Molecules

21 pages, 4915 KiB

Open AccessArticle

Interplay of Anisotropic Exchange Interactions and Single-Ion Anisotropy in Single-Chain Magnets Built from Ru/Os Cyanidometallates(III) and Mn(III) Complex

by Vladimir S. Mironov, Eugenia V. Peresypkina and Kira E. Vostrikova

Molecules 2023, 28(3), 1516; https://doi.org/10.3390/molecules28031516 - 3 Feb 2023

Cited by 4 | Viewed by 2301

Abstract

Two novel 1D heterobimetallic compounds {[Mn^III(SB²⁺)M^III(CN)₆]·4H₂O}_n (SB²⁺ = N,N′-ethylenebis(5-trimethylammoniomethylsalicylideneiminate) based on orbitally degenerate cyanidometallates [Os^III(CN)₆]³⁻ (1) and [Ru^III(CN)₆]³⁻ ( [...] Read more.

Two novel 1D heterobimetallic compounds {[Mn^III(SB²⁺)M^III(CN)₆]·4H₂O}_n (SB²⁺ = N,N′-ethylenebis(5-trimethylammoniomethylsalicylideneiminate) based on orbitally degenerate cyanidometallates [Os^III(CN)₆]³⁻ (1) and [Ru^III(CN)₆]³⁻ (2) and Mn^III Schiff base complex were synthesized and characterized structurally and magnetically. Their crystal structures consist of electrically neutral, well-isolated chains composed of alternating [M^III(CN)₆]³⁻ anions and square planar [Mn^III(SB²⁺)]³⁺ cations bridged by cyanide groups. These -ion magnetic anisotropy of Mn^III centers. These results indicate that the presence of compounds exhibit single-chain magnet (SCM) behavior with the energy barriers of Δτ₁/k_B = 73 K, Δτ₂/k_B = 41.5 K (1) and Δτ₁/k_B = 51 K, Δτ₂ = 27 K (2). Blocking temperatures of T_B = 2.8, 2.1 K and magnetic hysteresis with coercive fields (at 1.8 K) of 8000, 1600 Oe were found for 1 and 2, respectively. Theoretical analysis of the magnetic data reveals that their single-chain magnet behavior is a product of a complicated interplay of extremely anisotropic triaxial exchange interactions in M^III(4d/5d)–CN–Mn^III fragments: −J_xS_M^xS_Mn^x−J_yS_M^yS_Mn^y−J_zS_M^zS_Mn^z, with opposite sign of exchange parameters J_x = −22, J_y = +28, J_z = −26 cm⁻¹ and J_x = −18, J_y = +20, J_z = −18 cm⁻¹ in 1 and 2, respectively) and single orbitally degenerate [Os^III(CN)₆]³⁻ and [Ru^III(CN)₆]³⁻ spin units with unquenched orbital angular momentum in the chain compounds 1 and 2 leads to a peculiar regime of slow magnetic relaxation, which is beyond the scope of the conventional Glaubers’s 1D Ising model and anisotropic Heisenberg model. Full article

(This article belongs to the Section Inorganic Chemistry)

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17 pages, 3010 KiB

Open AccessArticle

Synthesis and Catalytic Activity of Bifunctional Phase-Transfer Organocatalysts Based on Camphor

by Luka Ciber, Franc Požgan, Helena Brodnik, Bogdan Štefane, Jurij Svete, Mario Waser and Uroš Grošelj

Molecules 2023, 28(3), 1515; https://doi.org/10.3390/molecules28031515 - 3 Feb 2023

Cited by 4 | Viewed by 2385

Abstract

Ten novel bifunctional quaternary ammonium salt phase-transfer organocatalysts were synthesized in four steps from (+)-camphor-derived 1,3-diamines. These quaternary ammonium salts contained either (thio)urea or squaramide hydrogen bond donor groups in combination with either trifluoroacetate or iodide as the counteranion. Their organocatalytic activity was [...] Read more.

Ten novel bifunctional quaternary ammonium salt phase-transfer organocatalysts were synthesized in four steps from (+)-camphor-derived 1,3-diamines. These quaternary ammonium salts contained either (thio)urea or squaramide hydrogen bond donor groups in combination with either trifluoroacetate or iodide as the counteranion. Their organocatalytic activity was evaluated in electrophilic heterofunctionalizations of β-keto esters and in the Michael addition of a glycine Schiff base with methyl acrylate. α-Fluorination and chlorination of β-keto esters proceeded with full conversion and low enantioselectivities (up to 29% ee). Similarly, the Michael addition of a glycine Schiff base with methyl acrylate proceeded with full conversion and up to 11% ee. The new catalysts have been fully characterized; the stereochemistry at the C-2 chiral center was unambiguously determined. Full article

(This article belongs to the Special Issue New Approaches to Synthetic Organic Chemistry)

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17 pages, 4890 KiB

Open AccessArticle

Silymarin Encapsulated Liposomal Formulation: An Effective Treatment Modality against Copper Toxicity Associated Liver Dysfunction and Neurobehavioral Abnormalities in Wistar Rats

by Tuba Maryam, Nosheen Fatima Rana, Sultan M. Alshahrani, Farhat Batool, Misha Fatima, Tahreem Tanweer, Salma Saleh Alrdahe, Yasmene F. Alanazi, Ifat Alsharif, Fatima S. Alaryani, Amer Sohail Kashif and Farid Menaa

Molecules 2023, 28(3), 1514; https://doi.org/10.3390/molecules28031514 - 3 Feb 2023

Cited by 11 | Viewed by 3053

Abstract

Wilson’s disease causes copper accumulation in the liver and extrahepatic organs. The available therapies aim to lower copper levels by various means. However, a potent drug that can repair the damaged liver and brain tissue is needed. Silymarin has hepatoprotective, antioxidant, and cytoprotective [...] Read more.

Wilson’s disease causes copper accumulation in the liver and extrahepatic organs. The available therapies aim to lower copper levels by various means. However, a potent drug that can repair the damaged liver and brain tissue is needed. Silymarin has hepatoprotective, antioxidant, and cytoprotective properties. However, poor oral bioavailability reduces its efficacy. In this study, a “thin film hydration method” was used for synthesizing silymarin-encapsulated liposome nanoparticles (SLNPs) and evaluated them against copper toxicity, associated liver dysfunction and neurobehavioral abnormalities in Wistar rats. After copper toxicity induction, serological and behavioral assays were conducted to evaluate treatment approaches. Histological examination of the diseased rats revealed severe hepatocyte necrosis and neuronal vacuolation. These cellular degenerations were mild in rats treated with SLNPs and a combination of zinc and SLNPs (ZSLNPs). SLNPs also decreased liver enzymes and enhanced rats’ spatial memory significantly (p = 0.006) in the diseased rats. During forced swim tests, SLNPs treated rats exhibited a 60-s reduction in the immobility period, indicating reduced depression. ZSLNPs were significantly more effective than traditional zinc therapy in decreasing the immobility period (p = 0.0008) and reducing liver enzymes, but not in improving spatial memory. Overall, SLNPs enhanced oral silymarin administration and managed copper toxicity symptoms. Full article

(This article belongs to the Special Issue Polymeric Systems Loaded with Natural Bioactive Compounds)

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24 pages, 4192 KiB

Open AccessArticle

Study on Dissociation and Chemical Structural Characteristics of Areca Nut Husk

by Jianbo Yuan, Haonan Zhang, Hui Zhao, Hao Ren and Huamin Zhai

Molecules 2023, 28(3), 1513; https://doi.org/10.3390/molecules28031513 - 3 Feb 2023

Cited by 5 | Viewed by 3020

Abstract

From the perspective of full-component utilization of woody fiber biomass resources, areca nut husk is an excellent woody fiber biomass feedstock because of its fast regeneration, significant regeneration ability, sustainability, low cost, and easy availability. In this study, fiber cell morphologies, chemical compositions, [...] Read more.

