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Chemical & Pharmaceutical Bulletin 2013A new method for the analysis of selected nitropolycyclic aromatic hydrocarbons (NPAHs) at ultra-trace levels in water samples is proposed. Particulate NPAHs were...
A new method for the analysis of selected nitropolycyclic aromatic hydrocarbons (NPAHs) at ultra-trace levels in water samples is proposed. Particulate NPAHs were collected on a GC glass fiber filter. Soluble NPAHs were collected on a C18 Empore disk. After simple clean-up and concentration of NPAHs in both phases, the NPAHs were analyzed using HPLC equipped with clean-up, reducer, concentration and chemiluminescence detection units. The proposed method showed good linear calibration curves with correlation coefficients (r(2)) ranging from 0.9954 to 0.9998. The limits of detection ranged from 0.013 to 0.15 nmol/L (soluble NPAHs) and from 0.01 to 0.13 nmol/L (particulate NPAHs) for 5 NPAHs [(9-nitroanthracene, 1-nitropyrene, 6-nitrochrysene (6-NC), 7-nitrobenz[a]anthracene and 6-nitrobenzo[a]pyrene] having 3 to 5 rings analyzed, when 1.5 L of water sample was used. The repeatability for soluble NPAHs ranged between 4.2 and 6.8% (n=5), while for particulate NPAHs, it varied between 2.2 and 2.8% (n=5). The proposed method successfully determined the above NPAHs expect 6-NC in river water samples, suggesting that this method is suitable for the ultra-trace analysis of NPAHs in water samples.
Topics: Anthracenes; Calibration; Chromatography, High Pressure Liquid; Chrysenes; Environmental Monitoring; Limit of Detection; Nitro Compounds; Polycyclic Aromatic Hydrocarbons; Pyrenes; Rivers; Water Pollutants, Chemical
PubMed: 24292788
DOI: 10.1248/cpb.c13-00547 -
PloS One 2021The Ultraviolet-visible (UV-Vis) spectra indicate that anthracenyl chalcones (ACs) have high maximum wavelengths and good transparency windows for optical applications...
The Ultraviolet-visible (UV-Vis) spectra indicate that anthracenyl chalcones (ACs) have high maximum wavelengths and good transparency windows for optical applications and are suitable for optoelectronic applications owing to their HOMO-LUMO energy gaps (2.93 and 2.76 eV). Different donor substituents on the AC affect their dipole moments and nonlinear optical (NLO) responses. The positive, negative, and neutral electrostatic potential regions of the molecules were identified using molecular electrostatic potential (MEP). The stability of the molecule on account of hyperconjugative interactions and accompanying charge delocalization was analyzed using natural bond orbital (NBO) analysis. Open and closed aperture Z-scans were performed using a continuous-wave frequency-doubled diode-pumped solid-state (DPSS) laser to measure the nonlinear absorption and nonlinear refractive index coefficients, respectively. The valley-to-peak profile of AC indicated a negative nonlinear refractive index coefficient. The obtained single crystals possess reverse saturation absorption due to excited-state absorption. The structural and nonlinear optical properties of the molecules have been discussed, along with the role of anthracene substitution for enhancing the nonlinear optical properties. The calculated third-order susceptibility value was 1.10 x10-4 esu at an intensity of 4.1 kW/cm2, higher than the reported values for related chalcone derivatives. The NLO response for both ACs offers excellent potential in optical switching and limiting applications.
Topics: Anthracenes; Chalcones; Crystallography, X-Ray; Density Functional Theory; Fused-Ring Compounds; Molecular Structure; Quantum Theory
PubMed: 34582495
DOI: 10.1371/journal.pone.0257808 -
Chemistry, An Asian Journal Dec 2020A straightforward modification route to obtain mono- and di-substituted anthroyl ester bridge functionalized dinuclear Au(I) bis-N-heterocyclic carbene complexes is...
