing in situ human lung adenocarcinoma cell culture. The results showed that the average particle size of G4 and G5 nanocomposites were 200 nm and 224.8 nm, with polydispersity index values of 0.05 and 0.300, zeta potential values of 11.54 and 4.26 mV of G4 and G5 PAMAM dendrimer, respectively. Comparative in situ study showed that cationic G4 erlotinib-loaded dendrimer was more selective and had higher antiproliferation activity against A549 lung cells compared to neutral G5 erlotinib-loaded dendrimers and erlotinib alone. These conclusions highlight the potential effect of cationic G4 dendrimer as a targeting-sustained-release carrier for erlotinib. Full article

(This article belongs to the Special Issue Nanomedicine Based Drug Delivery Systems: Recent Developments and Future Prospects)

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14 pages, 2400 KiB

Open AccessArticle

Aroma Characterization of Roasted Meat and Meat Substitutes Using Gas Chromatography–Mass Spectrometry with Simultaneous Selective Detection and a Dedicated Software Tool, AromaMS

by Nitzan Tzanani, Ariel Hindi and Dana Marder

Molecules 2023, 28(9), 3973; https://doi.org/10.3390/molecules28093973 - 08 May 2023

Viewed by 1440

Abstract

The development of healthier and more sustainable food products, such as plant-based meat substitutes (PBMSs), have received significant interest in recent years. A thorough understanding of the aroma composition can support efforts to improve the sensory properties of PBMS products and promote their [...] Read more.

The development of healthier and more sustainable food products, such as plant-based meat substitutes (PBMSs), have received significant interest in recent years. A thorough understanding of the aroma composition can support efforts to improve the sensory properties of PBMS products and promote their consumer acceptability. Here, we developed an integrated hardware and software approach for aroma analysis of roasted food based on simultaneous analysis with three complementary detectors. Following the standard procedure of aroma headspace sampling and separation using solid-phase microextraction-gas chromatography, the column flow was split into three channels for the following detectors for the selective detection of nitrogen and sulfur (N/S)-containing compounds: an electron ionization-mass spectrometry for identification through a library search, a nitrogen-phosphorous detector, and a flame-photometric detector (FPD)/pulsed-FPD. Integration of results from the different types of detectors was achieved using a software tool, called AromaMS, developed in-house for data processing. As stipulated by the user, AromaMS performed either non-targeted screening for all volatile organic compounds (VOCs) or selective screening for N/S-containing VOCs that play a major role in the aroma experience. User-defined parameters for library matching and the retention index were applied to further eliminate false identifications. This new approach was successfully applied for comparative analysis of roasted meat and PBMS samples. Full article

(This article belongs to the Special Issue Analysis of Volatile and Odor Compounds in Foods—Second Edition)

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11 pages, 2793 KiB

Open AccessArticle

Comparison between Cashew-Based and Petrochemical Hydroxyoximes: Insights from Molecular Simulations

by Cuong V. Nguyen, Chi M. Phan, Son A. Hoang and Shin-ichi Yusa

Molecules 2023, 28(9), 3971; https://doi.org/10.3390/molecules28093971 - 08 May 2023

Cited by 1 | Viewed by 1281

Abstract

Solvent extraction has been ubiquitously used to recover valuable metals from wastes such as spent batteries and electrical boards. With increasing demands for energy transition, there is a critical need to improve the recycling rate of critical metals, including copper. Therefore, the sustainability [...] Read more.

Solvent extraction has been ubiquitously used to recover valuable metals from wastes such as spent batteries and electrical boards. With increasing demands for energy transition, there is a critical need to improve the recycling rate of critical metals, including copper. Therefore, the sustainability of reagents is critical for the overall sustainability of the process. Yet, the recycling process relies on functional organic compounds based on the hydroxyoxime group. To date, hydroxyoxime extractants have been produced from petrol-based chemical feedstocks. Recently, natural-based cardanol has been used to produce an alternative hydroxyoxime. The natural-based oxime has been employed to recover valuable metals (Ga, Ni, Co) via a liquid/liquid extraction process. The natural compound has a distinctive structure with 15 carbons in the alkyl tail. In contrast, petrol-based hydroxyoximes have only 12 or fewer carbons. However, the molecular advantages of this natural-based compound over the current petrol-based ones remain unclear. In this study, molecular dynamics simulation was employed to investigate the effect of extractant hydrocarbon chains on the extraction of copper ions. Two hydroxyoxime extractants with 12 and 15 carbons in the alkyl chain were found to have similar interactions with Cu²⁺ ions. Yet, a slight molecular binding increase was observed when the carbon chain was increased. In addition, lengthening the carbon chain made the extracting stage easier and the stripping stage harder. The binding would result in a lower pH in the extraction step and a lower pH in the stripping step. The insights from this molecular study would help design the extraction circuit using natural-based hydroxyoxime extractants. A successful application of cashew-based cardanol will improve the environmental benefits of the recycling process. With cashew-producing regions in developing countries, the application also improves these regions’ social and economic sustainability. Full article

(This article belongs to the Special Issue Development of Analytical Methodologies for Selective Extraction, Separation, Identification, and Purification of Valuable Compounds)

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13 pages, 2663 KiB

Open AccessReview

Non-Native Structures of Apomyoglobin and Apoleghemoglobin in Folding Intermediates Related to the Protein Misfolding

by Chiaki Nishimura and Takeshi Kikuchi

Molecules 2023, 28(9), 3970; https://doi.org/10.3390/molecules28093970 - 08 May 2023

Viewed by 1260

Abstract

Protein folding is essential for a polypeptide chain to acquire its proper structure and function. Globins are a superfamily of ubiquitous heme-binding α-helical proteins whose function is principally to regulate oxygen homoeostasis. In this review, we explore the hierarchical helical formation in the [...] Read more.

Protein folding is essential for a polypeptide chain to acquire its proper structure and function. Globins are a superfamily of ubiquitous heme-binding α-helical proteins whose function is principally to regulate oxygen homoeostasis. In this review, we explore the hierarchical helical formation in the globin proteins apomyoglobin and leghemoglobin, and we discuss the existence of non-native and misfolded structures occurring during the course of folding to its native state. This review summarizes the research aimed at characterizing and comparing the equilibrium and kinetic intermediates, as well as delineating the complete folding pathway at a molecular level, in order to answer the following questions: “What is the mechanism of misfolding via a folding intermediate? Does the non-native structure stabilize the contemporary intermediate structure? Does the non-native structure induce slower folding?” The role of the non-native structures in the folding intermediate related to misfolding is also discussed. Full article

(This article belongs to the Special Issue Protein Folding, towards the Comprehensive Understanding from Various Aspects)

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29 pages, 4605 KiB

Open AccessArticle

Mechanistic Studies of Arene–Ruthenium(II) Complexes with Carbothioamidopyrazoles as Alternative Cancer Drugs

by Paweł Hikisz, Ewelina Namiecińska, Piotr Paneth and Elzbieta Budzisz

Molecules 2023, 28(9), 3969; https://doi.org/10.3390/molecules28093969 - 08 May 2023

Cited by 3 | Viewed by 1619

Abstract

Arene–ruthenium(II) complexes with carbothioamidopyrazoles at the C-2 and C-5 positions have been recognized as chemotherapeutic agent alternatives to cisplatin and its oxaliplatin analogs. The aim of this study was to continue research on the biological aspect of arene–ruthenium(II) complexes and their anticancer activity. [...] Read more.