From the perspective of full-component utilization of woody fiber biomass resources, areca nut husk is an excellent woody fiber biomass feedstock because of its fast regeneration, significant regeneration ability, sustainability, low cost, and easy availability. In this study, fiber cell morphologies, chemical compositions, lignin structures, and carbohydrate contents of areca nut husks were analyzed and compared with those of rice straw, and the application potentials of these two materials as biomass resources were compared. We found that areca nut husk fibers were shorter and wider than those of rice straw; areca nut husk contained more lignin and less ash, as well as less holocellulose than rice straw; areca nut husk and rice straw lignin were obtained by ball milling and phase separation, and areca nut husk lignin was found to be a typical GHS-type lignin. Herein, the yield of lignocresol was higher than that of milled wood lignin for both raw materials, and the molecular size was more homogeneous. Tricin structural monomers were discovered in the lignin of areca nut husk, similar to those present in other types of herbaceous plants. Structures of areca nut husk MWL (AHMWL) and AHLC were comprehensively characterized by quantitative NMR techniques (that is, ¹H NMR, ³¹P NMR, and 2D NMR). The molecular structure of AHLC was found to be closer to the linear structure with more functional groups exposed on the molecular surface, and the hydroxyl-rich p-cresol grafting structure was successfully introduced into the lignin structure. In addition, the carbohydrate content in the aqueous layer of the phase separation system was close to the carbohydrate content in the raw material, indicating that the phase separation method can precisely separate lignin from carbohydrates. These experimental results indicate that the phase separation method as a method for lignin utilization and structure study has outstanding advantages in lignin structure regulation and yield, and areca nut husk lignin is suitable for application in the same phase separation systems as short-period herbs, such as rice straw and wheat grass, and has the advantages of low ash content and high lignification degree, which will provide guidance for the high-value utilization of areca nut husk in the future. Full article

(This article belongs to the Section Bioorganic Chemistry)

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14 pages, 5341 KiB

Open AccessArticle

Biodiesel Purification by Solvent-Aided Crystallization Using 2-Methyltetrahydrofuran

by Wan Nur Aisyah Wan Osman, Nur Athirah Izzati Badrol and Shafirah Samsuri

Molecules 2023, 28(3), 1512; https://doi.org/10.3390/molecules28031512 - 3 Feb 2023

Cited by 5 | Viewed by 2025

Abstract

The previous biodiesel purification by Solvent-Aided Crystallization (SAC) using 1-butanol as assisting agent and parameters for SAC were optimized such as coolant temperature, cooling time and stirring speed. Meanwhile, 2-Methyltetrahydrofuran (2-MeTHF) was selected as an alternative to previous organic solvents for this study. [...] Read more.

The previous biodiesel purification by Solvent-Aided Crystallization (SAC) using 1-butanol as assisting agent and parameters for SAC were optimized such as coolant temperature, cooling time and stirring speed. Meanwhile, 2-Methyltetrahydrofuran (2-MeTHF) was selected as an alternative to previous organic solvents for this study. In this context, it is used to replace solvent 1-butanol from a conducted previous study. This study also focuses on the technological improvements in the purification of biodiesel via SAC as well as to produce an even higher purity of biodiesel. Experimental works on the transesterification process to produce crude biodiesel were performed and SAC was carried out to purify the crude biodiesel. The crude biodiesel content was analyzed by using Gas Chromatography–Mass Spectrometry (GC-MS) and Differential Scanning Calorimetry (DSC) to measure the composition of Fatty Acid Methyl Esters (FAME) present. The optimum value to yield the highest purity of FAME for parameters coolant temperature, cooling time, and stirring speed is −4 °C, 10 min and 210 rpm, respectively. It can be concluded that the assisting solvent 2-MeTHF has a significant effect on the process parameters to produce purified biodiesel according to the standard requirement. Full article

(This article belongs to the Special Issue Recent Advances in Green Solvents)

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14 pages, 3230 KiB

Open AccessArticle

Removal of Methylene Blue from Water Using Magnetic GTL-Derived Biosolids: Study of Adsorption Isotherms and Kinetic Models

by Shifa Zuhara, Snigdhendubala Pradhan, Yahya Zakaria, Akshath Raghu Shetty and Gordon McKay

Molecules 2023, 28(3), 1511; https://doi.org/10.3390/molecules28031511 - 3 Feb 2023

Cited by 3 | Viewed by 1893

Abstract

Global waste production is significantly rising with the increase in population. Efforts are being made to utilize waste in meaningful ways and increase its economic value. This research makes one such effort by utilizing gas-to-liquid (GTL)-derived biosolids, a significant waste produced from the [...] Read more.

Global waste production is significantly rising with the increase in population. Efforts are being made to utilize waste in meaningful ways and increase its economic value. This research makes one such effort by utilizing gas-to-liquid (GTL)-derived biosolids, a significant waste produced from the wastewater treatment process. To understand the surface properties, the biosolid waste (BS) that is activated directly using potassium carbonate, labelled as KBS, has been characterized using scanning electron microscopy and energy dispersive X-ray spectroscopy (SEM-EDS), X-ray photoelectron spectroscopy (XPS), X-ray powder diffraction (XRD), and Brunauer–Emmett–Teller (BET). The characterization shows that the surface area of BS increased from 0.010 to 156 m²/g upon activation. The EDS and XPS results show an increase in the metal content after activation (especially iron); additionally, XRD revealed the presence of magnetite and potassium iron oxide upon activation. Furthermore, the magnetic field was recorded to be 0.1 mT using a tesla meter. The magnetic properties present in the activated carbon show potential for pollutant removal. Adsorption studies of methylene blue using KBS show a maximum adsorption capacity of 59.27 mg/g; the adsorption process is rapid and reaches equilibrium after 9 h. Modelling using seven different isotherm and kinetic models reveals the best fit for the Langmuir-Freundlich and Diffusion-chemisorptionmodels, respectively. Additional thermodynamic calculations conclude the adsorption system to be exothermic, spontaneous, and favoring physisorption. Full article

(This article belongs to the Special Issue Innovative Adsorbents for Water Treatment)

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24 pages, 941 KiB

Open AccessReview

Current Status of the Bioactive Properties of Royal Jelly: A Comprehensive Review with a Focus on Its Anticancer, Anti-Inflammatory, and Antioxidant Effects

by Sara Botezan, Gabriela-Maria Baci, Lilla Bagameri, Claudia Pașca and Daniel Severus Dezmirean

Molecules 2023, 28(3), 1510; https://doi.org/10.3390/molecules28031510 - 3 Feb 2023

Cited by 33 | Viewed by 8972

Abstract

Royal jelly (RJ) has been one of the most widely used natural products in alternative medicine for centuries. Being produced by both hypopharyngeal and mandibular glands, RJ exhibits an extraordinary complexity in terms of its composition, including proteins, lipids, carbohydrates, polyphenols, vitamins, and [...] Read more.

