Disease relevance of phenanthrene

• Equilibrium constants (K(de)) are reported for the dehydration of hydrates of benzene, naphthalene, phenanthrene, and anthracene [1].
• Phenotypic and genotypic characterization of phenanthrene-degrading fluorescent Pseudomonas biovars [2].
• The analysis of Sphingomonas population structures of several PAH-contaminated soils by the new PCR-DGGE method revealed that soils containing the highest phenanthrene concentrations showed the lowest Sphingomonas diversity [3].
• Mineralization of phenanthrene by a Mycobacterium sp [4].
• Other closely related Burkholderia sp. populations, some of which utilized phenanthrene, were detected in sand and control enrichment cultures [5].

Psychiatry related information on phenanthrene

• We are developing a phenotyping approach to assessing individual differences in PAH metabolism by quantifying human urinary metabolites of the ubiquitous PAH phenanthrene (1) [6].

High impact information on phenanthrene

• The structure reveals that the phenanthrene ring system is stacked with the base pair immediately 3' to the modified guanine, thereby occluding the normal binding site for the correct incoming nucleoside triphosphate [7].
• Treatment of primary mixed fibroblasts and epithelial cell cultures with methylcholanthrene, but not phenanthrene, led to development of actively growing fibroblastic cultures with many heteroploid cells [8].
• Subsurface microorganisms detected at a former manufactured gas plant site contaminated with coal tars mineralized significant amounts of naphthalene (8-43%) and phenanthrene (3-31%) in sediment-water microcosms incubated for 4 weeks under aerobic conditions [9].
• These results indicate that the position of a nitrogen heteroatom in phenanthrene (the analogous carbocyclic aromatic hydrocarbon) not only has a marked effect on the mutagenic activities of the diol epoxide derivatives, but also can alter the metabolic activation pathways of the parent hydrocarbon [10].
• A structurally related noncarcinogenic polycyclic aromatic hydrocarbon, phenanthrene, had no effect on [3H]spiperone binding or PRL release [11].

Chemical compound and disease context of phenanthrene

• When overproduced in Escherichia coli, Pdo1 and Pdo2 showed distinctive selectivities towards PAH substrates, with the former enzyme catalyzing the dihydroxylation of both pyrene and phenanthrene and the latter preferentially oxidizing phenanthrene [12].
• Fifteen strains of polycyclic aromatic hydrocarbon (PAH)-catabolizing bacteria, identified as Pseudoalteromonas spp. were isolated from Eagle Harbor, Puget Sound, USA, using a most probable number procedure in which naphthalene or phenanthrene was the sole carbon and energy source [13].
• Cultures of Mycobacterium sp. strain PYR-1 were dosed with anthracene or phenanthrene and after 14 days of incubation had degraded 92 and 90% of the added anthracene and phenanthrene, respectively [14].
• Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp [15].
• To clone the dioxygenase genes involved in PAH degradation, two-dimensional (2D) gel electrophoresis of PAH-induced proteins from cultures of Mycobacterium sp. strain PYR-1 was used to detect proteins that increased after phenanthrene, dibenzothiophene, and pyrene exposure [16].

Biological context of phenanthrene

• The molecular modeling study is augmented by benchmark ab initio calculations on the bay-region triol carbocation of phenanthrene [17].
• We suggest that sorption of phenanthrene to these soil components may result in a higher concentration of substrate in the vicinity of the bacterial cells and therefore may increase its bioavailability [18].
• Earlier, we presented mechanistic models of the effects of surfactants on phenanthrene dissolution and on the biodegradation kinetics of phenanthrene solubilized in surfactant micelles [19].
• Plasmids of approximately 21, 58, and 77 megadaltons were detected in cells grown with phenanthrene but not in those which, after growth on nutrient media, lost the phenanthrene-degrading phenotype [4].
• Cloning and characterization of a chromosomal gene cluster, pah, that encodes the upper pathway for phenanthrene and naphthalene utilization by Pseudomonas putida OUS82 [20].

