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Journal of the American Chemical Society Jul 2022Catenanes composed of two achiral rings that are oriented (C symmetry) because of the sequence of atoms they contain are referred to as topologically chiral. Here, we...
Catenanes composed of two achiral rings that are oriented (C symmetry) because of the sequence of atoms they contain are referred to as topologically chiral. Here, we present the synthesis of a highly enantioenriched catenane containing a related but overlooked "co-conformationally 'topologically' chiral" stereogenic unit, which arises when a bilaterally symmetric C ring is desymmetrized by the position of an oriented macrocycle.
Topics: Anthracenes; Catenanes
PubMed: 35763555
DOI: 10.1021/jacs.2c02029 -
Journal of Materials Chemistry. B Jan 2020We synthesized an anthracene derivative with solvatochromic properties to be used as a molecular probe for membrane dynamics and supramolecular organization. A nine... (Comparative Study)
Comparative Study
We synthesized an anthracene derivative with solvatochromic properties to be used as a molecular probe for membrane dynamics and supramolecular organization. A nine carbon atom acyl chain and a dimethylamino substitution were introduced at positions 2 and 6 of the anthracene ring, respectively. This derivative, 2-nonanoyl-6-(dimethylamino)anthracene (termed CAPRYDAA), is a molecular probe designed to mimic the well-known membrane probe LAURDAN's location and response in the lipid membranes. Due to the larger distance between the electron donor and acceptor groups, its absorption and emission bands are red-shifted according to the polarity of the media. The photophysical behavior of CAPRYDAA was measured in homogeneous media, synthetic bilayer and cells, both in a cuvette and in a fluorescence microscope, using one and two-photon excitation. Our results show a comparable physicochemical behavior of CAPRYDAA with LAURDAN, but with the advantage of using visible light (488 nm) as an excitation source. CAPRYDAA was also excitable by two-photon laser sources, making it easy to combine CAPRYDAA with either blue or red emission probes. In GUVs or cells, CAPRYDAA can discriminate the lipid phases and liquid-liquid phase heterogeneity. This new membrane probe shows the bathochromic properties of the PRODAN-based probes designed by Weber, overcoming the need for UV or two-photon excitation and facilitating the studies on the membrane properties using regular confocal microscopes.
Topics: 2-Naphthylamine; Animals; Anthracenes; Cell Membrane; Fluorescent Dyes; Membrane Lipids; Mice; Microscopy, Fluorescence; NIH 3T3 Cells; Spectrometry, Fluorescence
PubMed: 31769463
DOI: 10.1039/c9tb01738k -
Molecules (Basel, Switzerland) Mar 2023The ability to degrade aromatic hydrocarbons, including (i) benzene, toluene, xylene, naphthalene, anthracene, phenanthrene, benzo[a]anthracene, and benzo[a]pyrene; (ii)...
The ability to degrade aromatic hydrocarbons, including (i) benzene, toluene, xylene, naphthalene, anthracene, phenanthrene, benzo[a]anthracene, and benzo[a]pyrene; (ii) polar substituted derivatives of benzene, including phenol and aniline; (iii) N-heterocyclic compounds, including pyridine; 2-, 3-, and 4-picolines; 2- and 6-lutidine; 2- and 4-hydroxypyridines; (iv) derivatives of aromatic acids, including coumarin, of 133 strains from the Regional Specialized Collection of Alkanotrophic Microorganisms was demonstrated. The minimal inhibitory concentrations of these aromatic compounds for varied in a wide range from 0.2 up to 50.0 mM. Xylene and polycyclic aromatic hydrocarbons (PAHs) were the less-toxic and preferred aromatic growth substrates. bacteria introduced into the PAH-contaminated model soil resulted in a 43% removal of PAHs at an initial concentration 1 g/kg within 213 days, which was three times higher than that in the control soil. As a result of the analysis of biodegradation genes, metabolic pathways for aromatic hydrocarbons, phenol, and nitrogen-containing aromatic compounds in , proceeding through the formation of catechol as a key metabolite with its following ortho-cleavage or via the hydrogenation of aromatic rings, were verified.
