Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Polycyclic Compounds”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 451 records · Page 25Linked to original sources
PubMedDate not supplied

Relationship between resonance energy and carcinogenicity of azaarenes.

Resonance energy per pi-electron (REPE) of azaarenes were calculated by Aihara's theory of resonance energy (TRE). Consequently, it was shown that the REPE values for the cationic species not having the carbon, or nitrogen atom with the highest approximate superdelocalizability (Sr'(E)) in the parent skeleton were more unstable than those of their parent skeleton. Some correlations seem to exist between the REPE values for the cationic species not having the atom with the highest value of (Sr'(E)) in parent skeleton and carcinogenic activity. Other types of correlations can be assumed in the case of carbazoles 7H-benzo[g]pyrido[2,3-a]carbazole (14), 13H-dibenzo[a]pyrido[3,2-i]carbazole (17), and 7H-benzo[c]pyrido[2,3-g]carbazole (20) although there are some exceptions, i.e., 7H-benzo[g]pyrido[3,2-a]carbazole (15) and 7H-dibenzo[c,g]-carbazole (18). The bond-order affected carcinogenicity induction in some ways as well.

Acridines↗
PubMed1987

Contribution of polycyclic aromatic hydrocarbons and nitro-derivatives to the carcinogenic impact of diesel engine exhaust condensate evaluated by implantation into the lungs of rats.

Diesel exhaust condensate was separated by a liquid-liquid distribution into a hydrophilic (I; about 25% by weight of the total condensate) and a hydrophobic part (II; about 75%-wt.). To evaluate the carcinogenicity, the proportionately dosed fractions have been implanted into the lungs of Osborne Mendel rats and compared with several doses of benzo[a]pyrene and the vehicle, a mixture of trioctanoin plus beeswax. Only the hydrophobic part which contained polycyclic aromatic compounds (PAC) resulted in 5 malignant tumors in a group of 35 animals. In addition, the hydrophobic part was separated by column chromatography on Sephadex LH 20 and subsequently on silica gel into several fractions, such as non-aromatic compounds plus PAC with 2 and 3 rings (IIa; 72%-wt of the total condensate), polycyclic aromatic compounds (PAH) with 4 and more rings (IIb; 0.8%-wt), polar PAC (IIc; 1.1%-wt) and nitro-PAH (IId; 0.7%-wt). PAH consisting of 4 and more rings (IIb) were found to be the most potent subfraction and provoked when proportionately dosed 6 carcinomas in a group of 35 rats. Only a low contribution to the carcinogenicity was observed by the subfraction of nitro-PAH (IId) which produced 1 carcinoma/35 rats. The polar PAC (IIc) and the fraction of non-aromatics plus PAC with 2 and 3 rings (IIa), although the main subfraction (72%-wt of the total condensate) did not provoke any tumors. The reconstitution of all hydrophobic subfractions (IIa-d) resulted in the same carcinogenic potency as the unfractionated hydrophobics (II), provoking 7 carcinoma in 35 rats. It may be concluded from these findings that most of the carcinogenicity of diesel exhaust originates from the PAH consisting of 4 or more rings.

Animals↗
PubMed2004

Isolation and characterization of Xanthobacter polyaromaticivorans sp. nov. 127W that degrades polycyclic and heterocyclic aromatic compounds under extremely low oxygen conditions.

Two bacterial strains, 127W and T102, were isolated from anoxic crude oil tank sludge as effective degraders of dibenzothiophene (DBT), a model sulfur containing heterocyclic aromatic compound in crude oil. Strain 127W was more tolerant to oxygen limitation than T102 and was capable of degrading two- and three-ring polycyclic and heterocyclic aromatic compounds under both aerobic and low oxygen conditions. Strain 127W degraded 0.082, 0.055, and 0.064 mM of DBT, naphthalene, and anthracene, respectively, in one week with dissolved oxygen < or =0.2ppm (0.006 mM). Degradation by 127W cell-free extracts for DBT was increased by addition of sodium hydrogencarbonate under this oxygen concentration. Phylogenetic analysis of the 16S rRNA gene sequence and physiological characteristics indicate that the strains 127W and T102 belong to new species of the genus Xanthobacter and Pseudomonas stutzeri, respectively. We propose X. polyaromaticivorans sp. nov. 127W.

Biodegradation, Environmental↗
PubMed1994

Bioaccumulation of aromatic hydrocarbons from sediments: a dose-response study with flounder (Pseudopleuronectes americanus).

