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The Importance of Substituent Position for Antibacterial Activity in the Group of Thiosemicarbazide Derivatives
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Probing Non-Covalent Interactions through Molecular Balances: A REG-IQA Study
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Synthesis and Dynamic Behavior of Ce(IV) Double-Decker Complexes of Sterically Hindered Phthalocyanines
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Chemical-Vapor-Deposition-Synthesized Two-Dimensional Non-Stoichiometric Copper Selenide (β-Cu2−xSe) for Ultra-Fast Tetracycline Hydrochloride Degradation under Solar Light
Journal Description
Molecules
Molecules
is the leading international, peer-reviewed, open access journal of chemistry. Molecules is published semimonthly online by MDPI. The International Society of Nucleosides, Nucleotides & Nucleic Acids (IS3NA), the Spanish Society of Medicinal Chemistry (SEQT) and the International Society of Heterocyclic Chemistry (ISHC) are affiliated with Molecules and their members receive a discount on the article processing charges.
- Open Access— free for readers, with article processing charges (APC) paid by authors or their institutions.
- High Visibility: indexed within Scopus, SCIE (Web of Science), PubMed, MEDLINE, PMC, Reaxys, CaPlus / SciFinder, MarinLit, AGRIS, and other databases.
- Journal Rank: JCR - Q2 (Chemistry, Multidisciplinary) / CiteScore - Q1 (Chemistry (miscellaneous))
- Rapid Publication: manuscripts are peer-reviewed and a first decision is provided to authors approximately 14.6 days after submission; acceptance to publication is undertaken in 2.7 days (median values for papers published in this journal in the second half of 2023).
- Recognition of Reviewers: reviewers who provide timely, thorough peer-review reports receive vouchers entitling them to a discount on the APC of their next publication in any MDPI journal, in appreciation of the work done.
- Sections: published in 26 topical sections.
- Testimonials: See what our editors and authors say about Molecules.
- Companion journals for Molecules include: Foundations and Photochem.
Impact Factor:
4.2 (2023);
5-Year Impact Factor:
4.6 (2023)
Latest Articles
Solid Lipid Nanoparticles Encapsulating a Benzoxanthene Derivative in a Model of the Human Blood–Brain Barrier: Modulation of Angiogenic Parameters and Inflammation in Vascular Endothelial Growth Factor-Stimulated Angiogenesis
Molecules 2024, 29(13), 3103; https://doi.org/10.3390/molecules29133103 (registering DOI) - 28 Jun 2024
Abstract
Lignans, a class of secondary metabolites found in plants, along with their derivatives, exhibit diverse pharmacological activities, including antioxidant, antimicrobial, anti-inflammatory, and antiangiogenic ones. Angiogenesis, the formation of new blood vessels from pre-existing ones, is a crucial process for cancer growth and development.
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Lignans, a class of secondary metabolites found in plants, along with their derivatives, exhibit diverse pharmacological activities, including antioxidant, antimicrobial, anti-inflammatory, and antiangiogenic ones. Angiogenesis, the formation of new blood vessels from pre-existing ones, is a crucial process for cancer growth and development. Several studies have elucidated the synergistic relationship between angiogenesis and inflammation in various inflammatory diseases, highlighting a correlation between inflammation and vascular endothelial growth factor (VEGF)-induced angiogenesis. Thus, the identification of novel molecules capable of modulating VEGF effects presents promising prospects for developing therapies aimed at stabilizing, reversing, or even arresting disease progression. Lignans often suffer from low aqueous solubility and, for their use, encapsulation in a delivery system is needed. In this research, a bioinspired benzoxantene has been encapsulated in solid lipid nanoparticles that have been characterized for their pharmacotechnical properties and their thermotropic behavior. The effects of these encapsulated nanoparticles on angiogenic parameters and inflammation in VEGF-induced angiogenesis were evaluated using human brain microvascular endothelial cells (HBMECs) as a human blood–brain barrier model.
Full article
(This article belongs to the Special Issue Preparation, Characterization, and Effect of Lipid Nanoparticles Used in Different Application Fields IV)
Open AccessArticle
Synthesis and Evaluation of the First 68Ga-Labeled C-Terminal Hydroxamate-Derived Gastrin-Releasing Peptide Receptor-Targeted Tracers for Cancer Imaging with Positron Emission Tomography
by
Lei Wang, Hsiou-Ting Kuo, Chao-Cheng Chen, Devon Chapple, Nadine Colpo, Pauline Ng, Wing Sum Lau, Shireen Jozi, François Bénard and Kuo-Shyan Lin
Molecules 2024, 29(13), 3102; https://doi.org/10.3390/molecules29133102 (registering DOI) - 28 Jun 2024
Abstract
Gastrin-releasing peptide receptor (GRPR), overexpressed in many solid tumors, is a promising imaging marker and therapeutic target. Most reported GRPR-targeted radioligands contain a C-terminal amide. Based on the reported potent antagonist D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-NHOH, we synthesized C-terminal hydroxamate-derived [68Ga]Ga-LW02075 ([68
[...] Read more.