Royal jelly (RJ) has been one of the most widely used natural products in alternative medicine for centuries. Being produced by both hypopharyngeal and mandibular glands, RJ exhibits an extraordinary complexity in terms of its composition, including proteins, lipids, carbohydrates, polyphenols, vitamins, and hormones. Due to its heterogeneous structure, RJ displays various functional roles for honeybees, including being involved in nutrition, learning, memory, and social behavior. Furthermore, a wide range of studies reported its therapeutic properties, including anticancer, anti-inflammatory, and antioxidant activities, to name a few. In this direction, there is a wide range of health-related problems for which the medical area specialists and researchers are continuously trying to find a cure, such as cancer, atherosclerosis, or infertility. For the mentioned diseases and more, it has been proven that RJ is a key player in finding a valuable treatment. In this review, the great impact of RJ as an alternative medicine agent is highlighted, with a focus on its anticancer, anti-inflammatory, and antioxidant activities. Moreover, we link it to its apitherapeutic potential by discussing its composition. Herein, we discuss a wide range of novel studies and present the latest research work. Full article

(This article belongs to the Special Issue Quality Control of Bee Products: Functional and Chemical Properties)

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22 pages, 3040 KiB

Open AccessArticle

Cytotoxic and Antioxidant Activity of Hypericum perforatum L. Extracts against Human Melanoma Cells from Different Stages of Cancer Progression, Cultured under Normoxia and Hypoxia

by Aleksandra Brankiewicz, Sara Trzos, Magdalena Mrożek, Małgorzata Opydo, Elżbieta Szostak, Michał Dziurka, Monika Tuleja, Agnieszka Łoboda and Ewa Pocheć

Molecules 2023, 28(3), 1509; https://doi.org/10.3390/molecules28031509 - 3 Feb 2023

Cited by 9 | Viewed by 3164

Abstract

Oxidative stress and the hypoxic microenvironment play a key role in the progression of human melanoma, one of the most aggressive skin cancers. The aim of our study was to evaluate the effect of Hypericum perforatum extracts of different origins (both commercially available [...] Read more.

Oxidative stress and the hypoxic microenvironment play a key role in the progression of human melanoma, one of the most aggressive skin cancers. The aim of our study was to evaluate the effect of Hypericum perforatum extracts of different origins (both commercially available (HpEx2) and laboratory-prepared from wild grown (HpEx12) and in vitro cultured (HpEx13) plants) and hyperforin salt on WM115 primary and WM266-4 lymph node metastatic human melanoma cells cultured under normoxic and hypoxic conditions. The polyphenol content, radical scavenging activity, and hyperforin concentration were determined in the extracts, while cell viability, apoptosis, ROS production, and expression of NRF2 and HO-1, important oxidative stress-related factors, were analyzed after 24 h of cell stimulation with HpExs and hyperforin salt. We found that cytotoxic, pro-apoptotic and antioxidant effects depend on the extract composition, the stage of melanoma progression, and the oxygen level. Hyperforin salt showed lower activity than H. perforatum extracts. Our study for the first time showed that the anticancer activity of H. perforatum extracts differs in normoxia and hypoxia. Importantly, the composition of extracts of various origins, including in vitro cultured, resulting in their unique properties, may be important in the selection of plants for therapeutic application. Full article

(This article belongs to the Special Issue Bioactive Compounds and Antioxidant Activity of Extracts from Different Natural Plants)

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12 pages, 4975 KiB

Open AccessArticle

Investigation on Gold–Ligand Interaction for Complexes from Gold Leaching: A DFT Study

by Na Zhang, Jue Kou and Chunbao Sun

Molecules 2023, 28(3), 1508; https://doi.org/10.3390/molecules28031508 - 3 Feb 2023

Cited by 5 | Viewed by 2490

Abstract

Gold leaching is an important process to extract gold from ore. Conventional alkaline cyanide process and alternative nontoxic lixiviants including thiosulfate, thiourea, thiocyanate, and halogen have been widely investigated. However, density functional theory (DFT) study on the gold complexes Au(CN)₂⁻, [...] Read more.

Gold leaching is an important process to extract gold from ore. Conventional alkaline cyanide process and alternative nontoxic lixiviants including thiosulfate, thiourea, thiocyanate, and halogen have been widely investigated. However, density functional theory (DFT) study on the gold complexes Au(CN)₂⁻, Au(S₂O₃)₂³⁻, Au[SC(NH₂)₂]₂⁺, Au(SCN)₂⁻, and AuCl₂⁻ required for discovering and designing new highly efficient and environmentally friendly gold leaching reagents is lacking, which is expected to support constructive information for the discovery and designation of new high-efficiency and environmentally friendly gold leaching reagents. In this study, the structure information, electron-transferring properties, orbital interaction, and chemical bond composition for complexes Au(CN)₂⁻, Au(S₂O₃)₂³⁻, Au[SC(NH₂)₂]₂⁺, Au(SCN)₂⁻, and AuCl₂⁻ depending on charge decomposition analysis (CDA), natural bond orbital (NBO), natural resonance theory (NRT), electron localization function (ELF), and energy decomposition analysis (EDA) were performed based on DFT calculation. The results indicate that there is not only σ-donation from ligand to Au⁺, but also electron backdonation from Au⁺ to ligands, which strengthens the coordinate bond between them. Compared with Cl⁻, ligands CN⁻, S₂O₃²⁻, SC(NH₂)₂, and SCN⁻ have very large covalent contribution to the coordinate bond with Au⁺, which explains the special stability of Au-CN and Au-S bonds. The degree of covalency and bond energy in Au–ligand bonding decreases from Au(CN)₂⁻, Au(S₂O₃)₂³⁻, Au[SC(NH₂)₂]₂⁺, Au(SCN)₂⁻, to AuCl₂⁻, which interprets the stability of the five complexes: Au(CN)₂⁻ > Au(S₂O₃)₂³⁻ > Au[SC(NH₂)₂]₂⁺ > Au(SCN)₂⁻ > AuCl₂⁻. Full article

(This article belongs to the Special Issue Advances in Density Functional Theory (DFT) Calculation)

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23 pages, 5644 KiB

Open AccessArticle

Improved Antioxidant and Mechanical Properties of Food Packaging Films Based on Chitosan/Deep Eutectic Solvent, Containing Açaí-Filled Microcapsules

by Barbara E. Teixeira-Costa, Willian Hermogenes Ferreira, Francisco M. Goycoolea, Brent S. Murray and Cristina T. Andrade

Molecules 2023, 28(3), 1507; https://doi.org/10.3390/molecules28031507 - 3 Feb 2023

Cited by 15 | Viewed by 3606

Abstract

The development of biobased antioxidant active packaging has been valued by the food industry for complying with environmental and food waste concerns. In this work, physicochemical properties for chitosan composite films as a potential active food packaging were investigated. Chitosan films were prepared [...] Read more.

The development of biobased antioxidant active packaging has been valued by the food industry for complying with environmental and food waste concerns. In this work, physicochemical properties for chitosan composite films as a potential active food packaging were investigated. Chitosan films were prepared by solution casting, plasticized with a 1:2 choline chloride: glycerol mixture as a deep eutectic solvent (DES) and incorporated with 0–10% of optimized açaí oil polyelectrolyte complexes (PECs). Scanning electron microscopy and confocal laser scanning microscopy revealed that the chitosan composite films were continuous and contained well-dispersed PECs. The increased PECs content had significant influence on the thickness, water vapor permeability, crystallinity (CrD) and mechanical and dynamic behavior of the films, as well as their antioxidant properties. The tensile strength was reduced in the following order: 11.0 MPa (control film) > 0.74 MPa (5% DES) > 0.63 MPa (5% DES and 5% PECs). Films containing 2% of PECs had an increased CrD, ~6%, and the highest elongation at break, ~104%. Films with 1% of PECs displayed the highest antioxidant properties against the ABTS and DPPH radicals, ~6 and ~17 mg TE g⁻¹, respectively, and highest equivalent polyphenols content (>0.5 mg GAE g⁻¹). Films with 2% of particles were not significantly different. These results suggested that the chitosan films that incorporated 1–2% of microparticles had the best combined mechanical and antioxidant properties as a potential material for food packaging. Full article

(This article belongs to the Special Issue Antioxidant/Antimicrobial Packaging Films)

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32 pages, 2620 KiB

Open AccessReview

Recent Advances in Well-Designed Therapeutic Nanosystems for the Pancreatic Ductal Adenocarcinoma Treatment Dilemma

by Xiao-Yan Yang, Yuan-Fei Lu, Jian-Xia Xu, Yong-Zhong Du and Ri-Sheng Yu

Molecules 2023, 28(3), 1506; https://doi.org/10.3390/molecules28031506 - 3 Feb 2023

Cited by 4 | Viewed by 2918

Abstract

Pancreatic ductal adenocarcinoma (PDAC) is a highly malignant tumor with an extremely poor prognosis and low survival rate. Due to its inconspicuous symptoms, PDAC is difficult to diagnose early. Most patients are diagnosed in the middle and late stages, losing the opportunity for [...] Read more.