A straightforward modification route to obtain mono- and di-substituted anthroyl ester bridge functionalized dinuclear Au(I) bis-N-heterocyclic carbene complexes is presented. The functionalization can be achieved starting from a hydroxyl-functionalized ligand precursor followed by transmetallation of the corresponding Ag complex or via esterification of the hydroxyl-functionalized gold complex. The compounds are characterized by NMR-spectroscopy, ESI-MS, elemental analysis and SC-XRD. The mono-ester Au complex shows quantum yields around 18%. In contrast, the corresponding syn-di-ester Au complex, exhibits significantly lower quantum yields of around 8%. Due to insufficient water solubility of the di-ester, only the mono-ester complex has been tested regarding its antiproliferative activity against HeLa- (cervix) and MCF-7- (breast) cancer cell lines and a healthy fibroblast cell line (V79). IC values of 7.26 μM in the HeLa cell line and 7.92 μM in the MCF-7 cell line along with selectivity indices of 8.8 (HeLa) and 8.0 (MCF-7) are obtained. These selectivity indices are significantly higher than those obtained for the reference drugs cisplatin or auranofin.
Topics: Anthracenes; Cell Line; Cell Proliferation; Coordination Complexes; Gold; HeLa Cells; Humans; Imidazolidines; MCF-7 Cells; Methane; Molecular Conformation; Spectrophotometry, Ultraviolet
PubMed: 33405335
DOI: 10.1002/asia.202001104 -
Scientific Reports Dec 2023The northeastern Pacific (NEP) Ocean spans the coast of British Columbia (Canada) and is impacted by anthropogenic activities including oil pipeline developments,...
The northeastern Pacific (NEP) Ocean spans the coast of British Columbia (Canada) and is impacted by anthropogenic activities including oil pipeline developments, maritime fossil fuel tanker traffic, industrial chemical effluents, agricultural and urban emissions in tandem with stormwater and wastewater discharges, and forest wildfires. Such events may expose surrounding marine environments to toxic polycyclic aromatic hydrocarbons (PAHs) and impact critical habitats of threatened killer whales (Orcinus orca). We analyzed skeletal muscle and liver samples from stranded Bigg's killer whales and endangered Southern Resident killer whales (SRKWs) for PAH contamination using LRMS. C3-phenanthrenes/anthracenes (mean: 632 ng/g lw), C4-dibenzothiophenes (mean: 334 ng/g lw), and C4-phenanthrenes/anthracenes (mean: 248 ng/g lw) presented the highest concentrations across all tissue samples. Diagnostic ratios indicated petrogenic-sourced contamination for SRKWs and pyrogenic-sourced burdens for Bigg's killer whales; differences between ecotypes may be attributed to habitat range, prey selection, and metabolism. A mother-fetus skeletal muscle pair provided evidence of PAH maternal transfer; low molecular weight compounds C3-fluorenes, dibenzothiophene, and naphthalene showed efficient and preferential exposure to the fetus. This indicates in-utero exposure of PAH-contamination to the fetus. Our results show that hydrocarbon-related anthropogenic activities are negatively impacting these top predators; preliminary data found here can be used to improve oil spill and other PAH pollution management and regulation efforts, and inform policy to conserve killer whale habitats in the NEP.
Topics: Animals; Polycyclic Aromatic Hydrocarbons; Whale, Killer; British Columbia; Phenanthrenes; Anthracenes; Environmental Monitoring
PubMed: 38114485
DOI: 10.1038/s41598-023-45306-w -
Journal of the American Chemical Society Oct 2016We report a functional synthetic model for studying the noncovalent networks (NCNs) required for complex protein functions. The model [2]-catenane is self-assembled from...
We report a functional synthetic model for studying the noncovalent networks (NCNs) required for complex protein functions. The model [2]-catenane is self-assembled from dipeptide building blocks and contains an extensive network of hydrogen bonds and aromatic interactions. Perturbations to the catenane cause compensating changes in the NCNs structure and dynamics, resulting in long-distance changes reminiscent of a protein. Key findings include the notion that NCNs require regions of negative cooperativity, or "frustrated" noncovalent interactions, as a source of potential energy for driving the response. We refer to this potential energy as latent free energy and describe a mechanistic and energetic model for responsive systems.