Gastrin-releasing peptide receptor (GRPR), overexpressed in many solid tumors, is a promising imaging marker and therapeutic target. Most reported GRPR-targeted radioligands contain a C-terminal amide. Based on the reported potent antagonist D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-NHOH, we synthesized C-terminal hydroxamate-derived [68Ga]Ga-LW02075 ([68Ga]Ga-DOTA-pABzA-DIG-D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-NHOH) and [68Ga]Ga-LW02050 ([68Ga]Ga-DOTA-Pip-D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-NHOH), and compared them with the closely related and clinically validated [68Ga]Ga-SB3 ([68Ga]Ga-DOTA-pABzA-DIG-D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-NHEt). Binding affinities (Ki) of Ga-SB3, Ga-LW02075, and Ga-LW02050 were 1.20 ± 0.31, 1.39 ± 0.54, and 8.53 ± 1.52 nM, respectively. Both Ga-LW02075 and Ga-LW02050 were confirmed to be GRPR antagonists by calcium release assay. Imaging studies showed that PC-3 prostate cancer tumor xenografts were clearly visualized at 1 h post injection by [68Ga]Ga-SB3 and [68Ga]Ga-LW02050 in PET images, but not by [68Ga]Ga-LW02075. Ex vivo biodistribution studies conducted at 1 h post injection showed that the tumor uptake of [68Ga]Ga-LW02050 was comparable to that of [68Ga]Ga-SB3 (5.38 ± 1.00 vs. 6.98 ± 1.36 %ID/g), followed by [68Ga]Ga-LW02075 (3.97 ± 1.71 %ID/g). [68Ga]Ga-SB3 had the highest pancreas uptake (37.3 ± 6.90 %ID/g) followed by [68Ga]Ga-LW02075 (17.8 ± 5.24 %ID/g), while the pancreas uptake of [68Ga]Ga-LW02050 was only 0.53 ± 0.11 %ID/g. Our data suggest that [68Ga]Ga-LW02050 is a promising PET tracer for detecting GRPR-expressing cancer lesions.
Full article
(This article belongs to the Special Issue New Advances in Radiopharmaceutical Sciences)
Open AccessArticle
Equilibrium Values for the Si-H Bond Length and Equilibrium Structures of Silyl Iodide and Halosilylenes
by
Jean Demaison and Jacques Liévin
Molecules 2024, 29(13), 3101; https://doi.org/10.3390/molecules29133101 (registering DOI) - 28 Jun 2024
Abstract
The equilibrium structures of silyl iodide, SiH3I, and silylene halides, SiHX (X = F, Cl, Br, I), were determined by using the mixed regression method, where approximate values of the rotational constants are supplemented by the structural parameters of a different
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The equilibrium structures of silyl iodide, SiH3I, and silylene halides, SiHX (X = F, Cl, Br, I), were determined by using the mixed regression method, where approximate values of the rotational constants are supplemented by the structural parameters of a different origin. For this goal, it is shown that the r(Si-H) bond length can be determined by using the isolated SiH stretching frequency and that an accurate estimation of the bond angles is obtained by an MP2 calculation with a basis set of triple zeta quality. To check the accuracy of the experimental structures, they were also optimized by means of all electron CCSD(T) calculations using basis sets of quadruple zeta quality.
Full article
(This article belongs to the Special Issue From Spectroscopic Insights to Structural Wonders: A Theme Issue Dedicated to Professor Jaan Laane)
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Graphical abstract
Open AccessArticle
Lattice Matching and Microstructure of the Aromatic Amide Fatty Acid Salts Nucleating Agent on the Crystallization Behavior of Recycled Polyethylene Terephthalate
by
Tianjiao Zhao, Fuhua Lin, Yapeng Dong, Meizhen Wang, Dingyi Ning, Xinyu Hao, Jialiang Hao, Yanli Zhang, Dan Zhou, Yuying Zhao, Jun Luo, Jingqiong Lu and Bo Wang
Molecules 2024, 29(13), 3100; https://doi.org/10.3390/molecules29133100 (registering DOI) - 28 Jun 2024
Abstract
To solve the decrease in the crystallization, mechanical and thermal properties of recycled polyethylene terephthalate (rPET) during mechanical recycling, the aromatic amide fatty acid salt nucleating agents Na-4-ClBeAmBe, Na-4-ClBeAmGl and Na-4-ClAcAmBe were synthesized and the rPET/nucleating agent blend was prepared by melting blending.
[...] Read more.
To solve the decrease in the crystallization, mechanical and thermal properties of recycled polyethylene terephthalate (rPET) during mechanical recycling, the aromatic amide fatty acid salt nucleating agents Na-4-ClBeAmBe, Na-4-ClBeAmGl and Na-4-ClAcAmBe were synthesized and the rPET/nucleating agent blend was prepared by melting blending. The molecular structure, the thermal stability, the microstructure and the crystal structure of the nucleating agent were characterized in detail. The differential scanning calorimetry (DSC) result indicated that the addition of the nucleating agent improved the crystallization temperature and accelerated the crystallization rate of the rPET. The nucleation efficiencies (NE) of the Na-4-ClBeAmBe, Na-4-ClBeAmGl and Na-4-ClAcAmBe were increased by 87.2%, 87.3% and 41.7% compared with rPET which indicated that Na-4-ClBeAmBe and Na-4-ClBeAmGl, with their long-strip microstructures, were more conducive to promoting the nucleation of rPET. The equilibrium melting points ( ) of rPET/Na-4-ClBeAmBe, rPET/Na-4-ClBeAmGl and rPET/Na-4-ClAcAmBe were increased by 11.7 °C, 18.6 °C and 1.9 °C compared with rPET, which illustrated that the lower mismatch rate between rPET and Na-4-ClBeAmGl (0.8% in b-axis) caused Na-4-ClBeAmGl to be the most capable in inducing the epitaxial crystallization and orient growth along the b-axis direction of the rPET. The small angle X-ray diffraction (SAXS) result proved this conclusion. Meanwhile, the addition of Na-4-ClBeAmGl caused the clearest increase in the rPET of its flexural strength and heat-distortion temperature (HDT) at 20.4% and 46.7%.
Full article
(This article belongs to the Special Issue Molecular Insights into Soft Materials)
Open AccessArticle
Modified Halloysite as An Adsorbent for the Removal of Cu(II) Ions and Reactive Red 120 Dye from Aqueous Solutions
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Krzysztof Kuśmierek, Andrzej Świątkowski, Ewa Wierzbicka and Izabella Legocka
Molecules 2024, 29(13), 3099; https://doi.org/10.3390/molecules29133099 (registering DOI) - 28 Jun 2024
Abstract
The adsorption of copper ions and Reactive Red 120 azo dye (RR-120) as models of water pollutants on unmodified halloysite (H-NM), as well as halloysites modified with sulfuric acid (H-SA) and (3-aminopropyl)triethoxysilane (H-APTES), was investigated. The results showed that adsorption of both the
[...] Read more.