Topics: Benzene; Rhodococcus; Polycyclic Aromatic Hydrocarbons; Hydrocarbons, Aromatic; Anthracenes; Biodegradation, Environmental; Phenols; Soil; Soil Pollutants
PubMed: 36903638
DOI: 10.3390/molecules28052393 -
British Journal of Pharmacology May 2018Although chloride channels are involved in several physiological processes and acquired diseases, the availability of compounds selectively targeting CLC proteins is...
BACKGROUND AND PURPOSE
Although chloride channels are involved in several physiological processes and acquired diseases, the availability of compounds selectively targeting CLC proteins is limited. ClC-1 channels are responsible for sarcolemma repolarization after an action potential in skeletal muscle and have been associated with myotonia congenita and myotonic dystrophy as well as with other muscular physiopathological conditions. To date only a few ClC-1 blockers have been discovered, such as anthracene-9-carboxylic acid (9-AC) and niflumic acid (NFA), whereas no activator exists. The absence of a ClC-1 structure and the limited information regarding the binding pockets in CLC channels hamper the identification of improved modulators.
EXPERIMENTAL APPROACH
Here we provide an in-depth characterization of drug binding pockets in ClC-1 through an integrated in silico and experimental approach. We first searched putative cavities in a homology model of ClC-1 built upon an eukaryotic CLC crystal structure, and then validated in silico data by measuring the blocking ability of 9-AC and NFA on mutant ClC-1 channels expressed in HEK 293 cells.
KEY RESULTS
We identified four putative binding cavities in ClC-1. 9-AC appears to interact with residues K231, R421 and F484 within the channel pore. We also identified one preferential binding cavity for NFA and propose R421 and F484 as critical residues.
CONCLUSIONS AND IMPLICATIONS
This study represents the first effort to delineate the binding sites of ClC-1. This information is fundamental to discover compounds useful in the treatment of ClC-1-associated dysfunctions and might represent a starting point for specifically targeting other CLC proteins.
Topics: Algorithms; Anthracenes; Binding Sites; Chloride Channels; HEK293 Cells; Humans; Ligands; Molecular Docking Simulation; Mutation; Niflumic Acid
PubMed: 29500929
DOI: 10.1111/bph.14192 -
Organic Letters May 2006[reaction: see text] The synthesis, photophysical properties, and structural characterization of a photodimerizable ditopic ligand are described. Upon irradiation at 366...
[reaction: see text] The synthesis, photophysical properties, and structural characterization of a photodimerizable ditopic ligand are described. Upon irradiation at 366 nm, ligand 1 dimerizes to the head-to-tail tetra-bpy ligand 2. This thermally stable photodimer can be dissociated back to 1 using higher energy irradiation (254 nm).
Topics: Anthracenes; Crystallization; Crystallography, X-Ray; Heterocyclic Compounds, 4 or More Rings; Ligands; Molecular Conformation; Molecular Structure; Photochemistry
PubMed: 16671763
DOI: 10.1021/ol060253i -
Journal of Applied Microbiology Aug 2008The metabolism of phenanthrene and anthracene by a moderate thermophilic Nocardia otitidiscaviarum strain TSH1 was examined.
AIMS
The metabolism of phenanthrene and anthracene by a moderate thermophilic Nocardia otitidiscaviarum strain TSH1 was examined.
METHODS AND RESULTS
When strain TSH1 was grown in the presence of anthracene, four metabolites were identified as 1,2-dihydroxy-1,2-dihydroanthracene, 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid, 2,3-dihydroxynaphthalene and benzoic acid using gas chromatography-mass spectrometry (GC-MS), reverse phase-high performance liquid chromatography (RP-HPLC) and thin-layer chromatography (TLC). Degradation studies with phenanthrene revealed 2,2'-diphenic acid, phthalic acid, 4-hydroxyphenylacetic acid, o-hydroxyphenylacetic acid, benzoic acid, a phenanthrene dihydrodiol, 4-[1-hydroxy(2-naphthyl)]-2-oxobut-3-enoic acid and 1-hydroxy-2-naphthoic acid (1H2NA), as detectable metabolites.
