-
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 -
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 -
Natural Product Research May 2021An unusual, new anthracene natural product named filamentos A (), two new anthraquinone derivatives named filamentos B () and C (), together with sixteen known compounds...
An unusual, new anthracene natural product named filamentos A (), two new anthraquinone derivatives named filamentos B () and C (), together with sixteen known compounds (-), were isolated from the roots of the tree . Their structures were identified by analysis of mass and spectroscopic data (IR, 1D and 2D NMR). Twelve metabolites (-, , -, -) showed moderate antibacterial activities against a wide range of Gram-positive and Gram-negative bacteria such as . , . , . , . , . and . .
Topics: Anthracenes; Anthraquinones; Anti-Bacterial Agents; Bacteria; Carbon-13 Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Plant Roots; Proton Magnetic Resonance Spectroscopy; Rubiaceae
PubMed: 31177846
DOI: 10.1080/14786419.2019.1627352 -
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... Dec 1983
Topics: Animals; Anthracenes; Carcinogens, Environmental; Chemical Phenomena; Chemistry; Cocarcinogenesis; Female; Humans; Male; Mice; Mutagenicity Tests; Neoplasms, Experimental; Pregnancy; Rats; Reproduction; Risk; Skin Neoplasms
PubMed: 6586640
DOI: No ID Found -
Science (New York, N.Y.) Dec 1950
Topics: Anthracenes; Radioisotopes
PubMed: 14787505
DOI: 10.1126/science.112.2920.718 -
Journal of the American Chemical Society Apr 2020Collisional intermolecular interactions between excited states form short-lived dimers and complexes that lead to the emergence of excimer/exciplex emission of lower...
Collisional intermolecular interactions between excited states form short-lived dimers and complexes that lead to the emergence of excimer/exciplex emission of lower energy, a phenomenon which must be differentiated from the photoluminescence (PL) arising from the monomeric molecules. Although the utilization of noncovalent bonding interactions, leading to the generation of excimer/exciplex PL, has been investigated extensively, precise control of the aggregates and their persistence at very low concentrations remains a rare phenomenon. In the search for a fresh approach, we sought to obtain exciplex PL from permanent structures by incorporating anthracene moieties into pyridinium-containing mechanically interlocked molecules. Beyond the optical properties of the anthracene moieties, their π-extended nature enforces [π···π] stacking that can overcome the Coulombic repulsion between the pyridinium units, affording an efficient synthesis of an octacationic homo[2]catenane. Notably, upon increasing the ionic strength by adding tetrabutylammonium hexafluorophosphate, the catenane yield increases significantly as a result of the decrease in Coulombic repulsions between the pyridinium units. Although the ground-state photophysical properties of the free cyclophane and the catenane are similar and show a charge-transfer band at ∼455 nm, their PL characters are distinct, denoting different excited states. The cyclophane emits at ∼562 nm (quantum yield ϕ = 3.6%, emission lifetime τ = 3 ns in MeCN), which is characteristic of a disubstituted anthracene-pyridinium linker. By contrast, the catenane displays an exciplex PL at low concentration (10 M) with an emission band centered on 650 nm (ϕ = 0.5%, τ = 14 ns) in MeCN and at 675 nm in aqueous solution. Live-cell imaging performed in MIAPaCa-2 prostate cancer cells confirmed that the catenane exciplex emission can be detected at micromolar concentrations.
Topics: Anthracenes; Humans; Molecular Structure
PubMed: 32233402
DOI: 10.1021/jacs.0c02128 -
Journal of Materials Chemistry. B May 2023Two novel anthracene derivatives were synthesized, and detailed photo-physical and biological investigations were carried out using a variety of spectroscopy techniques....
Two novel anthracene derivatives were synthesized, and detailed photo-physical and biological investigations were carried out using a variety of spectroscopy techniques. The effect of cyano (-CN) substitution was found to be effective to alter the charge population and frontier orbital energy levels Density Functional Theory (DFT) calculations. Particularly, the introduction of styryl and triphenylamine groups attached to the anthracene core helped to increase the conjugation relative to the anthracene moiety. The results revealed that the molecules have intramolecular charge transfer (ICT) properties, occurring from the electron donating triphenylamine to the electron accepting anthracene moiety in solutions. In addition, the photo-physical properties are strongly cyano-dependent, where the cyano-substituted (/)-(2-anthracen-9-yl)-3-(4'-(diphenylamino)biphenyl-4yl)acrylonitrile molecule showed stronger electron affinity due to the enhanced internal steric hindrance compared to the ()-4'-(2-(anthracen-9-yl)vinyl)-,-diphenylbiphenyl-4-amine molecule, which resulted in a lower photoluminescence quantum yield (PLQY) value and a shorter lifetime in the molecule. Besides, the Molecular Docking approach was used to investigate possible cellular staining targets to confirm cellular imaging potential of the compounds. Moreover, cell viability analyses put forth that synthesized molecules do not exhibit significant cytotoxicity under 125 μg mL concentration on the human dermal fibroblast cell line (HDFa). Moreover, both of the compounds showed great potential in cellular imaging of HDFa cells. Compared to Hoechst 33258, a common fluorescent dye used for nuclear staining, the compounds showed higher magnification of cellular structure imaging capacity by staining the whole cellular compartment. On the other hand, bacterial staining showed that ethidium bromide has higher resolution in monitoring () cell culture.
