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Nature Communications Sep 2022Self-complementary assembly is one of the most promising phenomena for the formation of discrete assemblies, e.g., proteins and capsids. However, self-complementary...
Self-complementary assembly is one of the most promising phenomena for the formation of discrete assemblies, e.g., proteins and capsids. However, self-complementary assembly based on multiple host-guest systems has been scarcely reported due to the difficulty in controlling each assembly. Herein, we report a dual interaction system in which the key assembly direction is well regulated by both π-π stacking and hydrogen bonding to construct a self-complementary macrocycle. Continuous host-guest behavior of anthracene-based molecular tweezers during crystallization leads to successful construction of a cyclic hexamer, which is reminiscent of Kekulé's monkey model. Furthermore, the cyclic hexamer in a tight and triple-layered fashion shows hierarchical assembly into cuboctahedron and rhombohedral assemblies in the presence of trifluoroacetic acid. Our findings would be potentially one of metal-free strategies for constructing anthracene-based supramolecular assemblies with higher-order structure.
Topics: Anthracenes; Hydrogen Bonding; Trifluoroacetic Acid
PubMed: 36163173
DOI: 10.1038/s41467-022-33357-y -
Molecules (Basel, Switzerland) Oct 2022Leishmaniasis is a vector-borne disease caused by protozoal Leishmania parasites. Previous studies have shown that endoperoxides (EP) can selectively kill Leishmania in...
Leishmaniasis is a vector-borne disease caused by protozoal Leishmania parasites. Previous studies have shown that endoperoxides (EP) can selectively kill Leishmania in host cells. Therefore, we studied in this work a set of new anthracene-derived EP (AcEP) together with their non-endoperoxidic analogs in model systems of Leishmania tarentolae promastigotes (LtP) and J774 macrophages for their antileishmanial activity and selectivity. The mechanism of effective compounds was explored by studying their reaction with iron (II) in chemical systems and in Leishmania. The correlation of structural parameters with activity demonstrated that in this compound set, active compounds had a LogPOW larger than 3.5 and a polar surface area smaller than 100 Å2. The most effective compounds (IC50 in LtP < 2 µM) with the highest selectivity (SI > 30) were pyridyl-/tert-butyl-substituted AcEP. Interestingly, also their analogs demonstrated activity and selectivity. In mechanistic studies, it was shown that EP were activated by iron in chemical systems and in LtP due to their EP group. However, the molecular structure beyond the EP group significantly contributed to their differential mitochondrial inhibition in Leishmania. The identified compound pairs are a good starting point for subsequent experiments in pathogenic Leishmania in vitro and in animal models.
Topics: Animals; Antiprotozoal Agents; Leishmania; Structure-Activity Relationship; Anthracenes; Iron
PubMed: 36296439
DOI: 10.3390/molecules27206846 -
Scientific Reports 2013Walkable dual emissions, in which the emission bands of the walker reversibly cross or leave those of the stationary ones depending on temperature and concentration,...
Walkable dual emissions, in which the emission bands of the walker reversibly cross or leave those of the stationary ones depending on temperature and concentration, have been demonstrated in cyclic dimeric lanthanide complexes [Ln(hfac)3(PAnPO2)]2 (Ln = Eu(III), Tb(III); hfac(-) = hexafluoroacetylacetonate; PAnPO2 = 9,10-bis(diphenylphosphino) anthracene dioxide), providing a concept model for signals exchanging and dispatching. Additionally, good linear relationships are observed between the maximum emission bands of the walker vs the concentrations {lg(M)} and the measurement temperatures (K), implying such materials could be served as potential concentration and temperature sensors.
Topics: Anthracenes; Hydrocarbons, Fluorinated; Lanthanoid Series Elements; Molecular Conformation; Pentanones; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry; X-Ray Diffraction
PubMed: 23857434
DOI: 10.1038/srep02199 -
Journal of the American Chemical Society Jun 2018The transfer of protons and electrons is key to energy conversion and storage, from photosynthesis to fuel cells. Increased understanding and control of these processes...
The transfer of protons and electrons is key to energy conversion and storage, from photosynthesis to fuel cells. Increased understanding and control of these processes are needed. A new anthracene-phenol-pyridine molecular triad was designed to undergo fast photoinduced multiple-site concerted proton-electron transfer (MS-CPET), with the phenol moiety transferring an electron to the photoexcited anthracene and a proton to the pyridine. Fluorescence quenching and transient absorption experiments in solutions and glasses show rapid MS-CPET (3.2 × 10 s at 298 K). From 5.5 to 90 K, the reaction rate and kinetic isotope effect (KIE) are independent of temperature, with zero Arrhenius activation energy. From 145 to 350 K, there are only slight changes with temperature. This MS-CPET reaction thus occurs by tunneling of both the proton and electron, in different directions. Since the reaction proceeds without significant thermal activation energy, the rate constant indicates the magnitude of the electron/proton double tunneling probability.
