-
Molecules (Basel, Switzerland) Jan 2024Enhanced oil recovery (EOR) processes are technologies used in the oil and gas industry to maximize the extraction of residual oil from reservoirs after primary and... (Review)
Review
Enhanced oil recovery (EOR) processes are technologies used in the oil and gas industry to maximize the extraction of residual oil from reservoirs after primary and secondary recovery methods have been carried out. The injection into the reservoir of surface-active substances capable of reducing the surface tension between oil and the rock surface should favor its extraction with significant economic repercussions. However, the most commonly used surfactants in EOR are derived from petroleum, and their use can have negative environmental impacts, such as toxicity and persistence in the environment. Biosurfactants on the other hand, are derived from renewable resources and are biodegradable, making them potentially more sustainable and environmentally friendly. The present review intends to offer an updated overview of the most significant results available in scientific literature on the potential application of biosurfactants in the context of EOR processes. Aspects such as production strategies, techniques for characterizing the mechanisms of action and the pros and cons of the application of biosurfactants as a principal method for EOR will be illustrated and discussed in detail. Optimized concepts such as the HLD in biosurfactant choice and design for EOR are also discussed. The scientific findings that are illustrated and reviewed in this paper show why general emphasis needs to be placed on the development and adoption of biosurfactants in EOR as a substantial contribution to a more sustainable and environmentally friendly oil and gas industry.
Topics: Anthracenes; Industry; Petroleum; Surface Tension
PubMed: 38257213
DOI: 10.3390/molecules29020301 -
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 -
PloS One 2016Mixing soil or adding earthworms (Eisenia fetida (Savigny, 1826)) accelerated the removal of anthracene, a polycyclic aromatic hydrocarbon, from a pasture and an arable...
Mixing soil or adding earthworms (Eisenia fetida (Savigny, 1826)) accelerated the removal of anthracene, a polycyclic aromatic hydrocarbon, from a pasture and an arable soil, while a non-ionic surfactant (Surfynol® 485) inhibited the removal of the contaminant compared to the untreated soil. It was unclear if the treatments affected the soil bacterial community and consequently the removal of anthracene. Therefore, the bacterial community structure was monitored by means of 454 pyrosequencing of the 16S rRNA gene in the pasture and arable soil mixed weekly, amended with Surfynol® 485, E. fetida or organic material that served as food for the earthworms for 56 days. In both soils, the removal of anthracene was in the order: mixing soil weekly (100%) > earthworms applied (92%) > organic material applied (77%) > untreated soil (57%) > surfactant applied (34%) after 56 days. There was no clear link between removal of anthracene from soil and changes in the bacterial community structure. On the one hand, application of earthworms removed most of the contaminant from the arable soil and had a strong effect on the bacterial community structure, i.e. a decrease in the relative abundance of the Acidobacteria, Chloroflexi and Gemmatimonadetes, and an increase in that of the Proteobacteria compared to the unamended soil. Mixing the soil weekly removed all anthracene from the arable soil, but had little or no effect on the bacterial community structure. On the other hand, application of the surfactant inhibited the removal of anthracene from the arable soil compared to the untreated soil, but had a strong effect on the bacterial community structure, i.e. a decrease in the relative abundance of Cytophagia (Bacteroidetes), Chloroflexi, Gemmatimonadetes and Planctomycetes and an increase in that of the Flavobacteria (Bacteroidetes) and Proteobacteria. Additionally, the removal of anthracene was similar in the different treatments of both the arable and pasture soil, but the effect of application of carrot residue, earthworms or the surfactant on the bacterial community structure was more accentuated in the arable soil than in the pasture soil. It was found that removal of anthracene was not linked to changes in the bacterial community structure.
Topics: Acidobacteria; Animals; Anthracenes; Bacteria; Bacteroidetes; Chloroflexi; DNA, Bacterial; Oligochaeta; Principal Component Analysis; Proteobacteria; RNA, Ribosomal, 16S; Sequence Analysis, DNA; Soil Microbiology; Soil Pollutants; Surface-Active Agents
PubMed: 27727277
DOI: 10.1371/journal.pone.0160991 -
Molecules (Basel, Switzerland) Jan 2024The 1,8-Diazaanthracene-2,9,10-triones, their 5,8-dihydro derivatives, and 1,8-diazaanthracene-2,7,9,10-tetraones, structurally related to the diazaquinomycin family of...
The 1,8-Diazaanthracene-2,9,10-triones, their 5,8-dihydro derivatives, and 1,8-diazaanthracene-2,7,9,10-tetraones, structurally related to the diazaquinomycin family of natural products, were synthesized in a regioselective fashion employing Diels-Alder strategies. These libraries were studied for their cytotoxicity in a variety of human cancer cell lines in order to establish structure-activity relationships. From the results obtained, we conclude that some representatives of the 1,8-diazaanthracene-2,9,10-trione framework show potent and selective cytotoxicity against solid tumors. Similar findings were made for the related 1-azaanthracene-2,9,10-trione derivatives, structurally similar to the marcanine natural products, which showed improved activity over their natural counterparts. An enantioselective protocol based on the use of a SAMP-related chiral auxiliary derived was developed for the case of chiral 5-substituted 1,8-diazaanthracene-2,9,10-triones, and showed that their cytotoxicity was not enantiospecific.
