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Keywords = imidazole N-oxides

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18 pages, 3370 KiB  
Article
Exploring a Novel Anti-Inflammatory Therapy for Diabetic Retinopathy Based on Glyco-Zeolitic-Imidazolate Frameworks
by Elena Díaz-Paredes, Francisco Martín-Loro, Rocío Rodríguez-Marín, Laura Gómez-Jaramillo, Elena M. Sánchez-Fernández, Carolina Carrillo-Carrión and Ana I. Arroba
Pharmaceutics 2025, 17(6), 791; https://doi.org/10.3390/pharmaceutics17060791 - 17 Jun 2025
Viewed by 692
Abstract
Background/Objectives: Diabetic retinopathy is an ocular disease caused by changes in the expression of inflammatory mediators and increased oxidative stress in the retina and is the leading cause of vision loss in diabetic patients. Currently, there is no treatment capable of reversing retinal [...] Read more.
Background/Objectives: Diabetic retinopathy is an ocular disease caused by changes in the expression of inflammatory mediators and increased oxidative stress in the retina and is the leading cause of vision loss in diabetic patients. Currently, there is no treatment capable of reversing retinal damage, which represents a significant burden on the quality of life of patients. (1R)-1-Dodecylsulfonyl-5N,6O-oxomethylidenenojirimycin stands outs as a prototype of the sp2-iminoglycolipids family for its beneficial neuroprotective effect against this chronic eye disease. Critical issues related to the low solubility and bioavailability of this glycolipid in biological settings are overcome by its encapsulation in a Zeolitic-Imidazolate Framework (ZIF) structure, resulting in homogeneous and biocompatible GlycoZIF nanoparticles. Cell studies show an enhanced cellular uptake compared with the free glycolipid, and importantly, its bioactivity is preserved once released inside cells. Methods: Extensive in vitro and ex vivo assays with diabetic retinopathy models unveil the mechanistic pathways of the designed GlycoZIF. Results: A reduction in proinflammatory mediators, increased heme oxygenase-1 level, inhibition of NLRP3 inflammasome, and reduced reactive gliosis is shown. Conclusions: These findings demonstrate for the first time the potential of Glyco-modified ZIFs for the treatment of diabetes-related ocular problems by controlling the immune-mediated inflammatory response. Full article
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19 pages, 2197 KiB  
Article
Antimicrobial Activity of Anionic Bis(N-Heterocyclic Carbene) Silver Complexes
by Carlos J. Carrasco, Francisco Montilla, Eduardo Villalobo, Manuel Angulo, Eleuterio Álvarez and Agustín Galindo
Molecules 2024, 29(19), 4608; https://doi.org/10.3390/molecules29194608 - 27 Sep 2024
Cited by 5 | Viewed by 1200
Abstract
The antimicrobial properties of a series of anionic bis(carbene) silver complexes Na3[Ag(NHCR)2] were investigated (2a2g and 2c′, where NHCR is a 2,2′-(imidazol-2-ylidene)dicarboxylate-type N-heterocyclic carbene). The complexes were synthesized by the interaction [...] Read more.