Pancreatic ductal adenocarcinoma (PDAC) is a highly malignant tumor with an extremely poor prognosis and low survival rate. Due to its inconspicuous symptoms, PDAC is difficult to diagnose early. Most patients are diagnosed in the middle and late stages, losing the opportunity for surgery. Chemotherapy is the main treatment in clinical practice and improves the survival of patients to some extent. However, the improved prognosis is associated with higher side effects, and the overall prognosis is far from satisfactory. In addition to resistance to chemotherapy, PDAC is significantly resistant to targeted therapy and immunotherapy. The failure of multiple treatment modalities indicates great dilemmas in treating PDAC, including high molecular heterogeneity, high drug resistance, an immunosuppressive microenvironment, and a dense matrix. Nanomedicine shows great potential to overcome the therapeutic barriers of PDAC. Through the careful design and rational modification of nanomaterials, multifunctional intelligent nanosystems can be obtained. These nanosystems can adapt to the environment’s needs and compensate for conventional treatments’ shortcomings. This review is focused on recent advances in the use of well-designed nanosystems in different therapeutic modalities to overcome the PDAC treatment dilemma, including a variety of novel therapeutic modalities. Finally, these nanosystems’ bottlenecks in treating PDAC and the prospect of future clinical translation are briefly discussed. Full article

(This article belongs to the Special Issue Recent Advances in Nano-Based Drug Delivery System)

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11 pages, 780 KiB

Open AccessArticle

Intraspecific Variability of Stinging Nettle (Urtica dioica L.)

by Sylwia Koczkodaj, Jarosław L. Przybył, Olga Kosakowska, Zenon Węglarz and Katarzyna B. Bączek

Molecules 2023, 28(3), 1505; https://doi.org/10.3390/molecules28031505 - 3 Feb 2023

Cited by 11 | Viewed by 2910

Abstract

The purpose of the work was to determine the intraspecific variability of the stinging nettle, in respect of the mass of leaves and their chemical composition, including the content of phenolic compounds and assimilative pigments. The objects of the study were 10 populations [...] Read more.

The purpose of the work was to determine the intraspecific variability of the stinging nettle, in respect of the mass of leaves and their chemical composition, including the content of phenolic compounds and assimilative pigments. The objects of the study were 10 populations of nettle, originating from the eastern and southern part of Poland. The results obtained indicate a high level of variability between and within the populations investigated but not strictly related to their geographical locations. The mass of the leaves ranged from 0.19 to 0.28 kg dry weight (DW)/plant (Coefficient of variation (CV) = 16.33%). Using HPLC–DAD, four phenolic acids were detected, i.e., caffeoylmalic (570.97–1367.40 mg/100 g DW), chlorogenic (352.79–1070.83 mg/100 g DW), neochlorogenic (114.56–284.77 mg/100 g DW) and cichoric (58.31–189.52 mg/100 g DW) acids, with the last one differentiating populations to the highest degree (CV = 48.83%). All of the analyzed populations met the requirements of the European Pharmacopoeia (Ph Eur 10th) concerning the minimum content of caffeoylmalic and chlorogenic acids in nettle leaves (not less than 0.3%). Within the flavonoid fraction, two compounds were identified, namely rutoside (917.05–1937.43 mg/100 g DW, CV = 21.32%) and hyperoside (42.01–289.45 mg/100 g DW; CV = 55.26%). The level of chlorophyll a ranged from 3.82 to 4.49 mg/g DW, chlorophyll b from 1.59 to 2.19 mg/g DW, while the content of carotenoids varied from 2.34 to 2.60 mg/100 g DW. Given all the traits investigated, the level of a population’s polymorphism (CV) was visibly higher within a population than between populations. Population no. 4 was distinguished by the highest mass of leaves, and the highest content of rutoside, while population no. 2 was distinguished by the highest content of hyperoside, caffeoylmalic and chlorogenic acid. Full article

(This article belongs to the Special Issue Bioactive Phenolic and Polyphenolic Compounds-2nd Edition)

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15 pages, 1704 KiB

Open AccessArticle

Proximate Composition and Nutritional Values of Selected Wild Plants of the United Arab Emirates

by Mohammad Shahid, Rakesh Kumar Singh and Sumitha Thushar

Molecules 2023, 28(3), 1504; https://doi.org/10.3390/molecules28031504 - 3 Feb 2023

Cited by 10 | Viewed by 3473

Abstract

Wild plants supply food and shelter to several organisms; they also act as important sources of many nutrients and pharmaceutical agents for mankind. These plants are widely used in traditional medicinal systems and folk medicines. The present study analyzed the nutritional and proximate [...] Read more.

Wild plants supply food and shelter to several organisms; they also act as important sources of many nutrients and pharmaceutical agents for mankind. These plants are widely used in traditional medicinal systems and folk medicines. The present study analyzed the nutritional and proximate composition of various compounds in selected wild plants available in the UAE, viz., Chenopodium murale L., Dipterygium glaucum Decne., Heliotropium digynum Asch. ex C.Chr., Heliotropium kotschyi Gürke., Salsola imbricata Forssk., Tribulus pentandrus Forssk., Zygophyllum qatarense Hadidi. The predominant amino acids detected in the plants were glycine, threonine, histidine, cysteine, proline, serine, and tyrosine; the highest quantities were observed in H. digynum and T. pentandrus. The major fatty acids present were long-chain saturated fatty acids; however, lauric acid was only present in S. imbricata. The presence of essential fatty acids such as oleic acid, α-Linoleic acid, and linolenic acid was observed in H. digynum, S. imbricata, and H. kotschyi. These plants also exhibited higher content of nutrients such as carbohydrates, proteins, fats, ash, and fiber. The predominant vitamins in the plants were vitamin B complex and vitamin C. C. murale had higher vitamin A, whereas vitamin B complex was seen in T. pentandrus and D. glaucum. The phosphorus and zinc content were high in T. pentandrus; the nitrogen, calcium, and potassium contents were high in H. digynum, and D. glaucum. Overall, these plants, especially H. digynum and T. pentandrus contain high amounts of nutritionally active compounds and important antioxidants including trace elements and vitamins. The results from the experiment provide an understanding of the nutritional composition of these desert plant species and can be better utilized as important agents for pharmacological drug discovery, food, and sustainable livestock production in the desert ecosystem. Full article

(This article belongs to the Special Issue Natural Bioactive Compounds and Human Health)

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14 pages, 1696 KiB

Open AccessFeature PaperArticle

Developing a Compost Quality Index (CQI) Based on the Electrochemical Quantification of Cd (HA) Reactivity

by Ana C. Silva, Pedro Rocha, Dulce Geraldo, Ana Cunha, Juan Antelo, José P. Pinheiro, Sarah Fiol and Fátima Bento

Molecules 2023, 28(3), 1503; https://doi.org/10.3390/molecules28031503 - 3 Feb 2023

Cited by 2 | Viewed by 1976

Abstract

The present work demonstrates the use of Cd²⁺ as a reactivity probe of the fulvic acids (FAs), humic acids (HAs) and dissolved organic matter (DOM) compost extracts. Significant differences were observed between the extracts, with the HA extract showing the highest reactivity. [...] Read more.