Topics: Humans; Anthracenes; Biological Products; Cell Line; Structure-Activity Relationship
PubMed: 38257402
DOI: 10.3390/molecules29020489 -
Nature Communications Dec 2022Due to the interest in the origin of life and the need to synthesize new functional materials, the study of the origin of chirality has been given significant attention....
Due to the interest in the origin of life and the need to synthesize new functional materials, the study of the origin of chirality has been given significant attention. The mechanism of chirality transfer at molecular and supramolecular levels remains underexplored. Herein, we study the mechanism of chirality transfer of N, N'-bis (octadecyl)---(anthracene-9-carboxamide)-glutamic diamide (--GAn) supramolecular chiral self-assembled at the air/water interface by chiral sum-frequency generation vibrational spectroscopy (chiral SFG) and molecular dynamics (MD) simulations. We observe long-range chirality transfer in the systems. The chirality of C-H is transferred first to amide groups and then transferred to the anthracene unit, through intermolecular hydrogen bonds and π-π stacking to produce an antiparallel β-sheet-like structure, and finally it is transferred to the end of hydrophobic alkyl chains at the interface. These results are relevant for understanding the chirality origin in supramolecular systems and the rational design of supramolecular chiral materials.
Topics: Stereoisomerism; Spectrum Analysis; Protein Conformation, beta-Strand; Hydrogen Bonding; Anthracenes
PubMed: 36517528
DOI: 10.1038/s41467-022-35548-z -
Molecules (Basel, Switzerland) Oct 2020The intermediacy of short-lived isoindenes, generated in the course of metallotropic or silatropic shifts over the indene skeleton, can be shown by Diels-Alder trapping... (Review)
Review
Diels-Alder Additions as Mechanistic Probes-Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings.
The intermediacy of short-lived isoindenes, generated in the course of metallotropic or silatropic shifts over the indene skeleton, can be shown by Diels-Alder trapping with tetracyanoethylene, leading to the complete elucidation of the dynamic behaviour of a series of polyindenylsilanes. Cyclopentadienones, bearing ferrocenyl and multiple phenyl or naphthyl substituents undergo [4 + 2] cycloadditions with diaryl acetylenes or triphenylcyclopropene to form the corresponding polyarylbenzenes or cycloheptatrienes. The heptaphenyltropylium cation, [CPh], was shown to adopt a nonplanar shallow boat conformation. In contrast, the attempted Diels-Alder reaction of tetracyclone and phenethynylfluorene yielded electroluminescent tetracenes. Finally, benzyne addition to 9-(2-indenyl)anthracene, and subsequent incorporation of a range of organometallic fragments, led to development of an organometallic molecular brake.
Topics: Anthracenes; Benzene Derivatives; Crystallography, X-Ray; Cycloaddition Reaction; Ethylenes; Indenes; Molecular Structure; Nitriles; Organometallic Compounds; Polymers; Stereoisomerism; Tropolone
PubMed: 33076359
DOI: 10.3390/molecules25204730 -
Journal of Applied Microbiology Aug 2008The metabolism of phenanthrene and anthracene by a moderate thermophilic Nocardia otitidiscaviarum strain TSH1 was examined.
AIMS
The metabolism of phenanthrene and anthracene by a moderate thermophilic Nocardia otitidiscaviarum strain TSH1 was examined.
METHODS AND RESULTS
When strain TSH1 was grown in the presence of anthracene, four metabolites were identified as 1,2-dihydroxy-1,2-dihydroanthracene, 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid, 2,3-dihydroxynaphthalene and benzoic acid using gas chromatography-mass spectrometry (GC-MS), reverse phase-high performance liquid chromatography (RP-HPLC) and thin-layer chromatography (TLC). Degradation studies with phenanthrene revealed 2,2'-diphenic acid, phthalic acid, 4-hydroxyphenylacetic acid, o-hydroxyphenylacetic acid, benzoic acid, a phenanthrene dihydrodiol, 4-[1-hydroxy(2-naphthyl)]-2-oxobut-3-enoic acid and 1-hydroxy-2-naphthoic acid (1H2NA), as detectable metabolites.
CONCLUSIONS
Strain TSH1 initiates phenanthrene degradation via dioxygenation at the C-3 and C-4 or at C-9 and C-10 ring positions. Ortho-cleavage of the 9,10-diol leads to formation of 2,2'-diphenic acid. The 3,4-diol ring is cleaved to form 1H2NA which can subsequently be degraded through o-phthalic acid pathway. Benzoate does not fit in the previously published pathways from mesophiles. Anthracene metabolism seems to start with a dioxygenation at the 1 and 2 positions and ortho-cleavage of the resulting diol. The pathway proceeds probably through 2,3-dicarboxynaphthalene and 2,3-dihydroxynaphthalene. Degradation of 2,3-dihydroxynaphthalene to benzoate and transformation of the later to catechol is a possible route for the further degradation of anthracene.