Arene–ruthenium(II) complexes with carbothioamidopyrazoles at the C-2 and C-5 positions have been recognized as chemotherapeutic agent alternatives to cisplatin and its oxaliplatin analogs. The aim of this study was to continue research on the biological aspect of arene–ruthenium(II) complexes and their anticancer activity. The present paper includes an additional 12 new tumor cells, analyzed by MTT, and employs a series of extended bioassays to better understand their potential mechanism of antitumor activity. The following tests were conducted: membrane permeability studies, intramolecular reactive oxygen and nitrogen species (ROS/RNS) assays, mitochondrial potential changes, DNA analysis by comet assay using the electrophoresis method, measurement of cleaved PARP protein levels, and determination of apoptotic and necrotic cell fractions by fluorescence microscopy. Additionally, the article presents lipophilicity studies based on RP-TLC and molecular docking studies. We hope that the presented data will prove useful in practical treatment, especially for patients with cancer. Full article

(This article belongs to the Special Issue Supramolecular and Coordination Metal-Based Molecules for Biomedical Applications)

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11 pages, 2605 KiB

Open AccessArticle

A Series of Polymer-Supported Polyoxometalates as Heterogeneous Photocatalysts for Degradation of Organic Dye

by Fan Yang, Xiaojiao He, Tingting Xin, Huizhen Yang, Lijie Bai, Lihua Gao and Yibo Wang

Molecules 2023, 28(9), 3968; https://doi.org/10.3390/molecules28093968 - 08 May 2023

Cited by 1 | Viewed by 947

Abstract

Photocatalytic degradation technology has developed rapidly in the treatment of organic pollutants due to its high efficiency, mild reaction conditions and easy control. In this paper, a series of heterogeneous photocatalysts, BWZ-en-R (BWZ = [BW₁₁Z(H₂O)O₃₉]⁷⁻, [...] Read more.

Photocatalytic degradation technology has developed rapidly in the treatment of organic pollutants due to its high efficiency, mild reaction conditions and easy control. In this paper, a series of heterogeneous photocatalysts, BWZ-en-R (BWZ = [BW₁₁Z(H₂O)O₃₉]⁷⁻, Z = Zn, Cd, Mn, en = ethylenediamine, R = Merrifield resin), were prepared by using ethanediamine as a linker to immobilize Keggin-type transition elements substituting tungstoborates on Merrifield resin and characterized by Fourier transform infrared spectroscopy, X-ray powder diffraction, scanning electron microscopy and energy-dispersive X-ray spectroscopy. The photocatalytic properties of BWZ-en-R (Z = Zn, Cd, Mn) for the degradation of methyl red (MR) were investigated. The results show that the BWZ-en-R (Z = Zn, Cd, Mn) photocatalysts exhibited high photodegradation ability for MR under the irradiation of ultraviolet light, and were easily separated from the reaction media. The maximum degradation rate (%) of MR (40 mL, 25 μM, pH = 2) reached 96.4% for the BWMn-en-R photocatalyst (40 mg) after being irradiated for 30 min, making this a promising photocatalyst candidate for dye degradation. Moreover, the influences of some factors, such as the Z-substituted elements in the BWZ, the BWZ-en-R dosage and the MR initial concentration, on the photocatalytic degradation rate of MR were also examined. Full article

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33 pages, 7569 KiB

Open AccessArticle

Fingerprinting Chemical Markers in the Mediterranean Orange Blossom Honey: UHPLC-HRMS Metabolomics Study Integrating Melissopalynological Analysis, GC-MS and HPLC-PDA-ESI/MS

by Konstantinos M. Kasiotis, Eirini Baira, Styliani Iosifidou, Electra Manea-Karga, Despina Tsipi, Sofia Gounari, Ioannis Theologidis, Theodora Barmpouni, Pier Paolo Danieli, Filippo Lazzari, Daniele Dipasquale, Sonia Petrarca, Souad Shairra, Naglaa A. Ghazala, Aida A. Abd El-Wahed, Seham M. A. El-Gamal and Kyriaki Machera

Molecules 2023, 28(9), 3967; https://doi.org/10.3390/molecules28093967 - 08 May 2023

Cited by 3 | Viewed by 2161

Abstract

(1) Background: Citrus honey constitutes a unique monofloral honey characterized by a distinctive aroma and unique taste. The non-targeted chemical analysis can provide pivotal information on chemical markers that differentiate honey based on its geographical and botanical origin. (2) Methods: Within the PRIMA [...] Read more.

(1) Background: Citrus honey constitutes a unique monofloral honey characterized by a distinctive aroma and unique taste. The non-targeted chemical analysis can provide pivotal information on chemical markers that differentiate honey based on its geographical and botanical origin. (2) Methods: Within the PRIMA project “PLANT-B”, a metabolomics workflow was established to unveil potential chemical markers of orange blossom honey produced in case study areas of Egypt, Italy, and Greece. In some of these areas, aromatic medicinal plants were cultivated to enhance biodiversity and attract pollinators. The non-targeted chemical analysis and metabolomics were conducted using ultra-high-performance liquid chromatography high-resolution mass spectrometry (UHPLC-HRMS). (3) Results: Forty compounds were disclosed as potential chemical markers, enabling the differentiation of the three orange blossom honeys according to geographical origin. Italian honey showed a preponderance of flavonoids, while in Greek honey, terpenoids and iridoids were more abundant than flavonoids, except for hesperidin. In Egyptian honey, suberic acid and a fatty acid ester derivative emerged as chemical markers. New, for honey, furan derivatives were identified using GC-MS in Greek samples. (4) Conclusions: The application of UHPLC-HRMS metabolomics combined with an elaborate melissopalynological analysis managed to unveil several potential markers of Mediterranean citrus honey potentially associated with citrus crop varieties and the local indigenous flora. Full article

(This article belongs to the Special Issue Chemometrics in Analytical Chemistry)

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12 pages, 2330 KiB

Open AccessArticle

Modelling the Encapsulation of 3-Hydroxyflavone with Cyclodextrin and Octa Acid and Comparing Their Differences

by Ka Wa Fan, Hoi Ling Luk and David Lee Phillips

Molecules 2023, 28(9), 3966; https://doi.org/10.3390/molecules28093966 - 08 May 2023

Viewed by 983

Abstract

The 3-hydroxyflavone (3-HF) is one of the common fluorescence probes. It has two distinct fluorescence bands: normal form and tautomer form. However, 3-hydroxyflavone has poor performance in water because of hydrogen bonding perturbation. The utilization of supramolecular chemistry would improve the fluorescence performance [...] Read more.