CONCLUSIONS
Strain TSH1 initiates phenanthrene degradation via dioxygenation at the C-3 and C-4 or at C-9 and C-10 ring positions. Ortho-cleavage of the 9,10-diol leads to formation of 2,2'-diphenic acid. The 3,4-diol ring is cleaved to form 1H2NA which can subsequently be degraded through o-phthalic acid pathway. Benzoate does not fit in the previously published pathways from mesophiles. Anthracene metabolism seems to start with a dioxygenation at the 1 and 2 positions and ortho-cleavage of the resulting diol. The pathway proceeds probably through 2,3-dicarboxynaphthalene and 2,3-dihydroxynaphthalene. Degradation of 2,3-dihydroxynaphthalene to benzoate and transformation of the later to catechol is a possible route for the further degradation of anthracene.
SIGNIFICANCE AND IMPACT OF THE STUDY
For the first time, metabolism of phenanthrene and anthracene in a thermophilic Nocardia strain was investigated.
Topics: Anthracenes; Benzoates; Biodegradation, Environmental; Catechols; Gas Chromatography-Mass Spectrometry; Hot Temperature; Nocardia; Oxidation-Reduction; Phenanthrenes; Soil Microbiology; Soil Pollutants; Species Specificity
PubMed: 18312570
DOI: 10.1111/j.1365-2672.2008.03753.x -
Scientific Reports Feb 2018A Schiff base ligand (SBL), N, N-bis (anthracen-9-ylmethylene) pyridine-2, 3-diamine, was synthesized through the condensation of 2,6-diaminopyridine and...
A Schiff base ligand (SBL), N, N-bis (anthracen-9-ylmethylene) pyridine-2, 3-diamine, was synthesized through the condensation of 2,6-diaminopyridine and anthracene-9-carbaldehyde using a 1:2 ratio. H NMR spectra confirmed the observation of non-involvement aromatic carboxylic proton in SBL. A novel series of lanthanide (i.e., praseodymium (Pr), erbium (Er), and ytterbium (Yb))-based SBL metal complexes was successfully synthesized, and their functional groups were elaborately demonstrated using UV-visible, Fourier transform infrared (FT-IR), and fluorescence spectroscopy analyses. FT-IR spectral studies revealed that SBL behaved as a bidentate ligand and it was structured with metal ions by the two azomethine nitrogens. The synthesized SBL-based metal complexes were elaborately performed for cytotoxicity activity versus Vero, human breast cancer (MCF7), and cervical (HeLa) anticancer cell lines.
Topics: Anthracenes; Cell Line, Tumor; Coordination Complexes; Diamines; Electron Spin Resonance Spectroscopy; Humans; Lanthanoid Series Elements; Ligands; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Pyridines; Schiff Bases; Spectrophotometry, Infrared; Spectroscopy, Fourier Transform Infrared
PubMed: 29445233
DOI: 10.1038/s41598-018-21366-1 -
Journal of the American Chemical Society Jan 2020Inverted region behavior for concerted proton-coupled electron transfer (PCET) was recently demonstrated for biomimetic anthracene-phenol-pyridine molecular triads....
Inverted region behavior for concerted proton-coupled electron transfer (PCET) was recently demonstrated for biomimetic anthracene-phenol-pyridine molecular triads. Photoexcitation of the anthracene to a locally excited state (LES) is followed by concerted electron transfer from the phenol to the anthracene and proton transfer from the phenol to the pyridine, forming a relatively long-lived charge separated state (CSS). The long-lived CSS and the inverted region behavior associated with the decay from the CSS to the ground state through charge recombination were experimentally observed only for triads with certain substituents on the anthracene and the pyridine. To explain this distinction, we computed the proton potential energy curves in four substituted triads using the complete active space self-consistent-field method and multireference perturbation theory, including solvent effects with a dielectric continuum model. The calculations revealed a local electron-proton transfer (LEPT) state, in which both the electron and proton transfer from the phenol to the pyridine. When the LEPT state is lower in energy than the CSS, it may provide an alternative pathway for fast decay from the LES to the ground state and thereby preclude detection of the CSS and the inverted region behavior. These calculations predict that substituents stabilizing negative charge on the pyridine and destabilizing negative charge on the anthracene will favor the LEPT pathway, while substituents with the reverse effects will favor the CSS pathway, which could exhibit inverted region behavior. These insights about the stabilization of energy-storing charge-separated states have implications for designing and controlling PCET reactions in artificial photosynthetic systems and other energy conversion processes.
