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PubMed1984

3-Methylcholanthrene does not induce in vitro xenobiotic metabolism in spiny lobster hepatopancreas, or affect in vivo disposition of benzo[a]pyrene.

Administration of 3-methylcholanthrene (10 mg/kg) i.m. to spiny lobsters, Panulirus argus, did not cause induction of the cytochrome P-450 content of hepatopancreas microsomes. The rate of oxidation of benzo[a]pyrene or 7-ethoxyresorufin in reductase-fortified preparations of hepatopancreas microsomes was the same for corn oil-treated or 3-methylcholanthrene-treated lobsters. Administration of 3-methylcholanthrene (10 mg/kg) i.m. to spiny lobsters one week prior to an i.v. dose of [14C]benzo[a]pyrene (1 mg/kg) did not influence the disposition of the radiolabelled benzo[a]pyrene in lobsters. At one week after the dose of [14C]benzo[a]pyrene, approximately 40% of the dose of [14C]benzo[a]pyrene remained in the lobsters, regardless of treatment. The digestive tract (hepatopancreas, intestinal contents, stomach and intestine) contained most (86%) of the 14C remaining in the lobsters.

Animals↗
PubMed2005

Transcriptional signatures of environmentally relevant exposures in normal human mammary epithelial cells: benzo[a]pyrene.

Changes in gene expression in a panel of primary normal human mammary epithelial cell strains, developed from healthy breast tissue obtained at reduction mammoplasty from different donors, in response to benzo[a]pyrene exposure have been investigated. It was expected that both gene expression changes common to cell strains derived from different donors as well as inter-individual variation would be observed. Therefore, the strategy that has been adopted is to identify potentially important changes, or useful changes from a biomonitoring perspective, using gene-array technology and a small number of donors; then investigate selected transcription responses using a large number of tissue donors and a cheaper method of transcript detection (real-time polymerase chain reaction). Here we report results from four primary normal human mammary epithelial cell strains that were treated with benzo[a]pyrene in vitro for either 6 or 24 h. Transcription was monitored using high-density oligonucleotide arrays (Affymetrix HuGeneFL). Total RNA was used for the preparation of labeled targets that were hybridized to microarrays containing probes representing more than 6800 human genes and expressed sequence tags. Gene expression data were analyzed using the GeneChip software (MAS 5.0). Altered gene expression patterns were observed in response to benzo[a]pyrene in human mammary epithelial cell strains from different donors. Specifically, the dioxin inducible cytochrome P450 CYP1B1 was consistently induced in response to 6 and 24 h exposure to benzo[a]pyrene in cell strains from all four donors. Two other genes that were relatively consistently induced were IL1beta and MMP1. Less consistent changes in other metabolism genes (CYP1A1, CYP11B2, and NQO1) and certain cell cycle control genes GOS2 and AF1Q were also induced, while EGR1 was suppressed. Although no change in p53 transcription was observed, an accumulation of p53 protein was detected using antibodies. A similar accumulation of Waf1 (p21) was also observed using immunohistochemistry, this was expected since p53 is p21's transcription factor. Significant inter-individual variations in both the levels and patterns of gene expression were observed, in response to benzo[a]pyrene exposure. These studies provide a complementary approach to molecular epidemiology for the investigation of differential susceptibility to chemical carcinogens, and specifically polycyclic aromatic hydrocarbons.

Air Pollutants↗
PubMed2005

Conditions for effective removal of pyrene from an artificially contaminated soil using Pseudomonas aeruginosa 57SJ rhamnolipids.

The efficacy of a new rhamnolipid biosurfactants mixture to enhance the removal of pyrene from a soil artificially contaminated was investigated. The molar solubilization ratio (MSR) and the partition coefficient between the micelles and water (log K(m)) were found to be 7.5 x 10(-3) and 5.7, respectively. From soil column studies, the pyrene removal increased linearly with the concentration of the injected biosurfactants solution above the effective critical micellar concentration (0.4 g L(-1)). Flushing with a 5.0 g L(-1) biosurfactants solution increased the pyrene concentration in the effluent by 178 times. At high biosurfactants' concentrations (2.5 and 5.0 g L(-1)), the cumulative pyrene recovery reached 70%. This pyrene remobilization takes place independently of the soil organic carbon solubilization. This study provides a combination of batch and column experiments in order to find the conditions for effective soil remediation using a new rhamnolipids mixture.

