Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “PHENANTHRENES”

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 19 recordsLinked to original sources
PubMed1999

Cometabolic oxidation of phenanthrene to phenanthrene trans-9,10-dihydrodiol by Mycobacterium strain S1 growing on anthracene in the presence of phenanthrene.

Mycobacterium strain S1, originally described as Rhodococcus strain S1 by chemotaxonomic criteria, was isolated by growth on anthracene, and is unable to use any of nine other polycyclic aromatic compounds as carbon source. Metabolism of phenanthrene during growth on anthracene as sole carbon source results in the accumulation of traces of a dihydrodiol metabolite in the growth medium, which, by comparison with authentic standards, has been tentatively identified as phenanthrene trans-9,10-dihydrodiol. Anthracene metabolites were ruled out on the basis of comparisons with authentic anthracene dihydrodiols from Pseudomonas fluorescens D1 and chemically synthesized anthrols. The original source of phenanthrene for dihydrodiol production was phenanthrene present as a < 1% contaminant in the anthracene used as carbon source. However, addition of further phenanthrene to the anthracene growth medium increased the level of phenanthrene trans-9,10-dihydrodiol formed. Mycobacterium strain S1 also produced phenanthrene trans-9,10-dihydrodiol when grown in a glucose-salts medium in the presence of phenanthrene. This dihydrodiol is a dead-end metabolite, and neither it nor its parent hydrocarbon are able to support the growth of Mycobacterium strain S1. Studies with metyrapone and ancimidol, which did not inhibit growth on anthracene but did inhibit formation of phenanthrene trans-9,10-dihydrodiol, suggest it is likely the product of a cytochrome P450 monooxygenase-like activity.

Anthracenes↗
PubMed1979

Mutagenicity of phenanthrene and phenanthrene K-region derivatives.

Phenanthrene and 9 K-region derivatives, most of them potential metabolites of phenanthrene, were tested for mutagenicity by the reversion of histidine-dependent Salmonella typhimurium TA1535, TA1537, TA1538, TA98 and TA100 and the rec assay with Bacillus subtilis H17 and M45. The strongest mutagenic effects in the reversion assay were observed with phenanthrene 9,10-oxide, 9-hydroxyphenanthrene and N-benzyl-phenanthrene-9,10-imine. Interestingly, the mutagenic potency of the arene imine was similar to that of the corresponding arene oxide. This is the first report on the mutagenicity of arene imine. The mutagenic effects of all these phenanthrene derivatives were much weaker than that of the positive control benzo[a]pyrene 4,5-oxide. Even weaker mutagenicty was found with cis-9,10-dihydroxy-9,10-dihydrophenanthrene and with trans-9,10-dihydroxy-9-10-dihydrophenanthrene. The other derivatives were inactive in this test. However, 9-10-dihydroxyphenanthrene and 9,10-phenanthrenequinone were more toxic to the rec- B. subtilis M45 strain than to the rec+ H17 strain. This was also true for phenanthrene 9,10-oxide and 9-hydroxyphenanthrene, but not with the other test compounds that reverted (9,10-dihydroxy-9,10-dihydrophenanthrenes; N-benzyl-phenanthrene 9,10-imine; benzo[a]pyrene 4,5-oxide) or did not revert (phenanthrene, 9,10-bis-(p-chlorophenyl)-phenanthrene 9,10-oxide, 9-10-diacetoxyphenanthrene) the Salmonella tester strains. Although the K region is a main site of metabolism and although all potential K-region metabolites were mutagenic, phenanthrene did not show a mutagenic effect in the presence of mouse-liver microsomes and an NADPH-generating system under standard conditions. However, uhen epoxide hydratase was inhibited, phenanthrene was activated to a mutagen that reverted his- S. typhimurium. This shows that demonstration of the mutagenic activity of metabolites together with the knowledge that a major metabolic route proceeds via these metabolites dose not automatically imply a mutagenic hazard of the mother compound, because the metabolites in question may not accumulate in sufficient quantities and therefore the presence and relative activities of enzymes that control the mutagenically active metabolites are crucial. N-Benzyl-phenanthrene 9.10-imine was mutagenic for the episome-containing S. typhimurium TA98 and TA100 but not for the precursor strains TA1538 and TA1535. This arene imine would therefore be useful as a positive control during routine testing to monitor in the former strains the presence of the episome which is rather easily lost.