The antimicrobial properties of a series of anionic bis(carbene) silver complexes Na3[Ag(NHCR)2] were investigated (2a2g and 2c′, where NHCR is a 2,2′-(imidazol-2-ylidene)dicarboxylate-type N-heterocyclic carbene). The complexes were synthesized by the interaction of imidazolium dicarboxylate compounds with silver oxide in the presence of aqueous sodium hydroxide. Complexes 2f,g were characterized analytically and spectroscopically, and the ligand precursor 1f and complexes 2c and 2g were structurally identified by X-ray diffraction methods. The anions of 2c and 2g, [Ag(NHCR)2]3−, showed a typical linear disposition of Ccarbene-Ag-Ccarbene atoms and an uncommonly eclipsed conformation of carbene ligands. The antimicrobial properties of complexes 2ag, which contains chiral (2b2e and 2c′) and non-chiral derivatives (2a,f,g), were evaluated against Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa, and a Gram-positive bacterium, Staphylococcus aureus. From the observed values of the minimal inhibitory concentration and minimal bactericidal concentration, complexes 2a and 2b showed the best antimicrobial activity against all strains. An interesting chirality–antimicrobial relationship was found, and eutomer 2c′ showed better activity than its enantiomer 2c against the three bacteria. Furthermore, these complexes were investigated experimentally and theoretically by 109Ag nuclear magnetic resonance, and the electronic and steric characteristics of the dianionic carbene ligands were also examined. Full article
(This article belongs to the Special Issue Exclusive Feature Papers on Molecular Structure)
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14 pages, 3940 KiB  
Article
Cobalt–Imidazole Complexes: Effect of Anion Nature on Thermochemical Properties
by Olga V. Netskina, Dmitry A. Sukhorukov, Kirill A. Dmitruk, Svetlana A. Mukha, Igor P. Prosvirin, Alena A. Pochtar, Olga A. Bulavchenko, Alexander A. Paletsky, Andrey G. Shmakov, Alexey P. Suknev and Oxana V. Komova
Materials 2024, 17(12), 2911; https://doi.org/10.3390/ma17122911 - 14 Jun 2024
Cited by 2 | Viewed by 1444
Abstract
A solvent-free method was proposed for the synthesis of hexaimidazolecobalt(II) nitrate and perchlorate complexes—[Co(C3H4N2)6](NO3)2 and [Co(C3H4N2)6](ClO4)2—by adding cobalt salts to [...] Read more.
A solvent-free method was proposed for the synthesis of hexaimidazolecobalt(II) nitrate and perchlorate complexes—[Co(C3H4N2)6](NO3)2 and [Co(C3H4N2)6](ClO4)2—by adding cobalt salts to melted imidazole. The composition, charge state of the metal, and the structure of the resulting complexes were confirmed by elemental analysis, XPS, IR spectroscopy, and XRD. The study of the thermochemical properties of the synthesized complexes showed that [Co(C3H4N2)6](NO3)2 and [Co(C3H4N2)6](ClO4)2 are thermally stable up to 150 and 170 °C, respectively. When the critical temperature of thermal decomposition is reached, oxidative two-stage gasification is observed. In this case, the organic component of the [Co(C3H4N2)6](NO3)2 complex undergoes almost complete gasification to form Co3O4 with a slight admixture of CoO, which makes it attractive as a component of gas-generation compositions, like airbags. Full article
(This article belongs to the Special Issue Advanced Materials: Process, Properties, and Applications)
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30 pages, 10231 KiB  
Article
Novel C3-Methylene-Bridged Indole Derivatives with and without Substituents at N1: The Influence of Substituents on Their Hemolytic, Cytoprotective, and Antimicrobial Activity
by Karolina Babijczuk, Natalia Berdzik, Damian Nowak, Beata Warżajtis, Urszula Rychlewska, Justyna Starzyk, Lucyna Mrówczyńska and Beata Jasiewicz
Int. J. Mol. Sci. 2024, 25(10), 5364; https://doi.org/10.3390/ijms25105364 - 14 May 2024
Cited by 5 | Viewed by 1632
Abstract
Alkaloids are natural compounds useful as scaffolds for discovering new bioactive molecules. This study utilized alkaloid gramine to synthesize two groups of C3-substituted indole derivatives, which were either functionalized at N1 or not. The compounds were characterized by spectroscopic methods. The protective effects [...] Read more.