Topics: Humans; Molecular Docking Simulation; Staphylococcus aureus; Fluorescent Dyes; Cell Survival; Anthracenes
PubMed: 37144344
DOI: 10.1039/d3tb00449j -
Journal of Hazardous Materials Jun 2024Anthracene, a polycyclic aromatic hydrocarbon (PAH), is a widespread environmental pollutant that poses potential risks to human health. Exposure to anthracene can...
Anthracene, a polycyclic aromatic hydrocarbon (PAH), is a widespread environmental pollutant that poses potential risks to human health. Exposure to anthracene can result in various adverse health effects, including skin-related disorders. Photo exposure sufficiently removes the anthracene from the environment but also generates more degradation products which can be more toxic. The goal of this study was to assess the change in anthracene dermotoxicity caused by photodegradation and understand the mechanism of this change. In the present study, over 99.99% of anthracene was degraded within 24 h of sunlight exposure, while producing many intermediate products including 9,10-anthraquinone and phthalic acid. The anthracene products with different durations of photo exposure were applied to 2D and 3D human keratinocyte cultures. Although the non-degraded anthracene significantly delayed the cell migration, the cell viability and differentiation decreased dramatically in the presence of the photodegraded anthracene. Anthracene photodegradation products also altered the expression patterns of a number of inflammation-related genes in comparison to the control cells. Among these genes, il1a, il1b, il8, cxcl2, s100a9, and mmp1 were upregulated whereas the tlr4 and mmp3 were downregulated by the photodegraded anthracene. Topical deliveries of the photodegraded and non-degraded anthracene to the dorsal skin of hairless mice showed more toxic effects by the photodegraded anthracene. The 4-hour photodegradation products of anthracene thickened the epidermal layer, increased the dermal cellularity, and induced the upregulation of inflammatory markers, il1a, il1b, s100a9, and mmp1. In addition, it also prevented the production of a gap junction protein, Connexin-43. All the evidence suggested that photodegradation enhanced the toxicities of anthracene to the skin. The 4-hour photodegradation products of anthracene led to clinical signs similar to acute inflammatory skin diseases, such as atopic and contact dermatitis, eczema, and psoriasis. Therefore, the potential risk of skin irritation by anthracene should be also considered when an individual is exposed to PAHs, especially in environments with strong sunlight.
Topics: Anthracenes; Humans; Keratinocytes; Photolysis; Animals; Skin; Cell Survival; Mice; Cell Movement; Sunlight; Mice, Hairless; Anthraquinones; Cell Differentiation
PubMed: 38663297
DOI: 10.1016/j.jhazmat.2024.134386 -
International Journal of Molecular... Jan 2020In this work, we studied the anthracene oxidation by hydroxyl radicals. Hydroxyl radical was generated by reaction of (TPPFe) with hydrogen peroxide under visible...
In this work, we studied the anthracene oxidation by hydroxyl radicals. Hydroxyl radical was generated by reaction of (TPPFe) with hydrogen peroxide under visible radiation at a nitrogen atmosphere. The TPPFe was synthesized by Adler Method followed by metal complexation with Fe (III) chloride hexahydrate. Hydroxyl radical was detected by fluorescence emission spectroscopy and we studied kinetic of anthracene selective oxidation by hydroxyl radicals through the differential method. The TPPFe was characterized by UV-Vis spectrophotometry, Dynamic Light Scattering (DLS) and Scanning Electron Microscopy (SEM) measurements. The results indicated that TPPFE was compound by micro-particles with a size distribution of around 2500 nm. Kinetic results showed that the apparent rate constant for the oxidation of anthracene increased exponentially on as temperature increases, furthermore, the activation energy for the Anthracene oxidation by hydroxyl radicals under visible irradiation was 51.3 kJ/mol. Finally, anthraquinone was the main byproduct generated after oxidation of anthracene by TPP-Fe under visible irradiation.
Topics: Anthracenes; Dynamic Light Scattering; Ferric Compounds; Hydrogen Peroxide; Hydroxyl Radical; Kinetics; Light; Microscopy, Electron, Scanning; Nitrogen; Oxidation-Reduction; Porphyrins; Spectrometry, Fluorescence
PubMed: 31948078
DOI: 10.3390/ijms21010353