The present work demonstrates the use of Cd²⁺ as a reactivity probe of the fulvic acids (FAs), humic acids (HAs) and dissolved organic matter (DOM) compost extracts. Significant differences were observed between the extracts, with the HA extract showing the highest reactivity. Comparing the different composts, the largest reactivity variation was again observed for HA then FA and finally DOM extracts. The Cd²⁺ binding extent was used to calculate the quality of composts and compared with a reference of uncomposted organic fertiliser (FLW), leading to the definition of an operational scale of compost quality. The parameter equivalent mass of fertiliser (m_EF) was used for this scale sorted the seven composts from 0.353 to 1.09 kg FLW, for compost of sewage sludge (CSS) and vermicompost of domestic waste (CVDW), respectively. The significance of this parameter was verified through a correlation analysis between binding extent and the effect of compost application on lettuce crop growth in a field trial. The results demonstrate the potentiality of FA and HA extracts as markers of compost bioactivity and the use of Cd²⁺ as a reactivity probe. Full article

(This article belongs to the Special Issue Electroanalytical Trace Metal Quantification and Speciation)

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8 pages, 10761 KiB

Open AccessCommunication

Hierarchical Pt-In Nanowires for Efficient Methanol Oxidation Electrocatalysis

by Zhao Lu, Lu Zou and Wulin Song

Molecules 2023, 28(3), 1502; https://doi.org/10.3390/molecules28031502 - 3 Feb 2023

Cited by 4 | Viewed by 1805

Abstract

Direct methanol fuel cells (DMFC) have attracted increasing research interest recently; however, their output performance is severely hindered by the sluggish kinetics of the methanol oxidation reaction (MOR) at the anode. Herein, unique hierarchical Pt-In NWs with uneven surface and abundant high-index facets [...] Read more.

Direct methanol fuel cells (DMFC) have attracted increasing research interest recently; however, their output performance is severely hindered by the sluggish kinetics of the methanol oxidation reaction (MOR) at the anode. Herein, unique hierarchical Pt-In NWs with uneven surface and abundant high-index facets are developed as efficient MOR electrocatalysts in acidic electrolytes. The developed hierarchical Pt₈₉In₁₁ NWs exhibit high MOR mass activity and specific activity of 1.42 A mg_Pt⁻¹ and 6.2 mA cm⁻², which are 5.2 and 14.4 times those of Pt/C, respectively, outperforming most of the reported MORs. In chronoamperometry tests, the hierarchical Pt₈₉In₁₁ NWs demonstrate a longer half-life time than Pt/C, suggesting the better CO tolerance of Pt₈₉In₁₁ NWs. After stability, the MOR activity can be recovered by cycling. XPS, CV measurement and CO stripping voltammetry measurements demonstrate that the outstanding catalytic activity may be attributed to the facile removal of CO due to the presence of In site-adsorbing hydroxyl species. Full article

(This article belongs to the Special Issue Energy-Relevant Advanced Materials)

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23 pages, 9984 KiB

Open AccessReview

Synthetic Studies on Tetracyclic Diquinane Lycopodium Alkaloids Magellanine, Magellaninone and Paniculatine

by Takeru Saito, John Mark Awad and Wei Zhang

Molecules 2023, 28(3), 1501; https://doi.org/10.3390/molecules28031501 - 3 Feb 2023

Cited by 2 | Viewed by 2405

Abstract

(–)-Magellanine, (+)-magellaninone, and (+)-paniculatine are three natural products isolated from the Lycopodium family that share a unique 6-5-5-6-fused tetracyclic diquinane core skeleton. Several members of this family have potent s anti-inflammatory and acetylcholinesterase-inhibitory properties and are under development for the treatment of Alzheimer’s [...] Read more.

(–)-Magellanine, (+)-magellaninone, and (+)-paniculatine are three natural products isolated from the Lycopodium family that share a unique 6-5-5-6-fused tetracyclic diquinane core skeleton. Several members of this family have potent s anti-inflammatory and acetylcholinesterase-inhibitory properties and are under development for the treatment of Alzheimer’s and other neurodegenerative diseases. Several research groups have undertaken the formal and total syntheses of this class of natural products. This review highlights over 20 reported total syntheses of these three alkaloids and the development of synthetic methods for the assembly of their core skeletons. Full article

(This article belongs to the Special Issue Design and Synthesis of Bioactive Organic Molecules)

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14 pages, 2607 KiB

Open AccessArticle

Accumulation of Antioxidative Phenolics and Carotenoids Using Thermal Processing in Different Stages of Momordica charantia Fruit

by Ji Hye Kim, You Jin Lim, Shucheng Duan, Tae Jung Park and Seok Hyun Eom

Molecules 2023, 28(3), 1500; https://doi.org/10.3390/molecules28031500 - 3 Feb 2023

Cited by 7 | Viewed by 2141

Abstract

The bitter taste of M. charantia fruit limits its consumption, although the health benefits are well known. The thermal drying process is considered as an alternative method to reduce the bitterness. However, processing studies have rarely investigated physiochemical changes in fruit stages. The [...] Read more.

The bitter taste of M. charantia fruit limits its consumption, although the health benefits are well known. The thermal drying process is considered as an alternative method to reduce the bitterness. However, processing studies have rarely investigated physiochemical changes in fruit stages. The antioxidant activities and physiochemical properties of various fruit stages were investigated using different thermal treatments. The color of the thermally treated fruit varied depending on the temperature. When heat-treated for 3 days, the samples from the 30 °C and 90 °C treatments turned brown, while the color of the 60 °C sample did not change significantly. The antioxidant activities were increased in the thermally processed samples in a temperature-dependent manner, with an increase in phenolic compounds. In the 90 °C samples, the 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity presented a 6.8-fold higher level than that of nonthermal treatment in mature yellow fruit (S3), whereas the activity showed about a 3.1-fold higher level in immature green (S1) and mature green (S2) fruits. Regardless of the stages, the carotenoid content tended to decrease with increasing temperature. In terms of antioxidant activities, these results suggested that mature yellow fruit is better for consumption using thermal processing. Full article

(This article belongs to the Special Issue Food Processing and Its Impact on Phenolic and Other Bioactive Constituents in Food – Second Edition)

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16 pages, 1361 KiB

Open AccessReview

Searching for the Best Values of NMR Shielding and Spin-Spin Coupling Parameters: CH_4-nF_n Series of Molecules as the Example

by Karol Jackowski and Mateusz A. Słowiński

Molecules 2023, 28(3), 1499; https://doi.org/10.3390/molecules28031499 - 3 Feb 2023

Cited by 2 | Viewed by 2333

Abstract

Attempts at the theoretical interpretation of NMR spectra have a very long and fascinating history. Present quantum chemical calculations of shielding and indirect spin-spin couplings permit modeling NMR spectra when small, isolated molecules are studied. Similar data are also available from NMR experiments [...] Read more.

Attempts at the theoretical interpretation of NMR spectra have a very long and fascinating history. Present quantum chemical calculations of shielding and indirect spin-spin couplings permit modeling NMR spectra when small, isolated molecules are studied. Similar data are also available from NMR experiments if investigations are performed in the gas phase. An interesting set of molecules is formed when a methane molecule is sequentially substituted by fluorine atoms—CH_4-nF_n, where n = 0, 1, 2, 3, or 4. The small molecules contain up to three magnetic nuclei, each with a one-half spin number. The spectral parameters of CH_4-nF_n can be easily observed in the gas phase and calculated with high accuracy using the most advanced ab initio methods of quantum chemistry. However, the presence of fluorine atoms makes the calculations of shielding and spin-spin coupling constants extremely demanding. Appropriate experimental ¹⁹F NMR parameters are good but also require some further improvements. Therefore, there is a real need for the comparison of existing NMR measurements with available state-of-the-art theoretical results for a better understanding of actual limits in the determination of the best shielding and spin-spin coupling values, and CH_4-nF_n molecules are used here as the exceptionally important case. Full article

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31 pages, 3499 KiB

Open AccessReview

A Review of Different Types of Liposomes and Their Advancements as a Form of Gene Therapy Treatment for Breast Cancer

by Gloria Yi Wei Tseu and Khairul Azfar Kamaruzaman

Molecules 2023, 28(3), 1498; https://doi.org/10.3390/molecules28031498 - 3 Feb 2023

Cited by 35 | Viewed by 5746

Abstract

Breast cancer incidence and mortality rates have increased exponentially during the last decade, particularly among female patients. Current therapies, including surgery and chemotherapy, have significant negative physical and mental impacts on patients. As a safer alternative, gene therapy utilising a therapeutic gene with [...] Read more.