Alkaloids are natural compounds useful as scaffolds for discovering new bioactive molecules. This study utilized alkaloid gramine to synthesize two groups of C3-substituted indole derivatives, which were either functionalized at N1 or not. The compounds were characterized by spectroscopic methods. The protective effects of the new compounds against in vitro oxidative hemolysis induced by standard oxidant 2,2′-azobis(2-amidinopropane dihydro chloride (AAPH) on human erythrocytes as a cell model were investigated. Additionally, the compounds were screened for antimicrobial activity. The results indicated that most of the indole derivatives devoid of the N1 substitution exhibited strong cytoprotective properties. The docking studies supported the affinities of selected indole-based ligands as potential antioxidants. Furthermore, the derivatives obtained exhibited potent fungicidal properties. The structures of the eight derivatives possessing indole moiety bridged to the imidazole-, benzimidazole-, thiazole-, benzothiazole-, and 5-methylbenzothiazoline-2-thiones were determined by X-ray diffraction. The C=S bond lengths in the thioamide fragment pointed to the involvement of zwitterionic structures of varying contribution. The predominance of zwitterionic mesomers may explain the lack of cytoprotective properties, while steric effects, which limit multiple the hydrogen-bond acceptor properties of a thione sulfur, seem to be responsible for the high hemolytic activity. Full article
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18 pages, 3933 KiB  
Article
Copper(II), Nickel(II) and Zinc(II) Complexes of Peptide Fragments of Tau Protein
by Zsuzsa Kastal, Adrienn Balabán, Szilvia Vida, Csilla Kállay, Lajos Nagy, Katalin Várnagy and Imre Sóvágó
Molecules 2024, 29(10), 2171; https://doi.org/10.3390/molecules29102171 - 7 May 2024
Cited by 7 | Viewed by 1381
Abstract
Copper(II), nickel(II) and zinc(II) complexes of various peptide fragments of tau protein were studied by potentiometric and spectroscopic techniques. All peptides contained one histidyl residue and represented the sequences of tau(91–97) (Ac-AQPHTEI-NH2), tau(385–390) (Ac-KTDHGA-NH2) and tau(404–409) (Ac-SPRHLS-NH2). [...] Read more.
Copper(II), nickel(II) and zinc(II) complexes of various peptide fragments of tau protein were studied by potentiometric and spectroscopic techniques. All peptides contained one histidyl residue and represented the sequences of tau(91–97) (Ac-AQPHTEI-NH2), tau(385–390) (Ac-KTDHGA-NH2) and tau(404–409) (Ac-SPRHLS-NH2). Imidazole-N donors of histidine were the primary metal binding sites for all peptides and all metal ions, but in the case of copper(II) and nickel(II), the deprotonated amide groups were also involved in metal binding by increasing pH. The most stable complexes were formed with copper(II) ions, but the presence of prolyl residues resulted in significant changes in the thermodynamic stability and speciation of the systems. It was also demonstrated that nickel(II) and especially zinc(II) complexes have relatively low thermodynamic stability with these peptides. The copper(II)-catalyzed oxidation of the peptides was also studied. In the presence of H2O2, the fragmentation of peptides was detected in all cases. In the simultaneous presence of H2O2 and ascorbic acid, the fragmentation of the peptide is less preferred, and the formation of 2-oxo-histidine also occurs. Full article
(This article belongs to the Section Medicinal Chemistry)
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14 pages, 6214 KiB  
Article
Investigation on Gold Dissolution Performance and Mechanism in Imidazolium Cyanate Ionic Liquids
by Na Zhang, Yuxin Zhang, Zhengyu Liu, Ziyuan Liu, Chunbao Sun, N. Emre Altun and Jue Kou
Molecules 2024, 29(4), 897; https://doi.org/10.3390/molecules29040897 - 18 Feb 2024
Cited by 2 | Viewed by 1962
Abstract
To explore green gold leaching reagents, a series of imidazolium cyanate ionic liquids (ILs), 1-ethyl-3-methyl-imidazolium cyanate ([C2MIM][OCN]), 1-propyl-3-methyl-imidazolium cyanate ([C3MIM][OCN]) and 1-butyl-3-methyl-imidazolcyanate ([C4MIM][OCN]) were synthesized and characterized by Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared Spectroscopy (FTIR) [...] Read more.