The 3-hydroxyflavone (3-HF) is one of the common fluorescence probes. It has two distinct fluorescence bands: normal form and tautomer form. However, 3-hydroxyflavone has poor performance in water because of hydrogen bonding perturbation. The utilization of supramolecular chemistry would improve the fluorescence performance of 3-hydroxyflavone in water. In this paper, it reviews supramolecular chemistry of 3-hydroxyflavone with cyclodextrin and octa acid. Past research has found that the addition of β-cyclodextrin to 3-hydroxyflavone in water would slightly improve the fluorescence intensity of the tautomer form. When adding γ-cyclodextrin to 3-hydroxyflavone in water, the green fluorescence intensity would be enhanced. Finally, the addition of octa acid creates a dry environment for the 3-hydroxyflavone, and it would only have a tautomer form. The ONIOM calculation shows the ways of self-assembly of β- and γ-cyclodextrin. It can explain the difference in ratio between the tautomer form and normal form after understanding the interaction. Full article

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18 pages, 4023 KiB

Open AccessArticle

Cyclopropane-Containing Specialized Metabolites from the Marine Cyanobacterium cf. Lyngbya sp.

by Nurul Farhana Salleh, Jiale Wang, Binu Kundukad, Emmanuel T. Oluwabusola, Delia Xin Yin Goh, Ma Yadanar Phyo, Jasmine Jie Lin Tong, Staffan Kjelleberg and Lik Tong Tan

Molecules 2023, 28(9), 3965; https://doi.org/10.3390/molecules28093965 - 08 May 2023

Viewed by 2084

Abstract

Marine cyanobacteria are known to produce structurally diverse bioactive specialized metabolites during bloom occurrence. These ecologically active allelochemicals confer chemical defense for the microalgae from competing microbes and herbivores. From a collection of a marine cyanobacterium, cf. Lyngbya sp., a small quantity of [...] Read more.

Marine cyanobacteria are known to produce structurally diverse bioactive specialized metabolites during bloom occurrence. These ecologically active allelochemicals confer chemical defense for the microalgae from competing microbes and herbivores. From a collection of a marine cyanobacterium, cf. Lyngbya sp., a small quantity of a new cyclopropane-containing molecule, benderadiene (2), and lyngbyoic acid (1) were purified and characterized using spectroscopic methods. Using live reporter quorum-sensing (QS) inhibitory assays, based on P. aeruginosa PAO1 lasB-gfp and rhlA-gfp strains, both compounds were found to inhibit QS-regulated gene expression in a dose-dependent manner. In addition to lyngbyoic acid being more active in the PAO1 lasB-gfp biosensor strain (IC₅₀ of 20.4 µM), it displayed anti-biofilm activity when incubated with wild-type P. aeruginosa. The discovery of lyngbyoic acid in relatively high amounts provided insights into its ecological significance as a defensive allelochemical in targeting competing microbes through interference with their QS systems and starting material to produce other related analogs. Similar strategies could be adopted by other marine cyanobacterial strains where the high production of other lipid acids has been reported. Preliminary evidence is provided from the virtual molecular docking of these cyanobacterial free acids at the ligand-binding site of the P. aeruginosa LasR transcriptional protein. Full article

(This article belongs to the Section Natural Products Chemistry)

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16 pages, 7069 KiB

Open AccessArticle

Quercetagitrin Inhibits Tau Accumulation and Reverses Neuroinflammation and Cognitive Deficits in P301S-Tau Transgenic Mice

by Suyue Zhong, Jinwang Ye, Yunsong Deng, Mohan Zhang, Miaozhan Zou, Xuanbao Yao and Shifeng Xiao

Molecules 2023, 28(9), 3964; https://doi.org/10.3390/molecules28093964 - 08 May 2023

Cited by 2 | Viewed by 1435

Abstract

Intracellular tau accumulation is a hallmark pathology of Alzheimer’s disease (AD) and other tauopathies. Tau protein, in the hyperphosphorylated form, is the component of paired helical filaments (PHFs) and neurofibrillary tangles (NFTs) in AD. Blocking tau aggregation and/or phosphorylation is currently a promising [...] Read more.

Intracellular tau accumulation is a hallmark pathology of Alzheimer’s disease (AD) and other tauopathies. Tau protein, in the hyperphosphorylated form, is the component of paired helical filaments (PHFs) and neurofibrillary tangles (NFTs) in AD. Blocking tau aggregation and/or phosphorylation is currently a promising strategy for AD treatment. Here, we elucidate that quercetagitrin, a natural compound derived from African marigold (Tagetes erecta), could inhibit tau aggregation and reduce tau phosphorylation at multiple disease-related sites in vitro. Moreover, the in vivo effect of quercetagitrin was assessed in P301S-tau transgenic via oral administration. The compound treatment restored the cognitive deficits and neuron loss in the mice. The formation of NFTs and tau phosphorylations in the hippocampus and cortex of the mice was also prevented by the compound. Moreover, quercetagitrin feeding displayed neuroinflammation protection through the inhibition of NF-κB activation in the mice. Together, our data reveal that quercetagitrin possesses the potential to further develop as a therapeutic medicine for AD and other tauopathies. Full article

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15 pages, 10931 KiB

Open AccessArticle

Extraction of Isoflavones, Alpha-Hydroxy Acids, and Allantoin from Soybean Leaves—Optimization by a Mixture Design of the Experimental Method

by Sławomir Dresler, Maciej Strzemski, Izabela Baczewska, Mateusz Koselski, Mohammad Bagher Hassanpouraghdam, Dariusz Szczepanek, Ireneusz Sowa, Magdalena Wójciak and Agnieszka Hanaka

Molecules 2023, 28(9), 3963; https://doi.org/10.3390/molecules28093963 - 08 May 2023

Cited by 2 | Viewed by 1652

Abstract

Soybeans are commonly known as a valuable source of biologically active compounds including isoflavones as well as allantoin and alpha-hydroxy acids. Since these compounds exhibit skin therapeutic effects, they are widely used in the cosmetic and pharmaceutical industries. The presented paper shows the [...] Read more.

Soybeans are commonly known as a valuable source of biologically active compounds including isoflavones as well as allantoin and alpha-hydroxy acids. Since these compounds exhibit skin therapeutic effects, they are widely used in the cosmetic and pharmaceutical industries. The presented paper shows the optimization of three solvent systems (ethanol, water, and 1,3-propanediol) to increase the extraction efficiency of isoflavones (daidzin, genistin, 6″-O-malonyldaidzin, 6″-O-malonylglycitin, 6″-O-malonylgenistin), allantoin, and alpha-hydroxy acids (citric acid, malic acid) from soybean leaves. A simplex centroid mixture design for three solvents with interior points was applied for the experimental plan creation. Based on the obtained results of metabolite extraction yield in relation to solvent composition, polynomial regression models were developed. All models were significant, with predicted R-squared values between 0.77 and 0.99, while in all cases the model’s lack of fit was not significant. The optimal mixture composition enabling the maximization of extraction efficiency was as follows: 32.9% ethanol, 53.9% water, and 13.3% propanediol (v/v/v). Such a mixture composition provided the extraction of 99%, 91%, 100%, 92%, 99%, 70%, 92%, and 69% of daidzin, genistin, 6″-O-malonyldaidzin, 6″-O-malonylglycitin, 6″-O-malonylgenistin, allantoin, citric acid, and malic acid, respectively. The solvent mixture composition developed provides a good extraction efficiency of the metabolites from soybean leaves and high antioxidant properties. Full article