Drug Evaluation, Preclinical↗
PubMed2003

Temporal change in culturable phenanthrene degraders in response to long-term exposure to phenanthrene in a soil column system.

Widespread environmental contamination by polycyclic aromatic hydrocarbons (PAH) has led to increased interest in the use of natural attenuation as a clean-up strategy. However, few bioremediation studies have investigated the behaviour of the indigenous PAH-degrading community after long-term exposure to a PAH. In this study, a column packed with sandy loam soil was exposed to a solution saturated with phenanthrene ( approximately 1.2 mg l-1) for a 6-month period to examine the temporal response of the indigenous phenanthrene-degrading community. Initial soil, effluent, and final soil samples were collected and analysed for phenanthrene concentration and culturable phenanthrene degraders. Phenanthrene-degrading isolates were grouped by colony morphology. For each unique group, 16S rDNA polymerase chain reaction was performed, and then sequencing analysis was used to identify the isolate at the genus level. Twenty-five phenanthrene-degrading isolates, potentially representing 19 genera, were obtained from this analysis. Of these, eight genera have not been reported previously to degrade phenanthrene, including Afipia, Janthinobacterium, Leptothrix, Massilia, Methylobacterium, Rhizobium, Sinorhizobium and Thiobacillus. Results indicate that the dominant phenanthrene-degrading population changed over the course of this 6-month experiment. Specifically, the isolates obtained initially from the soil were not subsequently found in either effluent samples or the soil at the end of the experiment. Furthermore, several isolates that were found in the soil at the end of the experiment were not observed in the soil initially or in the effluent samples. This study confirms earlier findings indicating that a diverse community participates in phenanthrene degradation in the environment, and also suggests that the composition of this community is temporally variable.

Bacteria↗
PubMed1996

Synthesis and mutagenicity of some cyclopenta[c]phenanthrenes and indeno[c]phenanthrenes.

An efficient two-step synthesis of 8(H)-9,10,11,12-tetra-hydrodicyclopenta[a,c]phenanthren-7-one, based on the high pressure Diels-Alder cycloaddition of 4-acetoxy-2-cyclopenten-1-one with 1-(1-naphthyl)cyclopentene and a subsequent dehydrogenation-aromatization reaction, is reported. Further, the synthesis of two cyclopenta[c]-phenanthrenes and indeno[c]phenanthrenes is described. Structural analysis of the new products by 1H and 13C NMR spectroscopy is presented. The mutagenic activity of the compounds in Salmonella typhimurium was estimated by Ames' test. Three compounds were shown to be mutagenic for the strain TA 100. The mutagenic activities exhibited by cyclopenta[c]phenanthrenes are compared with those shown by the related cyclopenta[a]phenanthrenes and then discussed with respect to the effect of the cyclopentane ring facing the bay region. Indeno[c]phenanthrenes are mostly inactive. The effect of benzoannulation on the mutagenic activities of cyclopenta[c]phenanthrenes is discussed.

Carbon Isotopes↗
PubMed2000

Effect of model sorptive phases on phenanthrene biodegradation: different enrichment conditions influence bioavailability and selection of phenanthrene-degrading isolates.

