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Fluorescence Recognition of Anions Using a Heteroditopic Receptor: Homogenous and Two-Phase Sensing.International Journal of Molecular... Dec 2021In contrast to monotopic receptor , the anthracene functionalized squaramide dual-host receptor is capable of selectively extracting sulfate salts, as was evidenced...
In contrast to monotopic receptor , the anthracene functionalized squaramide dual-host receptor is capable of selectively extracting sulfate salts, as was evidenced unambiguously by DOSY, mass spectrometry, fluorescent and ion chromatography measurements. The receptors were investigated in terms of anion and ion pair binding using the UV-vis and H NMR titrations method in acetonitrile. The reference anion receptor , lacking a crown ether unit, was found to lose the enhancement in anion binding induced by the presence of cations. Besides the ability to bind anions in an enhanced manner exhibited by ion pair receptors and , changing the 1-aminoanthracene substituent resulted in their exhibiting a lower anion affinity than receptor . By using receptor and adjusting the water content in organic phase it was possible to selectively detect sulfates both by "turn-off" and "turn-on" fluorescence, and to do so homogenously and under interfacial conditions. Such properties of receptor have allowed the development of a new type of sensor capable of recognizing and extracting potassium sulfate from the aqueous medium across a phase boundary, resulting in an appropriate fluorescent response in the organic solution.
Topics: Acetonitriles; Anions; Anthracenes; Cations; Crown Ethers; Crystallography, X-Ray; Fluorescence; Hydrogen Bonding; Magnetic Resonance Spectroscopy; Models, Molecular; Quinine; Sulfates
PubMed: 34948192
DOI: 10.3390/ijms222413396 -
Molecules (Basel, Switzerland) Mar 2024The catalytic properties of cytochrome (C) have captured great interest in respect to mitochondrial physiology and apoptosis, and hold potential for novel enzymatic...
The catalytic properties of cytochrome (C) have captured great interest in respect to mitochondrial physiology and apoptosis, and hold potential for novel enzymatic bioremediation systems. Nevertheless, its contribution to the metabolism of environmental toxicants remains unstudied. Human exposure to polycyclic aromatic hydrocarbons (PAHs) has been associated with impactful diseases, and animal models have unveiled concerning signs of PAHs' toxicity to mitochondria. In this work, a series of eight PAHs with ionization potentials between 7.2 and 8.1 eV were used to challenge the catalytic ability of C and to evaluate the effect of vesicles containing cardiolipin mimicking mitochondrial membranes activating the peroxidase activity of C. With moderate levels of HO and at pH 7.0, C catalyzed the oxidation of toxic PAHs, such as benzo[a]pyrene, anthracene, and benzo[a]anthracene, and the cardiolipin-containing membranes clearly increased the PAH conversions. Our results also demonstrate for the first time that C and C-cardiolipin complexes efficiently transformed the PAH metabolites 2-hydroxynaphthalene and 1-hydroxypyrene. In comparison to horseradish peroxidase, C was shown to reach more potent oxidizing states and react with PAHs with ionization potentials up to 7.70 eV, including pyrene and acenaphthene. Spectral assays indicated that anthracene binds to C, and docking simulations proposed possible binding sites positioning anthracene for oxidation. The results give support to the participation of C in the metabolism of PAHs, especially in mitochondria, and encourage further investigation of the molecular interaction between PAHs and C.
Topics: Animals; Humans; Polycyclic Aromatic Hydrocarbons; Cytochromes c; Cardiolipins; Hydrogen Peroxide; Anthracenes
PubMed: 38474641
DOI: 10.3390/molecules29051129 -
International Journal of Molecular... Mar 2022Conductive and porous nitrogen-rich materials have great potential as supercapacitor electrode materials. The exceptional efficiency of such compounds, however, is...
Conductive and porous nitrogen-rich materials have great potential as supercapacitor electrode materials. The exceptional efficiency of such compounds, however, is dependent on their larger surface area and the level of nitrogen doping. To address these issues, we synthesized a porous covalent triazine framework (An-CTFs) based on 9,10-dicyanoanthracene (An-CN) units through an ionothermal reaction in the presence of different molar ratios of molten zinc chloride (ZnCl) at 400 and 500 °C, yielding An-CTF-10-400, An-CTF-20-400, An-CTF-10-500, and An-CTF-20-500 microporous materials. According to N adsorption-desorption analyses (BET), these An-CTFs produced exceptionally high specific surface areas ranging from 406-751 m·g. Furthermore, An-CTF-10-500 had a capacitance of 589 F·g, remarkable cycle stability up to 5000 cycles, up to 95% capacity retention, and strong CO adsorption capacity up to 5.65 mmol·g at 273 K. As a result, our An-CTFs are a good alternative for both electrochemical energy storage and CO uptake.
