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Scientific Reports Apr 2021In order to analyze whether the marine macroalga Ulva lactuca can absorb and metabolize anthracene (ANT), the alga was cultivated with 5 µM ANT for 0-72 h, and the...
In order to analyze whether the marine macroalga Ulva lactuca can absorb and metabolize anthracene (ANT), the alga was cultivated with 5 µM ANT for 0-72 h, and the level of ANT was detected in the culture medium, and in the alga. The level of ANT rapidly decreased in the culture medium reaching a minimal level at 6 h, and rapidly increased in the alga reaching a maximal level at 12 h and then decreased to reach a minimal level at 48 h of culture. In addition, ANT induced an increase in hydrogen peroxide that remained until 72 h and a higher increase in superoxide anions that reach a maximal level at 24 h and remained unchanged until 72 h, indicating that ANT induced an oxidative stress condition. ANT induced an increase in lipoperoxides that reached a maximal level at 24 h and decreased at 48 h indicating that oxidative stress caused membrane damage. The activity of antioxidant enzymes SOD, CAT, AP, GR and GP increased in the alga treated with ANT whereas DHAR remained unchanged. The level of transcripts encoding these antioxidant enzymes increased and those encoding DHAR did not change. Inhibitors of monooxygenases, dioxygenases, polyphenol oxidases, glutathione-S-transferases and sulfotransferases induced an increase in the level of ANT in the alga cultivated for 24 h. These results strongly suggest that ANT is rapidly absorbed and metabolized in U. lactuca and the latter involves Phase I and II metabolizing enzymes.
Topics: Anthracenes; Antioxidants; Enzyme Activation; Enzymes; Hydrogen Peroxide; Oxidative Stress; Ulva
PubMed: 33833321
DOI: 10.1038/s41598-021-87147-5 -
International Journal of Molecular... Nov 2022In this work, we synthesized a polydimethylsiloxane membrane containing two emitter groups chemically attached to the membrane structure. For this, we attached the...
In this work, we synthesized a polydimethylsiloxane membrane containing two emitter groups chemically attached to the membrane structure. For this, we attached the anthracene group and the [Eu(bzac)] complex as blue and red emitters, respectively, in the matrix via hydrosilylation reactions. The synthesized membrane can be used as a bifunctional temperature and oxygen ratiometric optical probe by analyzing the effects that temperature changes and oxygen levels produce on the ratio of anthracene and europium(III) emission components. As a temperature probe, the system is operational in the 203-323 K range, with an observed maximum relative sensitivity of 2.06% K at 290 K and temperature uncertainties below 0.1 K over all the operational range. As an oxygen probe, we evaluated the ratiometric response at 25, 30, 35, and 40 °C. These results show an interesting approach to obtaining bifunctional ratiometric optical probes and also suggest the presence of an anthracene → europium(III) energy transfer, even though there is no chemical bonding between species.
Topics: Europium; Oxygen; Luminescence; Anthracenes
PubMed: 36498852
DOI: 10.3390/ijms232314526 -
Molecules (Basel, Switzerland) Nov 2021Every petroleum-processing plant produces sewage sludge containing several types of polycyclic aromatic hydrocarbons (PAHs). The degradation of PAHs via physical,...
Every petroleum-processing plant produces sewage sludge containing several types of polycyclic aromatic hydrocarbons (PAHs). The degradation of PAHs via physical, biological, and chemical methods is not yet efficient. Among biological methods, the use of marine sponge symbiont bacteria is considered an alternative and promising approach in the degradation of and reduction in PAHs. This study aimed to explore the potential performance of a consortium of sponge symbiont bacteria in degrading anthracene and pyrene. Three bacterial species ( strain GLB197, strain SLG510A3-8, and strain SLCDA 976) were mixed to form the consortium. The interaction between the bacterial consortium suspension and PAH components was measured at 5 day intervals for 25 days. The biodegradation performance of bacteria on PAH samples was determined on the basis of five biodegradation parameters. The analysis results showed a decrease in the concentration of anthracene (21.89%) and pyrene (7.71%), equivalent to a ratio of 3:1, followed by a decrease in the abundance of anthracene (60.30%) and pyrene (27.52%), equivalent to a ratio of 2:1. The level of pyrene degradation was lower than that of the anthracene due to fact that pyrene is more toxic and has a more stable molecular structure, which hinders its metabolism by bacterial cells. The products from the biodegradation of the two PAHs are alcohols, aldehydes, carboxylic acids, and a small proportion of aromatic hydrocarbon components.