Topics: Anthracenes; Biomimetic Materials; Glycine; Hydrogen Bonding; Models, Molecular; Molecular Conformation; Proteins; Thermodynamics
PubMed: 27631725
DOI: 10.1021/jacs.6b07833 -
Drug Design, Development and Therapy 2019Acute lung injury (ALI) is characterized by high prevalence and high mortality. Thus far, no effective pharmacological treatment has been made for ALI in clinics....
BACKGROUND
Acute lung injury (ALI) is characterized by high prevalence and high mortality. Thus far, no effective pharmacological treatment has been made for ALI in clinics. Inflammation is critical to the development of ALI. Curcumin analog C66, having reported as an inhibitor of c-Jun N-terminal kinase (JNK), exhibits anti-inflammatory property both in vitro and in vivo. However, whether C66 is capable of reducing lipopolysaccharide (LPS)-induced ALI through the inhibition of inflammation by targeting JNK remains unknown.
METHODS
Intratracheal injection of LPS was employed to build a mouse ALI model. H&E staining, wet/dry ratio, immunofluorescence staining, inflammatory cell detection, and inflammatory gene expression were used to evaluate lung injury and lung inflammation. In vitro, LPS was used to induce the expression of inflammatory cytokines both in protein and gene levels.
RESULTS
The results of our studies showed that the pretreatment with C66 and JNK inhibitor SP600125 was capable of attenuating the LPS-induced ALI by detecting pulmonary edema, pathological changes, total protein concentration, and inflammatory cell number in bronchoalveolar lavage fluid (BALF). Besides, C66 and SP600125 also suppressed LPS-induced inflammatory cytokine expression in BALF, serum, and lung tissue. In vitro, LPS-induced production of TNF-α and IL-6 and gene expression of TNF-α, IL-6, IL-1β, and COX-2 could be inhibited by the pretreatment with C66 and SP600125. It was found that C66 and SP600125 could inhibit LPS-induced phosphorylation of JNK both in vitro and in vivo.
CONCLUSION
In brief, our results suggested that C66 protects LPS-induced ALI through the inhibition of inflammation by targeting the JNK pathway. These findings further confirmed the pivotal role of JNK in ALI and implied that C66 is likely to serve as a potential therapeutic agent for ALI.
Topics: Acute Lung Injury; Animals; Anthracenes; Cells, Cultured; Curcumin; Disease Models, Animal; Dose-Response Relationship, Drug; Inflammation; Injections, Intravenous; JNK Mitogen-Activated Protein Kinases; Lipopolysaccharides; Male; Mice; Mice, Inbred C57BL; Molecular Structure; Phosphorylation; Structure-Activity Relationship
PubMed: 31849448
DOI: 10.2147/DDDT.S215712 -
Antimicrobial Agents and Chemotherapy Dec 2009Polyamine levels are greatly increased in alveolar macrophages (AMs) during Pneumocystis pneumonia (PCP), leading to increased production of H(2)O(2), which causes AMs...