Pseudopleuronectes americanus were chronically exposed to Hibernia crude oil in sediments, for 4 months. Oil was added to sediments at five concentrations between 0.09 and 4.5 mg/g (dry weight) and was 0.10-0.90 mg/g, at the termination of the exposure. Bioaccumulation measured in terms of fluorescence or in terms of the concentration of specific aromatic targets, increased with dosage. Accumulation of hydrocarbons was observed in muscle tissue (0.22 microgram/g, dry weight), when concentration of the sum of 27 polycyclic aromatic compounds (PAC) in sediments was of 0.65 microgram/g (E-50), at the end of the 4-month period. Of the 27 parental and alkylated polycyclic aromatic compounds analyzed, alkylated naphthalenes predominated in muscle (90-100%) and in sediments (30-60%). Bioaccumulation factors were derived for 13 compounds detected in muscle, at the three higher exposures. Liver concentrations (fluorescence) were higher than in muscle, but did not display a noticeable dose-response. Several alkylbenzenes, a C-2 biphenyl and C-4 acenaphthene were also detected in muscle extracts. The development of dose-response relationships for polycyclic aromatic hydrocarbons (PAH) present in sediment, in relation to bioaccumulation in flatfish, is of major interest for evaluating the environmental effects of oil contamination.

Animals↗
PubMed2003

Reversible binding of oxygen to aromatic compounds.

Many polycyclic aromatic hydrocarbons are able to trap singlet oxygen (1)O(2). Some of the endoperoxides, thus obtained, exhibit the exceptional feature of releasing oxygen, frequently in the excited singlet state, under heating or UV irradiation. In this Account, we provide a short summary of the present knowledge on these endoperoxides: preparation and thermal and photolytic decomposition, with a special emphasis on the structural requirements to favor cycloreversion. The profitable use of this property in the development of highly reversible photochromic systems and of specific sources or traps of (1)O(2) in aqueous media is also described.

Journal Article↗
PubMed1999

Polycyclic musk fragrances in the aquatic environment.

The polycyclic musk fragrances, mainly 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta(g)-2-ben zopyrane (HHCB) and 7-acetyl-1,1,3,4,4,6-hexamethyltetrahydronaphthalene (AHTN) are synthetic musk fragrances which are used in almost all scented consumer products, such as perfumes, cosmetics and laundry detergents. Concerning their chemical structures the polycyclic musks are indane and tetraline derivatives highly substituted mainly by methyl groups. Their production has been increased continuously during the last years with a world-wide production volume today of about 6000 t/year. After their application in private households they are dumped via the sewage treatment plants into the aquatic environment. In this review the analysis of polycyclic musk compounds in environmental samples is shortly presented and all published data of polycyclic musk compounds in water, sediment, suspended particulate matter (SPM), sewage sludge, and biota are summarized and discussed. The highest HHCB and AHTN concentrations were analysed in water (maximum concentrations: 6 microg HHCB/l, 4.4 microg AHTN/1) and sludge (maximum concentrations: 63 mg HHCB/kg dry matter, 34 mg AHTN/kg dry matter) from sewage plants, and in fish (maximum concentrations: 159 mg HHCB/kg lipid, 58 mg AHTN/kg lipid) from sewage ponds. In all other samples from different aquatic ecosystems these chemicals were unequivocally detected in varying concentrations dependent on the distance to sewage treatment plants. Even in marine water samples from the German Bight HHCB and AHTN could be quantified at the lower ng/l level. Very often HHCB and AHTN formed the major organic contaminants, in all samples their concentrations exceeded those of musk xylene and musk ketone. Also several by-products and impurities of the commercial polycyclic musks were analysed in river and waste water samples in not negligible amounts. The apparently ubiquitous distribution of polycyclic musks in the aquatic environment demonstrates the persistence and lipophilicity of these pollutants. The high log K(ow) values of HHCB and AHTN (5.7-5.9) do not directly correlate with their relatively low bioconcentration factors (BCFs) derived from fish experiments, this discrepancy may be explained by a particular metabolism in fish. There are indications of a possible species dependent metabolisation. For a general risk assessment of this new group of environmental pollutants besides the missing toxicological data, further studies on the distribution of the polycyclic musk fragrances including their by-products in the aquatic environment, on possible degradation processes in sediment/sludge as well as on the metabolism in fish are urgently needed.

Animals↗
PubMed1997

Mutagenicity testing of organic extracts of diesel exhaust particles after fractionation and recombination.