To explore green gold leaching reagents, a series of imidazolium cyanate ionic liquids (ILs), 1-ethyl-3-methyl-imidazolium cyanate ([C2MIM][OCN]), 1-propyl-3-methyl-imidazolium cyanate ([C3MIM][OCN]) and 1-butyl-3-methyl-imidazolcyanate ([C4MIM][OCN]) were synthesized and characterized by Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared Spectroscopy (FTIR) and thermogravimetric (TG) analysis. In this research, the imidazolium cyanates were utilized as a solute, which not only decreased the usage of ILs but also increased their gold dissolution capability. The gold dissolution performances of three imidazolium cyanates were characterized by dynamic leaching test and Scanning Electron Microscopy (SEM). The results show that the all three imidazolium cyanates had a gold dissolution ability, and the shorter the carbon chain on the imidazole ring in imidazolium cyanate, the faster the gold dissolution rate. The gold dissolution performance of [C2MIM][OCN] was the best, and the weight loss of gold leaf was 2.9 mg/cm2 at 40 °C after 120 h dissolution in [C2MIM][OCN] mixed with 10 wt. % water. Besides this, the gold dissolution rate increased with the increase in the concentration of imidazolium cyanates as well as the reaction temperature. The gold dissolution performances of imidazolium cyanates in different solvents including water, acetonitrile, dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) were also investigated, and the weaker the polarity of the solvent, the more conducive it was to the gold dissolution reaction. The mechanism of gold dissolution by imidazolium cyanates was investigated through NMR spectroscopy and Electrospray Ionization Mass Spectrometry (ESI-MS). It was inferred that during the process of gold dissolution, Au was oxidized to Au+ and the imidazolium cations were deprotonated to form N-heterocyclic carbenes, which coordinated with gold to form gold complexes and achieve gold dissolution. Full article
(This article belongs to the Section Electrochemistry)
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24 pages, 9582 KiB  
Review
Monofluoromethylation of N-Heterocyclic Compounds
by Mikhail Yu. Moskalik
Int. J. Mol. Sci. 2023, 24(24), 17593; https://doi.org/10.3390/ijms242417593 - 18 Dec 2023
Cited by 4 | Viewed by 2793
Abstract
The review focuses on recent advances in the methodologies for the formation or introduction of the CH2F moiety in N-heterocyclic substrates over the past 5 years. The monofluoromethyl group is one of the most versatile fluorinated groups used to modify [...] Read more.
The review focuses on recent advances in the methodologies for the formation or introduction of the CH2F moiety in N-heterocyclic substrates over the past 5 years. The monofluoromethyl group is one of the most versatile fluorinated groups used to modify the properties of molecules in synthetic medical chemistry. The review summarizes two strategies for the monofluoromethylation of N-containing heterocycles: direct monofluoromethylation with simple XCH2F sources (for example, ICH2F) and the assembly of N-heterocyclic structures from CH2F-containing substrates. The review describes the monofluoromethylation of pharmaceutically important three-, five- and six-membered N-heterocycles: pyrrolidines, pyrroles, indoles, imidazoles, triazoles, benzothiazoles, carbazoles, indazoles, pyrazoles, oxazoles, piperidines, morpholines, pyridines, quinolines and pyridazines. Assembling of 6-fluoromethylphenanthridine, 5-fluoromethyl-2-oxazolines, C5-monofluorinated isoxazoline N-oxides, and α-fluoromethyl-α-trifluoromethylaziridines is also shown. Fluoriodo-, fluorchloro- and fluorbromomethane, FCH2SO2Cl, monofluoromethyl(aryl)sulfoniummethylides, monofluoromethyl sulfides, (fluoromethyl)triphenylphosphonium iodide and 2-fluoroacetic acid are the main fluoromethylating reagents in recent works. The replacement of atoms and entire functional groups with a fluorine atom(s) leads to a change and often improvement in activity, chemical or biostability, and pharmacokinetic properties. The monofluoromethyl group is a bioisoster of -CH3, -CH2OH, -CH2NH2, -CH2CH3, -CH2NO2 and -CH2SH moieties. Bioisosteric replacement with the CH2F group is both an interesting task for organic synthesis and a pathway to modify drugs, agrochemicals and useful intermediates. Full article
(This article belongs to the Section Physical Chemistry and Chemical Physics)
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18 pages, 3392 KiB  
Article
5-Fluoro-1-Methyl-Pyrazol-4-yl-Substituted Nitronyl Nitroxide Radical and Its 3d Metal Complexes: Synthesis, Structure, and Magnetic Properties
by Ekaterina Kudryavtseva, Andrey Serykh, Bogdan Ugrak, Tatyana Dutova, Darina Nasyrova, Dmitrii Aleshin, Nikolay Efimov, Pavel Dorovatovskii, Artem Bogomyakov, Sergey Fokin, Galina Romanenko, Anna Sergeeva and Evgeny Tretyakov
Crystals 2023, 13(12), 1655; https://doi.org/10.3390/cryst13121655 - 30 Nov 2023
Cited by 4 | Viewed by 1775
Abstract
The metal–radical approach is a well-established synthetic way toward multi-spin systems that relies on the coordination of stable radical ligands with transition metal ions. The advantage offered by the use of paramagnetic ligands is that metal–radical magnetic exchange coupling is direct between the [...] Read more.