Polyamine levels are greatly increased in alveolar macrophages (AMs) during Pneumocystis pneumonia (PCP), leading to increased production of H(2)O(2), which causes AMs to undergo apoptosis. One of the mechanisms by which polyamine levels in AMs are elevated is enhanced uptake of exogenous polyamines. In this study, the possibility of targeting polyamine uptake as a treatment for PCP was examined. Four anthracene- and one benzene-polyamine conjugates that are potential polyamine transport inhibitors, including N1-anthracen-9-ylmethyl-butane-1,4-diamine; N-(4-aminobutyl)-N-anthracen-9-ylmethylbutane-1,4-diamine; N-[4-(4-aminobutylamino)butyl]-N-anthracen-9-ylmethylbutane-1,4-diamine; N-(4-amino-butyl)-N'-(10-[[4-(4-amino-butylamino)butylamino]-methyl]anthracen-9-ylmethyl)butane-1,4-diamine (44-Ant-44); and benzene-polyamine conjugate N-(4-amino-butyl)-N'-(4-[[4-(4-amino-butylamino)butylamino]-methyl]benzyl)butane-1,4-diamine (44-Bn-44), were tested. Compounds 44-Ant-44 and 44-Bn-44 were found to have a very low toxicity to AMs in vitro and were evaluated for their therapeutic effect on PCP in vivo. Sprague-Dawley rats infected with P. carinii for 28 days were intranasally instilled with 50 microl of a 1 mM solution of 44-Bn-44 or 44-Ant-44 every 2 days. Twenty-one days after initiation of the treatment, three to five rats from each group were sacrificed and examined for lung pathology, organism burden, and apoptosis of AMs. Both 44-Bn-44 and 44-Ant-44 reduced organism burdens; however, only 44-Ant-44 decreased the severity of the infection with reduced lung inflammation, increased clearance of exudates, increased air space, and decreased apoptosis of AMs. 44-Ant-44 also significantly prolonged the survival of treated animals. These results suggest that polyamine uptake is a potential target for treatment of PCP.
Topics: Animals; Anthracenes; Antifungal Agents; Apoptosis; Benzene; Biological Transport; Female; Injections, Intramuscular; Macrophages, Alveolar; Molecular Structure; Pneumocystis carinii; Pneumonia, Pneumocystis; Polyamines; Rats; Rats, Sprague-Dawley
PubMed: 19805570
DOI: 10.1128/AAC.00662-09 -
Asian Pacific Journal of Cancer... Feb 2023With increasing incidence of cancers globally and limited resources in some affected countries, repurposing existing drugs for reducing tumorigenesis is highly...
OBJECTIVE
With increasing incidence of cancers globally and limited resources in some affected countries, repurposing existing drugs for reducing tumorigenesis is highly important. Artemisinin and caffeine have potent anti-oxidative and anti-tumor properties but are therapies for other diseases. This study evaluated the biochemical and p53 gene modulatory effects of doses of artemisinin-caffeine combination on breast, lungs and liver tissues in rats induced with DMBA.
METHODS
After due ethical approval, 30 animals were treated with 40mg/kg single dose of 7,12-dimethylbenzene anthracene (DMBA) as a model for DNA damage and induction of carcinogenesis. Five animals each received normal saline (normal), low dose artemisinin (Art; 4mg/kg), low dose caffeine (Caff; 25mg/kg), low dose combination of caff + art (25+4mg/kg), high dose combination of caff + art (50+8mg/kg) or no treatment (DMBA). All treatment doses were orally administered daily for two weeks post DMBA treatment. Nitric oxide levels and p53 relative gene expression was carried out using primer-specific RT-PCR, GAPDH was used as loading control and amplicons were resolved by gel electrophoresis.
RESULTS
DMBA induced lesions in breast, liver, and lung tissues evident from histology analysis, compared to normal group. In all 3 tissues, caffeine (25mg/kg) and combination of caff + art (25+4mg/kg) significantly reduced p53 gene expression (p < 0.05), but there was significant increase in the group treated with low dose art (4mg/kg) and high dose caff + art, which were similar to DMBA group (p<0.05). In lungs, nitric oxide (NO) increased in all groups but not in caffeine, in the liver NO decreased with caffeine or its combination with art, compared to DMBA group.
CONCLUSIONS
This study shows a dose-dependent synergistic anticancer effects of caffeine and artemisinin combination on p53 gene and nitric oxide regulation hence can mitigate tumor development.
