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المؤلفون: Kåre B. Jørgensen, Daniela M. Pampanin, Roger Lille-Langøy, Magne O. Sydnes, Anders Goksøyr, Odd André Karlsen
المصدر: Environmental Science and Technology
15123-15135مصطلحات موضوعية: chemistry.chemical_classification, Chrysene, biology, Stereochemistry, Landbruks- og Fiskerifag: 900 [VDP], Aryl, General Chemistry, Phenanthrene, biology.organism_classification, Aryl hydrocarbon receptor, chemistry.chemical_compound, Hydrocarbon, chemistry, Biotransformation, biology.protein, Environmental Chemistry, Gadus, Matematikk og Naturvitenskap: 400::Kjemi: 440 [VDP], Naphthalene
الوصف: Polycyclic aromatic hydrocarbons (PAHs) are among the most toxic and bioavailable components found in petroleum and represent a high risk to aquatic organisms. The aryl hydrocarbon receptor (Ahr) is a ligand-activated transcription factor that mediates the toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and other planar aromatic hydrocarbons, including certain PAHs. Ahr acts as a xenosensor and modulates the transcription of biotransformation genes in vertebrates, such as cytochrome P450 1A (cyp1a). Atlantic cod (Gadus morhua) possesses two Ahr proteins, Ahr1a and Ahr2a, which diverge in their primary structure, tissue-specific expression, ligand affinities, and transactivation profiles. Here, a luciferase reporter gene assay was used to assess the sensitivity of the Atlantic cod Ahrs to 31 polycyclic aromatic compounds (PACs), including two- to five-ring native PAHs, a sulfur-containing heterocyclic PAC, as well as several methylated, methoxylated, and hydroxylated congeners. Notably, most parent compounds, including naphthalene, phenanthrene, and partly, chrysene, did not act as agonists for the Ahrs, while hydroxylated and/or alkylated versions of these PAHs were potent agonists. Importantly, the greater potencies of substituted PAH derivatives and their ubiquitous occurrence in nature emphasize that more knowledge on the toxicity of these environmentally and toxicologically relevant compounds is imperative. publishedVersion
وصف الملف: application/pdf
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::58f16f28ca88da23effc70dd25c4c1f9Test
https://hdl.handle.net/11250/2832035Test -
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المؤلفون: Edward S. Chen, Edward C. M. Chen
المصدر: Rapid Communications in Mass Spectrometry. 32:230-234
مصطلحات موضوعية: Chrysene, Anthracene, Stereochemistry, 010401 analytical chemistry, Organic Chemistry, Phenanthrene, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, chemistry.chemical_compound, Tetracene, chemistry, Electron affinity, Excited state, Pyrene, Physical chemistry, Ground state, Spectroscopy
الوصف: Rationale The anion mass spectral lifetimes for several aromatic hydrocarbons reported in the subject article were related to significantly different electron affinities. The different values are rationalized using negative ion mass spectral data. Methods Electron affinities for polycyclic aromatic hydrocarbons are reported from the temperature dependence of unpublished electron capture detector data. These are compared with published values and the largest values are assigned to the ground state. Results The ground state adiabatic electron affinities: (eV) pentacene, 1.41 (3); tetracene, 1.058 (5); benz(a)pyrene, 0.82 (4); benz(a) anthracene, 0.69 (2) anthracene, 0.68 (2); and pyrene, 0.59 (1) are used to assign excited state adiabatic electron affinities: (eV) tetracene: 0.88 (4); anthracene 0.53 (1); pyrene, 0.41 (1); benz(a)anthracene, 0.39 (10); chrysene, 0.32 (1); and phenanthrene, 0.12 (2) and ground state adiabatic electron affinities: (eV) dibenz(a,j)anthracene, 0.69 (3); dibenz(a,h)anthracene, 0.68 (3); benz(e)pyrene, 0.60 (3); and picene, 0.59 (3) from experimental data. The lifetime of benz(a)pyrene is predicted to be larger than 150 μs and for benzo(c)phenanthrene and picene about 40 μs, from ground state adiabatic electron affinities. Conclusions The assignments of adiabatic electron affinities of aromatic hydrocarbons determined from electron capture detector and mass spectrometric data to ground and excited states are supported by constant electronegativities. A set of consistent ground state adiabatic electron affinities for 15 polycyclic aromatic hydrocarbons is related to lifetimes from the subject article.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8535c307dd2193719bbf58b5e39975d9Test