Topics: Adsorption; Anthracenes; Carbon Dioxide; Metal-Organic Frameworks; Nitrogen; Triazines
PubMed: 35328595
DOI: 10.3390/ijms23063174 -
Journal of Natural Products Jun 2014Among the ciliates, Stentor amethystinus stands out for its conspicuous red-violet color compared to its blue- and red-colored relatives Stentor coeruleus and...
Among the ciliates, Stentor amethystinus stands out for its conspicuous red-violet color compared to its blue- and red-colored relatives Stentor coeruleus and Blepharisma japonicum. Rich blooms in German lakes allowed us to collect sufficient organisms to isolate the pigments and elucidate the structure of the main component amethystin (4) by spectroscopic methods as a carboxy derivative of blepharismin. Depending on conditions, the carboxy group appears as an orthoester or as a mixture of the orthoester and small amounts of a hydroxylactone. Derivatives of both isomeric forms were obtained by acetylation and methylation supporting the proposed structures. On reaction of amethystin with base in the presence of oxygen, oxyamethystin and, under vigorous conditions, p-hydroxybenzoic acid were formed. In addition to 4, two homologues, an isomer of amethystin, and stentorin F (1b) were identified in the primary extract. Further, a biosynthetic scheme is proposed linking stentorin, blepharismin, and amethystin type compounds to the hypothetical protostentorin as a common intermediate.
Topics: Anthracenes; Ciliophora; Coloring Agents; Germany; Lakes; Molecular Structure; Perylene; Polycyclic Compounds
PubMed: 24882688
DOI: 10.1021/np5001363 -
Microbiology Spectrum Oct 2022Streptococcus mutans and Candida albicans exhibit strong cariogenicity through cross-kingdom biofilm formation during the pathogenesis of dental caries. Caffeic acid...
Streptococcus mutans and Candida albicans exhibit strong cariogenicity through cross-kingdom biofilm formation during the pathogenesis of dental caries. Caffeic acid phenethyl ester (CAPE), a natural compound, has potential antimicrobial effects on each species individually, but there are no reports of its effect on this dual-species biofilm. This study aimed to explore the effects of CAPE on cariogenic biofilm formation by S. mutans and C. albicans and the related mechanisms. The effect of CAPE on planktonic cell growth was investigated, and crystal violet staining, the anthrone-sulfuric acid assay and confocal laser scanning microscopy were used to evaluate biofilm formation. The structures of the formed biofilms were observed using scanning electron microscopy. To explain the antimicrobial effect of CAPE, quantitative real-time PCR (qRT-PCR) was applied to monitor the relative expression levels of cariogenic genes. Finally, the biocompatibility of CAPE in human oral keratinocytes (HOKs) was evaluated using the CCK-8 assay. The results showed that CAPE suppressed the growth, biofilm formation and extracellular polysaccharides (EPS) synthesis of C. albicans and S. mutans in the coculture system of the two species. The expression of the gene was also suppressed by CAPE. The efficacy of CAPE was concentration dependent, and the compound exhibited acceptable biocompatibility. Our research lays the foundation for further study of the application of the natural compound CAPE as a potential antimicrobial agent to control dental caries-associated cross-kingdom biofilms. Severe dental caries is a multimicrobial infectious disease that is strongly induced by the cross-kingdom biofilm formed by S. mutans and C. albicans. This study aimed to investigate the potential of caffeic acid phenethyl ester (CAPE) as a natural product in the prevention of severe caries. This study clarified the inhibitory effect of CAPE on cariogenic biofilm formation and the control of cariogenic genes. It deepens our understanding of the synergistic cariogenic effect of S. mutans and C. albicans and provides a new perspective for the prevention and control of dental caries with CAPE. These findings may contribute to the development of CAPE as a promising antimicrobial agent targeting this caries-related cross-kingdom biofilm.
Topics: Humans; Streptococcus mutans; Candida albicans; Gentian Violet; Dental Caries; Biofilms; Anti-Infective Agents; Polysaccharides; Biological Products; Anthracenes
PubMed: 35980199
DOI: 10.1128/spectrum.01578-22 -
Chemistry (Weinheim An Der Bergstrasse,... Jul 2022A series of bis-(4'-pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis-N-methylpyridinium compounds were...