The sorption of organic contaminants by natural organic matter (NOM) often limits substrate bioavailability and is an important factor affecting microbial degradation rates in soils and sediments. We hypothesized that reduced substrate bioavailability might influence which microbial assemblages are responsible for contaminant degradation under enrichment culture conditions. Our primary goal was to characterize enrichments in which different model organic solid phases were used to establish a range of phenanthrene bioavailabilities for soil microorganisms. Phenanthrene sorption coefficients (expressed as log K(D) values) ranged from 3.0 liters kg(-1) for Amberlite carboxylic acid cation-exchange resin (AMB) to 3.5 liters kg(-1) for Biobeads polyacrylic resin (SM7) and 4.2 liters kg(-1) for Biobeads divinyl benzene resin (SM2). Enrichment cultures were established for control (no sorptive phase), sand, AMB, SM7, and SM2 treatments by using two contaminated soils (from Dover, Ohio, and Libby, Mont.) as the initial inocula. The effects of sorption by model phases on the degradation of phenanthrene were evaluated for numerous transfers in order to obtain stable microbial assemblages representative of sorptive and nonsorptive enrichment cultures and to eliminate the effects of the NOM present in the initial inoculum. Phenanthrene degradation rates were similar for each soil inoculum and ranged from 4 to 5 micromol day(-1) for control and sand treatments to approximately 0.4 micromol day(-1) in the presence of the SM7 sorptive phase. The rates of phenanthrene degradation in the highly sorptive SM2 enrichment culture were insignificant; consequently, stable microbial populations could not be obtained. Bacterial isolates obtained from serial dilutions of enrichment culture samples exhibited significant differences in rates of phenanthrene degradation performed in the presence of SM7, suggesting that enrichments performed in the presence of a sorptive phase selected for different microbial assemblages than control treatments containing solid phase phenanthrene.

Adsorption↗
PubMed2004

Effect of n-alkyl chain length on the complexation of phenanthrene and 9-alkyl-phenanthrene with beta-cyclodextrin.

The characteristics of host-guest complexation between beta-cyclodextrin (beta-CD) and phenanthrene derivatives (phenanthrene, n-propyl, n-butyl and n-hexyl-phenanthrene) were investigated by fluorescence spectrometry. Linear and non-linear regression methods were used to estimate the formation constants (K1). A 1:1 stoichiometric ratio and an effect of n-alkyl chain length on the formation constant were observed for the binary inclusion complex between guest and beta-CD. The formation constant dramatically increases with the length of n-alkyl, it starts from the value of 140 l mol(-1) for the phenanthrene to reach the value of 580 l mol(-1) for hexyl-phenanthrene. The effect of the temperature on the fluorescence intensity of each complex (guest-host) was also studied; and then the thermodynamic parameters were calculated. The main inclusion site seems to be aromatic moiety for short chain molecules, and it moves toward the alkyl chain part, as the chain becomes longer.

Macromolecular Substances↗
PubMed1983

Replica plating method for estimating phenanthrene-utilizing and phenanthrene-cometabolizing microorganisms.

A replica plating method was developed for detecting and enumerating phenanthrene-degrading microorganisms. The method is designed to discriminate between aquatic organisms that utilize phenanthrene as the sole carbon and energy source and organisms that cometabolize phenanthrene. The method was used to demonstrate that phenanthrene utilizers and phenanthrene cometabolizers coexist in estuarine sediments.

Journal Article↗
PubMed1997

A New and Concise Synthesis of 3-Hydroxybenzo[c]phenanthrene and 12-Hydroxybenzo[g]chrysene, Useful Intermediates for the Synthesis of Fjord-Region Diol Epoxides of Benzo[c]phenanthrene and Benzo[g]chrysene.