Topics: Anthracenes; Electrons; Fluorescence; Hydrogen Bonding; Kinetics; Molecular Structure; Phenols; Protons; Pyridines; Temperature; Ultraviolet Rays
PubMed: 29847111
DOI: 10.1021/jacs.8b04455 -
International Journal of Molecular... May 2023In this study, we synthesized two conjugated microporous polymers (CMPs), An-Ph-TPA and An-Ph-Py CMPs, using the Suzuki cross-coupling reaction. These CMPs are organic...
In this study, we synthesized two conjugated microporous polymers (CMPs), An-Ph-TPA and An-Ph-Py CMPs, using the Suzuki cross-coupling reaction. These CMPs are organic polymers with p-conjugated skeletons and persistent micro-porosity and contain anthracene (An) moieties linked to triphenylamine (TPA) and pyrene (Py) units. We characterized the chemical structures, porosities, thermal stabilities, and morphologies of the newly synthesized An-CMPs using spectroscopic, microscopic, and N adsorption/desorption isotherm techniques. Our results from thermogravimetric analysis (TGA) showed that the An-Ph-TPA CMP displayed better thermal stability with T = 467 °C and char yield of 57 wt% compared to the An-Ph-Py CMP with T = 355 °C and char yield of 54 wt%. Furthermore, we evaluated the electrochemical performance of the An-linked CMPs and found that the An-Ph-TPA CMP had a higher capacitance of 116 F g and better capacitance stability of 97% over 5000 cycles at 10 A g. In addition, we assessed the biocompatibility and cytotoxicity of An-linked CMPs using the MTT assay and a live/dead cell viability assay and observed that they were non-toxic and biocompatible with high cell viability values after 24 or 48 h of incubation. These findings suggest that the An-based CMPs synthesized in this study have potential applications in electrochemical testing and the biological field.
Topics: Polymers; Amines; Adsorption; Anthracenes
PubMed: 37240313
DOI: 10.3390/ijms24108966 -
ChemistryOpen May 2020Two new families of -nucleoside analogues containing the anthracene moiety introduced through the nitrosocarbonyl ene reaction with allylic alcohols were prepared. The...
Two new families of -nucleoside analogues containing the anthracene moiety introduced through the nitrosocarbonyl ene reaction with allylic alcohols were prepared. The core structure is an isoxazolidine heterocycle that introduces either atom either a phenyl ring or dimethyl moiety at the C3 carbon. Different heterobases were inserted at the position 5 of the heterocyclic ring. One of the synthesized compounds demonstrated a good capacity to induce cell death and an appreciable nuclear fragmentation was evidenced in treated cells.
Topics: Anthracenes; Apoptosis; Humans; Models, Molecular; Molecular Structure; Nucleosides; Oxazoles; Propanols; Structure-Activity Relationship; U937 Cells
PubMed: 32373422
DOI: 10.1002/open.202000034 -
International Journal of Molecular... Feb 201070 years have passed since the first isolation of the naphthodianthrones hypericin and pseudohypericin from Hypericum perforatum L. Today, they continue to be one of the... (Review)
Review
70 years have passed since the first isolation of the naphthodianthrones hypericin and pseudohypericin from Hypericum perforatum L. Today, they continue to be one of the most promising group of polyphenols, as they fascinate with their physical, chemical and important biological properties which derive from their unique chemical structure. Hypericins and their derivatives have been extensively studied mainly for their antitumor, antiviral and antidepressant properties. Notably, hypericin is one of the most potent naturally occurring photodynamic agents. It is able to generate the superoxide anion and a high quantum yield of singlet oxygen that are considered to be primarily responsible for its biological effects. The prooxidant photodynamic properties of hypericin have been exploited for the photodynamic therapy of cancer (PDT), as hypericin, in combination with light, very effectively induces apoptosis and/or necrosis of cancer cells. The mechanism by which these activities are expressed continues to be a main topic of discussion, but according to scientific data, different modes of action (generation of ROS & singlet oxygen species, antiangiogenesis, immune responces) and multiple molecular pathways (intrinsic/extrinsic apoptotic pathway, ERK inhibition) possibly interrelating are implicated. The aim of this review is to analyse the most recent advances (from 2005 and thereof) in the chemistry and biological activities (in vitro and in vivo) of the pure naphthodianthrones, hypericin and pseudohypericin from H. perforatum. Extracts from H. perforatum were not considered, nor pharmakokinetic or clinical data. Computerised literature searches were performed using the Medline (PubMed), ChemSciFinder and Scirus Library databases. No language restrictions were imposed.