SIGNIFICANCE AND IMPACT OF THE STUDY
For the first time, metabolism of phenanthrene and anthracene in a thermophilic Nocardia strain was investigated.
Topics: Anthracenes; Benzoates; Biodegradation, Environmental; Catechols; Gas Chromatography-Mass Spectrometry; Hot Temperature; Nocardia; Oxidation-Reduction; Phenanthrenes; Soil Microbiology; Soil Pollutants; Species Specificity
PubMed: 18312570
DOI: 10.1111/j.1365-2672.2008.03753.x -
Molecules (Basel, Switzerland) Jul 2021-glucosidase is a major enzyme that is involved in starch digestion and type 2 diabetes mellitus. In this study, the inhibition of hypericin by α-glucosidase and its...
-glucosidase is a major enzyme that is involved in starch digestion and type 2 diabetes mellitus. In this study, the inhibition of hypericin by α-glucosidase and its mechanism were firstly investigated using enzyme kinetics analysis, real-time interaction analysis between hypericin and -glucosidase by surface plasmon resonance (SPR), and molecular docking simulation. The results showed that hypericin was a high potential reversible and competitive α-glucosidase inhibitor, with a maximum half inhibitory concentration (IC) of 4.66 ± 0.27 mg/L. The binding affinities of hypericin with -glucosidase were assessed using an SPR detection system, which indicated that these were strong and fast, with balances dissociation constant (KD) values of 6.56 × 10 M and exhibited a slow dissociation reaction. Analysis by molecular docking further revealed that hydrophobic forces are generated by interactions between hypericin and amino acid residues Arg-315 and Tyr-316. In addition, hydrogen bonding occurred between hypericin and -glucosidase amino acid residues Lys-156, Ser-157, Gly-160, Ser-240, His-280, Asp-242, and Asp-307. The structure and micro-environment of α-glucosidase enzymes were altered, which led to a decrease in α-glucosidase activity. This research identified that hypericin, an anthracene ketone compound, could be a novel α-glucosidase inhibitor and further applied to the development of potential anti-diabetic drugs.
Topics: Anthracenes; Binding Sites; Fungal Proteins; Glycoside Hydrolase Inhibitors; Humans; Hydrogen Bonding; Hydrophobic and Hydrophilic Interactions; Hypoglycemic Agents; Kinetics; Molecular Docking Simulation; Nitrophenylgalactosides; Perylene; Protein Binding; Protein Conformation, alpha-Helical; Protein Conformation, beta-Strand; Protein Interaction Domains and Motifs; Saccharomyces cerevisiae; Surface Plasmon Resonance; alpha-Glucosidases
PubMed: 34361714
DOI: 10.3390/molecules26154566 -
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 -
Molecules (Basel, Switzerland) Mar 2023The ability to degrade aromatic hydrocarbons, including (i) benzene, toluene, xylene, naphthalene, anthracene, phenanthrene, benzo[a]anthracene, and benzo[a]pyrene; (ii)...
The ability to degrade aromatic hydrocarbons, including (i) benzene, toluene, xylene, naphthalene, anthracene, phenanthrene, benzo[a]anthracene, and benzo[a]pyrene; (ii) polar substituted derivatives of benzene, including phenol and aniline; (iii) N-heterocyclic compounds, including pyridine; 2-, 3-, and 4-picolines; 2- and 6-lutidine; 2- and 4-hydroxypyridines; (iv) derivatives of aromatic acids, including coumarin, of 133 strains from the Regional Specialized Collection of Alkanotrophic Microorganisms was demonstrated. The minimal inhibitory concentrations of these aromatic compounds for varied in a wide range from 0.2 up to 50.0 mM. Xylene and polycyclic aromatic hydrocarbons (PAHs) were the less-toxic and preferred aromatic growth substrates. bacteria introduced into the PAH-contaminated model soil resulted in a 43% removal of PAHs at an initial concentration 1 g/kg within 213 days, which was three times higher than that in the control soil. As a result of the analysis of biodegradation genes, metabolic pathways for aromatic hydrocarbons, phenol, and nitrogen-containing aromatic compounds in , proceeding through the formation of catechol as a key metabolite with its following ortho-cleavage or via the hydrogenation of aromatic rings, were verified.
Topics: Benzene; Rhodococcus; Polycyclic Aromatic Hydrocarbons; Hydrocarbons, Aromatic; Anthracenes; Biodegradation, Environmental; Phenols; Soil; Soil Pollutants
PubMed: 36903638
DOI: 10.3390/molecules28052393