(This article belongs to the Section Natural Products Chemistry)

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16 pages, 4264 KiB

Open AccessArticle

Mitochondria-Targeted Fluorescent Nanoparticles with Large Stokes Shift for Long-Term BioImaging

by Xiao Li, Tao Zhang, Xuebo Diao, Li Yu, Yue Su, Jiapei Yang, Zibo Shang, Shuai Liu, Jia Zhou, Guolin Li and Huirong Chi

Molecules 2023, 28(9), 3962; https://doi.org/10.3390/molecules28093962 - 08 May 2023

Cited by 4 | Viewed by 1583

Abstract

Mitochondria (MITO) play a significant role in various physiological processes and are a key organelle associated with different human diseases including cancer, diabetes mellitus, atherosclerosis, Alzheimer’s disease, etc. Thus, detecting the activity of MITO in real time is becoming more and more important. [...] Read more.

Mitochondria (MITO) play a significant role in various physiological processes and are a key organelle associated with different human diseases including cancer, diabetes mellitus, atherosclerosis, Alzheimer’s disease, etc. Thus, detecting the activity of MITO in real time is becoming more and more important. Herein, a novel class of amphiphilic aggregation-induced emission (AIE) active probe fluorescence (AC-QC nanoparticles) based on a quinoxalinone scaffold was developed for imaging MITO. AC-QC nanoparticles possess an excellent ability to monitor MITO in real-time. This probe demonstrated the following advantages: (1) lower cytotoxicity; (2) superior photostability; and (3) good performance in long-term imaging in vitro. Each result of these indicates that self-assembled AC-QC nanoparticles can be used as effective and promising MITO-targeted fluorescent probes. Full article

(This article belongs to the Special Issue Aggregation-Induced Emission: From Fundamental to Application)

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15 pages, 2650 KiB

Open AccessReview

Strictinin: A Key Ingredient of Tea

by Jason T. C. Tzen

Molecules 2023, 28(9), 3961; https://doi.org/10.3390/molecules28093961 - 08 May 2023

Cited by 1 | Viewed by 2075

Abstract

Strictinin is a relatively tiny ellagitannin, which is found in many plants as a minor constituent. Catechins are known as the major constituents in the young leaves of most tea plants, while strictinin was found as a major constituent in the Pu’er tea [...] Read more.

Strictinin is a relatively tiny ellagitannin, which is found in many plants as a minor constituent. Catechins are known as the major constituents in the young leaves of most tea plants, while strictinin was found as a major constituent in the Pu’er tea plant. In some Pu’er tea varieties, strictinin was identified as the most abundant phenolic compound rather than catechins. In the past decade, strictinin was demonstrated to possess several functional activities, including antiviral, antibacterial, anti-obesity, laxative, anticaries, anti-allergic, antipsoriatic, antihyperuricemia, antidiabetic, and anticancer effects. These functional activities were in accordance with the therapeutic effects empirically perceived for Pu’er tea. Evidently, strictinin is the key ingredient in Pu’er tea that acts as a herbal medicine. In functionally-based applications, an instant powder of Pu’er tea infusion was formulated as an active raw material to be supplemented in food, cosmetics, and beverages; a new type of tea named Bitter Citrus Tzen Tea was developed by combining three teas empirically consumed to expel the cold, and new edible oral care products were designed for caries prevention by supplementation with Pu’er tea extract. More functional activities and practical applications of strictinin are scientifically anticipated in follow-up research. Full article

(This article belongs to the Special Issue Advances in Functional Foods)

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14 pages, 4427 KiB

Open AccessArticle

Anti-Atopic Effect of Isatidis Folium Water Extract in TNF-α/IFN-γ-Induced HaCaT Cells and DNCB-Induced Atopic Dermatitis Mouse Model

by Ga-Yul Min, Tae In Kim, Ji-Hye Kim, Won-Kyung Cho, Ju-Hye Yang and Jin Yeul Ma

Molecules 2023, 28(9), 3960; https://doi.org/10.3390/molecules28093960 - 08 May 2023

Viewed by 2143

Abstract

Isatidis folium or Isatis tinctoria L. is a flowering plant of the Brassicaceae family, commonly known as woad, with an ancient and well-documented history as an indigo dye and medicinal plant. This study aimed to evaluate the anti-atopic dermatitis (AD) effects of Isatidis [...] Read more.

Isatidis folium or Isatis tinctoria L. is a flowering plant of the Brassicaceae family, commonly known as woad, with an ancient and well-documented history as an indigo dye and medicinal plant. This study aimed to evaluate the anti-atopic dermatitis (AD) effects of Isatidis folium water extract (WIF) using a 2,4-dinitrochlorobenzene (DNCB)-induced AD-like mouse model and to investigate the underlying mechanism using tumor necrosis factor-α (TNF-α) and interferon-γ (IFN-γ)-activated HaCaT cells. Oral administration of WIF reduced spleen weight, decreased serum IgE and TNF-α levels, reduced epidermal and dermal thickness, and inhibited eosinophil and mast cell recruitment to the dermis compared to DNCB-induced control groups. Furthermore, oral WIF administration suppressed extracellular signal-regulated kinase and p38 mitogen-activated protein kinase protein expression levels, p65 translocation from the cytoplasm to the nucleus, and mRNA expression of TNF-α, IFN-γ, interleukin (IL)-6, and IL-13 in skin lesion tissues. In HaCaT cells, WIF suppressed the production of regulated upon activation, normal T cell expressed and secreted (RANTES), thymus and activation-regulated chemokine (TARC), macrophage-derived chemokine (MDC), MCP-1, and MIP-3a, which are inflammatory cytokines and chemokines related to AD, and inhibited the mRNA expression of RANTES, TARC, and MDC in TNF-α/IFN-γ-stimulated HaCaT cells. Overall, the results revealed that WIF ameliorated AD-like skin inflammation by suppressing proinflammatory cytokine and chemokine production via nuclear factor-κB pathway inhibition, suggesting WIF as a potential candidate for AD treatment. Full article

(This article belongs to the Special Issue Anti-inflammatory Activity of Natural Products and Alternative Medicine)

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19 pages, 30528 KiB

Open AccessArticle

Cytotoxic Activity, Topoisomerase I Inhibition and In Silico Studies of New Sesquiterpene-aryl Ester Derivatives of (-) Drimenol

by Ileana Araque, Javiera Ramírez, Rut Vergara, Jaime Mella, Pablo Aránguiz, Luis Espinoza, Waleska Vera, Iván Montenegro, Cristian O. Salas, Joan Villena and Mauricio A. Cuellar

Molecules 2023, 28(9), 3959; https://doi.org/10.3390/molecules28093959 - 08 May 2023

Viewed by 1608

Abstract

In this study, we aimed to evaluate two sets of sesquiterpene-aryl derivatives linked by an ester bond, their cytotoxic activities, and their capacity to activate caspases 3/7 and inhibit human topoisomerase I (TOP1). A total of 13 compounds were synthesized from the natural [...] Read more.