Topics: Acinetobacter calcoaceticus; Animals; Anthracenes; Bacillus pumilus; Biodegradation, Environmental; Microbiota; Porifera; Pseudomonas stutzeri; Pyrenes; Symbiosis
PubMed: 34833943
DOI: 10.3390/molecules26226851 -
Molecules (Basel, Switzerland) Nov 2020genus consists of shrubs and small trees. Four toxic compounds have been isolated from plants, which were typified as dimeric anthracenones and named T496, T514, T516,... (Review)
Review
genus consists of shrubs and small trees. Four toxic compounds have been isolated from plants, which were typified as dimeric anthracenones and named T496, T514, T516, and T544. Moreover, several related compounds have been isolated and characterized. Here we review the toxicity of the fruit of plants when ingested (accidentally or experimentally), as well as the toxicity of its isolated compounds. Additionally, we analyze the probable antineoplastic effect of T514. Toxins cause damage mainly to nervous system, liver, lung, and kidney. The pathophysiological mechanism has not been fully understood but includes metabolic and structural alterations that can lead cells to apoptosis or necrosis. T514 has shown selective toxicity in vitro against human cancer cells. T514 causes selective and irreversible damage to peroxisomes; for this reason, it was renamed peroxisomicine A1 (PA1). Since a significant number of malignant cell types contain fewer peroxisomes than normal cells, tumor cells would be more easily destroyed by PA1 than healthy cells. Inhibition of topoisomerase II has also been suggested to play a role in the effect of PA1 on malignant cells. More research is needed, but the evidence obtained so far indicates that PA1 could be an effective anticancer agent.
Topics: Anthracenes; Antineoplastic Agents, Phytogenic; Drug-Related Side Effects and Adverse Reactions; Humans; Karwinskia; Neoplasms
PubMed: 33261194
DOI: 10.3390/molecules25235590 -
Ecotoxicology and Environmental Safety Jan 2021The study explored the polycyclic aromatic hydrocarbon tolerance of indigenous biosurfactant producing microorganisms. Three bacterial species were isolated from crude...
The study explored the polycyclic aromatic hydrocarbon tolerance of indigenous biosurfactant producing microorganisms. Three bacterial species were isolated from crude oil contaminated sites of Haldia, West Bengal. The three species were screened for biosurfactant production and identified by 16S rRNA sequencing as Brevundimonas sp. IITISM 11, Pseudomonas sp. IITISM 19 and Pseudomonas sp. IITISM 24. The strains showed emulsification activities of 51%, 57% and 63%, respectively. The purified biosurfactants were characterised using FT-IR, GC-MS and NMR spectroscopy and found to have structural similarities to glycolipopeptides, cyclic lipopeptides and glycolipids. The biosurfactants produced were found to be stable under a wide range of temperature (0-100 °C), pH (4-12) and salinity (up to 20% NaCl). Moreover, the strains displayed tolerance to high concentrations (275 mg/L) of anthracene and fluorene and showed a good amount of cell surface hydrophobicity with different hydrocarbons. The study reports the production and characterisation of biosurfactant by Brevundimonas sp. for the first time. Additionally, the kinetic parameters of the bacterial strains grown on up to 300 mg/L concentration of anthracene and fluorene, ranged between 0.0131 and 0.0156 µ (h), while the K(mg/L) ranged between 59.28 and 102.66 for Monod's Model. For Haldane-Andrew's model, µ (h) varied between 0.0168 and 0.0198. The inhibition constant was highest for Pseudomonas sp. IITISM 19 on anthracene and Brevundimonas sp. IITISM 11 on fluorene. The findings of the study suggest that indigenous biosurfactant producing strains have tolerance to high PAH concentrations and can be exploited for bioremediation purposes.