Breast cancer incidence and mortality rates have increased exponentially during the last decade, particularly among female patients. Current therapies, including surgery and chemotherapy, have significant negative physical and mental impacts on patients. As a safer alternative, gene therapy utilising a therapeutic gene with the potential to treat various ailments is being considered. Delivery of the gene generally utilises viral vectors. However, immunological reactions and even mortality have been recorded as side effects. As a result, non-viral vectors, such as liposomes, a system composed of lipid bilayers formed into nanoparticles, are being studied. Liposomes have demonstrated tremendous potential due to their limitless ability to combine many functions into a system with desirable characteristics and functionality. This article discusses cationic, anionic, and neutral liposomes with their stability, cytotoxicity, transfection ability, cellular uptake, and limitation as a gene carrier suitable for gene therapy specifically for cancer. Due to the more practical approach of employing electrostatic contact with the negatively charged nucleic acid and the cell membrane for absorption purposes, cationic liposomes appear to be more suited for formulation for gene delivery and therapy for breast cancer treatment. As the other alternatives have numerous complicated additional modifications, attachments need to be made to achieve a functional gene therapy system for breast cancer treatment, which were also discussed in this review. This review aimed to increase understanding and build a viable breast cancer gene therapy treatment strategy. Full article

(This article belongs to the Special Issue Lipids in Drug Delivery and Therapeutics)

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13 pages, 2575 KiB

Open AccessArticle

Effect of Wide-Spectrum Monochromatic Lights on Growth, Phytochemistry, Nutraceuticals, and Antioxidant Potential of In Vitro Callus Cultures of Moringa oleifera

by Muhammad Naeem Bajwa, Mehnaz Khanum, Gouhar Zaman, Muhammad Asad Ullah, Umar Farooq, Muhammad Waqas, Nisar Ahmad, Christophe Hano and Bilal Haider Abbasi

Molecules 2023, 28(3), 1497; https://doi.org/10.3390/molecules28031497 - 3 Feb 2023

Cited by 7 | Viewed by 2706

Abstract

Moringa oleifera, also called miracle tree, is a pharmaceutically important plant with a multitude of nutritional, medicinal, and therapeutic attributes. In the current study, an in-vitro-based elicitation approach was used to enhance the commercially viable bioactive compounds in an in vitro callus [...] Read more.

Moringa oleifera, also called miracle tree, is a pharmaceutically important plant with a multitude of nutritional, medicinal, and therapeutic attributes. In the current study, an in-vitro-based elicitation approach was used to enhance the commercially viable bioactive compounds in an in vitro callus culture of M. oleifera. The callus culture was established and exposed to different monochromatic lights to assess the potentially interactive effects on biomass productions, biosynthesis of pharmaceutically valuable secondary metabolites, and antioxidant activity. Optimum biomass production (16.7 g/L dry weight), total phenolic contents (TPC: 18.03 mg/g), and flavonoid contents (TFC: 15.02 mg/g) were recorded in callus cultures placed under continuous white light (24 h), and of other light treatments. The highest antioxidant activity, i.e., ABTS (550.69 TEAC µM) and FRAP (365.37 TEAC µM), were also noted under white light (24 h). The analysis of phytochemicals confirmed the significant impact of white light exposures on the enhanced biosynthesis of plant secondary metabolites. The enhanced levels of secondary metabolites, i.e., kaempferol (1016.04 µg/g DW), neochlorogenic acid (998.38 µg/g DW), quercetin (959.92 µg/g DW), and minor compounds including luteolin, apigenin, and p-coumaric acid were observed as being highest in continuous white light (24 h with respect to the control (photoperiod). Similarly, blue light enhanced the chlorogenic acid accumulation. This study shows that differential spectral lights demonstrate a good approach for the enhancement of nutraceuticals along with novel pharmacologically important metabolites and antioxidants in the in vitro callus culture of M. oleifera. Full article

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82 pages, 34708 KiB

Open AccessReview

Organometallic Chemistry within the Structured Environment Provided by the Macrocyclic Cores of Carbaporphyrins and Related Systems

by Timothy D. Lash

Molecules 2023, 28(3), 1496; https://doi.org/10.3390/molecules28031496 - 3 Feb 2023

Cited by 5 | Viewed by 2513

Abstract

The unique environment within the core of carbaporphyrinoid systems provides a platform to explore unusual organometallic chemistry. The ability of these structures to form stable organometallic derivatives was first demonstrated for N-confused porphyrins but many other carbaporphyrin-type systems were subsequently shown to exhibit [...] Read more.

The unique environment within the core of carbaporphyrinoid systems provides a platform to explore unusual organometallic chemistry. The ability of these structures to form stable organometallic derivatives was first demonstrated for N-confused porphyrins but many other carbaporphyrin-type systems were subsequently shown to exhibit similar or complementary properties. Metalation commonly occurs with catalytically active transition metal cations and the resulting derivatives exhibit widely different physical, chemical and spectroscopic properties and range from strongly aromatic to nonaromatic and antiaromatic species. Metalation may trigger unusual, highly selective, oxidation reactions. Alkyl group migration has been observed within the cavity of metalated carbaporphyrins, and in some cases ring contraction of the carbocyclic subunit takes place. Over the past thirty years, studies in this area have led to multiple synthetic routes to carbaporphyrinoid ligands and remarkable organometallic chemistry has been reported. An overview of this important area is presented. Full article

(This article belongs to the Special Issue Featured Reviews in Organometallic Chemistry)

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23 pages, 3522 KiB

Open AccessArticle

Synthesis of Novel 1-Oxo-2,3,4-trisubstituted Tetrahydroisoquinoline Derivatives, Bearing Other Heterocyclic Moieties and Comparative Preliminary Study of Anti-Coronavirus Activity of Selected Compounds

by Meglena I. Kandinska, Nikola T. Burdzhiev, Diana V. Cheshmedzhieva, Sonia V. Ilieva, Peter P. Grozdanov, Neli Vilhelmova-Ilieva, Nadya Nikolova, Vesela V. Lozanova and Ivanka Nikolova

Molecules 2023, 28(3), 1495; https://doi.org/10.3390/molecules28031495 - 3 Feb 2023

Cited by 4 | Viewed by 2034

Abstract

A series of novel 1-oxo-2,3,4-trisubstituted tetrahydroisoquinoline (THIQ) derivatives bearing other heterocyclic moieties in their structure were synthesized based on the reaction between homophthalic anhydride and imines. Initial studies were carried out to establish the anti-coronavirus activity of some of the newly obtained THIQ-derivatives [...] Read more.