https://doi.org/10.1002/rcm.8021Test -
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المؤلفون: W. H. Laarhoven, J. B. M. Somers
المصدر: Recueil des Travaux Chimiques des Pays-Bas. 99:160-166
مصطلحات موضوعية: Chrysene, chemistry.chemical_compound, chemistry, Stereochemistry, Substituent, Triphenylene, General Chemistry, Phenanthrene, Ring (chemistry), Conformational isomerism, Cis–trans isomerism
الوصف: An NMR investigation of cis and trans isomers of styrylphenanthrene and some benzologues was performed, in which Δtrans-cis values (δtrans-δcis), temperature dependence (ΔT) in CS2 and ASIS effects were determined. It was concluded that in the series styryl-phenanthrene (2),-benzo[c]-phenanthrene (1),-dibenzo[c,g]triphenylene (10),-hexahelicene (9) only 1 exists mainly as a cis-synrotamer, whereas in the other compounds the cis-anti rotamer predominates in varying degrees. The introduction of an additional benzo group in 1 and 2 at the ring, containing the styryl substituent, which leads to the styryl-chrysene (11) and styryl-benzo[c]chrysene (12), shifts the conformational equilibrium to the cis-syn rotamer. The introduction of polar substituents at the para-position of 2-styrylbenzo[c]phenanthrene has only a small influence on the syn-anti equilibrium. The observed effects are discussed.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_________::253ea09c722f808f9af3ba7780edcaa7Test
https://doi.org/10.1002/recl.19800990504Test -
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المؤلفون: Bengt Jernström, Ulla Stenius, Åse Mattsson, Maria Malmlöf, Albrecht Seidel
المصدر: Polycyclic Aromatic Compounds. 28:392-401
مصطلحات موضوعية: Chrysene, Polymers and Plastics, Stereochemistry, DNA damage, Organic Chemistry, Histone H2AX, Phenanthrene, Adduct, chemistry.chemical_compound, Biochemistry, chemistry, Materials Chemistry, DNA, Carcinogen, Nucleotide excision repair
الوصف: The human lung cancer cell line A549 was exposed to diol epoxides (DEs) and the effect on DNA damage signaling proteins was studied. The DEs used were derived from the bay-region PAHs chrysene; CDE and dibenz[a,h]anthracene; DBADE, or the fjord-region PAHs benzo[c]chrysene; B[c]CDE, benzo[g]chrysene; B[g]CDE and benzo[c]phenanthrene; B[c]PhDE. All DEs induced a rapid response on Mdm2, p53 and histone H2AX phosphorylation, where Mdm2 was the most sensitive marker of DNA damage. Fjord-region DEs induced a stronger and more persistent effect on the proteins studied than the bay-region DEs. This variance is likely to reflect differences in adduct recognition and handling by nucleotide excision repair. The stimulating effect of DEs on histone H2AX phosphorylation demonstrated that, in addition to DNA strand breaks and UV-induced photoproducts, stable and bulky DNA-adducts also possess this capacity.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_________::8b036e3e7f43015fccef1ffd3dda465cTest
https://doi.org/10.1080/10406630802374937Test -
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المؤلفون: Trevor M. Penning, Carol A. Shultz, Ronald G. Harvey, Dipti Mangal, Ian A. Blair, Nisha T. Palackal
المصدر: Chemical Research in Toxicology. 21:668-677
مصطلحات موضوعية: Models, Molecular, Chrysene, Circular dichroism, Stereochemistry, Benzo(c)phenanthrene, Stereoisomerism, In Vitro Techniques, Toxicology, Article, Chrysenes, Mass Spectrometry, Substrate Specificity, Structure-Activity Relationship, chemistry.chemical_compound, Animals, Humans, Chromatography, High Pressure Liquid, Mercaptoethanol, chemistry.chemical_classification, Alanine, biology, Chemistry, Circular Dichroism, Active site, General Medicine, Phenanthrenes, Rats, Inbred F344, Recombinant Proteins, Rats, Alcohol Oxidoreductases, Kinetics, Enzyme, Liver, Mutation, biology.protein, Indicators and Reagents, Enantiomer, Oxidoreductases