Topics: Anthracenes; Phenol; Photochemical Processes; Pyridines; Solvents
PubMed: 31846322
DOI: 10.1021/jacs.9b11425 -
Molecules (Basel, Switzerland) Jul 2021-glucosidase is a major enzyme that is involved in starch digestion and type 2 diabetes mellitus. In this study, the inhibition of hypericin by α-glucosidase and its...
-glucosidase is a major enzyme that is involved in starch digestion and type 2 diabetes mellitus. In this study, the inhibition of hypericin by α-glucosidase and its mechanism were firstly investigated using enzyme kinetics analysis, real-time interaction analysis between hypericin and -glucosidase by surface plasmon resonance (SPR), and molecular docking simulation. The results showed that hypericin was a high potential reversible and competitive α-glucosidase inhibitor, with a maximum half inhibitory concentration (IC) of 4.66 ± 0.27 mg/L. The binding affinities of hypericin with -glucosidase were assessed using an SPR detection system, which indicated that these were strong and fast, with balances dissociation constant (KD) values of 6.56 × 10 M and exhibited a slow dissociation reaction. Analysis by molecular docking further revealed that hydrophobic forces are generated by interactions between hypericin and amino acid residues Arg-315 and Tyr-316. In addition, hydrogen bonding occurred between hypericin and -glucosidase amino acid residues Lys-156, Ser-157, Gly-160, Ser-240, His-280, Asp-242, and Asp-307. The structure and micro-environment of α-glucosidase enzymes were altered, which led to a decrease in α-glucosidase activity. This research identified that hypericin, an anthracene ketone compound, could be a novel α-glucosidase inhibitor and further applied to the development of potential anti-diabetic drugs.
Topics: Anthracenes; Binding Sites; Fungal Proteins; Glycoside Hydrolase Inhibitors; Humans; Hydrogen Bonding; Hydrophobic and Hydrophilic Interactions; Hypoglycemic Agents; Kinetics; Molecular Docking Simulation; Nitrophenylgalactosides; Perylene; Protein Binding; Protein Conformation, alpha-Helical; Protein Conformation, beta-Strand; Protein Interaction Domains and Motifs; Saccharomyces cerevisiae; Surface Plasmon Resonance; alpha-Glucosidases
PubMed: 34361714
DOI: 10.3390/molecules26154566 -
International Journal of Environmental... Feb 2020It has been reported that spinal deformity was induced in developing fish by the addition of polycyclic aromatic hydrocarbons (PAHs). To examine the mechanism of the...
It has been reported that spinal deformity was induced in developing fish by the addition of polycyclic aromatic hydrocarbons (PAHs). To examine the mechanism of the disruption of fish bone metabolism, the effect of benz[]anthracene (BaA), a kind of PAH, on plasma calcium, inorganic phosphorus, osteoblasts, and osteoclasts was investigated in this study. We also measured several plasma components to analyze the toxicity of BaA on other metabolisms. BaA (1 or 10 ng/g body weight) was intraperitoneally injected (four times) into nibbler fish during breeding, for 10 days, and it was indicated, for the first time, that injecting high doses of BaA to nibbler fish induced both hypocalcemia and hypophosphatemia. Furthermore, in the scales of nibbler fish treated with high doses of BaA, both osteoclastic and osteoblastic marker messengerRNA (mRNA) expressions decreased. These results are a cause of disruption of bone metabolism and, perhaps, the induction of spinal deformities. In addition, we found that total protein, metabolic enzymes in the liver, total cholesterol, free cholesterol, and high-density lipoprotein cholesterol levels significantly decreased in BaA-injected fish. These results indicate that BaA may affect liver diseases and emphasize the importance of prevention of aquatic PAH pollution.
Topics: Animals; Anthracenes; Bone and Bones; Fishes; Liver; Osteoclasts; Polycyclic Aromatic Hydrocarbons; Water Pollutants, Chemical
PubMed: 32098178
DOI: 10.3390/ijerph17041391