The metal–radical approach is a well-established synthetic way toward multi-spin systems that relies on the coordination of stable radical ligands with transition metal ions. The advantage offered by the use of paramagnetic ligands is that metal–radical magnetic exchange coupling is direct between the magnetic orbitals of the radical and metal ion. With the aim of further exploring this approach, crystals of four heterspin complexes, [M(hfac)2LF]2 {M = Mn, Co, or Ni and hfac = hexafluoroacetylacetonate} and [Cu(hfac)2LF]n, were obtained using a new fluorinated pyrazolyl-substituted nitronyl nitroxide radical, 4,4,5,5-tetramethyl-2-(5-fluoro-1-methyl-1H-pyrazol-4-yl)-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl (LF) as a ligand. The newly synthesized complexes were fully characterized, including X-ray crystallography and magnetometry. XRD analysis revealed that complexes [M(hfac)2LF]2 have similar dimer structures in which a metal ion is in a six-coordinated environment with four O atoms from the two hfac ligands, one radical O atom, and one pyrazole N atom from ligand LF. Nonetheless, the packing patterns of the complexes were found to be considerably different. In [Mn(hfac)2LF]2, there are no magnetically important short contacts between manganese dimers. By contrast, in [Co(hfac)2LF]2 and [Ni(hfac)2LF]2, there are short contacts between non-coordinate O atoms of nitronyl nitroxide moieties. Magnetic behaviors of [M(hfac)2LF]2 showed that the M ions and the directly coordinated radicals are strongly antiferromagnetically coupled (JMn-ON = −84.1 ± 1.5 cm−1, JCo-ON = −134.3 ± 2.6 cm−1, and JNi-ON = −276.2 ± 2.1 cm−1; H^=2JS^MS^NO). Notably, the magnetization of [Mn(hfac)2LF]2 having molecular structure proved to be accompanied by hysteresis. The [Cu(hfac)2LF]n complex has a chain-polymer structure with alternating magnetic fragments: three spin exchange clusters {ONO–Cu(II)–ONO} and {Cu(II)} ions. Despite the direct coordination of radicals, its magnetic properties are weakly ferromagnetic (JCu-ON = 14.8 ± 0.3 cm−1). Full article
(This article belongs to the Section Hybrid and Composite Crystalline Materials)
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12 pages, 2080 KiB  
Article
The Reactions of Alkenes with Phenyl-N-triflylimino-λ3-iodane: Solvent and Oxidant Impact
by Mikhail Yu. Moskalik, Anton S. Ganin and Bagrat A. Shainyan
Int. J. Mol. Sci. 2023, 24(21), 15947; https://doi.org/10.3390/ijms242115947 - 3 Nov 2023
Cited by 3 | Viewed by 1375
Abstract
The reactions of alkenes with phenyl-N-triflylimino-λ3-iodane PhI=NTf (1) have been studied in different conditions. In methylene chloride, in the presence of N-halosuccinimides, the products of mono and bis-triflamidation were obtained. In MeCN, the product of bromotriflamidation [...] Read more.