In this study, we aimed to evaluate two sets of sesquiterpene-aryl derivatives linked by an ester bond, their cytotoxic activities, and their capacity to activate caspases 3/7 and inhibit human topoisomerase I (TOP1). A total of 13 compounds were synthesized from the natural sesquiterpene (-)-drimenol and their cytotoxic activity was evaluated in vitro against three cancer cell lines: PC-3 (prostate cancer), HT-29 (colon cancer), MCF-7 (breast cancer), and an immortalized non-tumoral cell line (MCF-10). From the results, it was observed that 6a was the most promising compound due to its cytotoxic effect on three cancer cell lines and its selectivity, 6a was 100-fold more selective than 5-FU in MCF-7 and 20-fold in PC-3. It was observed that 6a also induced apoptosis by caspases 3/7 activity using a Capsase-Glo-3/7 assay kit and inhibited TOP1. A possible binding mode of 6a in a complex with TOP1-DNA was proposed by docking and molecular dynamics studies. In addition, 6a was predicted to have a good pharmacokinetic profile for oral administration. Therefore, through this study, it was demonstrated that the drimane scaffold should be considered in the search of new antitumoral agents. Full article

(This article belongs to the Special Issue Computational and Synthetic Approaches of Drug Discovery in Cancer and Neurological Disorders)

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14 pages, 4857 KiB

Open AccessArticle

Toxicity Effects of Polystyrene Nanoplastics with Different Sizes on Freshwater Microalgae Chlorella vulgaris

by Qingqing Xiang, Ying Zhou and Chengxia Tan

Molecules 2023, 28(9), 3958; https://doi.org/10.3390/molecules28093958 - 08 May 2023

Cited by 5 | Viewed by 1937

Abstract

The ubiquitous nature of plastics, particularly nanoplastics, raises concern about their potential effects on primary producer microalgae. Currently, the impacts and potential mechanisms of nanoplastics on microalgae are not fully understood. In this study, the effects of two plain commercial polystyrene nanoplastics (PS-NPs) [...] Read more.

The ubiquitous nature of plastics, particularly nanoplastics, raises concern about their potential effects on primary producer microalgae. Currently, the impacts and potential mechanisms of nanoplastics on microalgae are not fully understood. In this study, the effects of two plain commercial polystyrene nanoplastics (PS-NPs) with different sizes (50 nm and 70 nm) on C. vulgaris were assessed in a concentration range of 0–50 mg/L during 72 h exposure periods. Results revealed that both PS-NPs have dose-dependent toxicity effects on C. vulgaris, as confirmed by the decrease of growth rates, chlorophyll a and esterase activities, and the increase of ROS, MDA, and membrane damage. The membrane damage was caused by the agglomeration of PS-NPs on microalgae and may be the key reason for the toxicity. Compared with 70 nm PS-NPs (72 h EC₅₀ >50 mg/L), 50 nm PS-NPs posed greater adverse effects on algae, with an EC_50–72h of 19.89 mg/L. FTIR results also proved the stronger variation of macromolecules in the 50 nm PS-NPs treatment group. This phenomenon might be related to the properties of PS-NPs in exposure medium. The lower absolute zeta potential value of 50 nm PS-NPs induced the stronger interaction between PS-NPs and algae as compared to 70 nm PS-NPs, leading to severe membrane damage and the loss of esterase activity as well as settlement. These findings emphasized the importance of considering the impacts of commercial PS-NPs properties in toxicity evaluation. Full article

(This article belongs to the Topic Antioxidant Activity in Plants, Plant-Derived Bioactive Compounds and Foods)

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14 pages, 7196 KiB

Open AccessArticle

Robust Self-Supported SnO₂-Mn₂O₃@CC Electrode for Efficient Electrochemical Degradation of Cationic Blue X-GRRL Dye

by Caiyun Li, Peng Yi, Junwei Sun, Xi-Ao Wang, Rongzhan Liu and Jiankun Sun

Molecules 2023, 28(9), 3957; https://doi.org/10.3390/molecules28093957 - 08 May 2023

Cited by 3 | Viewed by 1240

Abstract

Exploration of highly efficient and robust catalyst is pivotal for electrocatalytic degradation of dye wastewater, but it still is a challenge. Here, we develop a three-dimensional self-supported SnO₂-Mn₂O₃ hybrid nanosheets grown on carbon cloth (noted by SnO₂ [...] Read more.

Exploration of highly efficient and robust catalyst is pivotal for electrocatalytic degradation of dye wastewater, but it still is a challenge. Here, we develop a three-dimensional self-supported SnO₂-Mn₂O₃ hybrid nanosheets grown on carbon cloth (noted by SnO₂-Mn₂O₃@CC) electrode via a simple hydrothermal method and annealing treatment. Benefitting from the interlaced nanosheets architecture that enlarges the surface area and the synergetic component effect that accelerates the interfacial electronic transfer, SnO₂-Mn₂O₃@CC electrode exhibits a superior electrocatalytic degradation efficiency for cationic blue X-GRRL dye in comparison with the single metal oxide electrode containing SnO₂@CC and Mn₂O₃@CC. The degradation efficiency of cationic blue X-GRRL on SnO₂-Mn₂O₃@CC electrode can reach up to 97.55% within 50 min. Furthermore, self-supported architecture of nanosheets on carbon cloth framework contributes to a robust stability compared with the traditional electrode via the multiple dip/brush coating accompanied by the thermal decomposition method. SnO₂-Mn₂O₃@CC electrode exhibits excellent recyclability, which can still retain a degradation efficiency of 94.12% after six cycles. This work may provide a new pathway for the design and exploration of highly efficient and robust electrooxidation catalysts for dye degradation. Full article

(This article belongs to the Special Issue Recent Progress in Nanomaterials in Electrochemistry)

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14 pages, 1059 KiB

Open AccessArticle

Phytochemical Characterization of Purple Coneflower Roots (Echinacea purpurea (L.) Moench.) and Their Extracts

by Ani Petrova, Manol Ognyanov, Nadezhda Petkova and Petko Denev

Molecules 2023, 28(9), 3956; https://doi.org/10.3390/molecules28093956 - 08 May 2023

Cited by 1 | Viewed by 1695

Abstract

Echinacea purpurea is a perennial plant that belongs to the Asteraceae family. It has a wide range of applications mainly in the treatment and prevention of inflammations in the respiratory system. The current study aimed to perform a phytochemical characterization of purple coneflower [...] Read more.