Anatomical context of phenanthrene

• The comparative hydration of styrene 7,8-oxide, octene 1,2-oxide, naphthalene 1,2-oxide, phenanthrene 9,10-oxide, benzo[a]anthracene 5,6-oxide, 3-methylcholanthrene 11,12-oxide, dibenzo[a,h]anthracene 5,6-oxide, and benzo[a, 7,8-, 9,10-, and 11,12-oxides to their respective dihydrodiols was investigated in microsomes from nine human autopsy livers [21].
• The MAbs obtained from four of the 16 hybridomas exhibited strong inhibitory activity to CYP2A6-catalysed phenanthrene metabolism [22].
• This study has evaluated the effect of boldine (B), and two phenanthrene alkaloids semisynthesized by us, secoboldine (SB) and boldine methine (BM), on Ang-II-induced neutrophil recruitment [23].
• The results indicate that there are differences in both the regio- and stereoselective metabolism of anthracene and phenanthrene between the fungus C. elegans and rat liver microsomes [24].
• We conducted an experiment in two-compartment devices to show the selection of bacterial communities by root exudates and phenanthrene as a function of distance to roots [25].

Associations of phenanthrene with other chemical compounds

• However, phenanthrene quinone was a potent inhibitor (approximate K(i) = 6.3 +/- 1 microm) [26].
• Along the reaction pathway, desolvation of the thiolate sulfur of glutathione is observed, in agreement with solvent isotope experiments, as well as increased solvation of the epoxide oxygen of phenanthrene 9,10-oxide, illustrating an important stabilizing role for active site solvent molecules [27].
• We developed a liquid chromatography-tandem mass spectrometry method for the determination of phenolic metabolites of naphthalene, fluorene, phenanthrene, and pyrene in human urine [28].
• In this work, stir bar sorptive extraction and liquid desorption was combined with MEKC and diode-array detection (SBSE-LD-MEKC-DAD) for the determination of polynuclear aromatic hydrocarbons (PAHs) in aqueous medium, using biphenyl, fluorene, anthracene, phenanthrene, fluoranthene and pyrene as model compounds [29].
• There were three exceptions, namely benzo[e]pyrene, phenanthrene and perylene (each possessing a bay region), which were not mutagenic [30].

Gene context of phenanthrene

• It is reported that CYP3A4-catalyzed phenanthrene metabolism is activated by 7,8-benzoflavone and that 7,8-benzoflavone serves as a substrate for CYP3A4 [31].
• Here, the application of rat and human CYP1A1 and CYP1A2 is demonstrated for comparative studies on the oxidation of polycyclic aromatic hydrocarbons, such as phenanthrene, benz[a]anthracene, and benzo[a]pyrene [32].
• 7, 8-Benzoflavone activation of phenanthrene metabolism by CYP3A4 and dapsone activation of flurbiprofen and naproxen metabolism by CYP2C9 were also observed [33].
• Species and cytochrome P450 specific metabolite profiles were also observed for phenanthrene and benz[a]anthracene [32].
• GSH conjugates of phenanthrene 9(S),10(R)-oxide and 4,5-diazaphenanthrene 9(S),10(R)-oxide were docked into the active site of both GST 3-3 and GST 4-4 [34].

Analytical, diagnostic and therapeutic context of phenanthrene

• Partial purification of the LH-20 beta inhibitor component by high performance liquid chromatography and gas-liquid chromatography-mass spectrometric analysis suggests the putative inhibitor activity is not steroidal in nature and consists of two very similar phenanthrene-like molecules (molecular weights 302 and 304) [35].
• The disappearance of phenanthrene from the extracellular medium and mycelia was determined by using gas chromatography [36].
• PAH compounds are not estrogenic, and indeed, stomach and small intestine digestions of 62.5 nmol naphthalene, phenanthrene, pyrene, and benzo(a)pyrene showed no estrogenic effects in the human estrogen receptor bioassay [37].
• A new green fluorescent protein-based bacterial biosensor for analysing phenanthrene fluxes [38].
• Comparison of the circular dichroism spectra of the phenanthrene trans-1,2- and trans-3,4-dihydrodiols formed by C. elegans to those formed by mammalian enzymes indicated that each of the dihydrodiols formed by C. elegans had an S,S absolute configuration [24].

References