A series of bis-(4'-pyridylethynyl)arenes (arene=benzene, tetrafluorobenzene, and anthracene) were synthesized and their bis-N-methylpyridinium compounds were investigated as a class of π-extended methyl viologens. Their structures were determined by single crystal X-ray diffraction, and their photophysical and electrochemical properties (cyclic voltammetry), as well as their interactions with DNA/RNA were investigated. The dications showed bathochromic shifts in emission compared to the neutral compounds. The neutral compounds showed very small Stokes shifts, which are a little larger for the dications. All of the compounds showed very short fluorescence lifetimes (<4 ns). The neutral compound with an anthracene core has a quantum yield of almost unity. With stronger acceptors, the analogous bis-N-methylpyridinium compound showed a larger two-photon absorption cross-section than its neutral precursor. All of the dicationic compounds interact with DNA/RNA; while the compounds with benzene and tetrafluorobenzene cores bind in the grooves, the one with an anthracene core intercalates as a consequence of its large, condensed aromatic linker moiety, and it aggregates within the polynucleotide when in excess over DNA/RNA. Moreover, all cationic compounds showed highly specific CD spectra upon binding to ds-DNA/RNA, attributed to the rare case of forcing the planar, achiral molecule into a chiral rotamer, and negligible toxicity toward human cell lines at ≤10 μM concentrations. The anthracene-analogue exhibited intracellular accumulation within lysosomes, preventing its interaction with cellular DNA/RNA. However, cytotoxicity was evident at 1 μM concentration upon exposure to light, due to singlet oxygen generation within cells. These multi-faceted features, in combination with its two-photon absorption properties, suggest it to be a promising lead compound for development of novel light-activated theranostic agents.
Topics: Anthracenes; Benzene; Biology; DNA; Humans; Molecular Structure; Paraquat; RNA
PubMed: 35502627
DOI: 10.1002/chem.202200753 -
The American Journal of Pathology Nov 1978Seven aromatic polycyclic hydrocarbons (PCHs) were investigated for their toxic effects on respiratory mucosa: benzo(e)pyrene (BeP), pyrene, anthracene,... (Comparative Study)
Comparative Study
Seven aromatic polycyclic hydrocarbons (PCHs) were investigated for their toxic effects on respiratory mucosa: benzo(e)pyrene (BeP), pyrene, anthracene, benz(a)anthracene(BaA), dibenz(a,c)anthracene(DBacA), benzo (a)pyrene (BaP), and dimethylbenz(a)anthracene (DMBA). The compounds were chosen because they comprise a spectrum of PCHs ranging from noncarcinogens, to initiators, to weak and strong carcinogens. All of them except DMBA are environmentally relevant chemicals. The chemicals were tested over an 8-week period. Heterotopic tracheal transplants were continously exposed and the histopathologic effects induced by the various PCHs were periodically assessed semiquantitatively. All PCHs exhibited varying degrees of toxicity for respiratory epithelium and submucosa. BeP clearly showed the least toxicity followed by pyrene and anthracene. BaA and DBacA caused marked epithelial and submucosal changes. In addition to epithelial hyperplasia, undifferentiated epithelium and squamous metaplasia developed. Marked mononuclear infiltration occurred in the subepithelial connective tissue. With BaP the epithelial and submucosal changes were similar but were much stronger. DMBA was the most toxic substance, causing epithelial necrosis followed by generalized keratinizing squamous metaplasia; the subepithelial changes consisted of an early acellular exudate and, later (at 8 weeks), marked condensation and hyalinization of the lamina propria. The toxic response pattern of the tracheal mucosa to carcinogenic agents was characterized by the chronicity of epithelial and connective tissue damage, as opposed to the short-lived hyperplastic and inflammatory response elicited by the noncarcinogens and weak initiators.
Topics: 9,10-Dimethyl-1,2-benzanthracene; Animals; Anthracenes; Benz(a)Anthracenes; Benzopyrenes; Hyperplasia; Male; Metaplasia; Mucous Membrane; Necrosis; Pyrenes; Rats; Trachea
PubMed: 102204
DOI: No ID Found -
British Medical Journal Jul 1978
Comparative Study
Topics: Anthracenes; Anthralin; Ficusin; Humans; Photochemotherapy; Psoriasis
PubMed: 697982
DOI: 10.1136/bmj.2.6131.206-a -
Molecules (Basel, Switzerland) Jul 2018Leishmaniasis is a vector-borne disease caused by protozoal . Because of resistance development against current drugs, new antileishmanial compounds are urgently needed....