Biodegradation, Environmental↗
PubMed2004

Solubilization of pyrene by anionic-nonionic mixed surfactants.

Surfactant-enhanced remediation (SER) is an effective approach for the removal of sorbed hydrophobic organic compounds from contaminated soils. The solubilization of pyrene by four anionic-nonionic mixed surfactants, sodium dodecyl sulfate (SDS) with Triton X-405 (TX405), Brij35, Brij58, and Triton X-100 (TX100), has been studied from measurements of the molar solubilization ratio (MSR), the micelle-water partition coefficient (Kmc), and the critical micelle concentration (CMC). The MSRs of pyrene in mixed surfactants are found to be larger than those predicted according to an ideal mixing rule. The mixing effect of anionic and nonionic surfactants on MSR for pyrene follows the order of SDS-TX405 > SDS-Brij35 > SDS-Brij58 > SDS-TX100 and increases with an increase in the hydrophile-lipophile balance (HLB) value of nonionic surfactant in mixed systems. In addition, the mixture of anionic and nonionic surfactants cause the Kmc value for pyrene to be greater than the ideal value in SDS-TX405 mixed system, but to be smaller than the ideal value in SDS-Brij35, SDS-Brij58, and SDS-TX100 mixed systems. Meanwhile, in the four mixed systems, the experimental CMCs are lower than the ideal CMCs at almost all mixed surfactant solution compositions. The mixing effect of anionic and nonionic surfactants on MSR for pyrene can be attributed to the conjunct or the net result of the negative deviation of the CMCs from ideal mixture and the increasing or decreasing Kmc.

Anions↗
PubMed2005

Mycelial pellet formation by Penicillium ochrochloron species due to exposure to pyrene.

Five indigenous fungal strains with characteristics of the genus Penicillium capable of degrading and utilizing pyrene, as sole carbon source were isolated from soil of a former gas work site. Two strains were identified as Penicillium ochrochloron. One of the strains was able to degrade a maximum of 75% of 50 mg l(-1) pyrene at 22 degrees C during 28 days of incubation. The presence of pyrene in the medium resulted in an aggregation of hyphae into pellets by the two Penicillium ochrochloron strains. Formation of pellets was observed after 48 h of incubation with difference in size and texture between the two strains. This indicated the individual variation within the same genus of fungi. However, remaining strains did not show this behavior even though they were capable of utilizing pyrene as sole carbon source. The macro- and microscopic morphology of fungal pellets was studied using scanning electron microscopy. It was found that the addition of varying concentration of pyrene ranging from 10 to 50 mg l(-1) in the medium influenced shape and structure of the mycelial pellets. A two-fold increase in hyphal branching (with concomitant decrease in the average hyphal growth unit) was observed at a concentration of 10mg l(-1). The relevance of fungal growth and morphology for bioremediation of polycyclic aromatic hydrocarbons (PAHs) contaminated sites are discussed.

Biodegradation, Environmental↗
PubMed2006

Effect of the high polycyclic aromatic hydrocarbon, benzo[a]pyrene, on the lipid content of Fusarium solani.

The purpose of the present paper was to study the effect of the high polycyclic aromatic hydrocarbon (PAH), benzo[a]pyrene, on the lipid [fatty acid (FA) and sterol] composition and content of the fungi Fusarium solani and F. oxysporum, respectively recognized as good and poor PAH degraders. The major FAs and the major sterol that characterized the tested Fusarium strains were C16:0, C18:1, C18:2, and ergosterol. Lipid profiles of F. solani remained unchanged with the addition of benzo[a]pyrene in the culture media at all concentrations and duration of treatment. However, in the presence of benzo[a]pyrene, significant decreases in FA content, which reached 18% in young cultures and 28% in mature colonies, were registered. Similarly, the sterol content of F. solani was reduced by 27% in the presence of benzo[a]pyrene. In contrast, no modification in lipid profile and lipid content were observed with F. oxysporum, a strain recognized as a low benzo[a]pyrene degrader.