A new strategy for the evaluation of mixtures is presented. The mixture used was the organic extract of diesel exhaust particles (DEP). After extraction with dichloromethane (DCM), the crude extract was fractionated according to polarity into five fractions: aliphatic hydrocarbons, polycyclic aromatic hydrocarbons (PAHs), nitro-PAHs, dinitro-PAHs, and polar compounds. After dissolving in dimethylsulphoxide (DMSO), the three fractions containing the primary mutagens (fractions 3-5) were recombined in different combinations to create new extracts. The blend matrix was obtained using a mixture design at three dose levels to support an empirical model with linear, interaction, and quadratic terms (Taylor polynome). The recombined extracts were tested in the Ames Salmonella assay using strain TA100. Multivariate data analysis was performed with projections to latent structures (PLS). The best model describing the relation between the mutagenicity (response) and the three fractions (variables) contained two interaction terms. The model showed high correlation (r2) and prediction properties (Q2), the latter obtained after cross validation. Interaction terms are only indications of possible synergism or antagonism and have to be evaluated with respect to dose-additivity and response-additivity. The incorporation of dose in the design reduced the number of samples (recombined extracts) significantly, compared to determining dose-response curves on each sample (i.e. the recombined extracts in different dilutions). Furthermore, instead of running two independent experiments as required in the standard procedure for the Ames test, predictions and verifications of a few new samples were used. The principle of fractionation and recombination, and the use of mixture design may in principle be extended to an unlimited number of variables. An adaptation of mixture design to the isobole method is discussed.

Hydrocarbons↗
PubMed2005

Preparation and characterization of spherical polymer packings from polybutadiene for size-exclusion chromatography.

Porous polymer spherical particles for column packings in nonaqueous size-exclusion chromatography (SEC) were prepared from 1,2-syndiotactic polybutadiene by suspension and evaporation method. The polymer microbeads obtained were crosslinked by radical reaction between 2-vinyl groups in polybutadiene with ultraviolet radiation, to render them insoluble. These microbeads have wider chromatographic separation width than polystyrene column packings. In addition, the polybutadiene microbeads did not show the excessive retention observed with commercial polystyrene columns for polycyclic aromatic compounds. Therefore, a close correlation between the elution volume and M, for polycyclic aromatic compounds was observed with polybutadiene microbeads columns.

Butadienes↗
PubMed2003

Biomarker responses and chemical analyses in fish indicate leakage of polycyclic aromatic hydrocarbons and other compounds from car tire rubber.

Rubber tire material contains toxic compounds including oils rich in polycyclic aromatic hydrocarbons (PAH), so-called highly aromatic (HA) oils, as well as other reactive additives used as antioxidants, antiozonants, and vulcanization accelerators. The toxicity of rubber tire leachates to aquatic organisms has been demonstrated before. However, previous studies have focused on lethal rather than sublethal effects. We kept rainbow trout (Oncorhynchus mykiss) in tanks with two types of tires: a tire containing HA oils in the tread or a tire free of HA oils in the tread. After 1 d of exposure, an induction of cytochrome P4501A1 (CYP1A1) was evident in both exposed groups, measured as elevated ethoxyresorufin-O-deethylase (EROD) activity and increased CYP1A1 mRNA levels. After two weeks of exposure, EROD activity and CYP1A1 mRNA were still high in fish exposed to leachate from HA oil-containing tire, whereas the effect was somewhat lower in fish exposed to leachate from HA oil-free tread tire. Compounds in the tire leachates also affected antioxidant parameters. Total glutathione concentration in liver as well as hepatic glutathione reductase, glutathione S-transferase, and glucose-6-phosphate dehydrogenase activities were markedly elevated after two weeks of exposure in both groups. The responses were greater in the group exposed to leachate from HA oil-free tread tire. Vitellogenin measurements did not indicate leakage of estrogenic compounds from the tires. Chemical analyses of bile from exposed fish revealed the presence of hydroxylated PAH as well as aromatic nitrogen compounds indicating uptake of these compounds by the fish.

Animals↗
PubMed2001

Antiestrogenicity of clarified slurry oil and two crude oils in a human breast-cancer cell assay.