A series of novel 1-oxo-2,3,4-trisubstituted tetrahydroisoquinoline (THIQ) derivatives bearing other heterocyclic moieties in their structure were synthesized based on the reaction between homophthalic anhydride and imines. Initial studies were carried out to establish the anti-coronavirus activity of some of the newly obtained THIQ-derivatives against two strains of human coronavirus-229E and OC-43. Their antiviral activity was compared with that of their close analogues, piperidinones and thiomorpholinones, previously synthesized in our group, with aim to expand the range of the tested representative sample and to obtain valuable preliminary information about biological properties of a wider variety of compounds. Full article

(This article belongs to the Special Issue Synthesis of Tetrahydroisoquinoline and Protoberberine Derivatives)

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17 pages, 4332 KiB

Open AccessArticle

Identification of New L-Fucosyl and L-Galactosyl Amides as Glycomimetic Ligands of TNF Lectin Domain of BC2L-C from Burkholderia cenocepacia

by Sarah Mazzotta, Giulia Antonini, Francesca Vasile, Emilie Gillon, Jon Lundstrøm, Annabelle Varrot, Laura Belvisi and Anna Bernardi

Molecules 2023, 28(3), 1494; https://doi.org/10.3390/molecules28031494 - 3 Feb 2023

Cited by 4 | Viewed by 2249

Abstract

The inhibition of carbohydrate-lectin interactions is being explored as an efficient approach to anti adhesion therapy and biofilm destabilization, two alternative antimicrobial strategies that are being explored against resistant pathogens. BC2L-C is a new type of lectin from Burkholderia cenocepacia that binds (mammalian) fucosides [...] Read more.

The inhibition of carbohydrate-lectin interactions is being explored as an efficient approach to anti adhesion therapy and biofilm destabilization, two alternative antimicrobial strategies that are being explored against resistant pathogens. BC2L-C is a new type of lectin from Burkholderia cenocepacia that binds (mammalian) fucosides at the N-terminal domain and (bacterial) mannosides at the C-terminal domain. This double carbohydrate specificity allows the lectin to crosslink host cells and bacterial cells. We have recently reported the design and generation of the first glycomimetic antagonists of BC2L-C, β-C- or β-N-fucosides that target the fucose-specific N-terminal domain (BC2L-C-Nt). The low water solubility of the designed N-fucosides prevented a full examination of this promising series of ligands. In this work, we describe the synthesis and biophysical evaluation of new L-fucosyl and L-galactosyl amides, designed to be water soluble and to interact with BC2L-C-Nt. The protein–ligand interaction was investigated by Saturation Transfer Difference NMR, Isothermal Titration Calorimetry and crystallographic studies. STD-NMR experiments showed that both fucosyl and galactosyl amides compete with α-methyl fucoside for lectin binding. A new hit compound was identified with good water solubility and an affinity for BC2L-C-Nt of 159 μM (ITC), which represents a one order of magnitude gain over α-methyl fucoside. The x-ray structure of its complex with BC2L-C-Nt was solved at 1.55 Å resolution. Full article

(This article belongs to the Special Issue Carbohydrate Chemistry II)

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10 pages, 1080 KiB

Open AccessArticle

Novel Indane Derivatives with Antioxidant Activity from the Roots of Anisodus tanguticus

by Chun-Wang Meng, Hao-Yu Zhao, Huan Zhu, Cheng Peng, Qin-Mei Zhou and Liang Xiong

Molecules 2023, 28(3), 1493; https://doi.org/10.3390/molecules28031493 - 3 Feb 2023

Cited by 9 | Viewed by 2017

Abstract

Four novel indane derivatives, anisotindans A–D (1–4), were isolated from the roots of Anisodus tanguticus. Their structures were established using comprehensive spectroscopic analyses, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations and single-crystal X-ray [...] Read more.

Four novel indane derivatives, anisotindans A–D (1–4), were isolated from the roots of Anisodus tanguticus. Their structures were established using comprehensive spectroscopic analyses, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction analyses. Anisotindans C and D (3 and 4) are two unusual indenofuran analogs. ABTS^•+ and DPPH^•+ assays of radical scavenging activity reveal that all compounds (1–4) are active. Specifically, the ABTS^•+ assay results show that anisotindan A (1) exhibits the best antioxidant activity with an IC₅₀ value of 15.62 ± 1.85 μM (vitamin C, IC₅₀ = 22.54 ± 5.18 μM). Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources II)

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20 pages, 5212 KiB

Open AccessArticle

The Development and Optimization of Lipid-Based Self-Nanoemulsifying Drug Delivery Systems for the Intravenous Delivery of Propofol

by Mohsin Kazi, Athba Alqahtani, Majed Alharbi, Ajaz Ahmad, Muhammad Delwar Hussain, Hani Alothaid and Mohammed S. Aldughaim

Molecules 2023, 28(3), 1492; https://doi.org/10.3390/molecules28031492 - 3 Feb 2023

Cited by 7 | Viewed by 3246

Abstract

Purpose: Propofol is a relatively short-acting potent anesthetic lipophilic drug used during short surgical procedures. Despite the success of propofol intravenous emulsions, drawbacks to such formulations include inherent emulsion instability, the lack of a safe vehicle to prevent sepsis, and concern regarding hyperlipidemia-related [...] Read more.

Purpose: Propofol is a relatively short-acting potent anesthetic lipophilic drug used during short surgical procedures. Despite the success of propofol intravenous emulsions, drawbacks to such formulations include inherent emulsion instability, the lack of a safe vehicle to prevent sepsis, and concern regarding hyperlipidemia-related side effects. The aim of the current investigation was to develop a novel, lipid-based self-nanoemulsifying drug delivery system (SNEDDS) for propofol with improved stability and anesthetic activity for human use. Methods: A series of SNEDDS formulations were developed using naturally obtained medium-chain/long-chain mono-, di-, and triglycerides, glyceryl monocaprylate, and water-soluble cosolvents with hydrogenated castor oil constructing ternary phase diagrams for propofol. The developed SNEDDS formulations were characterized using visual observation, particle size analysis, zeta potential, transmission electron microscopy, equilibrium solubility, in vitro dynamic dispersion and stability, and in vivo sleeping disorder studies in rats. The in vivo bioavailability of the SNEDDSs in rats was also studied to compare the representative formulations with the marketed product Diprivan^®. Results: Medium-chain triglycerides (M810) with mono-diglycerides (CMCM) as an oil blend and hydrogenated castor oil (KHS15) as a surfactant were selected as key ingredients in ternary phase diagram studies. The nanoemulsifying regions were identified from the studies and a number of SNEDDSs were formulated. Results from the characterization studies demonstrated the formation of efficient nanosized particles (28–45 nm globule size, 0.10–0.20 PDI) in the optimized SNEDDS with a drug loading of 50 mg/g, which is almost 500-fold higher than free propofol. TEM analysis showed the formation of spherical and homogeneous nanoparticles of less than 50 nm. The dissolution rate of the representative SNEDDS was faster than raw propofol and able to maintain 99% propofol in aqueous solution for around 24 h. The optimized liquid SNEDDS formulation was found to be thermodynamically stable. The intravenous administration of the SNEDDS in male Wistar rats induced a sleeping time of 73–88 min. The mean plasma concentrations after the IV administration of propofol nano-formulations PF2-SNEDDS and PF8-SNEDDS were 1348.07 ± 27.31 and 1138.66 ± 44.97 µg/mL, as compared to 891.44 ± 26.05 µg/mL (p = 0.05) observed after the IV administration of raw propofol. Conclusion: Propofol-loaded SNEDDS formulations could be a potential pharmaceutical product with improved stability, bioavailability, and anesthetic activity. Full article

(This article belongs to the Special Issue Lipids in Drug Delivery and Therapeutics)

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12 pages, 2758 KiB

Open AccessReview

Microbial Production of Human Milk Oligosaccharides

by Dileep Sai Kumar Palur, Shannon R. Pressley and Shota Atsumi

Molecules 2023, 28(3), 1491; https://doi.org/10.3390/molecules28031491 - 3 Feb 2023

Cited by 4 | Viewed by 6115

Abstract

Human milk oligosaccharides (HMOs) are complex nonnutritive sugars present in human milk. These sugars possess prebiotic, immunomodulatory, and antagonistic properties towards pathogens and therefore are important for the health and well-being of newborn babies. Lower prevalence of breastfeeding around the globe, rising popularity [...] Read more.