Benzo(a)pyrene↗
PubMed2001

Characteristics of pyrene phospholipid/gamma-cyclodextrin complex.

Recently, it was demonstrated that gamma-cyclodextrins (gamma-CDs) greatly accelerates transfer of hydrophobic pyrene-labeled and other fluorescent phospholipid derivatives from vesicles to cells in culture (). To understand better the characteristics of this process, we studied the interaction of gamma-CD with pyrene-labeled phosphatidylcholines (PyrPCs) using a variety of physical methods. Either one or both of the acyl chains of PC was labeled with a pyrene moiety (monoPyrPCs and diPyrPCs, respectively), and the length of the labeled chain(s) varied from 4 to 14 carbons. Fluorescent binding assays showed that the association constant decreases strongly with increasing acyl chain length. PyrPC/gamma-CD stoichiometry was 1:2 for the shorter chain species, but changed to 1:3 when the acyl chain length exceeded 8 (diPyrPCs) or 10 (monoPyrPCs) carbons. The activation energy for the formation of diPyr(10)PC/gamma-CD complex was high, i.e., +92 kJ/mol, indicating that the phospholipid molecule has to fully emerge from the bilayer before complex formation can take place. The free energy, enthalpy, and entropy of transfer of monoPyrPC from bilayer to gamma-CD complex were close to zero. The absorption, Fourier transform infrared, and fluorescence spectral measurements and lifetime analysis indicated that the pyrene moiety lies inside the CD cavity and is conformationally restricted, particularly when the labeled chain is short. The acyl chains of a PyrPC molecule seem to share a CD cavity rather than occupy different ones. The present data provide strong evidence that the ability of gamma-CD to enhance intermembrane transfer of pyrene-labeled phospholipids is based on the formation of stoichiometric complexes in the aqueous phase. This information should help in designing CD derivatives that are more efficient lipid carriers then those available at present.

Acylation↗
PubMed2001

Molecular mechanism of lateral diffusion of py(10)-PC and free pyrene in fluid DMPC bilayers.

From the study of the kinetics of the fluorescence self-quenching of pyrene in multilamellar vesicles of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) in the fluid phase we obtain the molecular diffusion parameters, diffusion coefficients, and activation energies for lateral diffusion for three probes: 1-palmitoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphocholine (py(10)-PC), pyrene, and 1-pyrenebutanoic acid (py-but). The experiments are done in a range of temperatures for which the reversibility of excimer formation is negligible and the probe/phospholipid ratios used are low, avoiding non-ideal mixing of the probe. The time-resolved fluorescence decays are, in all cases, accurately and consistently described by the two-dimensional (2D) formalism for bimolecular diffusion-controlled reactions. From the parameters obtained in this way we conclude that the primary step of the diffusion of the pyrene-labeled phospholipid involves the simultaneous jump of phospholipid and fluorophore moieties, and also that although in the case of py(10)-PC the pyrene from molecules pertaining to different layers may interact during the lifetime of the exited state, this is not the case for free pyrene.

Biophysical Phenomena↗
PubMedDate not supplied

Regioselectivity in rat microsomal metabolism of benzo[a]pyrene: evidence for involvement of two distinct binding sites.

The metabolic profile of benzo[a]pyrene (BP) in cumene hydroperoxide-(CHP)-dependent reaction by male rat liver microsomes was dependent on CHP concentration. At 0.05 mM CHP, 3-hydroxy-BP was the major metabolite. Increase in CHP reduced 3-hydroxy-BP formation but increased BP quinone formation simultaneously. This change in metabolic profile was reversed by preincubation with pyrene. Pyrene (PY) selectively inhibited quinone formation but enhanced 3-hydroxy-BP formation. Naphthalene (NP) had no effect on BP quinone formation but inhibited BP 3-hydroxylation. Phenanthrene (PA) and benz[a]anthracene (BA) inhibited effectively 3-hydroxy-BP formation but only slightly quinone formation. BP binding to microsomal protein correlated to quinone formation and not BP 3-hydroxylation. BP metabolism by female rat liver microsomes also depended on CHP concentration but was much less efficient than the male. Quinones were consistently predominant metabolites and their formation was also inhibited by pyrene. Our data provide evidence that regioselectivity in BP metabolism involves at least two distinct binding sites. One site recognizes the benzo region of BP in BP 3-hydroxylation and the other recognizes the pyrene region in quinone formation. The different ratios of 3-hydroxy-BP to quinone formation by male and female rat liver microsomes suggest that the two binding sites are probably located at separate cytochrome P-450 isozymes.