A new strategy which involves a palladium-catalyzed cross-coupling reaction has been developed for the rapid synthesis of 3-hydroxybenzo[c]phenanthrene (5) and 12-hydroxybenzo[g]chrysene (6). These phenolic compounds are the key intermediates for the synthesis of highly carcinogenic fjord-region diol epoxide metabolites 3 and 4 of benzo[c]phenanthrene (1) and benzo[g]chrysene (2). The cross-coupling reaction of 2-bromo-5-methoxybenzaldehyde (9) with naphthalene-1-boronic acid (7) and phenanthrene-9-boronic acid (8) produced 2-(1-naphthyl)-5-methoxybenzaldehyde (10) and 2-(9-phenanthryl)-5-methoxybenzaldehyde (11), respectively, in quantitative yields. After reaction of these aldehydes with trimethylsulfonium iodide under phase-transfer conditions or with the Wittig reagent obtained from (methoxymethyl)triphenylphosphonium bromide and phenyllithium to generate an oxiranyl or methoxyethene side chain, the acid-catalyzed cyclization with methanesulfonic acid (or boron trifluoride) produced 3-methoxybenzo[c]phenanthrene (16) and 12-methoxybenzo[g]chrysene (17) in 61-64% yields. Finally, demethylation of these methoxy derivatives 16 and 17 with boron tribromide resulted in the formation of the hydroxy analogues 5 and 6, respectively. The availability of this short and high-yielding regiospecific method for the synthesis of phenols 5 and 6 should allow the preparative-scale synthesis of the fjord-region diol epoxides 3 and 4. These diol epoxides are required as starting compounds for the synthesis of site-specifically modified oligonucleotides which are critically needed to elucidate the mechanism of carcinogenesis at the molecular level.

Journal Article↗
PubMed2001

Biotransformation of phenanthrene and 1-methoxynaphthalene with Streptomyces lividans cells expressing a marine bacterial phenanthrene dioxygenase gene cluster.

The phdABCD gene cluster in a marine bacterium Nocardioides sp. strain KP7 codes for the multicomponent enzyme phenanthrene dioxygenase. phdA encoding an iron-sulfur protein large subunit alpha, phdB encoding its small subunit beta, phdC encoding ferredoxin, and phdD encoding ferredoxin reductase, were replaced in such a way that the termination codons of the preceding open reading frames were overlapped with the initiation codons of the following genes. This manipulated phdABCD gene cluster was positioned downstream of the thiostrepton-inducible promoter PtipA in a high-copy-number vector pIJ6021, and introduced into the gram-positive, soil-inhabiting, filamentous bacterium Streptomyces lividans. The recombinant S. lividans cells converted phenanthrene into a cis-diol form, which was determined to be cis-3,4-dihydroxy-3,4-dihydrophenanthrene by its UV spectral data as well as HPLC property, using the authentic sample for comparison. This biotransformation proceeded very efficiently; 200 microM and 2 mm of phenanthrene were almost completely converted to its cis-diol form in 6 h and 32 h, respectively. In addition, the S. lividans cells carrying the phdABCD gene cluster were found to transform 1-methoxynaphthalene to two products, which were identified to be 8-methoxy-2-naphthol in addition to 8-methoxy-1,2-dihydro-1,2-naphthalenediol by their EI-MS, 1H- and 13C-NMR spectral data.

Actinomycetales↗
PubMedDate not supplied

Phenanthrene degradation in soils co-inoculated with phenanthrene-degrading and biosurfactant-producing bacteria.

Contaminant sorption within the soil matrix frequently limits biodegradation. However, contaminant bioavailability can be species-specific. This study investigated bioavailability of phenanthrene (PHE) to two PHE-degrading bacteria (Pseudomonas strain R and isolate P5-2) in the presence of rhamnolipid biosurfactant and/or a biosurfactant-producing bacterium, Pseudomonas aeruginosa ATCC 9027. Pseudomonas strain R mineralized more soil-sorbed PHE than strain P5-2, but in aqueous cultures the rate and extent of PHE mineralization by P5-2 exceeded that by P. strain R. In Fallsington sandy loam (fine-loamy, mixed, active, mesic Typic Endoaquult) (high PHE-sorption capacity) the addition of rhamnolipid increased PHE mineralization by P. strain R. Phenanthrene mineralization in soils inoculated with P5-2 was minimal and no enhancement in PHE degradation was observed when biosurfactant was added. Co-inoculation of Fallsington sandy loam with the biosurfactant producer did not affect PHE mineralization by isolate P5-2, but significantly enhanced PHE mineralization by P. strain R. The enhancement of PHE mineralization could not be explained by P. aeruginosa-mediated PHE degradation. The addition of rhamnolipid at concentrations above the critical micelle concentration (CMC) resulted in enhanced PHE release from test soils. These results suggest that the PHE-degrading strains were able to access different pools of PHE and that the biosurfactant-enhanced release of PHE from soils did not result in enhanced biodegradation. The results also demonstrated that bacteria with the catabolic potential to degrade sorbed hydrophobic contaminants could interact commensally with surfactant-producing strains by an unknown mechanism to hasten the biodegradation of aromatic hydrocarbons. Thus, understanding interactions among microbes may provide opportunities to further enhance biodegradation of soil-bound organic contaminants.