The adsorption of copper ions and Reactive Red 120 azo dye (RR-120) as models of water pollutants on unmodified halloysite (H-NM), as well as halloysites modified with sulfuric acid (H-SA) and (3-aminopropyl)triethoxysilane (H-APTES), was investigated. The results showed that adsorption of both the adsorbates was pH-dependent and increased with the increase in halloysite dosage. The adsorption kinetics were evaluated and the results demonstrated that the adsorption followed the pseudo-second-order model. The adsorption isotherms of Cu(II) ions and RR-120 dye on the halloysites were described satisfactorily by the Langmuir model. The maximum adsorption capacities for the Cu(II) ions were 0.169, 0.236, and 0.507 mmol/g, respectively, for H-NM, H-SA, and H-APTES indicating that the NH2-functionalization rather than the surface area of the adsorbents was responsible for the enhanced adsorption. The adsorption capacities for RR-120 dye were found to be 9.64 μmol/g for H-NM, 75.76 μmol/g for H-SA, and 29.33 μmol/g for H-APTES. The results demonstrated that APTES-functionalization and sulfuric acid activation are promising modifications, and both modified halloysites have good application potential for heavy metals as well as for azo dye removal.
Full article
(This article belongs to the Special Issue Efficient Chemical Technologies and Adsorbents for Environmental Pollution Removal and Wastes Recycling II)
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Graphical abstract
Open AccessArticle
Vanillic Acid Nanocomposite: Synthesis, Characterization Analysis, Antimicrobial, and Anticancer Potentials
by
Baskar Venkidasamy, Umadevi Subramanian, Hesham S. Almoallim, Sulaiman Ali Alharbi, Rahul Raj Chennam Lakshmikumar and Muthu Thiruvengadam
Molecules 2024, 29(13), 3098; https://doi.org/10.3390/molecules29133098 (registering DOI) - 28 Jun 2024
Abstract
Recently, nanoparticles have received considerable attention owing to their efficiency in overcoming the limitations of traditional chemotherapeutic drugs. In our study, we synthesized a vanillic acid nanocomposite using both chitosan and silver nanoparticles, tested its efficacy against lung cancer cells, and analyzed its
[...] Read more.
Recently, nanoparticles have received considerable attention owing to their efficiency in overcoming the limitations of traditional chemotherapeutic drugs. In our study, we synthesized a vanillic acid nanocomposite using both chitosan and silver nanoparticles, tested its efficacy against lung cancer cells, and analyzed its antimicrobial effects. We used several characterization techniques such as ultraviolet–visible spectroscopy (UV-Vis), field emission scanning electron microscopy (FESEM), energy-dispersive X-ray spectroscopy (EDAX), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC) to determine the stability, morphological characteristics, and properties of the biosynthesized vanillic acid nanocomposites. Furthermore, the vanillic acid nanocomposites were tested for their antimicrobial effects against Escherichia coli and Staphylococcus aureus, and Candida albicans. The data showed that the nanocomposite effectively inhibited microbes, but its efficacy was less than that of the individual silver and chitosan nanoparticles. Moreover, the vanillic acid nanocomposite exhibited anticancer effects by increasing the expression of pro-apoptotic proteins (BAX, Casp3, Casp7, cyt C, and p53) and decreasing the gene expression of Bcl-2. Overall, vanillic acid nanocomposites possess promising potential against microbes, exhibit anticancer effects, and can be effectively used for treating diseases such as cancers and infectious diseases.
Full article
(This article belongs to the Special Issue Advances in Nanomaterials for Biomedical Applications)
Open AccessArticle
Inhibition of Monoamine Oxidases by Pyridazinobenzylpiperidine Derivatives
by
Jong Min Oh, Yaren Nur Zenni, Zeynep Özdemir, Sunil Kumar, Semanur Kılıç, Mevlüt Akdağ, Azime Berna Özçelik, Hoon Kim and Bijo Mathew
Molecules 2024, 29(13), 3097; https://doi.org/10.3390/molecules29133097 (registering DOI) - 28 Jun 2024
Abstract
Monoamine oxidase inhibitors (MAOIs) have been crucial in the search for anti-neurodegenerative medications and continued to be a vital source of molecular and mechanistic diversity. Therefore, the search for selective MAOIs is one of the main areas of current drug development. To increase
[...] Read more.
Monoamine oxidase inhibitors (MAOIs) have been crucial in the search for anti-neurodegenerative medications and continued to be a vital source of molecular and mechanistic diversity. Therefore, the search for selective MAOIs is one of the main areas of current drug development. To increase the effectiveness and safety of treating Parkinson’s disease, new scaffolds for reversible MAO-B inhibitors are being developed. A total of 24 pyridazinobenzylpiperidine derivatives were synthesized and evaluated for MAO. Most of the compounds showed a higher inhibition of MAO-B than of MAO-A. Compound S5 most potently inhibited MAO-B with an IC50 value of 0.203 μM, followed by S16 (IC50 = 0.979 μM). In contrast, all compounds showed weak MAO-A inhibition. Among them, S15 most potently inhibited MAO-A with an IC50 value of 3.691 μM, followed by S5 (IC50 = 3.857 μM). Compound S5 had the highest selectivity index (SI) value of 19.04 for MAO-B compared with MAO-A. Compound S5 (3-Cl) showed greater MAO-B inhibition than the other derivatives with substituents of -Cl > -OCH3 > -F > -CN > -CH3 > -Br at the 3-position. However, the 2- and 4-position showed low MAO-B inhibition, except S16 (2-CN). In addition, compounds containing two or more substituents exhibited low MAO-B inhibition. In the kinetic study, the Ki values of S5 and S16 for MAO-B were 0.155 ± 0.050 and 0.721 ± 0.074 μM, respectively, with competitive reversible-type inhibition. Additionally, in the PAMPA, both lead compounds demonstrated blood–brain barrier penetration. Furthermore, stability was demonstrated by the 2V5Z-S5 complex by pi–pi stacking with Tyr398 and Tyr326. These results suggest that S5 and S16 are potent, reversible, selective MAO-B inhibitors that can be used as potential agents for the treatment of neurological disorders.