Echinacea purpurea is a perennial plant that belongs to the Asteraceae family. It has a wide range of applications mainly in the treatment and prevention of inflammations in the respiratory system. The current study aimed to perform a phytochemical characterization of purple coneflower (Echinacea purpurea) roots and their extracts (water, 40%, 50%, 60% ethanol, and 60% glycerol). Phytochemical characterization was carried out by gravimetric, spectrophotometric, and chromatographic methods. Echinacea roots were characterized by a low lipid (0.8%) content. In contrast, carbohydrates (45%) and proteins (20%) occupied a large part of the dry matter. Amongst the extracts, the highest yield was obtained using water as a solvent (53%). Water extract was rich in protein and carbohydrates as fructans (inulin) were the most abundant carbohydrate constituent. The most exhaustive recovery of the phenolic components was conducted by extraction with 40% ethanol and 60% glycerol. It was found that water is the most suitable extractant for obtaining a polysaccharide-containing complex (PSC) (8.87%). PSC was composed mainly of fructans (inulin) and proteins with different molecular weight distributions. The yield of PSC decreased with an increasing ethanol concentration (40% > 50% > 60%) but the lowest yield was obtained from 60% glycerol extract. The obtained results showed that Echinacea roots contained a large amount of biologically active substances—phenolic components and polysaccharides and that glycerol was equally efficient to ethanol in extracting caffeic acid derivatives from purple coneflower roots. The data can be used for the preparation of extracts having different compositions and thus easily be incorporated into commercial products. Full article

(This article belongs to the Special Issue Extraction and Application of Nutrients and Functional Compounds from Food)

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21 pages, 5835 KiB

Open AccessArticle

Thermo-Chemical Modification of Cellulose for the Adsorptive Removal of Titan Yellow from Wastewater

by Ubaid Ur Rahman, Muhammad Humayun, Abbas Khan, Saima Farooq, Muhammad Sadiq, Mohamed Bououdina and Nasrullah Shah

Molecules 2023, 28(9), 3955; https://doi.org/10.3390/molecules28093955 - 08 May 2023

Cited by 6 | Viewed by 1277

Abstract

This research work focuses on the isolation and thermo-chemical modification of cellulose and its application as an adsorbent for the removal of organic pollutants. The used cellulose was collected from a locally available plant (Olive Europa) commonly called Zaitoon. The stem [...] Read more.

This research work focuses on the isolation and thermo-chemical modification of cellulose and its application as an adsorbent for the removal of organic pollutants. The used cellulose was collected from a locally available plant (Olive Europa) commonly called Zaitoon. The stem branches of Zaitoon were collected and then kept in water for 40–45 days at room temperature to extract the cellulose fibers. These cellulose fibers were then kept in the Soxhlet apparatus for washing in n-hexane for 72 h. The purified cellulose was divided into three parts: one part was subjected to thermal activation (TAC), the second was modified chemically (CMC) with Benzyl Chloride, while the last one remained un-functionalized (UFC). All the three forms of cellulose were characterized via FTIR and SEM, then utilized for the removal of Titan Yellow (TY) dye from aqueous media via adsorption process by varying the contact time, temperature, concentration of dye and type, and dose of adsorbent. The adsorption efficiencies of all adsorbents were compared under different experimental variables. Thermally activated cellulose showed the best results for the removal of TY compared with other materials. The calculated removal percentage of TY was found to be 97.69, 94.83, 94.83, and 98% under equilibrium conditions of contact time, temperature, adsorbent dose, and TY concentration. Similarly, the uptake capacities of TAC under optimal experimental conditions were found to be 19.56, 18.96, 18.52, and 18.75 mg/g. Thermodynamic studies of TAC, CMC, and UFC showed that the values of ΔG are negative, while those of ΔH and ΔS are positive in all cases and at all temperatures. This indicates that the TY elimination process is endothermic and spontaneous with an entropy-driven nature. The obtained results indicate that the as-fabricated low-cost biomaterials can effectively remove dyes from wastewater through physicochemical interactions. The removal process was influenced by the nature of the adsorbent and the operating variables. Full article

(This article belongs to the Special Issue Wastewater Treatment: Functional Materials and Advanced Technology)

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17 pages, 5282 KiB

Open AccessArticle

Ultrafine Kaolinite Removal in Recycled Water from the Overflow of Thickener Using Electroflotation: A Novel Application of Saline Water Splitting in Mineral Processing

by Felipe M. Galleguillos Madrid, María P. Arancibia-Bravo, Felipe D. Sepúlveda, Freddy A. Lucay, Alvaro Soliz and Luis Cáceres

Molecules 2023, 28(9), 3954; https://doi.org/10.3390/molecules28093954 - 08 May 2023

Cited by 3 | Viewed by 1328

Abstract

The presence of ultrafine clay particles that are difficult to remove by conventional filtration creates many operational problems in mining processing systems. In this work, the removal of clay suspensions has been investigated using an electroflotation (EF) process with titanium electrodes. The results [...] Read more.

The presence of ultrafine clay particles that are difficult to remove by conventional filtration creates many operational problems in mining processing systems. In this work, the removal of clay suspensions has been investigated using an electroflotation (EF) process with titanium electrodes. The results show that EF is a viable and novel alternative for removing ultrafine particles of kaolinite-type clay present in sedimentation tank overflows with low salt concentrations (<0.1 mol/L) in copper mining facilities based on the saline water splitting concept. Maximum suspended solid removal values of 91.4 and 83.2% in NaCl and KCl solutions, respectively, were obtained under the experimental conditions of the constant applied potential of 20 V/SHE, salinity concentration of 0.1 mol/L, and electroflotation time of 10 and 20 min in NaCl and KCl solutions, respectively. Furthermore, the visual evidence of particle aggregation by flocculation during the experiments indicates a synergy between EF and electrocoagulation (EC) that enhances the removal of ultrafine particles of kaolinite. Full article

(This article belongs to the Topic Insight into Liquid/Fluid Interfaces)

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17 pages, 3190 KiB

Open AccessArticle

Untreated Opuntia ficus indica for the Efficient Adsorption of Ni(II), Pb(II), Cu(II) and Cd(II) Ions from Water

by Marcella Barbera, Serena Indelicato, David Bongiorno, Valentina Censi, Filippo Saiano and Daniela Piazzese

Molecules 2023, 28(9), 3953; https://doi.org/10.3390/molecules28093953 - 08 May 2023

Cited by 2 | Viewed by 1541

Abstract

The raw cladode of Opuntia ficus indica (OFI) was evaluated as a sustainable biosorbent for the removal of heavy metals (Ni, Pb, Cu, and Cd) from aqueous solutions. The functional groups of OFI were identified by employing DRIFT-FTIR and CP-MAS-NMR techniques before and [...] Read more.