Topics: Anthracenes; Anti-Infective Agents; Antidepressive Agents; Cell Survival; Humans; Hypericum; Neoplasms; Perylene; Photochemotherapy; Photosensitizing Agents
PubMed: 20386655
DOI: 10.3390/ijms11020562 -
Nutrients Jan 2023Traditionally, Curcuma xanthorriza (CX), black cumin seed (BC), and honey have been used by the Indonesian people as medicinal ingredients to treat various health...
Herbal Honey Preparations of Curcuma Xanthorriza and Black Cumin Protect against Carcinogenesis through Antioxidant and Immunomodulatory Activities in Sprague Dawley (SD) Rats Induced with Dimethylbenz(a)anthracene.
BACKGROUND
Traditionally, Curcuma xanthorriza (CX), black cumin seed (BC), and honey have been used by the Indonesian people as medicinal ingredients to treat various health symptoms. CX extracts and BC have been proven in the laboratory as chemopreventive agents, antioxidants, and immunomodulators. In this study, we developed CX extract, BC oil, and honey into herbal honey preparations (CXBCH) and hypothesized that the preparations show chemopreventive activity. The purpose of the study was to determine the CXBCH potential as chemopreventive, antioxidant, and immunomodulatory.
METHOD
In this experimental laboratory research, antioxidant, immunomodulatory, and cytotoxic activities were tested on human mammary cancer cell lines (T47D cells) while the chemopreventive activity of the CXBCH preparations on Sprague Dawley (SD) rats induced with dimethylbenzene(a)anthracene (DMBA).
RESULTS
CXBCH preparations demonstrated immunomodulatory, antioxidant, and cytotoxic activities in T47D, Hela, and HTB-183 cells and in DMBA-induced SD rats, as the preparations inhibited tumor nodule formation, increased the number of CD4, CD8 and CD4CD25 cells, and glutathione-S-transferase (GST) activity, and decreased serum NO levels.
CONCLUSIONS
CXBCH preparations display chemopreventive, antioxidant, and immunomodulatory properties.
Topics: Rats; Animals; Humans; Rats, Sprague-Dawley; Antioxidants; 9,10-Dimethyl-1,2-benzanthracene; Curcuma; Honey; Nigella sativa; Carcinogenesis; Anthracenes; Mammary Neoplasms, Experimental; Carcinogens
PubMed: 36678242
DOI: 10.3390/nu15020371 -
PloS One 2018Biodegradation of hazardous pollutants is of immense importance for maintaining a clean environment. However, the concentration of such contaminants/pollutants can be...
Biodegradation of hazardous pollutants is of immense importance for maintaining a clean environment. However, the concentration of such contaminants/pollutants can be minimized with the help of microorganisms that has the ability to degrade the toxic pollutants into non-toxic metabolites. In the current study, 23 bacterial isolates were purified from the rhizospheric soil of Sysimbrium irio, growing as a wild plant in the vicinity of gas filling stations in Peshawar city. The isolated strains were initially screened on solid nutrient agar and further purified by culturing it on anthracene amended mineral media (PNR). The bacterial growth and anthracene disappearance were observed by calculating optical density (OD). The isolates showed a concentration-dependent growth on anthracene amended PNR media at 30°C and pH7. Also, an increase in bacterial OD from 0.351 to 1.80 with increased shaking speed was noticed. On the contrary, alternate carbon sources (glucose, fructose, sucrose) or nitrogen sources (KNO3, NaNO3, NH4NO3 and CaNO3) posed inhibitory effect on bacterial growth during anthracene degradation. The recorded efficiency of anthracene degradation by the selected bacterial isolate (1.4×1023 CFUmL-1 and 1.80 OD) was 82.29%, after 120 h of incubation. The anthracene was degraded to 9, 10, dihydroxy-anthracene and anthraquinone, detected through GC-MS. The efficient bacterial isolate was identified as S13, a new strain of Bacillus cereus, using 16S rRNA analysis, showing 98% homology. The isolated bacterial strain S13 may be used as a potential tool for bioremediation of toxic hydrocarbons and to keep the environment free from PAH pollutants.
Topics: Anthracenes; Anthraquinones; Bacillus cereus; Biodegradation, Environmental; Gas Chromatography-Mass Spectrometry; Hydrogen-Ion Concentration; Phylogeny; RNA, Ribosomal, 16S; Soil Microbiology; Soil Pollutants; Temperature
PubMed: 30071070
DOI: 10.1371/journal.pone.0201620 -
IARC Monographs on the Evaluation of... 1989
Review
Topics: Animals; Benz(a)Anthracenes; Carcinogens; Chemical Phenomena; Chemistry; Humans; Mice; Mutagens; Neoplasms, Experimental; Nitro Compounds; Perylene; Risk
PubMed: 2697770
DOI: No ID Found