Topics: Animals; Rats; Caffeine; Nitric Oxide; Tumor Suppressor Protein p53; Xylenes; Carcinogenesis; Cell Transformation, Neoplastic; Liver; Artemisinins; Anthracenes; Lung; Gene Expression
PubMed: 36853292
DOI: 10.31557/APJCP.2023.24.2.451 -
Journal of Oleo Science 2009The objective of this work was to determine some beneficial and bioactive minor lipid components in wheat germ and grape seeds as a result of milling industry of wheat...
The objective of this work was to determine some beneficial and bioactive minor lipid components in wheat germ and grape seeds as a result of milling industry of wheat and pressing of grapes in wineries. Sterylglycosides (SG's) were isolated and fractionate into free and acylated SG's by TLC and were determine as their1-anthroylnitriles (1-AN) by HPLC. Moreover, 4-desmethylsterols were isolated, derivatized into their trimethyl silyl derivatives and analyzed by GLC. Tocopherols and tocotrienols were directly analyzed by HPLC. In addition, fatty acids composition by GLC was accomplished. The results were compared to three conventional edible oils, namely, corn, sunflower and cottonseed. It was found that the wheat germ oil (WGO) and grape seed oil (GSO) contained reasonable amounts of whole sterols. Sterylglycosides fraction (SG), which have not been evaluated, it was found that the two by-products contained high amounts of SG's and they were rich in free and acylated campe/stigma SG as well as free and acylated beta-sito SG. Total tocopherols and tocotrienols components were found in very high amounts in WGO (1300 ppm) and GSO (380 ppm). It is noteworthy to mention that GSO contained significant amounts of alpha- and gamma-tocotrienols which prevent cardiovascular diseases and contained reasonable amounts of alpha- and gamma-tocopherols. On the other side, it was found that WG and GS oils were enrich in linoleic acid (omega-6), while linolenic acid (omega-3) was present in higher quantity in WGO.
Topics: Anthracenes; Chemical Fractionation; Chromatography, Gas; Chromatography, High Pressure Liquid; Fatty Acids; Phytosterols; Plant Oils; Seeds; Tocopherols; Tocotrienols; Triticum; Vitis
PubMed: 19367078
DOI: 10.5650/jos.58.227 -
Scientific Reports Sep 2015Halophilic Martelella strain AD-3, isolated from highly saline petroleum-contaminated soil, can efficiently degrade polycyclic aromatic hydrocarbons (PAHs), such as...
Halophilic Martelella strain AD-3, isolated from highly saline petroleum-contaminated soil, can efficiently degrade polycyclic aromatic hydrocarbons (PAHs), such as phenanthrene and anthracene, in 3-5% salinity. Gentisic acid is a key intermediate in the microbial degradation of PAH compounds. However, there is little information on PAH degradation by moderately halophilic bacteria. In this study, a 1,077-bp long gene encoding gentisate 1,2-dioxygenase (GDO) from a halophilic Martelella strain AD-3 was cloned, sequenced, and expressed in Escherichia coli. The recombinant enzyme GDO was purified and characterized in detail. By using the (18)O isotope experiment and LC-MS analysis, the sources of the two oxygen atoms added onto maleylpyruvate were identified as H2O and O2, respectively. The Km and kcat values for gentisic acid were determined to be 26.64 μM and 161.29 s(-1), respectively. In addition, optimal GDO activity was observed at 30 °C, pH 7.0, and at 12% salinity. Site-directed mutagenesis demonstrated the importance of four highly conserved His residues at positions 155, 157, 167, and 169 for enzyme activity. This finding provides new insights into mechanism and variety of gentisate 1,2-dioxygenase for PAH degradation in high saline conditions.
Topics: Alphaproteobacteria; Amino Acid Sequence; Anthracenes; Base Sequence; Biodegradation, Environmental; Cloning, Molecular; Dioxygenases; Escherichia coli; Petroleum Pollution; Phenanthrenes; Pimelic Acids; Salinity; Sequence Alignment; Sequence Analysis, DNA; Sodium Chloride; Soil; Soil Microbiology; Soil Pollutants
PubMed: 26394696
DOI: 10.1038/srep14307