Human milk oligosaccharides (HMOs) are complex nonnutritive sugars present in human milk. These sugars possess prebiotic, immunomodulatory, and antagonistic properties towards pathogens and therefore are important for the health and well-being of newborn babies. Lower prevalence of breastfeeding around the globe, rising popularity of nutraceuticals, and low availability of HMOs have inspired efforts to develop economically feasible and efficient industrial-scale production platforms for HMOs. Recent progress in synthetic biology and metabolic engineering tools has enabled microbial systems to be a production system of HMOs. In this regard, the model organism Escherichia coli has emerged as the preferred production platform. Herein, we summarize the remarkable progress in the microbial production of HMOs and discuss the challenges and future opportunities in unraveling the scope of production of complex HMOs. We focus on the microbial production of five HMOs that have been approved for their commercialization. Full article

(This article belongs to the Special Issue Feature Papers in Chemical Biology—Edition of 2022-2023)

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19 pages, 12464 KiB

Open AccessArticle

A Knowledge-Graph-Based Multimodal Deep Learning Framework for Identifying Drug–Drug Interactions

by Jing Zhang, Meng Chen, Jie Liu, Dongdong Peng, Zong Dai, Xiaoyong Zou and Zhanchao Li

Molecules 2023, 28(3), 1490; https://doi.org/10.3390/molecules28031490 - 3 Feb 2023

Cited by 8 | Viewed by 3685

Abstract

The identification of drug–drug interactions (DDIs) plays a crucial role in various areas of drug development. In this study, a deep learning framework (KGCN_NFM) is presented to recognize DDIs using coupling knowledge graph convolutional networks (KGCNs) with neural factorization machines (NFMs). A KGCN [...] Read more.

The identification of drug–drug interactions (DDIs) plays a crucial role in various areas of drug development. In this study, a deep learning framework (KGCN_NFM) is presented to recognize DDIs using coupling knowledge graph convolutional networks (KGCNs) with neural factorization machines (NFMs). A KGCN is used to learn the embedding representation containing high-order structural information and semantic information in the knowledge graph (KG). The embedding and the Morgan molecular fingerprint of drugs are then used as input of NFMs to predict DDIs. The performance and effectiveness of the current method have been evaluated and confirmed based on the two real-world datasets with different sizes, and the results demonstrate that KGCN_NFM outperforms the state-of-the-art algorithms. Moreover, the identified interactions between topotecan and dantron by KGCN_NFM were validated through MTT assays, apoptosis experiments, cell cycle analysis, and molecular docking. Our study shows that the combination therapy of the two drugs exerts a synergistic anticancer effect, which provides an effective treatment strategy against lung carcinoma. These results reveal that KGCN_NFM is a valuable tool for integrating heterogeneous information to identify potential DDIs. Full article

(This article belongs to the Topic Bioinformatics in Drug Design and Discovery)

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22 pages, 4867 KiB

Open AccessArticle

Synthesis and Optical Properties of a Series of Push-Pull Dyes Based on Pyrene as the Electron Donor

by Thanh-Tuân Bui, Sébastien Péralta and Frédéric Dumur

Molecules 2023, 28(3), 1489; https://doi.org/10.3390/molecules28031489 - 3 Feb 2023

Cited by 2 | Viewed by 2829

Abstract

Fifteen push-pull dyes comprising the tetracyclic polyaromatic pyrene have been designed and synthesized. The optical properties of the fifteen dyes have been examined in twenty-two solvents of different polarities. Surprisingly, contrarily to what is classically observed for push-pull dyes of D-π-A structures, a [...] Read more.

Fifteen push-pull dyes comprising the tetracyclic polyaromatic pyrene have been designed and synthesized. The optical properties of the fifteen dyes have been examined in twenty-two solvents of different polarities. Surprisingly, contrarily to what is classically observed for push-pull dyes of D-π-A structures, a negative solvatochromism could be found for numerous dyes. The photoluminescence and thermal properties of the dyes were also examined. Theoretical calculations were carried out to support the experimental results. Full article

(This article belongs to the Section Colorants)

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24 pages, 866 KiB

Open AccessReview

Antioxidant and Anti-Inflammatory Compounds from Edible Plants with Anti-Cancer Activity and Their Potential Use as Drugs

by Sofía Isabel Cuevas-Cianca, Cristian Romero-Castillo, José Luis Gálvez-Romero, Zaida Nelly Juárez and Luis Ricardo Hernández

Molecules 2023, 28(3), 1488; https://doi.org/10.3390/molecules28031488 - 3 Feb 2023

Cited by 21 | Viewed by 6068

Abstract

Food is our daily companion, performing numerous beneficial functions for our bodies. Many of them can help to alleviate or prevent ailments and diseases. In this review, an extensive bibliographic search is conducted in various databases to update information on unprocessed foods with [...] Read more.

Food is our daily companion, performing numerous beneficial functions for our bodies. Many of them can help to alleviate or prevent ailments and diseases. In this review, an extensive bibliographic search is conducted in various databases to update information on unprocessed foods with anti-inflammatory and antioxidant properties that can aid in treating diseases such as cancer. The current state of knowledge on inflammatory processes involving some interleukins and tumor necrosis factor-alpha (TNF-α) is reviewed. As well as unprocessed foods, which may help reduce inflammation and oxidative stress, both of which are important factors in cancer development. Many studies are still needed to take full advantage of the food products we use daily. Full article

(This article belongs to the Special Issue The Role of Natural Products in Promoting Well-being: From Foods to Drugs)

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20 pages, 3051 KiB

Open AccessReview

Fundamentals of Rhenium-188 Radiopharmaceutical Chemistry

by Janke Kleynhans, Adriano Duatti and Cristina Bolzati

Molecules 2023, 28(3), 1487; https://doi.org/10.3390/molecules28031487 - 3 Feb 2023

Cited by 10 | Viewed by 3352

Abstract

The β⁻ emitter, rhenium-188 (¹⁸⁸Re), has long been recognized as an attractive candidate for targeted cancer radionuclide therapy (TRNT). This transition metal shares chemical similarities with its congener element technetium, whose nuclear isomer technetium-99m (^99mTc) is the current [...] Read more.

The β⁻ emitter, rhenium-188 (¹⁸⁸Re), has long been recognized as an attractive candidate for targeted cancer radionuclide therapy (TRNT). This transition metal shares chemical similarities with its congener element technetium, whose nuclear isomer technetium-99m (^99mTc) is the current workhorse of diagnostic nuclear medicine. The differences between these two elements have a significant impact on the radiolabelling methods and should always receive critical attention. This review aims to highlight what needs to be considered to design a successful radiopharmaceutical incorporating ¹¹⁸Re. Some of the most effective strategies for preparing therapeutic radiopharmaceuticals with ¹⁸⁸Re are illustrated and rationalized using the concept of the inorganic functional group (core) and a simple ligand field theoretical model combined with a qualitative definition of frontiers orbitals. Of special interest are the Re(V) oxo and Re(V) nitrido functional groups. Suitable ligands for binding to these cores are discussed, successful clinical applications are summarized, and a prediction of viable future applications is presented. Rhenium-188 decays through the emission of a high energy beta particle (2.12 MeV max energy) and a half-life of 16.9 h. An ideal biological target would therefore be a high-capacity target site (transporters, potential gradients, tumour microenvironment) with less emphasis on saturable targets such as overexpressed receptors on smaller metastases. Full article

(This article belongs to the Special Issue Technetium and Rhenium in Chemistry and Their Advanced Applications)

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