The reactions of alkenes with phenyl-N-triflylimino-λ3-iodane PhI=NTf (1) have been studied in different conditions. In methylene chloride, in the presence of N-halosuccinimides, the products of mono and bis-triflamidation were obtained. In MeCN, the product of bromotriflamidation (with NBS) with solvent interception or of bis-triflamidation (with NIS) is formed. The reaction with trans-stilbene in acetonitrile with NBS gave rise to cyclization to 2-methyl-4,5-diphenyl-1-triflyl-4,5-dihydro-1H-imidazole. In contrast, with NIS as an oxidant, both in CH2Cl2 and MeCN, the major product was 2,3-diphenyl-1-triflylaziridine formed in good yield. With NBS, aziridine is also formed but as a minor product, the major one being a mixture of diastereomers of the product of bromotriflamidation. The reaction of compound 1 with vinylcyclohexane in methylene chloride affords the mixtures of regioisomers of the products of halotriflamidation, whereas in acetonitrile, the products of solvent interception and cyclization to the imidazoline are formed. A mechanism explaining the formation of all isolated products is proposed. Full article
(This article belongs to the Special Issue Recent Advances on Fluorine Chemistry)
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25 pages, 5829 KiB  
Article
Synthesis and Characterization of Bipyridyl-(Imidazole)n Mn(II) Compounds and Their Evaluation as Potential Precatalysts for Water Oxidation
by Ge Mu, Ryan B. Gaynor, Baylee N. McIntyre, Bruno Donnadieu and Sidney E. Creutz
Molecules 2023, 28(20), 7221; https://doi.org/10.3390/molecules28207221 - 23 Oct 2023
Viewed by 2569
Abstract
Metalloenzymes make extensive use of manganese centers for oxidative catalysis, including water oxidation; the need to develop improved synthetic catalysts for these processes has long motivated the development of bioinspired manganese complexes. Herein, we report a series of bpy-(imidazole)n (n = 1 [...] Read more.
Metalloenzymes make extensive use of manganese centers for oxidative catalysis, including water oxidation; the need to develop improved synthetic catalysts for these processes has long motivated the development of bioinspired manganese complexes. Herein, we report a series of bpy-(imidazole)n (n = 1 or 2) (bpy = 2,2′-bipyridyl) ligands and their Mn2+ complexes. Four Mn2+ complexes are structurally characterized using single-crystal X-ray diffraction, revealing different tridentate and tetradentate ligand coordination modes. Cyclic voltammetry of the complexes is consistent with ligand-centered reductions and metal-centered oxidations, and UV-vis spectroscopy complemented by TD-DFT calculations shows primarily ligand-centered transitions with minor contributions from charge-transfer type transitions at higher energies. In solution, ESI-MS studies provide evidence for ligand reorganization, suggesting complex speciation behavior. The oxidation of the complexes in the presence of water is probed using cyclic voltammetry, but the low stability of the complexes in aqueous solution leads to decomposition and precludes their ultimate application as aqueous electrocatalysts. Possible reasons for the low stability and suggestions for improvement are discussed. Full article
(This article belongs to the Section Inorganic Chemistry)
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14 pages, 2879 KiB  
Article
Multiscale Porous Carbon Materials by In Situ Growth of Metal–Organic Framework in the Micro-Channel of Delignified Wood for High-Performance Water Purification
by Youngho Jeon, Dabum Kim, Suji Lee, Kangyun Lee, Youngsang Ko, Goomin Kwon, Jisoo Park, Ung-Jin Kim, Sung Yeon Hwang, Jeonghun Kim and Jungmok You
Nanomaterials 2023, 13(19), 2695; https://doi.org/10.3390/nano13192695 - 3 Oct 2023
Cited by 1 | Viewed by 2566
Abstract
Porous carbon materials are suitable as highly efficient adsorbents for the treatment of organic pollutants in wastewater. In this study, we developed multiscale porous and heteroatom (O, N)-doped activated carbon aerogels (CAs) based on mesoporous zeolitic imidazolate framework-8 (ZIF-8) nanocrystals and wood using [...] Read more.
Porous carbon materials are suitable as highly efficient adsorbents for the treatment of organic pollutants in wastewater. In this study, we developed multiscale porous and heteroatom (O, N)-doped activated carbon aerogels (CAs) based on mesoporous zeolitic imidazolate framework-8 (ZIF-8) nanocrystals and wood using 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) oxidation, in situ synthesis, and carbonization/activation. The surface carboxyl groups in a TEMPO-oxidized wood (TW) can provide considerably large nucleation sites for ZIF-8. Consequently, ZIF-8, with excellent porosity, was successfully loaded into the TW via in situ growth to enhance the specific surface area and enable heteroatom doping. Thereafter, the ZIF-8-loaded TW was subjected to a direct carbonization/activation process, and the obtained activated CA, denoted as ZIF-8/TW-CA, exhibited a highly interconnected porous structure containing multiscale (micro, meso, and macro) pores. Additionally, the resultant ZIF-8/TW-CA exhibited a low density, high specific surface area, and excellent organic dye adsorption capacity of 56.0 mg cm−3, 785.8 m2 g−1, and 169.4 mg g−1, respectively. Given its sustainable, scalable, and low-cost wood platform, the proposed high-performance CA is expected to enable the substantial expansion of strategies for environmental protection, energy storage, and catalysis. Full article
(This article belongs to the Topic Porous Materials for Energy and Environment Applications)
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13 pages, 2046 KiB  
Article
Ratio-Metric Fluorescence/Colorimetric and Smartphone-Assisted Visualization for the Detection of Dopamine Based on Cu-MOF with Catecholase-like Activity
by Yushuang Guo, Mingli Chen, Ting Yang and Jianhua Wang
Chemosensors 2023, 11(8), 431; https://doi.org/10.3390/chemosensors11080431 - 3 Aug 2023
Cited by 8 | Viewed by 2643
Abstract
As the most abundant catecholamine neurotransmitter in the brain, dopamine plays an important role in the normal physiological process, and its level in urine also changes during human pathological processes. In clinic, the detection of dopamine in urine is a potential marker for [...] Read more.