Full article
(This article belongs to the Special Issue Drug Design and Development for Dementia, Epilepsy, and Other Neurological Disorder Diseases)
Open AccessArticle
Optimizing Photoelectrochemical UV Imaging Photodetection: Construction of Anatase/Rutile Heterophase Homojunctions and Oxygen Vacancies Engineering in MOF-Derived TiO2
by
Yueying Ma, Yuewu Huang, Ju Huang, Zewu Xu, Yanbin Yang, Changmiao Xie, Bingke Zhang, Guanghong Ao, Zhendong Fu, Aimin Li, Dongbo Wang and Liancheng Zhao
Molecules 2024, 29(13), 3096; https://doi.org/10.3390/molecules29133096 (registering DOI) - 28 Jun 2024
Abstract
Self-powered photoelectrochemical (PEC) ultraviolet photodetectors (UVPDs) are promising for next-generation energy-saving and highly integrated optoelectronic systems. Constructing a heterojunction is an effective strategy to increase the photodetection performance of PEC UVPDs because it can promote the separation and transfer of photogenerated carriers. However,
[...] Read more.
Self-powered photoelectrochemical (PEC) ultraviolet photodetectors (UVPDs) are promising for next-generation energy-saving and highly integrated optoelectronic systems. Constructing a heterojunction is an effective strategy to increase the photodetection performance of PEC UVPDs because it can promote the separation and transfer of photogenerated carriers. However, both crystal defects and lattice mismatch lead to deteriorated device performance. Here, we introduce a structural regulation strategy to prepare TiO2 anatase-rutile heterophase homojunctions (A-R HHs) with oxygen vacancies (OVs) photoanodes through an in situ topological transformation of titanium metal–organic framework (Ti-MOF) by pyrolysis treatment. The cooperative interaction between A-R HHs and OVs suppresses carrier recombination and accelerates carrier transport, thereby significantly enhancing the photodetection performance of PEC UVPDs. The obtained device realizes a high on/off ratio of 10,752, a remarkable responsivity of 24.15 mA W−1, an impressive detectivity of 3.28 × 1011 Jones, and excellent cycling stability. More importantly, under 365 nm light illumination, a high-resolution image of “HUST” (the abbreviation of Harbin University of Science and Technology) was obtained perfectly, confirming the excellent optical imaging capability of the device. This research not only presents an advanced methodology for constructing TiO2-based PEC UVPDs, but also provides strategic guidance for enhancing their performance and practical applications.
Full article
(This article belongs to the Special Issue Recent Progress in Nanomaterials in Electrochemistry)
Open AccessArticle
Identification of Novel GANT61 Analogs with Activity in Hedgehog Functional Assays and GLI1-Dependent Cancer Cells
by
Dina Abu Rabe, Lhoucine Chdid, David R. Lamson, Christopher P. Laudeman, Michael Tarpley, Naglaa Elsayed, Ginger R. Smith, Weifan Zheng, Maria S. Dixon and Kevin P. Williams
Molecules 2024, 29(13), 3095; https://doi.org/10.3390/molecules29133095 (registering DOI) - 28 Jun 2024
Abstract
Aberrant activation of hedgehog (Hh) signaling has been implicated in various cancers. Current FDA-approved inhibitors target the seven-transmembrane receptor Smoothened, but resistance to these drugs has been observed. It has been proposed that a more promising strategy to target this pathway is at
[...] Read more.
Aberrant activation of hedgehog (Hh) signaling has been implicated in various cancers. Current FDA-approved inhibitors target the seven-transmembrane receptor Smoothened, but resistance to these drugs has been observed. It has been proposed that a more promising strategy to target this pathway is at the GLI1 transcription factor level. GANT61 was the first small molecule identified to directly suppress GLI-mediated activity; however, its development as a potential anti-cancer agent has been hindered by its modest activity and aqueous chemical instability. Our study aimed to identify novel GLI1 inhibitors. JChem searches identified fifty-two compounds similar to GANT61 and its active metabolite, GANT61-D. We combined high-throughput cell-based assays and molecular docking to evaluate these analogs. Five of the fifty-two GANT61 analogs inhibited activity in Hh-responsive C3H10T1/2 and Gli-reporter NIH3T3 cellular assays without cytotoxicity. Two of the GANT61 analogs, BAS 07019774 and Z27610715, reduced Gli1 mRNA expression in C3H10T1/2 cells. Treatment with BAS 07019774 significantly reduced cell viability in Hh-dependent glioblastoma and lung cancer cell lines. Molecular docking indicated that BAS 07019774 is predicted to bind to the ZF4 region of GLI1, potentially interfering with its ability to bind DNA. Our findings show promise in developing more effective and potent GLI inhibitors.
Full article
(This article belongs to the Special Issue Small-Molecule Modulators Targeting Emerging Therapeutic Pathways: Design, Synthesis and Biological Evaluation)
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Open AccessArticle
Increasing 1,4-Diaminobutane Production in Escherichia coli by Optimization of Cofactor PLP and NADPH Synthesis
by
Tong Sun, Yongcan Zhao, Jinjin Wang, Wenke Kang, Xiangxiang Sun, Yanling Sun, Meixue Chu, Zhengyu Liu, Fuping Lu and Ming Li
Molecules 2024, 29(13), 3094; https://doi.org/10.3390/molecules29133094 (registering DOI) - 28 Jun 2024
Abstract
1,4-diaminobutane is widely used in the industrial production of polymers, pharmaceuticals, agrochemicals and surfactants. Owing to economic and environmental concerns, there has been a growing interest in using microbes to produce 1,4-diaminobutane. However, there is lack of research on the influence of cofactors
[...] Read more.