Exposure to crude oil and certain petroleum products can be a serious health hazard. Clarified slurry oil (CSO) is a complex mixture of hydrocarbons derived from the processing of crude oil, and is a known systemic and developmental toxicant, mutagen, and carcinogen. In the present study, CSO and two crude oils, Belridge heavy crude oil (BHCO) and Lost Hills light crude oil (LHLCO), were examined for their estrogenic and antiestrogenic properties in a human breast-cancer cell (MCF-7) assay. The MCF-7 focus assay is based on postconfluent cell growth and tissue restructuring, measured as the postconfluent development of multicellular nodules or foci. The mutagenicity indices of BHCO and LHLCO also were determined in a modified Ames Salmonella assay. Oil samples were prepared in dimethyl sulfoxide, resulting in extraction of virtually all of the aromatic compounds including the sulfur- and nitrogen-substituted three- to seven-ring polycyclic aromatic compounds comprising 62.2% of the CSO, 9% of the BHCO, and 2% of the LHLCO by total weight. None of the three samples was estrogenic in the MCF-7 focus assay. In contrast, all of the samples were antiestrogenic; that is, they inhibited the development of foci induced by 1 nM 17beta-estradiol (E2). The potencies of the oil samples for both antiestrogenicity and mutagenicity were correlated with the percent of polycyclic aromatic compounds they contained. Two potential mechanisms for the observed antiestrogenicity were examined. Radiometric analysis of the catabolism of [3H]E2 in MCF-7 cell cultures demonstrated that all three samples increased catabolism of E2. Results from a whole-cell estrogen-receptor (ER) binding assay suggested that metabolites of compounds in the oil samples might have competed with [3H]E2 for ER in the MCF-7 cultures. Thus the antiestrogenicity of the oil samples may occur through at least two mechanisms, increased catabolism of E2 and antagonistic binding to ER.

Binding, Competitive↗
PubMed2000

Enantioselective formation of arene oxides by direct oxidation of the arene.

Polycyclic aromatic compounds may be metabolized in humans to materials which are carcinogenic. These metabolites frequently contain an arene oxide group which is implicated in binding the metabolite to important biological substrates such as DNA. These enzymatic processes produce arene oxides in a highly enantioselective fashion. Direct oxidation of arenes by typical oxidants gives racemic oxide. We have been interested in converting arenes to arene oxides by direct oxidation in an enantioselective reaction. Three oxidation systems have been used to convert a variety of polycyclic aromatic compounds to arene oxides in processes which gives modest enantiomeric excesses.

Catalysis↗
PubMed1994

Lignin peroxidase oxidation of aromatic compounds in systems containing organic solvents.

Lignin peroxidase from Phanerochaete chrysosporium was used to study the oxidation of aromatic compounds, including polycyclic aromatic hydrocarbons and heterocyclic compounds, that are models of moieties of asphaltene molecules. The oxidations were done in systems containing water-miscible organic solvents, including methanol, isopropanol, N, N-dimethylformamide, acetonitrile, and tetrahydrofuran. Of the 20 aromatic compounds tested, 9 were oxidized by lignin peroxidase in the presence of hydrogen peroxide. These included anthracene, 1-, 2-, and 9-methylanthracenes, acenaphthene, fluoranthene, pyrene, carbazole, and dibenzothiophene. Of the compounds studied, lignin peroxidase was able to oxidize those with ionization potentials of <8 eV (measured by electron impact). The reaction products contain hydroxyl and keto groups. In one case, carbon-carbon bond cleavage, yielding anthraquinone from 9-methylanthracene, was detected. Kinetic constants and stability characteristics of lignin peroxidase were determined by using pyrene as the substrate in systems containing different amounts of organic solvent. Benzyl alkylation of lignin peroxidase improved its activity in a system containing water-miscible organic solvent but did not increase its resistance to inactivation at high solvent concentrations.

Journal Article↗
PubMed1977

[Comparative studies on the contamination of foods by cancerogenic hydrocarbons in the Soviet Union and in the GDR (author's transl)].

Investigations on the relationship of the environmental contamination with cancer are shown to be necessary. Epidemiologic investigations point to a connection of the increased occurence of cancer in the gastro-intestinal tract with dietetic factors. The high cancer rate in the gastro-intestinal tract (amongst other factors) is discussed as a result of the uptake of exogenic foreign matterns with the food. The possibilities of the contamination by cancerogenic compounds are summarized. The necessity of international co-operation in the field of finding out, as far as possible, sources and degree of food contamination by cancerogenic compounds is motivated beginning with polycyclic aromatic compounds, whereby at present benzo-(a)-pyrene comes into question as a reference substance. The laying down of controllable hygienic norms as preliminarily tolerable limits in the proper sense of an unavoidable dose are discussed. They could be a basis of oncological preventive measures (minimization or elimination of cancerogenic compounds in foods).