As the most abundant catecholamine neurotransmitter in the brain, dopamine plays an important role in the normal physiological process, and its level in urine also changes during human pathological processes. In clinic, the detection of dopamine in urine is a potential marker for the diagnosis and the treatment of endocrine-related diseases. In this work, a copper metal organic framework with catecholase-like activity was prepared via the precipitation of Cu2+ and imidazole, simulating the N-Cu coordination environment in the active site of catecholase. Cu-MOF (the copper–metal organic framework) can catalyze the oxidation of DA (dopamine) to dopaquinone using O2 in the air. The oxidation product can further react with 1,3-dihydroxynaphthalene to produce a fluorophore product. Based on the above reaction, a multimodal sensing platform with three signal outputs, including ratio-metric fluorescence, absorbance and digital information extracted from smartphone images for simple and sensitive determination of DA, was proposed, with detection limits of 0.0679, 0.3206, and 0.3718 μM, respectively. This multimodal sensing platform was able to detect DA in body fluid in a self-correcting way, as demonstrated by the successful determination of DA in normal human urine samples, and samples with a high level of interference. Full article
(This article belongs to the Special Issue Nanoparticles in Chemical and Biological Sensing)
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11 pages, 1347 KiB  
Article
Metal-Free Eliminative C-H Arylthiolation of 2H-Imidazole N-Oxides with Thiophenols
by Egor A. Nikiforov, Nailya F. Vaskina, Timofey D. Moseev, Mikhail V. Varaksin, Valery N. Charushin and Oleg N. Chupakhin
Chemistry 2023, 5(3), 1477-1487; https://doi.org/10.3390/chemistry5030100 - 24 Jun 2023
Cited by 5 | Viewed by 2015
Abstract
A synthetic strategy based on reactions of cyclic imine oxides, namely 2H-imidazole 1-oxides, with thiophenols mediated by acetyl chloride was successfully applied as a convenient tool to obtain a series of novel azaheterocyclic molecules, including water-soluble hydrochloride forms. Optimized reaction conditions [...] Read more.
A synthetic strategy based on reactions of cyclic imine oxides, namely 2H-imidazole 1-oxides, with thiophenols mediated by acetyl chloride was successfully applied as a convenient tool to obtain a series of novel azaheterocyclic molecules, including water-soluble hydrochloride forms. Optimized reaction conditions found herein for the nucleophilic substitution of hydrogen (SNH) in non-aromatic azaheterocyclic substrates via the “addition-elimination” (SNH AE) scheme enabled 15 arylthiolated 2H-imidazoles to be prepared in yields of up to 90%. The developed methodology discloses an original synthetic way to obtain numerous azaheterocyclic molecules, which are of interest in the field of medicinal chemistry and materials science. Full article
(This article belongs to the Section Molecular Organics)
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20 pages, 3216 KiB  
Article
Novel 2-alkythio-4-chloro-N-[imino(heteroaryl)methyl]benzenesulfonamide Derivatives: Synthesis, Molecular Structure, Anticancer Activity and Metabolic Stability
by Beata Żołnowska, Jarosław Sławiński, Mariusz Belka, Tomasz Bączek, Jarosław Chojnacki and Anna Kawiak
Int. J. Mol. Sci. 2023, 24(11), 9768; https://doi.org/10.3390/ijms24119768 - 5 Jun 2023
Cited by 3 | Viewed by 3241
Abstract
A series of novel 2-alkythio-4-chloro-N-[imino-(heteroaryl)methyl]benzenesulfonamide derivatives, 824, were synthesized in the reaction of the N-(benzenesulfonyl)cyanamide potassium salts 17 with the appropriate mercaptoheterocycles. All the synthesized compounds were evaluated for their anticancer activity in HeLa, HCT-116 [...] Read more.