Leishmaniasis is a vector-borne disease caused by protozoal . Because of resistance development against current drugs, new antileishmanial compounds are urgently needed. Endoperoxides (EPs) are successfully used in malaria therapy, and experimental evidence of their potential against leishmaniasis exists. Anthracene endoperoxides (AcEPs) have so far been only technically used and not explored for their leishmanicidal potential. This study verified the in vitro efficiency and mechanism of AcEPs against both promastigotes and axenic amastigotes ( and ) as well as their toxicity in J774 macrophages. Additionally, the kinetics and radical products of AcEPs’ reaction with iron, the formation of radicals by AcEPs in , as well as the resulting impairment of parasite mitochondrial functions were studied. Using electron paramagnetic resonance combined with spin trapping, photometry, and fluorescence-based oximetry, AcEPs were demonstrated to (i) show antileishmanial activity in vitro at IC values in a low micromolar range, (ii) exhibit host cell toxicity in J774 macrophages, (iii) react rapidly with iron (II) resulting in the formation of oxygen- and carbon-centered radicals, (iv) produce carbon-centered radicals which could secondarily trigger superoxide radical formation in , and (v) impair mitochondrial functions in during parasite killing. Overall, the data of different AcEPs demonstrate that their structures besides the peroxo bridge strongly influence their activity and mechanism of their antileishmanial action.
Topics: Animals; Anthracenes; Cell Line; Cell Survival; Electron Spin Resonance Spectroscopy; Inhibitory Concentration 50; Iron; Leishmania; Mice; Mitochondria; Oxidation-Reduction; Oxygen Consumption; Peroxides; Superoxides
PubMed: 29996524
DOI: 10.3390/molecules23071680 -
The Journal of Biological Chemistry Jul 1984Absolute configurations of the arene 1,2-oxides formed from napththalene and anthracene by cytochrome P-450c, the predominant isozyme of cytochrome P-450 found in the...
Absolute configurations of the arene 1,2-oxides formed from napththalene and anthracene by cytochrome P-450c, the predominant isozyme of cytochrome P-450 found in the livers of rats treated with 3-methylcholanthrene, were determined via two different approaches. The first consisted of trapping the arene oxides with N-acetyl-L-cysteine to form S-conjugates, methylation of the conjugates with diazomethane, and separation of the resulting diastereomeric esters by reversed phase high performance liquid chromatography. Analysis by this procedure of the arene oxides formed from radioactive naphthalene and anthracene by a highly purified and reconstituted monooxygenase system containing cytochrome P-450c indicated that 73 and greater than or equal to 95%, respectively, of the metabolically formed arene oxides consisted of the (+)-(1R,2S)-enantiomer. In the second approach, each hydrocarbon was incubated with a reconstituted system containing both cytochrome P-450c and epoxide hydrolase. Under these conditions, the predominant metabolites are trans-1,2-dihydrodiols formed by epoxide hydrolase catalyzed trans-addition of water to the arene oxide intermediates. In both cases, the (-)-(1R,2R)-dihydrodiols predominated; 92% for naphthalene and 99% for anthracene. Enzyme-catalyzed addition of water to (+)- and (-)-anthracene 1,2-oxide and (+)-napthalene 1,2-oxide occurred exclusively (greater than 99%) at the allylic 2-position. The (-)-(1S,2R)-naphthalene 1,2-oxide, however, is converted to a 40:60 mixture of the (-)-(1R,2R)- and (+)-(1S,2S)-dihydrodiols by benzylic and allylic attack, respectively, resulting in increased enantiomeric purity of the dihydrodiol relative to the oxide. Thus, qualitatively and quantitatively both approaches indicate that the (+)-arene (1R,2S)-oxides predominate. The results are discussed in terms of the steric constraints of a proposed model for the catalytic binding site of cytochrome P-450c.
Topics: Animals; Anthracenes; Aroclors; Binding Sites; Carbon Radioisotopes; Chlorodiphenyl (54% Chlorine); Cytochrome P-450 Enzyme System; Epoxide Hydrolases; Liver; Microsomes, Liver; NADPH-Ferrihemoprotein Reductase; Naphthalenes; Rats; Tritium
PubMed: 6430894
DOI: No ID Found