1,4-diaminobutane is widely used in the industrial production of polymers, pharmaceuticals, agrochemicals and surfactants. Owing to economic and environmental concerns, there has been a growing interest in using microbes to produce 1,4-diaminobutane. However, there is lack of research on the influence of cofactors pyridoxal phosphate (PLP) and NADPH on the synthesis of 1,4-diaminobutane. PLP serves as a cofactor of ornithine decarboxylase in the synthesis of 1,4-diaminobutane. Additionally, the synthesis of 1 mol 1,4-diaminobutane requires 2 mol NADPH, thus necessitating consideration of NADPH balance in the efficient synthesis of 1,4-diaminobutane by Escherichia coli. The aim of this study was to enhance the synthesis efficiency of 1,4-diaminobutane through increasing production of PLP and NADPH. By optimizing the expression of the genes associated with synthesis of PLP and NADPH in E. coli, cellular PLP and NADPH levels increased, and the yield of 1,4-diaminobutane also increased accordingly. Ultimately, using glucose as the primary carbon source, the yield of 1,4-diaminobutane in the recombinant strain NAP19 reached 272 mg/L·DCW, by increased 79% compared with its chassis strain.
Full article
(This article belongs to the Special Issue Synthesis of Natural Products Using Engineered Plants and Microorganisms)
Open AccessArticle
Tailoring Fibroblast-Activation Protein Targeting for Theranostics: A Comparative Preclinical Evaluation of the 68Ga- and 177Lu-Labeled Monomeric and Dimeric Fibroblast-Activation Protein Inhibitors DOTA.SA.FAPi and DOTAGA.(SA.FAPi)2
by
Tilman Läppchen, Adrianna Bilinska, Eirinaios Pilatis, Elena Menéndez, Surachet Imlimthan, Euy Sung Moon, Ali Afshar-Oromieh, Frank Rösch, Axel Rominger and Eleni Gourni
Molecules 2024, 29(13), 3093; https://doi.org/10.3390/molecules29133093 (registering DOI) - 28 Jun 2024
Abstract
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Background: FAP radiopharmaceuticals show promise for cancer diagnosis; however, their limited tumor residency hinders treatment. This study compared two FAPi derivatives, DOTA.SA.FAPi and DOTAGA.(SA.FAPi)2, labeled with gallium-68 and lutetium-177, aiming to determine an optimum combination for creating theranostic pairs. Methods: The
[...] Read more.
Background: FAP radiopharmaceuticals show promise for cancer diagnosis; however, their limited tumor residency hinders treatment. This study compared two FAPi derivatives, DOTA.SA.FAPi and DOTAGA.(SA.FAPi)2, labeled with gallium-68 and lutetium-177, aiming to determine an optimum combination for creating theranostic pairs. Methods: The radiotracers were studied for lipophilicity, binding to human serum proteins, and binding to human cancer-associated fibroblasts (CAFs) in vitro, including saturation and internalization/externalization studies. PET/SPECT/CT and biodistribution studies were conducted in PC3 and U87MG xenografts for [68Ga]Ga-DOTA.SA.FAPi and [68Ga]Ga-DOTAGA.(SA.FAPi)2. [177Lu]Lu-DOTA.SA.FAPi and [177Lu]Lu-DOTAGA.(SA.FAPi)2, were evaluated in PC3 xenografts. Biodistribution studies of [68Ga]Ga-DOTA.SA.FAPi were performed in healthy male and female mice. Results: All radiotracers exhibited strong binding to FAP. Their internalization rate was fast while only [177Lu]Lu-DOTAGA.(SA.FAPi)2 was retained longer in CAFs. [68Ga]Ga-DOTAGA.(SA.FAPi)2 and [177Lu]Lu-DOTAGA.(SA.FAPi)2 displayed elevated lipophilicity and affinity for human serum proteins compared to [68Ga]Ga-DOTA.SA.FAPi and [177Lu]Lu-DOTA.SA.FAPi. In vivo studies revealed slower washout of [68Ga]Ga-DOTAGA.(SA.FAPi)2 within 3 h compared to [68Ga]Ga-DOTA.SA.FAPi. The tumor-to-tissue ratios of [68Ga]Ga-DOTAGA.(SA.FAPi)2 versus [68Ga]Ga-DOTA.SA.FAPi did not exhibit any significant differences. [177Lu]Lu-DOTAGA.(SA.FAPi)2 maintained a significant tumor uptake even after 96 h p.i. compared to [177Lu]Lu-DOTA.SA.FAPi. Conclusions: Dimeric compounds hold promise for therapy, while monomers are better suited for diagnostics. Finding the right combination is essential for effective disease management.
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Open AccessArticle
Analysis of the Variation in Antioxidant Activity and Chemical Composition upon the Repeated Thermal Treatment of the By-Product of the Red Ginseng Manufacturing Process
by
Yu-Dan Wang, Hui-E Zhang, Lu-Sheng Han, Gen-Yue Li, Kai-Li Yang, Yuan Zhao, Jia-Qi Wang, Yang-Bin Lai, Chang-Bao Chen and En-Peng Wang
Molecules 2024, 29(13), 3092; https://doi.org/10.3390/molecules29133092 (registering DOI) - 28 Jun 2024
Abstract
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Steamed ginseng water (SGW) is a by-product of the repeated thermal processing of red ginseng, which is characterized by a high bioactive content, better skin care activity, and a large output. However, its value has been ignored, resulting in environmental pollution and resource
[...] Read more.
Steamed ginseng water (SGW) is a by-product of the repeated thermal processing of red ginseng, which is characterized by a high bioactive content, better skin care activity, and a large output. However, its value has been ignored, resulting in environmental pollution and resource waste. In this study, UHPLC-Q-Exactive-MS/MS liquid chromatography–mass spectrometry and multivariate statistical analysis were conducted to characterize the compositional features of the repeated thermal-treated SGW. The antioxidant activity (DPPH, ABTS, FRAP, and OH) and chemical composition (total sugars, total saponins, and reducing and non-reducing sugars) were comprehensively evaluated based on the entropy weighting method. Four comparison groups (groups 1 and 3, groups 1 and 5, groups 1 and 7, and groups 1 and 9) were screened for 37 important common difference markers using OPLS-DA analysis. The entropy weight method was used to analyze the weights of the indicators; the seventh SGW sample was reported to have a significant weight. The results of this study suggest that heat treatment time and frequency can be an important indicator value for the quality control of SGW cycling operations, which have great potential in antioxidant products.
