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Analytical Sciences : the International... 2018The degradation of polycyclic aromatic hydrocarbons (PAHs) can generate AhR-binding compounds, exhibiting genotoxicity and carcinogenicity. In this investigation, aryl...
The degradation of polycyclic aromatic hydrocarbons (PAHs) can generate AhR-binding compounds, exhibiting genotoxicity and carcinogenicity. In this investigation, aryl hydrocarbon receptor (AhR) from carp and anthracene (Ant) were coupled as antigen to establish an indirect competition ELISA (ic-ELISA) with an AhR-Ant antibody. A standard curve was determined for the ic-ELISA concerning detection range and limit. Also, the specificity, stability and the recovery of the ic-ELISA were checked. Results indicate that the ratio of antibody to antigen titer is 1:64000. The resulting standard curve is Y = 21.326 × X + 1.8213. The detection range lies within 10 - 1000 ng mL and the limiting concentration is 2.43 ng mL. The cross reaction ratio (CR) between Ant and naphthalene (Nap), Ant and phenanthrene (Phe) or Ant and fluoranthene (Flu) were 5.7, 19.1 and less than 0.1%, respectively. The range of the coefficient of variance (C.V) amounts was from 4.2 up to 9.5% and the recovery range was from 90 to 115%. These results show that the AhR-Ant ic-ELISA is sensitive, and can be used as a technical support to quantify Ant in the environment.
Topics: Animals; Anthracenes; Biosensing Techniques; Carps; Ecotoxicology; Enzyme-Linked Immunosorbent Assay; Receptors, Aryl Hydrocarbon; Temperature; Water
PubMed: 29643304
DOI: 10.2116/analsci.17P389 -
ACS Applied Materials & Interfaces Sep 2023AIEgens have emerged as a promising alternative to molecular rotors in bioimaging applications. However, transferring the concept of aggregation-induced emission (AIE)...
AIEgens have emerged as a promising alternative to molecular rotors in bioimaging applications. However, transferring the concept of aggregation-induced emission (AIE) from solution to living systems remains a challenge. Given the highly heterogeneous nature and the compartmentalization of the cell, different approaches are needed to control the self-assembly within the crowded intricate cellular environment. Herein, we report for the first time the self-assembly mechanism of an anthracene-guanidine derivative (AG) forming the rare and highly emissive T-shaped dimer in breast cancer cell lines as a proof of concept. This process is highly sensitive to the local environment in terms of polarity, viscosity, and/or water quantity that should enable the use of the AG as a fluorescence lifetime imaging biosensor for intracellular imaging of cellular structures and the monitoring of intracellular state parameters. Different populations of the monomer and T-shaped and π-π dimers were observed in the cell membrane, cytoplasm, and nucleoplasm, related to the local viscosity and presence of water. The T-shaped dimer is formed preferentially in the nucleus because of the higher density and viscosity compared to the cytoplasm. The present results should serve as a precursor for the development of new design strategies for molecular systems for a wide range of applications such as cell viscosity, density, or temperature sensing and imaging.
Topics: Cytoplasm; Optical Imaging; Cell Membrane; Anthracenes; Polymers; Water
PubMed: 37699547
DOI: 10.1021/acsami.3c10823 -
Molecules (Basel, Switzerland) Dec 2020Two yellow bis-azo dyes containing anthracene and two azodiphenylether groups (BPA and BTA) were prepared, and an extensive investigation of their physical, thermal and...
Two yellow bis-azo dyes containing anthracene and two azodiphenylether groups (BPA and BTA) were prepared, and an extensive investigation of their physical, thermal and biological properties was carried out. The chemical structure was confirmed by the FTIR spectra, while from the UV-Vis spectra, the quantum efficiency of the laser fluorescence at the 476.5 nm was determined to be 0.33 (BPA) and 0.50 (BTA). The possible transitions between the energy levels of the electrons of the chemical elements were established, identifying the energies and the electronic configurations of the levels of transition. Both crystals are anisotropic, the optical phenomenon of double refraction of polarized light (birefringence) taking place. Images of maximum illumination and extinction were recorded when the crystals of the bis-azo compounds rotated by 90° each, which confirms their birefringence. A morphologic study of the thin films deposited onto glass surfaces was performed, proving the good adhesion of both dyes. By thermal analysis and calorimetry, the melting temperatures were determined (~224-225 °C for both of them), as well as their decomposition pathways and thermal effects (enthalpy variations during undergoing processes); thus, good thermal stability was exhibited. The interaction of the two compounds with collagen in the suede was studied, as well as their antioxidant activity, advocating for good chemical stability and potential to be safely used as coloring agents in the food industry.