Adsorption↗
PubMed1977

Mass spectrometry of cyclopenta[alpha]phenanthrenes. Metabolites formed in vitro and in vivo from the carcinogen 15,16-dihydro-11-methyl-cyclopenta[alpha]phenanthren-17-one.

The mass spectra of a number of synthetic cyclopenta[alpha]phenanthrenes are described, and identification of an in vitro metabolite of a carcinogen of this series is reported. The correlation of the mass spectra of the major urinary metabolite, its dehydration product and its triacetate with the structure assigned to the metabolite is described.

Animals↗
PubMed1994

Relative role of eukaryotic and prokaryotic microorganisms in phenanthrene transformation in coastal sediments.

THE RELATIVE ROLE OF EUKARYOTIC VERSUS PROKARYOTIC MICROORGANISMS IN PHENANTHRENE TRANSFORMATION WAS MEASURED IN SLURRIES OF COASTAL SEDIMENT BY TWO DIFFERENT APPROACHES: detection of marker metabolites and use of selective inhibitors on phenanthrene biotransformation. Phenanthrene biotransformation was measured by polar metabolite formation and CO(2) evolution from [9-C]phenanthrene. Radiolabeled metabolites were tentatively identified by high-performance liquid chromatography (HPLC) separation combined with UV/visible spectral analysis of HPLC peaks and comparison to authentic standards. Both yeasts and bacteria transformed phenanthrene in slurries of coastal sediment. Two products of phenanthrene oxidation by fungi, phenanthrene trans-3,4-dihydrodiol and 3-phenanthrol, were produced in yeast-inoculated sterile sediment. However, only products of phenanthrene oxidation typical of bacterial transformation, 1-hydroxy-2-naphthoic acid and phenanthrene cis-3,4-dihydrodiol, were isolated from slurries of coastal sediment with natural microbial populations. Phenanthrene trans-dihydrodiols or other products of fungal oxidation of phenanthrene were not detected in the slurry containing a natural microbial population. A predominant role for bacterial transformation of phenanthrene was also suggested from selective inhibitor experiments. Addition of streptomycin to slurries, at a concentration which suppressed bacterial viable counts and rates of [methyl-H]thymidine uptake, completely inhibited phenanthrene transformation. Treatment with colchicine, at a concentration which suppressed yeast viable counts, depressed phenanthrene transformation by 40%, and this was likely due to nontarget inhibition of bacterial activity. The relative contribution of eukaryotic microorganisms to phenanthrene transformation in inoculated sterile sediment was estimated to be less than 3% of the total activity. We conclude that the predominant degraders of phenanthrene in muddy coastal sediments are bacteria and not eukaryotic microorganisms.

Journal Article↗
PubMed2006

Visualizing the air-to-leaf transfer and within-leaf movement and distribution of phenanthrene: further studies utilizing two-photon excitation microscopy.