Full article
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Open AccessReview
Biological Activities of Novel Oleanolic Acid Derivatives from Bioconversion and Semi-Synthesis
by
Nahla Triaa, Mansour Znati, Hichem Ben Jannet and Jalloul Bouajila
Molecules 2024, 29(13), 3091; https://doi.org/10.3390/molecules29133091 (registering DOI) - 28 Jun 2024
Abstract
Oleanolic acid (OA) is a vegetable chemical that is present naturally in a number of edible and medicinal botanicals. It has been extensively studied by medicinal chemists and scientific researchers due to its biological activity against a wide range of diseases. A significant
[...] Read more.
Oleanolic acid (OA) is a vegetable chemical that is present naturally in a number of edible and medicinal botanicals. It has been extensively studied by medicinal chemists and scientific researchers due to its biological activity against a wide range of diseases. A significant number of researchers have synthesized a variety of analogues of OA by modifying its structure with the intention of creating more potent biological agents and improving its pharmaceutical properties. In recent years, chemical and enzymatic techniques have been employed extensively to investigate and modify the chemical structure of OA. This review presents recent advancements in medical chemistry for the structural modification of OA, with a special focus on the biotransformation, semi-synthesis and relationship between the modified structures and their biopharmaceutical properties.
Full article
(This article belongs to the Special Issue Synthesis of Bioactive Compounds: Volume II)
Open AccessArticle
Protective Effect of Polyphenolic Extracts from Hippophae rhamnoides L. and Reynoutria japonica Houtt. on Erythrocyte Membrane
by
Teresa Kaźmierczak, Katarzyna Męczarska, Sabina Lachowicz-Wiśniewska, Sylwia Cyboran-Mikołajczyk, Jan Oszmiański and Dorota Bonarska-Kujawa
Molecules 2024, 29(13), 3090; https://doi.org/10.3390/molecules29133090 (registering DOI) - 28 Jun 2024
Abstract
Sea buckthorn and Japanese knotweed are known in many traditional medicine systems to be a great source of bioactive substances. This research aims to compare the bioactivity and protective effects of the phenolic extracts of leaves from sea buckthorn and roots and leaves
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Sea buckthorn and Japanese knotweed are known in many traditional medicine systems to be a great source of bioactive substances. This research aims to compare the bioactivity and protective effects of the phenolic extracts of leaves from sea buckthorn and roots and leaves from the Japanese knotweed on erythrocytes. The polyphenol composition of the extract was analyzed using UPLC-PDA-ESI-MS/MS. The extracts’ toxicity and impact on the erythrocytes’ osmotic fragility were measured spectrophotometrically. The antioxidant activity was determined based on the inhibition of oxidation of erythrocytes and their membrane induced by 2,2′-Azobis(2-methylpropionamidine) dihydrochloride (AAPH),measured spectrophotometrically and using fluorimetry. To find the possible mechanism of the extracts’ action, extract-modified cells were observed under a microscope, and the potential localization of the extract’s phytochemical composition was checked using fluorescent probes. The results showed that the used extracts are not toxic to erythrocytes, increase their osmotic resistance, and successfully protect them against free radicals. Extract components localize on the outer part of the membrane, where they can scavenge the free radicals from the environment. Altogether, the presented extracts can greatly protect living organisms against free radicals and can be used to support the treatment of diseases caused by excess free radicals.
Full article
(This article belongs to the Special Issue Natural Polyphenols in Human Health (Volume II))
Open AccessArticle
Synthesis and Properties of Hydrophilic and Hydrophobic Deep Eutectic Solvents via Heating-Stirring and Ultrasound
by
María Isabel Martín, Irene García-Díaz, María Lourdes Rodríguez, María Concepción Gutiérrez, Francisco del Monte and Félix A. López
Molecules 2024, 29(13), 3089; https://doi.org/10.3390/molecules29133089 (registering DOI) - 28 Jun 2024
Abstract
Abstract: Deep eutectic solvents (DESs) have emerged as a greener alternative to other more polluting traditional solvents and have attracted a lot of interest in the last two decades. The DESs are less toxic dissolvents and have a lower environmental footprint. This paper
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Abstract: Deep eutectic solvents (DESs) have emerged as a greener alternative to other more polluting traditional solvents and have attracted a lot of interest in the last two decades. The DESs are less toxic dissolvents and have a lower environmental footprint. This paper presents an alternative synthesis method to the classical heating–stirring method. The ultrasound method is one of the most promising synthesis methods for DESs in terms of yield and energy efficiency. Therefore, the ultrasound synthesis method was studied to obtain hydrophobic (Aliquat 336:L-Menthol (3:7); Lidocaine:Decanoic acid (1:2)) and hydrophilic DESs based on choline chloride, urea, ethylene glycol and oxalic acid. The physical characterization of DESs via comparison of Fourier transform infrared (FTIR) spectra showed no difference between the DESs obtained by heating–stirring and ultrasound synthesis methods. The study and comparison of all the prepared DESs were carried out via nuclear magnetic resonance spectroscopy (NMR). The density and viscosity properties of DESs were evaluated. The density values were similar for both synthesis methods. However, differences in viscosity values were detected due to the presence of some water in hygroscopic DESs.