Topics: Anthracenes; Azo Compounds; Chemical Phenomena; Coloring Agents; Models, Theoretical; Molecular Structure; Spectroscopy, Fourier Transform Infrared; Spectrum Analysis; Temperature
PubMed: 33291331
DOI: 10.3390/molecules25235757 -
Nature Communications Aug 2022Reactions that lead to destruction of aromatic ring systems often require harsh conditions and, thus, take place with poor selectivities. Selective partial...
Reactions that lead to destruction of aromatic ring systems often require harsh conditions and, thus, take place with poor selectivities. Selective partial dearomatization of fused arenes is even more challenging but can be a strategic approach to creating versatile, complex polycyclic frameworks. Herein we describe a general organophotoredox approach for the chemo- and regioselective dearomatization of structurally diverse polycyclic aromatics, including quinolines, isoquinolines, quinoxalines, naphthalenes, anthracenes and phenanthrenes. The success of the method for chemoselective oxidative rupture of aromatic moieties relies on precise manipulation of the electronic nature of the fused polycyclic arenes. Mechanistic studies show that the addition of a hydrogen atom transfer (HAT) agent helps favor the dearomatization pathway over the more thermodynamically downhill aromatization pathway. We show that this strategy can be applied to rapid synthesis of biologically valued targets and late-stage skeletal remodeling en route to complex structures.
Topics: Anthracenes; Isoquinolines; Naphthalenes; Oxidation-Reduction; Phenanthrenes
PubMed: 35931700
DOI: 10.1038/s41467-022-32201-7 -
Applied and Environmental Microbiology Jun 1993The well-characterized plasmid-encoded naphthalene degradation pathway in Pseudomonas putida PpG7(NAH7) was used to investigate the role of the NAH plasmid-encoded...
The well-characterized plasmid-encoded naphthalene degradation pathway in Pseudomonas putida PpG7(NAH7) was used to investigate the role of the NAH plasmid-encoded pathway in mineralizing phenanthrene and anthracene. Three Pseudomonas strains, designated 5R, DFC49, and DFC50, were recovered from a polynuclear aromatic hydrocarbon-degrading inoculum developed from a manufactured gas plant soil slurry reactor. Plasmids pKA1, pKA2, and pKA3, approximately 100 kb in size, were isolated from these strains and characterized. These plasmids have homologous regions of upper and lower NAH7 plasmid catabolic genes. By conjugation experiments, these plasmids, including NAH7, have been shown to encode the genotype for mineralization of [9-14C]phenanthrene and [U-14C]anthracene, as well as [1-14C]naphthalene. One strain, Pseudomonas fluorescens 5RL, which has the complete lower pathway inactivated by transposon insertion in nahG, accumulated a metabolite from phenanthrene and anthracene degradation. This is the first direct evidence to indicate that the NAH plasmid-encoded catabolic genes are involved in degradation of polynuclear aromatic hydrocarbons other than naphthalene.
Topics: Anthracenes; Biodegradation, Environmental; Naphthalenes; Phenanthrenes; Plasmids; Pseudomonas; Soil Microbiology; Soil Pollutants
PubMed: 8328809
DOI: 10.1128/aem.59.6.1931-1937.1993 -
Reproductive Biology and Endocrinology... Mar 2022The purpose of this study was to investigate the effects of polycyclic aromatic hydrocarbons (PAHs) other than bisphenol A (BPA) and BPA substitutes on placental cells.
BACKGROUND
The purpose of this study was to investigate the effects of polycyclic aromatic hydrocarbons (PAHs) other than bisphenol A (BPA) and BPA substitutes on placental cells.
METHODS
HTR-8/SVneo cells were treated with anthracene, benzo[k]fluoranthene, benzo[a]pyrene, and 4,4-(9-fluorenylidene)diphenol, which is used as a substitute for BPA-free products. After confirming the dose response for each reagent using the prepared cells, the cells were incubated for 24, 48, and 72 h. Cell viability was confirmed using the XTT assay. Each experiment was performed with the minimum number of samples (n = 3) required for statistical analysis. The results were analyzed using t-tests; p < 0.05 was considered statistically significant.