Benzopyrenes↗
PubMed1997

Adsorption of mutagens to chlorophyllin-chitosan, an insoluble form of chlorophyllin.

Chlorophyllin, a water soluble derivative of chlorophyll is known to suppress the mutagenic and carcinogenic actions of compounds having polycyclic structures, e.g. heterocyclic amines and aflatoxin B1. There is evidence that this suppressing effect arises, at least in part, by a complex formation between the porphyrin-like structure of chlorophyllin and the planar molecular surfaces of these compounds. We report here that chlorophyllin can form an insoluble salt-like material when mixed with chitosan, a polyglucosamine, and that the solid chlorophyllin-chitosan thus prepared can efficiently trap polycyclic mutagenic compounds. The adsorbed polycyclic mutagens were elutable with buffers of acidic pH, but only to small extents. Chlorophyllin-chitosan may be expected to be useful as an intercepting agent against polycyclic mutagens and carcinogens.

Adsorption↗
PubMed1988

Genotoxicity and PAC analysis of particulate and vapour phases of environmental tobacco smoke.

Samples of indoor air were collected from an office room (88 m3) both before smoking and during experimental smoking of 96 cigarettes by 10 persons within 6 h. The particulates were collected on glass-fibre filters and the vapour-phase compounds on XAD-2 resin. The samples were extracted with acetone and analysed quantitatively for polycyclic aromatic compounds and qualitatively with GC-MS. The extracts of filters and XAD-2 resins were fractionated into neutral/acidic and 2 basic (strong and weak bases) fractions; all these fractions were tested with the sister-chromatid exchange (SCE) assay in Chinese hamster ovary (CHO) cells and with the Salmonella/microsome test (strain TA98). Total concentrations of PAC were 205 ng/m3 in the background sample and 1207 ng/m3 after contamination by cigarette smoking. The total PAC concentrations were 4-6 times higher in the vapour phase than in the particulate phase. The fractions of the particulate samples collected before smoking showed mainly marginal genotoxic activity, whereas after smoking their genotoxicity increased dramatically. The fractions of the vapour phase samples were not genotoxic before smoking, but after smoking the neutral/acidic and strong basic fractions induced responses in both assays. The SCE assay was more sensitive towards the vapour-phase mutagens of environmental tobacco smoke (ETS). The relative responses of the two basic fractions, whereas the fraction containing neutral and acidic compounds was the most potent in the SCE assay. In the Salmonella test, the mutagenic activity was mainly detected with metabolic activation, while the induction of SCE in CHO cells was also seen without an exogenous metabolic activation system.

Air Pollutants, Occupational↗
PubMed1998

Molecular epizootiology of genotoxic events in marine fish: linking contaminant exposure, DNA damage, and tissue-level alterations.

Molecular epizootiological studies are increasingly being used to investigate environmental effects of genotoxic contaminants. The assessment of damage to DNA and linking the damage to subsequent molecular, cellular, or tissue-level alterations is a central component of such studies. Our research has focused on the refinement of the 32P-postlabeling assay for measuring covalent DNA-xenobiotic adducts arising from exposure to polycyclic aromatic compounds, using DNA adducts as molecular dosimeters of genotoxic contaminant exposure in biomonitoring studies, and investigating the relationship of DNA adduct formation to toxicopathic liver disease, including neoplastic lesions. A combination of field and laboratory studies using the 32P-postlabeling assay has shown that DNA adducts in marine fish are effective molecular dosimeters of genotoxic contaminant exposure. Investigations of the relationship of DNA adduct formation to neoplastic liver disease have shown that elevated levels of DNA adducts in certain fish species from contaminated coastal sites are associated with increased prevalences of toxicopathic hepatic lesions, including neoplasms, and that the ability to assess DNA damage has helped to explain, in part, species differences in lesion prevalence. Moreover, in a study of a site in Puget Sound contaminated with polycyclic aromatic compounds, we have shown, for the first time, that elevated levels of hepatic DNA adducts are a significant risk factor for certain degenerative and preneoplastic lesions occurring early in the histogenesis of hepatic neoplasms in feral English sole (Pleuronectes vetulus). These latter findings coupled with our current studies of mutational events in the K-ras proto-oncogene should provide further mechanistic substantiation that mutagenic events resulting from exposure to complex mixtures of genotoxic polycyclic aromatic compounds are involved in the etiology of hepatic neoplasia in English sole.

Animals↗