Full article
(This article belongs to the Special Issue New Advances in Deep Eutectic Solvents)
Open AccessArticle
In Vitro Multi-Bioactive Potential of Enzymatic Hydrolysis of a Non-Toxic Jatropha curcas Cake Protein Isolate
by
Olloqui Enrique Javier, González-Rodríguez Maurilio Alejandro, Contreras-López Elizabeth, Pérez-Flores Jesús Guadalupe, Pérez-Escalante Emmanuel, Moreno-Seceña Juan Carlos and Martínez-Carrera Daniel
Molecules 2024, 29(13), 3088; https://doi.org/10.3390/molecules29133088 (registering DOI) - 28 Jun 2024
Abstract
The Jatropha curcas cake, a protein-rich by-product of biofuel production, was the subject of our study. We identified and quantified the ACE inhibitory, antioxidant, and antidiabetic activities of bioactive peptides from a Jatropha curcas L. var Sevangel protein isolate. The protein isolate (20.44%
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The Jatropha curcas cake, a protein-rich by-product of biofuel production, was the subject of our study. We identified and quantified the ACE inhibitory, antioxidant, and antidiabetic activities of bioactive peptides from a Jatropha curcas L. var Sevangel protein isolate. The protein isolate (20.44% recovered dry matter, 38.75% protein content, and 34.98% protein yield) was subjected to two enzyme systems for hydrolysis: alcalase (PEJA) and flavourzyme (PEJF), recording every 2 h until 8 h had passed. The highest proteolytic capacity in PEJA was reached at 2 h (4041.38 ± 50.89), while in PEJF, it was reached at 6 h (3435.16 ± 59.31). Gel electrophoresis of the PEJA and PEJF samples showed bands corresponding to peptides smaller than 10 kDa in both systems studied. The highest values for the antioxidant capacity (DPPH) were obtained at 4 h for PEJA (56.17 ± 1.14), while they were obtained at 6 h for PEJF (26.64 ± 0.52). The highest values for the antihypertensive capacity were recorded at 6 h (86.46 ± 1.85) in PEJF. The highest antidiabetic capacity obtained for PEJA and PEJF was observed at 6 h, 68.86 ± 8.27 and 52.75 ± 2.23, respectively. This is the first report of their antidiabetic activity. Notably, alcalase hydrolysate outperformed flavourzyme hydrolysate and the cereals reported in other studies, confirming its better multi-bioactivity.
Full article
(This article belongs to the Special Issue Bioactive Compounds from Functional Foods, 2nd Edition)
Open AccessArticle
Sedimentation of a Charged Soft Sphere within a Charged Spherical Cavity
by
Yong-Jie Lin and Huan J. Keh
Molecules 2024, 29(13), 3087; https://doi.org/10.3390/molecules29133087 (registering DOI) - 28 Jun 2024
Abstract
The sedimentation of a soft particle composed of an uncharged hard sphere core and a charged porous surface layer inside a concentric charged spherical cavity full of a symmetric electrolyte solution is analyzed in a quasi-steady state. By using a regular perturbation method
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The sedimentation of a soft particle composed of an uncharged hard sphere core and a charged porous surface layer inside a concentric charged spherical cavity full of a symmetric electrolyte solution is analyzed in a quasi-steady state. By using a regular perturbation method with small fixed charge densities of the soft sphere and cavity wall, a set of linearized electrokinetic equations relevant to the fluid velocity field, electrical potential profile, and ionic electrochemical potential energy distributions are solved. A closed-form formula for the sedimentation velocity of the soft sphere is obtained as a function of the ratios of core-to-particle radii, particle-to-cavity radii, particle radius-to-Debye screening length, and particle radius-to-porous layer permeation length. The existence of the surface charge on the cavity wall increases the settling velocity of the charged soft sphere, principally because of the electroosmotic enhancement of fluid recirculation within the cavity induced by the sedimentation potential gradient. When the porous layer space charge and cavity wall surface charge have the same sign, the particle velocity is generally enhanced by the presence of the cavity. When these fixed charges have opposite signs, the particle velocity will be enhanced/reduced by the presence of the cavity if the wall surface charge density is sufficiently large/small relative to the porous layer space charge density in magnitude. The effect of the wall surface charge on the sedimentation of the soft sphere increases with decreases in the ratios of core-to-particle radii, particle-to-cavity radii, and particle radius-to-porous layer permeation length but is not a monotonic function of the ratio of particle radius-to-Debye length.
Full article
(This article belongs to the Special Issue Electrokinetic Motions of Colloidal Particles and Polymeric Fluid Mechanics)
Open AccessArticle
Synthesis and In Silico Analysis of New Polyheterocyclic Molecules Derived from [1,4]-Benzoxazin-3-one and Their Inhibitory Effect against Pancreatic α-Amylase and Intestinal α-Glucosidase
by
Mohamed Ellouz, Aziz Ihammi, Abdellah Baraich, Ayoub Farihi, Darifa Addichi, Saliha Loughmari, Nada Kheira Sebbar, Mohamed Bouhrim, Ramzi A. Mothana, Omar M. Noman, Bruno Eto, Fatiha Chigr and Mohammed Chigr
Molecules 2024, 29(13), 3086; https://doi.org/10.3390/molecules29133086 (registering DOI) - 28 Jun 2024
Abstract
This study focuses on synthesizing a new series of isoxazolinyl-1,2,3-triazolyl-[1,4]-benzoxazin-3-one derivatives 5a–5o. The synthesis method involves a double 1,3-dipolar cycloaddition reaction following a “click chemistry” approach, starting from the respective [1,4]-benzoxazin-3-ones. Additionally, the study aims to evaluate the antidiabetic potential
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This study focuses on synthesizing a new series of isoxazolinyl-1,2,3-triazolyl-[1,4]-benzoxazin-3-one derivatives 5a–5o. The synthesis method involves a double 1,3-dipolar cycloaddition reaction following a “click chemistry” approach, starting from the respective [1,4]-benzoxazin-3-ones. Additionally, the study aims to evaluate the antidiabetic potential of these newly synthesized compounds through in silico methods. This synthesis approach allows for the combination of three heterocyclic components: [1,4]-benzoxazin-3-one, 1,2,3-triazole, and isoxazoline, known for their diverse biological activities. The synthesis procedure involved a two-step process. Firstly, a 1,3-dipolar cycloaddition reaction was performed involving the propargylic moiety linked to the [1,4]-benzoxazin-3-one and the allylic azide. Secondly, a second cycloaddition reaction was conducted using the product from the first step, containing the allylic part and an oxime. The synthesized compounds were thoroughly characterized using spectroscopic methods, including 1H NMR, 13C NMR, DEPT-135, and IR. This molecular docking method revealed a promising antidiabetic potential of the synthesized compounds, particularly against two key diabetes-related enzymes: pancreatic α-amylase, with the two synthetic molecules 5a and 5o showing the highest affinity values of 9.2 and 9.1 kcal/mol, respectively, and intestinal α-glucosidase, with the two synthetic molecules 5n and 5e showing the highest affinity values of −9.9 and −9.6 kcal/mol, respectively. Indeed, the synthesized compounds have shown significant potential as antidiabetic agents, as indicated by molecular docking studies against the enzymes α-amylase and α-glucosidase. Additionally, ADME analyses have revealed that all the synthetic compounds examined in our study demonstrate high intestinal absorption, meet Lipinski’s criteria, and fall within the required range for oral bioavailability, indicating their potential suitability for oral drug development.