Two-photon excitation microscopy (TPEM) was used to monitor the air-to-leaf transfer and within-leaf movement and distribution of phenanthrene in two plant species (maize and spinach) grown within a contaminated atmosphere. Phenanthrene was visualized within the leaf cuticle, epidermis, mesophyll, and vascular system of living maize and spinach plants. No detectable levels of phenanthrene were observed in the roots or stems of either species, suggesting phenanthrene entered the leaves only from the air. Phenanthrene was observed in both the abaxial and adaxial cuticles of both species. Particulate material (aerosols/dust) contaminated with phenanthrene was located at the surface of the cuticle and became encapsulated within the cuticularwaxes. Overtime, diffuse areas of phenanthrene formed within the adjacent cuticle. However, most of the visualized phenanthrene reaching the leaves arrived via gas-phase transfer. Phenanthrene was found within the wax plugs of stomata of both species and on the external surface of the stomatal pore, but not on the internal surface, or within the sub-stomatal cavity. Phenanthrene diffused through the cuticles of both species in 24-48 h, entering the epidermis to reside predominantly within the cell walls of maize (indicative of apoplastic transport) and the cellular cytoplasm of spinach (indicative of symplastic transport). Phenanthrene accumulated within the spinach cytoplasm where it concentrated into the vacuoles of the epidermal cells. Phenanthrene was not observed to accumulate in the cytoplasm of maize cells. Phenanthrene entered the internal mesophyll of both species, and was found within the mesophyll cell walls, at the surface of the chloroplasts, and within the cellular cytoplasm. Phenanthrene was observed within the xylem of maize following 12 days exposure. The cuticle and epidermis at the edges of spinach leaves had a systematically higher concentration of phenanthrene than the cuticle and epidermal cells at the center of the leaf. These results provide important new information about how such compounds enter, move, and distribute within leaves, and suggest that contemporary views of such processes based on data obtained from traditional analytical methods may need to be revised.

Adsorption↗
PubMed1985

Toxicity of polycyclic aromatic hydrocarbons. I. Effect of phenanthrene, pyrene, and their ozonized products on blood chemistry in rats.

Male Sprague-Dawley rats were treated with a single ip injection of physiological saline (3.0 ml/kg), dimethyl sulfoxide (DMSO, 3.0 ml/kg), phenanthrene (150 mg/kg), ozonized products of phenanthrene (150 mg/kg), pyrene (150 mg/kg), or ozonized products of pyrene (150 mg/kg). Phenanthrene, pyrene, and their ozonized products were dissolved in DMSO (50 mg/ml). Serum aspartate aminotransferase (AST) activity was increased significantly 24 hr after ip administration of DMSO when compared with physiological saline. Phenanthrene produced a significant elevation of serum AST and gamma-glutamyl transpeptidase (GGTP) levels related to physiological saline and DMSO-injected rats 24 hr after injection. However, GGTP levels for groups treated with DMSO or phenanthrene were not significantly increased when compared with saline groups 72 hr after injection. Ozonized products of phenanthrene produced a significant elevation of serum AST, alanine aminotransferase (ALT), GGTP, and bilirubin levels when compared with groups treated with physiological saline, DMSO, and phenanthrene 24 or 72 hr after injections. The ozonized products of phenanthrene also produced significant elevation of serum creatinine levels compared with physiological saline, DMSO, and phenanthrene groups at 24 hr after treatment and of blood urea nitrogen (BUN) levels at 24 and 72 hr. Although pyrene caused a small but significant increase in the serum AST and bilirubin levels 24 hr after treatment, no significant change in the serum AST, ALT, GGTP, BUN, and creatine levels were observed with the ozonized products of pyrene at 24 or 72 hr. This study demonstrates significant alterations in serum chemistry induced by reaction products of ozone with phenanthrene. No such effect was observed when the products of pyrene ozonation were administered. Although the ozonation products of pyrene were not toxic under the conditions of this study, phenanthrene products were more hepatotoxic than was phenanthrene itself. Nephrotoxicity was also an apparent effect of ozonized phenanthrene. Since ozone-polycyclic aromatic hydrocarbon (PAH) reactions may occur in the atmosphere, these reactions might produce compounds that are more toxic than either ozone or the PAH alone.

Alanine Transaminase↗