الوصف: This study demonstrates that benzo[g]chrysene-11,12-dihydrodiol (B[g]C-11,12-dihydrodiol) derived from the fjord-region parent hydrocarbon B[g]C is oxidized by rat AKR1C9 with a k c a t/ K m 100 times greater than that observed with the commonly studied bay-region benzo[ a]pyrene-7,8-dihydrodiol (B[a]P-7,8-dihydrodiol). Conversely, despite its strikingly similar structure to B[ g]C-11,12-dihydrodiol, benzo[ c]phenanthrene-3,4-dihydrodiol (B[ c]Ph-3,4-dihydrodiol) is consumed by AKR1C9 at sluggish rates comparable to those observed with B[ a]P-7,8-dihydrodiol. CD spectroscopy revealed that only the (+)-B[ g]C-11,12-dihydrodiol stereoisomer was oxidized, while AKR1C9 oxidized both stereoisomers of B[a]P-7,8-dihydrodiol and B[ c]Ph-3,4-dihydrodiol. The (+)- S, S- and (-)- R, R-stereoisomers of B[g]C-11,12-dihydrodiol were purified by chiral RP-HPLC. The 11 S,12 S-stereoisomer was oxidized at the same rate as the racemate. The 11 R,12 R-stereoisomer did not act as an inhibitor to AKR1C9, indicating that the (-)- R, R-stereoisomer was excluded from the active site. To understand the basis of stereochemical preference, we screened alanine-scanning mutants of active site residues of AKR1C9. These studies revealed that in comparison to the wild type, F129A, W227A, and Y310A enabled the oxidation of both the B[g]C-11 S,12 S-dihydrodiol and the B[g]C-11 R,12 R-dihydrodiol. Molecular modeling revealed that unlike B[a]P-7,8-dihydrodiol and B[ c]Ph-3,4-dihydrodiol, B[g]C-11,12-dihydrodiol enantiomers are significantly bent out of plane. As a consequence, the (-)- R, R-stereoisomer was prevented from binding to the active site because of unfavorable interactions with F129, W227, or Y310. Additionally, LC/MS validated that the product of the reaction of B[g]C-11,12-dihydrodiol oxidation catalyzed by AKR1C9 was B[g]C-11,12-dione, which was trapped in vitro with the nucleophile 2-mercaptoethanol. The similarity between rates of trans-dihydrodiol oxidation by the rat and human liver specific AKRs (AKR1C9 and AKR1C4) implicate these enzymes in hepatocarcinogenesis in rats observed with the fjord-region PAH.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::454dff842a8085080520e0afd37ddffbTest
https://doi.org/10.1021/tx7003695Test -
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المؤلفون: Volker J. Soballa, Gernot Grimmer, Jürgen Jacob, Gottfried Raab, Helmut Greim, Johannes Doehmer, Albrecht Seidel
المصدر: Polycyclic Aromatic Compounds. 10:1-9
مصطلحات موضوعية: Chrysene, Anthracene, Polymers and Plastics, Stereochemistry, Organic Chemistry, Benzo(c)phenanthrene, CYP1A2, respiratory system, Phenanthrene, Benz(a)anthracene, chemistry.chemical_compound, Benzo(a)pyrene, chemistry, polycyclic compounds, Materials Chemistry, Pyrene, heterocyclic compounds
الوصف: Phenanthrene, benz[a]anthracene, chrysene, benzo[c]phenanthrene, and benzo[a]pyrene have been studied for their regiospecific oxidation by five human (1A1, 1A2, 2A6, 2E1, 3A4) and three rat (1A1, 1A2, 2B1) CYP isoforms. All substrates are preferentially metabolized by CYP1A1 and CYP1A2 in human and rat. Other isoforms play a minor role if at all. Significant differences between human and rat CYP isoforms can be recognized with regard to the regiospecific oxidation of PAH. For instance, K-region oxidation is more pronounced in rat than in human CYP1A1 and CYP1A2. Hence, extrapolation from metabolism studies in rodents to human may be limited.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_________::11876bd474c9098fc074e92864cb3a9dTest
https://doi.org/10.1080/10406639608034673Test -
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المصدر: Carcinogenesis. 17:605-608
مصطلحات موضوعية: Bay-Region, Polycyclic Aromatic Hydrocarbon, Chrysene, Cancer Research, Stereochemistry, Guanine, Benzo(c)phenanthrene, Stereoisomerism, General Medicine, Phenanthrenes, Phenanthrene, Adduct, DNA Adducts, chemistry.chemical_compound, Spectrometry, Fluorescence, chemistry, Benzo(a)pyrene, Polycyclic Hydrocarbons, Polycyclic Aromatic Hydrocarbons, DNA