Full article
(This article belongs to the Special Issue Advances in Synthesis and Biological Activity of Novel Derivatives Based on Five-Membered Heterocyclic Scaffolds and Their Intermediates—Second Edition)
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Open AccessArticle
Hierarchical Y Zeolite-Based Catalysts for VGO Cracking: Impact of Carbonaceous Species on Catalyst Acidity and Specific Surface Area
by
Jayson Fals, Juan Francisco Garcia-Valencia, Esneyder Puello-Polo, Fernando Tuler and Edgar Márquez
Molecules 2024, 29(13), 3085; https://doi.org/10.3390/molecules29133085 (registering DOI) - 28 Jun 2024
Abstract
The performance of catalysts prepared from hierarchical Y zeolites has been studied during the conversion of vacuum gas oil (VGO) into higher-value products. Two different catalysts have been studied: CatY.0.00 was obtained from the standard zeolite (Y-0.00-M: without alkaline treatment) and CatY.0.20 was
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The performance of catalysts prepared from hierarchical Y zeolites has been studied during the conversion of vacuum gas oil (VGO) into higher-value products. Two different catalysts have been studied: CatY.0.00 was obtained from the standard zeolite (Y-0.00-M: without alkaline treatment) and CatY.0.20 was prepared from the desilicated zeolite (Y-0-20-M: treated with 0.20 M NaOH). The cracking tests were carried out in a microactivity test (MAT) unit with a fixed-bed reactor at 550 °C in the 20–50 s reaction time range, with a catalyst mass of 3 g and a mass flow rate of VGO of 2.0 g/min. The products obtained were grouped according to their boiling point range in dry gas (DG), liquefied petroleum gas (LPG), naphtha, and coke. The results showed a greater conversion and selectivity to gasoline with the CatY.0.20 catalyst, along with improved quality (RON) of the C5–C12 cut. Conversely, the CatY.0.00 catalyst (obtained from the Y-0.00-M zeolite) showed greater selectivity to gases (DG and LPG), attributable to the electronic confinement effect within the microporous channels of the zeolite. The nature of coke has been studied using different analysis techniques and the impact on the catalysts by comparing the properties of the fresh and deactivated catalysts. The coke deposited on the catalyst surfaces was responsible for the loss of activity; however, the CatY.0.20 catalyst showed greater resistance to deactivation by coke, despite showing the highest selectivity. Given that the reaction occurs in the acid sites of the zeolite and not in the matrix, the increased degree of mesoporosity of the zeolite in the CatY.0.20 catalyst facilitated the outward diffusion of products from the zeolitic channels to the matrix, thereby preserving greater activity.
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(This article belongs to the Special Issue New Insights into Porous Materials in Adsorption and Catalysis)
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Open AccessArticle
Effect of Electrolysis Conditions on Electrodeposition of Cobalt–Tin Alloys, Their Structure, and Wettability by Liquids
by
Ewa Rudnik, Grzegorz Włoch and Monika Walkowicz
Molecules 2024, 29(13), 3084; https://doi.org/10.3390/molecules29133084 (registering DOI) - 28 Jun 2024
Abstract
The aim of this study was a systematic analysis of the influence of anions (chloride and sulfate) on the electrochemical behavior of the Co-Sn system during codeposition from gluconate baths. The pH-dependent multiple equilibria in cobalt–tin baths were calculated using stability constants. The
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The aim of this study was a systematic analysis of the influence of anions (chloride and sulfate) on the electrochemical behavior of the Co-Sn system during codeposition from gluconate baths. The pH-dependent multiple equilibria in cobalt–tin baths were calculated using stability constants. The codeposition of the metals was characterized thermodynamically considering the formation of various CoxSny intermetallic phases. The alloys obtained at different potentials were characterized in terms of their elemental (EDS and anodic stripping) and phase compositions (XRD), the development of preferred orientation planes (texture coefficients), surface morphology (SEM), and wettability (water; diiodomethane; surface energy). The mass of the deposits and cathodic current efficiencies were strongly dependent on both the deposition potential and the bath composition. The morphology and composition of the alloys were mainly dependent on the deposition potential, while the effect of the anions was less emphasized. Two-phase alloys were produced at potentials −0.9 V (Ag/AgCl) and lower, and they consisted of a mixture of tetragonal tin and an uncommon tetragonal CoSn phase. The preferential orientation planes of tin grains were dependent on the cobalt incorporation into the deposits and anion type in the bath, while the latter did not affect the preferential orientation plane of the CoSn phase. The surface wettability of the alloys displayed hydrophobicity and oleophilicity originating from the hierarchical porous surface topography rather than the elemental or phase composition. The codeposition of the metals occurs within the progressive nucleation model, but at more electronegative potentials and in the presence of sulfate ions, a transition from progressive to instantaneous nucleation can be possible. This correlated well with the partial polarization curves of the alloy deposition and the texture of the tin phase.
Full article
(This article belongs to the Section Electrochemistry)
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