Topics: Anthracenes; Bacteria; Biodegradation, Environmental; Fluorenes; Glycolipids; Hydrocarbons; Kinetics; Petroleum; Polycyclic Aromatic Hydrocarbons; Pseudomonas; RNA, Ribosomal, 16S; Spectroscopy, Fourier Transform Infrared; Surface-Active Agents
PubMed: 33396141
DOI: 10.1016/j.ecoenv.2020.111621 -
Food Research International (Ottawa,... Jul 2022More than 5.8 million tonnes of oil have been spilled into the oceans. Some oil disasters marked history, causing multiple social and economic consequences in addition... (Review)
Review
More than 5.8 million tonnes of oil have been spilled into the oceans. Some oil disasters marked history, causing multiple social and economic consequences in addition to catastrophic environmental impacts. Recently, Brazil and Mauritius faced oil disasters that have severely impacted seafood sanitary credibility. One of the components of the oil composition are the polycyclic aromatic hydrocarbons (PAH), which are the main contamination markers of petrogenic origin. There is enough evidence to correlate the intake of food contaminated with PAH with increased risks of developing cancer. The set PAH4, composed of benzo[a]anthracene, benzo[a]pyrene, benzo[b]fluoranthene, and chrysene, and the set PAH8, composed of benzo[a]anthracene, benzo[a]pyrene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[ghi]perylene, chrysene, dibenzo[a,h]anthracene, and indeno[1,2,3-cd]pyrene are recognized as markers of food chemical contamination. After oil disasters in the oceans, the risk to the health of seafood consumers tends to be of special concern, Countries like the European Union set maximum levels for benzo[a]pyrene (5 µg kg) and PAH4 (30 µg kg) in bivalve mollusks. Levels of concern established by countries that have faced oil disasters are given special attention in this review. Laboratory analysis of PAH in food samples is very challenging because it deals with quite different kinds of matrices. Furthermore, analytical results are usually related to the closure or reopening of cultivated areas and fishing points. Therefore, the progress of the analytical methods for PAH in seafood is covered in detail. Chemical laboratory measurements provide essential data to assess the potential risks to human health due to consumption of seafood contaminated with PAH. The main human health risk assessment approaches in a seafood contamination scenario with PAH are reviewed and discussed, providing an insightful and guiding tool to each step of the risk assessment framework.
Topics: Anthracenes; Benzo(a)pyrene; Chrysenes; Disasters; Food Safety; Humans; Petroleum Pollution; Polycyclic Aromatic Hydrocarbons
PubMed: 35761626
DOI: 10.1016/j.foodres.2022.111366 -
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 -
Journal of Microbiology and... Jan 2019Lichens are generally known as self-sufficient, symbiotic life-forms between fungi and algae/cyanobacteria, and they also provide shelter for a wide range of beneficial...
Lichens are generally known as self-sufficient, symbiotic life-forms between fungi and algae/cyanobacteria, and they also provide shelter for a wide range of beneficial bacteria. Currently, bacterial-derived biodegradable polyhydroxyalkanoate (PHA) is grabbing the attention of many researchers as a promising alternative to non-degradable plastics. This study was conducted to develop a new method of PHA production using unexplored lichen-associated bacteria, which can simultaneously degrade two ubiquitous industrial toxins, anthracene and naphthalene. Here, 49 lichen-associated bacteria were isolated and tested for PHA synthesis. During the GC-MS analysis, a potential strain of EL19 was found to be a 3-hydroxyhexanoate (3-HHx) accumulator and identified as sp. based on the 16S rRNA sequencing. GC analysis revealed that EL19 was capable of accumulating 30.62% and 19.63% of 3-HHx from naphthalene and anthracene, respectively, resulting in significant degradation of 98% and 96% of naphthalene and anthracene, respectively, within seven days. Moreover, the highly expressed gene verified the genetic basis of PHA production under nitrogen starvation conditions. Thus, this study strongly supports the hypothesis that lichen-associated bacteria can detoxify naphthalene and anthracene, store energy for extreme conditions, and probably help the associated lichen to live in extreme conditions. So far, this is the first investigation of lichen-associated bacteria that might utilize harmful toxins as feasible supplements and convert anthracene and naphthalene into eco-friendly 3-HHx. Implementation of the developed method would reduce the production cost of PHA while removing harmful waste products from the environment.
Topics: Acyltransferases; Anthracenes; Biodegradation, Environmental; Caproates; Culture Media; Gene Expression; Lichens; Naphthalenes; Nitrogen; Phylogeny; Polyhydroxyalkanoates; Pseudomonas; RNA, Ribosomal, 16S; Sequence Analysis, DNA
PubMed: 30518016
DOI: 10.4014/jmb.1808.08037 -
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 -
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