الوصف: In the electrofluorescence method, a solution of DNA with covalently bound polycyclic hydrocarbons is placed in an electric field, and changes in the intensity of polarized fluorescence are observed. Under the correct conditions, these charges can be used to determine a value for the angle psi between the long axis of the hydrocarbon molecule and the axis of the DNA helix. For DNA or poly(dA-dT) treated with each stereoisomer of anti-benzo[c]phenanthrene diolepoxide, psi ranged from 55 degrees to 61 degrees, consistent with a mixture of quasi-intercalated adenine adducts and externally bound guanine adducts. Similar results were obtained with another set of 'fjord-region' diolepoxides, derived from benzo[c]chrysene. Adducts in DNA treated with diolepoxides derived from chrysene, 5-methylchrysene or 6-methylchrysene gave psi of about 53 degrees, so the predominant adducts are externally bound, probably in the minor groove of DNA.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::02173e94f2d5be5e6d94a87e1ea766a1Test
https://doi.org/10.1093/carcin/17.3.605Test -
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المؤلفون: Dawoon Jung, Chaok Seok, Won Joon Shim, Seongjin Hong, Kyungho Choi, Sangwoo Lee, Habyeong Kang, Woong-Hee Shin, John P. Giesy, Jong Seong Khim, Un Hyuk Yim
المصدر: Chemosphere. 139
مصطلحات موضوعية: Chrysene, Environmental Engineering, Alkylation, Stereochemistry, Health, Toxicology and Mutagenesis, Polycyclic aromatic hydrocarbon, Thiophenes, Chrysenes, Cell Line, chemistry.chemical_compound, Molecular descriptor, Environmental Chemistry, Bioassay, Humans, chemistry.chemical_classification, biology, Public Health, Environmental and Occupational Health, General Medicine, General Chemistry, Phenanthrene, Phenanthrenes, Aryl hydrocarbon receptor, Pollution, Molecular Docking Simulation, Petroleum, chemistry, Receptors, Aryl Hydrocarbon, Docking (molecular), biology.protein, Biological Assay, Environmental Pollutants
الوصف: Polycyclic aromatic hydrocarbons (PAHs) and their alkylated forms are important components of crude oil. Both groups of PAHs have been reported to cause dioxin-like responses, mediated by aryl hydrocarbon receptor (AhR). Thus, characterization of binding affinity to the AhR of unsubstituted or alkylated PAHs is important to understand the toxicological consequences of oil contamination on ecosystems. We investigated the potencies of major PAHs of crude oil, e.g., chrysene, phenanthrene and dibenzothiophene, and their alkylated forms (n=17) to upregulate expression of AhR-mediated processes by use of the H4IIE-luc transactivation bioassay. In addition, molecular descriptors of different AhR activation potencies among PAHs were investigated by use of computational molecular docking models. Based on responses of the H4IIE-luc in vitro assay, it was shown that potencies of PAHs were determined by alkylation in addition to the number and conformation of rings. Potencies of AhR-mediated processes were generally greater when a chrysene group was substituted, especially in 1-methyl-chrysene. Significant negative correlations were observed between the in vitro dioxin-like potency measured in H4IIE-luc cells and the binding distance estimated from the in silico modeling. The difference in relative potency for AhR activation observed among PAHs and their alkylated forms could be explained by differences among binding distances in the ligand binding domain of the AhR caused by alkylation. The docking model developed in the present study may have utility in predicting risks of environmental contaminants of which toxicities are mediated by AhR binding.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::abca305e62da7b584540281043b7facdTest
https://pubmed.ncbi.nlm.nih.gov/26037956Test -
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المؤلفون: Hester Jongepier, Anette V. Klomp, Paul A.F. de Bie, Nico W. van den Brink, A.T.C. Bosveld
المصدر: Chemosphere 49 (2002) 1