The raw cladode of Opuntia ficus indica (OFI) was evaluated as a sustainable biosorbent for the removal of heavy metals (Ni, Pb, Cu, and Cd) from aqueous solutions. The functional groups of OFI were identified by employing DRIFT-FTIR and CP-MAS-NMR techniques before and after contact with the ions in an aqueous media, showing a rearrangement of the biomass structure due to the complexation between the metal and the functional groups. The adsorption process was studied in both single- and multi-component systems under batch conditions at different pHs (4.0, 5.0, and 6.0), different metal concentrations, and different biomass amounts. The results show that the raw OFI had a removal capacity at room temperature of over 80% for all metals studied after only 30 min of contact time, indicating a rapid adsorption process. Biosorption kinetics were successfully fitted by the pseudo-second-order equation, while Freundlich correctly modelled the biosorption data at equilibrium. The results of this work highlight the potential use of the untreated cladode of OFI as an economical and environmentally friendly biosorbent for the removal of heavy metals from the contaminated aqueous solution. Full article

(This article belongs to the Special Issue Chemical Technologies for Environmental Analysis and Pollution Removal)

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16 pages, 4797 KiB

Open AccessArticle

Solubilization of Reactive Red 2 in the Mixed Micelles of Cetylpyridinium Chloride and TX-114

by Tayyba Yaqoob, Saadia Shaukat, Rasha Alonaizan, Ramzan Ullah, Imran Khan, Muhammad Faizan Nazar and Hafiz Muhammad Abd Ur Rahman

Molecules 2023, 28(9), 3952; https://doi.org/10.3390/molecules28093952 - 08 May 2023

Cited by 2 | Viewed by 1298

Abstract

Owing to their surface active properties, surfactants have numerous applications in different fields of life. In the present research work, the solubilization of reactive red 2 (RR2) has been studied in single and mixed micellar systems (MMS) using UV-visible spectroscopy and electrical conductivity [...] Read more.

Owing to their surface active properties, surfactants have numerous applications in different fields of life. In the present research work, the solubilization of reactive red 2 (RR2) has been studied in single and mixed micellar systems (MMS) using UV-visible spectroscopy and electrical conductivity measurements. The interaction of RR2 with ionic micelles of cetylpyridinium chloride (CPC) was investigated. In order to probe the interaction of RR2 in MMS, mixtures of CPC and TX-114 (Triton X-114, a nonionic surfactant) were used. UV-visible spectroscopy has been used to obtain the degree of solubilization of RR2 in terms of the partition coefficient (K_c) and Gibbs free energy of partitioning (ΔG^°_p). Electrical conductivity data have been employed to detect the critical micelle concentration (CMC) of the surfactant systems in the presence of RR2 and, accordingly, to calculate the thermodynamic parameters of the micellization. From the obtained data, it is concluded that the micellization is spontaneous at all studied temperatures. Moreover, the micellization was observed to be driven by both enthalpy and entropy. The results also indicated that MMS have better solubilizing power than single micellar solutions. Full article

(This article belongs to the Special Issue Surfactants & Detergents: Theory, Technology and Application)

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15 pages, 3696 KiB

Open AccessArticle

Microstructure, Physical and Biological Properties, and BSA Binding Investigation of Electrospun Nanofibers Made of Poly(AA-co-ACMO) Copolymer and Polyurethane

by Hanaa Mansour, Samia M. Elsigeny, Fawzia I. Elshami, Mohamed Auf, Shaban Y. Shaban and Rudi van Eldik

Molecules 2023, 28(9), 3951; https://doi.org/10.3390/molecules28093951 - 08 May 2023

Cited by 1 | Viewed by 1197

Abstract

In this study, poly(AA-co-ACMO) and polyurethane-based nanofibers were prepared in a ratio of 1:1 (NF11) and 2:1 (NF21) as antimicrobial carriers for chronic wound management. Different techniques were used to characterize the nanofibers, and poly(AA-co-ACMO) was mostly found on the surface of PU. [...] Read more.

In this study, poly(AA-co-ACMO) and polyurethane-based nanofibers were prepared in a ratio of 1:1 (NF11) and 2:1 (NF21) as antimicrobial carriers for chronic wound management. Different techniques were used to characterize the nanofibers, and poly(AA-co-ACMO) was mostly found on the surface of PU. With an increase in poly(AA-co-ACMO) dose from 0 (PU) and 1:1 (NF11) to 2:1 (NF21) in the casting solution, the contact angle (CA) was reduced from 137 and 95 to 24, respectively, and hydrophilicity was significantly increased. As most medications inhibit biological processes by binding to a specific protein, in vitro protein binding was investigated mechanistically using a stopped-flow technique. Both NF11 and NF21 bind to BSA via two reversible steps: a fast second-order binding followed by a slow first-order one. The overall parameters for NF11 (K_a = 1.1 × 10⁴ M⁻¹, K_d = 89.0 × 10⁻⁶, ΔG⁰ = −23.1 kJ mol⁻¹) and NF21 (K_a = 189.0 × 10⁴ M⁻¹, K_d = 5.3 × 10⁻⁶ M, ΔG⁰ = −27.5 kJ mol⁻¹) were determined and showed that the affinity for BSA is approximately (NF11)/(NF21) = 1/180. This indicates that NF21 has much higher BSA affinity than NF11, although BSA interacts with NF11 much faster. NF21 with higher hydrophilicity showed effective antibacterial properties compared to NF11, in agreement with kinetic data. The study provided an approach to manage chronic wounds and treating protein-containing wastewater. Full article

(This article belongs to the Special Issue Feature Papers in Applied Chemistry 2.0)

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18 pages, 3265 KiB

Open AccessArticle

Effect of Different Phosphates on Pyrolysis Temperature-Dependent Carbon Sequestration and Phosphorus Release Performance in Biochar

by Tianxia Bai, Wenge Ma, Wenhui Li, Jinling Jiang, Jiamin Chen, Rui Cao, Wenjie Yang, Dan Dong, Tingwu Liu and Yonggang Xu

Molecules 2023, 28(9), 3950; https://doi.org/10.3390/molecules28093950 - 08 May 2023

Cited by 1 | Viewed by 1352

Abstract

Carbon sequestration is the primary function of biochar. Hence, it is necessary to design biochar with high carbon (C) retention and low C loss. In this study, three P compounds, including KH₂PO₄, Ca(H₂PO₄)₂, [...] Read more.

Carbon sequestration is the primary function of biochar. Hence, it is necessary to design biochar with high carbon (C) retention and low C loss. In this study, three P compounds, including KH₂PO₄, Ca(H₂PO₄)₂, and NH₄H₂PO₄, were premixed with corn stalk (1:4, w/w), aiming to produce biochars (CSB+K, CSB+Ca, and CSB+N) with high C sequestration and slow release of P at three temperatures (300, 500, and 700 °C). The addition of all P sources obviously increased C retention, with the order of NH₄H₂PO₄ (65.6–83.5%) > Ca(H₂PO₄)₂ (60.4–78.2%) > KH₂PO₄ (50.1–76.1%), compared with the pristine biochar (47.8–73.6%). The addition of Ca(H₂PO₄)₂ and KH₂PO₄ led to an increase in aromaticity and graphitization, as evidenced by H/C, FTIR, Raman and XPS analysis, whereas an opposite result occurred on CSB+N. Furthermore, all three phosphates reduced C loss of biochars with H₂O₂ oxidation, and CSB+Ca showed the best effect. Ca(H₂PO₄)₂ and KH₂PO₄ pretreated biochars had higher resistance to K₂Cr₂O₇ oxidation and thermal treatment. In contrast, the C loss of NH₄H₂PO₄-added biochar at 500 and 700 °C with K₂Cr₂O₇ oxidation was increased by 54% and 36%, respectively. During the pyrolysis process, Ca(H₂PO₄)₂ was transformed into insoluble Ca₂P₂O₇, leading to the lowest P release rate of CSB+Ca. This study indicates that co-pyrolysis of corn stalk and Ca(H₂PO₄)₂ is optimal for increasing C retention, enhancing C stability and improving slow-release performance of P regardless of pyrolysis temperature. Full article