RESULTS
After treatment with anthracene, benzo[k]fluoranthene, benzo[a]pyrene, and 4,4-(9-fluorenylidene)diphenol, the absorbance measured using the XTT assay decreased significantly with increasing concentration. The absorbance decreased significantly over time following treatment with each endocrine disruptor at the concentration confirmed by the dose-response analysis.
CONCLUSIONS
This study showed that anthracene, benzo[k]fluoranthene, benzo[a]pyrene, and 4,4-(9-fluorenylidene)diphenol-a BPA substitute-affect cell viability and necrosis in the placental cell line. The study indicates the serious effects of PAHs that negatively affect pregnancy but were previously unknown. Further, this study would serve as a reference for the identification of harmful PAHs during pregnancy prognosis in women who are more susceptible to PAH exposure.
Topics: Anthracenes; Benzhydryl Compounds; Benzo(a)pyrene; Cell Differentiation; Cell Line; Cell Proliferation; Cell Survival; Dose-Response Relationship, Drug; Female; Fluorenes; Humans; Phenols; Placenta; Polycyclic Aromatic Hydrocarbons; Pregnancy; Time Factors
PubMed: 35260167
DOI: 10.1186/s12958-022-00920-7 -
Scientific Reports Oct 2019The freshwater flagellate alga Euglena agilis Carter was exposed to the polycyclic aromatic hydrocarbon (PAH) anthracene for 96 h under optimal photosynthetically...
The freshwater flagellate alga Euglena agilis Carter was exposed to the polycyclic aromatic hydrocarbon (PAH) anthracene for 96 h under optimal photosynthetically active radiation (PAR), and responses of growth, photosynthetic pigment production, and photosynthetic efficiency were assessed. Anthracene reduced the growth rate (μ) and levels of chlorophyll a (Chl a), chlorophyll b (Chl b), and total carotenoids. The growth rate was more sensitive than photosynthetic parameters, with a median effective concentration (EC) of 4.28 mg L. Between 5 and 15 mg L, anthracene inhibited the maximum quantum yield (F/F) of photosystem II (PSII) and the maximum photosynthetic electron transport rate through PSII (rETR) with EC values of 14.88 and 11.8 mg L, respectively. At all anthracene concentrations, intracellular reactive oxygen species (ROS) were elevated, indicating increased oxidative stress. Anthracene presumably reduced the PSII efficiency of photochemical energy regulation and altered the photochemistry through intracellular ROS formation. Acute exposure to PAHs may induce severe physiological changes in phytoplankton cells, which may influence vital ecological processes within the aquatic environments. Additionally, growth and Chl a content may serve as sensitive risk assessment parameters of anthracene toxicity in water management since EC values for both overlap with anthracene levels (8.3 mg L) permitted by the US Environmental Protection Agency (USEPA).
Topics: Anthracenes; Cell Proliferation; Dimethyl Sulfoxide; Euglena; Fluoresceins; Fluorescence; Fresh Water; Photosynthesis; Photosystem II Protein Complex; Pigments, Biological; Solvents
PubMed: 31653882
DOI: 10.1038/s41598-019-51451-y -
British Journal of Clinical Pharmacology 19831 High speed surface electrocardiograms were recorded in 35 patients during the baseline and after four weeks' treatment in a placebo-controlled trial of mianserin and... (Clinical Trial)
Clinical Trial Randomized Controlled Trial
1 High speed surface electrocardiograms were recorded in 35 patients during the baseline and after four weeks' treatment in a placebo-controlled trial of mianserin and maprotiline in primary depressive illness. 2 Measurements of the RR, PR and QT intervals, QRS width and T wave height were made blind to patient, drug and treatment interval and compared with plasma drug concentrations. The presence or absence of cardiac arrhythmias was recorded. 3 The only significant findings were an increased heart rate and PR interval and decreased QTc interval in the maprotiline group. Only one patient receiving maprotiline had a cardiac arrhythmia. There was no significant correlation between measurements of ECG parameters and plasma drug levels. 4 The results confirm the lack of cardiac effects of mianserin and show both anticholinergic activity and effects of an intracardiac conduction in the case of maprotiline. The mechanisms of these effects are discussed.