Chemosphere, 49(1), 75-83مصطلحات موضوعية: Chrysene, Environmental Engineering, milieu, Stereochemistry, Health, Toxicology and Mutagenesis, Models, Biological, Risk Assessment, chemistry.chemical_compound, Toxicity Tests, Cytochrome P-450 CYP1A1, polycyclic compounds, Animals, Humans, Environmental Chemistry, Potency, Bioassay, Receptors, Cholinergic, Polycyclic Aromatic Hydrocarbons, Toxic equivalency factor, Cells, Cultured, Carcinogen, Netherlands, Fluoranthene, Dose-Response Relationship, Drug, Chemistry, Ecologie en Milieu, biochemie, ecotoxicologie, Public Health, Environmental and Occupational Health, General Medicine, General Chemistry, Phenanthrene, Pollution, Diet, Rats, Environmental chemistry, Pyrene, Environmental Monitoring
الوصف: The ethoxy resorufin dealkylase (EROD) inducing potency of 10 polycyclic aromatic hydrocarbons (PAHs) is measured in the H4IIE in vitro bioassay and the results are compared to those reported in literature. The selected PAHs varied considerably in their potency to induce EROD activity. Anthracene (Ant) and phenanthrene (Phe) showed consistently no response. Naphthalene (Nap) showed no or a very weak response on EROD activity. Fluoranthene (Fla) and benzo[g,h,i]perylene (BghiP) showed weak responses at the highest doses. The other PAHs, including indeno[1,2,3-cd]pyrene (IP), benz[a]anthracene (BaA), benzo[a]pyrene (BaP), chrysene (Chr) and benzo[k]fluoranthene (BkF), showed full bell shaped dose-response curves. BaP EROD induction equivalency factors (BaP-1EF) were calculated and increased in the order Ant approximately PheFlaNapBghiPIPBaABaPChrBkF. Comparison of BaP-IEFs based on 50% effect concentration (EC50) or lowest effect concentration (LEC), yielded a significant relationship between both methods described by the equation log(BaPIEF(EC50) = 0.55 x log(BaPIEF(LEC)) + 0.07 (r2 = 0.913). BaP-IEFs as derived from our measurements and as reported in literature and measured in other in vitro assays deviated up to a factor of 17 among the different studies, but the potency rankings were comparable. For the PAH mixture as on average present in the human diet an overall tetrachlorodibenzo-p-dioxin (TCDD)-IEF of 1 x 10(-4) was estimated. The total PAH based TCDD induction equivalents (IEQ) intake then was calculated 300 pg/day, which is approximately 2 times higher then the PHAH based TCDD-EQ intake reported for humans.
وصف الملف: application/pdf; application/octet-stream
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::9a944a28c4c7fb0cb7d3880a1d47c5d5Test
https://doi.org/10.1016/s0045-6535Test(02)00161-3 -
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المؤلفون: Stephen Nesnow, Dhimant Desai, S. Amin, C. Davis
المصدر: Polycyclic Aromatic Compounds. 16:141-149
مصطلحات موضوعية: Chrysene, chemistry.chemical_compound, Polymers and Plastics, Benzo(a)pyrene, Chemistry, Stereochemistry, Organic Chemistry, Materials Chemistry, Pyrene, Phenanthrene, Dibenzopyrenes
الوصف: The morphological transforming activities in mouse embryo C3H10T1/2CL8 (C3H10T1/2) cells were examined for six PAHs: benzo[c]chrysene (B[c]C); benzo[g]chrysene (B[g]C); benzo[c]phenanthrene (B[c]P); dibenzo[a, l]pyrene (DB[a, l]P); dibenzo[a,e]pyrene (DB[a,e]P) and benzo[a]pyrene (B[a]P). C3H10T1/2 cells treated with B[c]P or B[g]C at concentrations of 0–3 μg/ml did not produce any transformed Type II or III foci after 24 hr of exposure. Concurrent cytotoxicity was observed. Under the same conditions, B[a]P and B[c]C were active, with B[c]C approximately one-half the activity of B[a]P. However, after a 48-hr treatment, B[c]P and B[g]C gave significant activity measured as both foci/dish or the number of dishes exhibiting foci. After a 24-hr treatment, comparison of B[a]P with two dibenzopyrenes, DB[a, l]P and DB[a,e]P, gave activities in the order: DB[a, l]P > B[a]P > DB[a,e]P. After 48 hr of treatment, both B[a]P and DB[a,e]P had similar activities.
الوصول الحر: https://explore.openaire.eu/search/publication?articleId=doi_________::3d273e6fc97ace55648f1d8bda4e80cbTest
https://doi.org/10.1080/10406639908020581Test