(This article belongs to the Collection Recycling of Biomass Resources: Biofuels and Biochemicals)

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27 pages, 12974 KiB

Open AccessArticle

β-Carboline-α-aminophosphonate Derivative: A Promising Antitumor Agent for Breast Cancer Treatment

by Caroline Pinto Zani, Aline Pinto Zani, Cristiane Melissa Thomazini, Karina Miyuki Retamiro, Aline Rufino de Oliveira, Débora Laís Gonçalves, Maria Helena Sarragiotto, Francielle Pelegrin Garcia, Sueli de Oliveira Silva, Celso Vataru Nakamura and Tania Ueda-Nakamura

Molecules 2023, 28(9), 3949; https://doi.org/10.3390/molecules28093949 - 08 May 2023

Viewed by 1547

Abstract

Breast cancer is the most common type of cancer and the leading cause of cancer mortality among women worldwide. Considering the limitations of the current treatments available, we analyzed the in vitro cytotoxic potential of ((4-Fluoro-phenyl)-{2-[(1-phenyl-9H-β-carboline-3-carbonyl)-amino]-ethylamino}-methyl)-phosphonic acid dibutyl ester (BCP-1) in [...] Read more.

Breast cancer is the most common type of cancer and the leading cause of cancer mortality among women worldwide. Considering the limitations of the current treatments available, we analyzed the in vitro cytotoxic potential of ((4-Fluoro-phenyl)-{2-[(1-phenyl-9H-β-carboline-3-carbonyl)-amino]-ethylamino}-methyl)-phosphonic acid dibutyl ester (BCP-1) in breast cancer cells (MCF-7 and MDA-MB-231) and in a non-tumor breast cell line (MCF-10A). BCP-1 has an α-aminophosphonate unit linked to the β-carboline nucleus, and the literature indicates that compounds of these classes have high biological potential. In the present study, the mechanism of action of BCP-1 was investigated through methods of spectrofluorimetry, flow cytometry, and protein expression analysis. It was found that BCP-1 inhibited the proliferation of both cancer cell lines. Furthermore, it induced oxidative stress and cell cycle arrest in G2/M. Upregulation of apoptosis-related proteins such as Bax, cytochrome C, and caspases, as well as a decrease in the anti-apoptotic protein Bcl-2, indicated potential induction of apoptosis in the MDA-MB-231 cells. While in MCF-7 cells, BCP-1 activated the autophagic death pathway, which was demonstrated by an increase in autophagic vacuoles and acidic organelles, in addition to increased expression of LC3I/LC3II and reduced SQSTM1/p62 expression. Further, BCP-1 demonstrated antimetastatic potential by reducing MMP-9 expression and cell migration in both breast cancer cell lines. In conclusion, BCP-1 is a promising candidate for breast cancer chemotherapy. Full article

(This article belongs to the Special Issue Discovery and Design for Novel Anti-cancer Products)

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11 pages, 1305 KiB

Open AccessArticle

Highly Efficient Synthesis of Chlorogenic Acid Oleyl Alcohol Ester under Non-Catalytic and Solvent-Free Conditions

by Cong Sun, Hui Liu, Yanran Chen, Xianzhi Wei and Shaohua Liang

Molecules 2023, 28(9), 3948; https://doi.org/10.3390/molecules28093948 - 08 May 2023

Cited by 1 | Viewed by 1244

Abstract

As a natural polyphenolic compound, chlorogenic acid (CGA) has attracted increasing attention for its various biological activities, such as antioxidant, liver protection, intestinal barrier protection, and effective treatment of obesity and type II diabetes. However, the poor solubility of CGA in hydrophobic media [...] Read more.

As a natural polyphenolic compound, chlorogenic acid (CGA) has attracted increasing attention for its various biological activities, such as antioxidant, liver protection, intestinal barrier protection, and effective treatment of obesity and type II diabetes. However, the poor solubility of CGA in hydrophobic media limits its application in the food, drug and cosmetic industries. In order to obtain new hydrophobic derivatives, a highly efficient synthesis approach of CGA oleyl alcohol ester (CGOA) under non-catalytic and solvent-free conditions was developed in this study. The influences of reaction temperature, reaction time, substrate molar ratio, and stirring rate on the CGA conversion were investigated. The results showed that the optimal conditions were as follows: reaction temperature 200 °C, reaction time 3 h, molar ratio of CGA to oleyl alcohol 1:20, and stirring rate 200 rpm. Under these conditions, the CGA conversion could reach 93.59%. Then, the obtained crude product was purified by solvent extraction and column chromatography, and the purify of CGOA was improved to 98.72%. Finally, the structure of CGOA was identified by FT-IR, HPLC-MS and NMR. This study provides a simple and efficient strategy for the preparation of CGOA with the avoidance of catalysts and solvents. Full article

(This article belongs to the Special Issue Insights for Food Lipids)

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20 pages, 1319 KiB

Open AccessArticle

Effect of the Harvest Season of Anthyllis henoniana Stems on Antioxidant and Antimicrobial Activities: Phytochemical Profiling of Their Ethyl Acetate Extracts

by Amani Ayachi, Amer Ben Younes, Ameni Ben Ammar, Bouthaina Bouzayani, Sonda Samet, Mariam Siala, Mohamed Trigui, Michel Treilhou, Nathan Téné and Raoudha Mezghani-Jarraya

Molecules 2023, 28(9), 3947; https://doi.org/10.3390/molecules28093947 - 07 May 2023

Cited by 1 | Viewed by 1740

Abstract

Anthyllis henoniana stems were harvested in two seasons: winter and spring (February and May 2021). In this study, we investigated the antioxidant (DPPH, ABTS, FRAP and TAC) and antimicrobial activities, total phenolic contents and total flavonoid contents of the obtained extracts (hexane, ethyl [...] Read more.

Anthyllis henoniana stems were harvested in two seasons: winter and spring (February and May 2021). In this study, we investigated the antioxidant (DPPH, ABTS, FRAP and TAC) and antimicrobial activities, total phenolic contents and total flavonoid contents of the obtained extracts (hexane, ethyl acetate and methanol). The results showed that ethyl acetate extract from stems harvested in winter exhibited the highest antioxidant activity, while ethyl acetate extract from the stems harvested in spring showed the most potent antibacterial and antifungal activities. To explain these differences, we investigated the phytochemical composition of these two extracts using liquid chromatography coupled with mass spectrometry. Therefore, 45 compounds were detected, from which we identified 20 compounds (flavonoids, triterpenoids, chalcones and phenolic acids); some were specific to the harvest month while others were common for both periods. Some of the major compounds detected in ethyl acetate (spring) were dihydrochalcone (Kanzonol Y, 8.2%) and flavanone (sophoraflavanone G, 5.9%), previously recognized for their antimicrobial effects. We therefore concluded that the difference in activities observed for the two harvest periods depends on the chemical composition of the extracts and the relative abundance of each compound. Full article

(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources)

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Molecules, Volume 28, Issue 9 (May-1 2023) – 331 articles

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