Topics: Adolescent; Adult; Anthracenes; Arrhythmias, Cardiac; Depressive Disorder; Dibenzazepines; Double-Blind Method; Electrocardiography; Female; Heart Conduction System; Heart Rate; Humans; Male; Maprotiline; Mianserin; Middle Aged
PubMed: 6824556
DOI: 10.1111/j.1365-2125.1983.tb05872.x -
Communications Biology Oct 2023Mammary cancer incidence varies greatly across species and underlying mechanisms remain elusive. We previously showed that mammosphere-derived epithelial cells from...
Mammary cancer incidence varies greatly across species and underlying mechanisms remain elusive. We previously showed that mammosphere-derived epithelial cells from species with low mammary cancer incidence, such as horses, respond to carcinogen 7, 12-Dimethylbenz(a)anthracene-induced DNA damage by undergoing apoptosis, a postulated anti-cancer mechanism. Additionally, we found that miR-214-3p expression in mammosphere-derived epithelial cells is lower in mammary cancer-resistant as compared to mammary cancer-susceptible species. Here we show that increasing miR-214 expression and decreasing expression of its target gene nuclear factor kappa B subunit 1 in mammosphere-derived epithelial cells from horses abolishes 7,12-Dimethylbenz(a)anthracene-induced apoptosis. A direct interaction of miR-214-3p with another target gene, unc-5 netrin receptor A, is also demonstrated. We propose that relatively low levels of miR-214 in mammosphere-derived epithelial cells from mammals with low mammary cancer incidence, allow for constitutive gene nuclear factor kappa B subunit 1 expression and apoptosis in response to 7, 12-Dimethylbenz(a)anthracene. Better understanding of the mechanisms regulating cellular responses to carcinogens improves our overall understanding of mammary cancer resistance mechanisms.
Topics: Animals; Horses; Carcinogens; 9,10-Dimethyl-1,2-benzanthracene; NF-kappa B; Epithelial Cells; MicroRNAs; Apoptosis; Anthracenes; Mammals; Neoplasms
PubMed: 37789172
DOI: 10.1038/s42003-023-05370-4 -
Molecular Pharmaceutics May 2020Necrosis targeting and imaging has significant implications for evaluating tumor growth, therapeutic response, and delivery of therapeutics to perinecrotic tumor zones....
Necrosis targeting and imaging has significant implications for evaluating tumor growth, therapeutic response, and delivery of therapeutics to perinecrotic tumor zones. Hypericin is a hydrophobic molecule with high necrosis affinity and fluorescence imaging properties. To date, the safe and effective delivery of hypericin to areas of necrosis in vivo remains a challenge because of its incompatible biophysical properties. To address this issue, we have developed a biodegradable nanoparticle (Hyp-NP) for delivery of hypericin to tumors for necrosis targeting and fluorescence imaging. The nanoparticle was developed using methoxy poly(ethylene glycol)--poly(ε-caprolactone) and hypericin by a modified solvent evaporation technique. The size of Hyp-NP was 19.0 ± 1.8 nm from cryo-TEM and 37.3 ± 0.7 nm from dynamic light-scattering analysis with a polydispersity index of 0.15 ± 0.01. The encapsulation efficiency of hypericin was 95.05% w/w by UV-vis absorption. After storage for 30 days, 91.4% hypericin was retained in Hyp-NP with nearly no change in hydrodynamic size, representing nanoparticle stability. In an ovarian cancer cell line, Hyp-NP demonstrated cellular internalization with intracellular cytoplasmic localization and preserved fluorescence and necrosis affinity. In a mouse subcutaneous tumor model, tumor accumulation was noted at 8 h postinjection, with near-complete clearance at 96 h postinjection. Hyp-NP was shown to be tightly localized within necrotic tumor zones. Histological analysis of harvested organs demonstrated no gross abnormalities, and in vitro, no hemolysis was observed. This proof-of-concept study demonstrates the potential clinical applications of Hyp-NP for necrosis targeting.
Topics: Animals; Anthracenes; Cell Line, Tumor; Female; Humans; Mice; Nanoparticles; Necrosis; Neoplasms; Optical Imaging; Perylene
PubMed: 32212709
DOI: 10.1021/acs.molpharmaceut.9b01238