A series of novel 2-alkythio-4-chloro-N-[imino-(heteroaryl)methyl]benzenesulfonamide derivatives, 824, were synthesized in the reaction of the N-(benzenesulfonyl)cyanamide potassium salts 17 with the appropriate mercaptoheterocycles. All the synthesized compounds were evaluated for their anticancer activity in HeLa, HCT-116 and MCF-7 cell lines. The most promising compounds, 1113, molecular hybrids containing benzenesulfonamide and imidazole moieties, selectively showed a high cytotoxic effect in HeLa cancer cells (IC50: 6–7 μM) and exhibited about three times less cytotoxicity against the non-tumor cell line HaCaT cells (IC50: 18–20 μM). It was found that the anti-proliferative effects of 11, 12 and 13 were associated with their ability to induce apoptosis in HeLa cells. The compounds increased the early apoptotic population of cells, elevated the percentage of cells in the sub-G1 phase of the cell cycle and induced apoptosis through caspase activation in HeLa cells. For the most active compounds, susceptibility to undergo first-phase oxidation reactions in human liver microsomes was assessed. The results of the in vitro metabolic stability experiments indicated values of the factor t½ for 1113 in the range of 9.1–20.3 min and suggested the hypothetical oxidation of these compounds to sulfenic and subsequently sulfinic acids as metabolites. Full article
(This article belongs to the Section Biochemistry)
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Article
Oxidative Stress, Cytotoxic and Inflammatory Effects of Azoles Combinatorial Mixtures in Sertoli TM4 Cells
by Sabrina Petricca, Veronica Carnicelli, Carla Luzi, Benedetta Cinque, Giuseppe Celenza and Roberto Iorio
Antioxidants 2023, 12(6), 1142; https://doi.org/10.3390/antiox12061142 - 24 May 2023
Cited by 11 | Viewed by 2787
Abstract
Triazole and imidazole fungicides are an emerging class of contaminants with an increasing and ubiquitous presence in the environment. In mammals, their reproductive toxicity has been reported. Concerning male reproduction, a combinatorial activity of tebuconazole (TEB; triazole fungicide) and econazole (ECO; imidazole compound) [...] Read more.
Triazole and imidazole fungicides are an emerging class of contaminants with an increasing and ubiquitous presence in the environment. In mammals, their reproductive toxicity has been reported. Concerning male reproduction, a combinatorial activity of tebuconazole (TEB; triazole fungicide) and econazole (ECO; imidazole compound) in inducing mitochondrial impairment, energy depletion, cell cycle arrest, and the sequential activation of autophagy and apoptosis in Sertoli TM4 cells (SCs) has recently been demonstrated. Given the strict relationship between mitochondrial activity and reactive oxygen species (ROS), and the causative role of oxidative stress (OS) in male reproductive dysfunction, the individual and combined potential of TEB and ECO in inducing redox status alterations and OS was investigated. Furthermore, considering the impact of cyclooxygenase (COX)-2 and tumor necrosis factor-alpha (TNF-α) in modulating male fertility, protein expression levels were assessed. In the present study, we demonstrate that azoles-induced cytotoxicity is associated with a significant increase in ROS production, a drastic reduction in superoxide dismutase (SOD) and GSH-S-transferase activity levels, and a marked increase in the levels of oxidized (GSSG) glutathione. Exposure to azoles also induced COX-2 expression and increased TNF-α production. Furthermore, pre-treatment with N-acetylcysteine (NAC) mitigates ROS accumulation, attenuates COX-2 expression and TNF-α production, and rescues SCs from azole-induced apoptosis, suggesting a ROS-dependent molecular mechanism underlying the azole-induced cytotoxicity. Full article
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