Animals↗
PubMed1987

Effect of ingested benzo[a]pyrene and cadmium on tissue accumulation, hydroxylase activity, and intestinal morphology of the black sea bass, Centropristis striata.

Black sea bass, Centropristis striata, were fed shrimp containing [14C]benzo[a]pyrene (200 ppb) in the presence and absence of cadmium (10 ppm) for 10 days. Concentrations of cadmium in muscle tissue were significantly higher when both cadmium and benzo[a]pyrene were ingested simultaneously by the fish. Results indicate that selected tissue concentrations of total benzo[a]pyrene compounds (parent and metabolites) were not affected by the presence of cadmium. The bile contained the majority of benzo[a]pyrene found for all treatments. Ingestion of both contaminants had no effect on hepatic benzo[a]pyrene hydroxylase activity. Histological evidence from the feeding study demonstrated the presence of subcellular inclusions in the intestinal columnar cells and the combined effects of both contaminants appeared greater than either alone.

Animals↗
PubMed1999

Inhibition by retinoids of benzo(A)pyrene metabolism catalyzed by 3-methylcholanthrene-induced rat cytochrome P-450 1A1.

Benzo(a)pyrene, a well-known procarcinogen, is believed to be activated by microsomal cytochrome P-450 1A1 (CYP 1A1). We recently reported that rat CYP 1A1 induced by 3-methylcholanthrene (3-MC) catalyzed the conversion of retinal to retinoic acid. In this study, we investigated retinoid inhibition of the metabolism of benzo(a)pyrene and 7-ethoxyresorufin, another specific substrate of CYP 1A1, using liver microsomes prepared from control and 3-MC-pretreated rats as the enzyme source. In 3-MC-treated rats, retinal and retinol, but not retinoic acid, inhibited benzo(a)pyrene metabolism. The 50% inhibitory concentration (IC50) of retinal was about 11.5 micromol/L and the inhibition was competitive, with a Ki value of 5.8 micromol/L. Retinol is a more potent inhibitor than retinal. The IC50 was about 5 micromol/L and the inhibition was mixed, with a Ki value of 19.2 micromol/L and a Ki' value of 4.2 micromol/L. Almost the same results were obtained for the reaction of 7-ethoxyresorufin deethylation. In contrast, the metabolic activity of both benzo(a)pyrene and 7-ethoxyresorufin was much lower in untreated versus 3-MC-treated rats, and only weak inhibition by the retinoids was observed. The results suggest that retinoids inhibit the activation of benzo(a)pyrene and that the substrate specificity of cytochrome P-450 isozymes associated with retinoid metabolism should be taken into account when studying the anticarcinogenic action of retinoids.

Animals↗
PubMed2001

Pyrene biodegradatin in aqueous solutions and soil slurries by Mycobacterium PYR-1 and enriched consortium.

To better understand complex bioavailability issues, pyrene degradation was examined in aqueous and soil slurry solutions using pure Mycobacterium sp. PYR-1 and a microbial consortium. The intrinsic rates of the aqueous pyrene degradation were very similar, 1.3 x 10(-9) microg pyrene/CFU-h for Mycobacterium sp. PYR-1 and 1.1 x 10(-9) microg pyrene/CFU-h for the consortium. Rates were much lower with the soil-slurry experiments, ranging from 1.2 x 10(-12) to 7.8 x 10(-10) microg/CFU-h, depicting the strong negative effects of soils on bioavailability. Supernatants from the slurry experiments were found to increase the aqueous-phase pyrene solubility significantly. Pyrene solubility was increased from 120.5 to over 230 microg/l. However, the linear adsorption constants of pyrene on the soil were reduced.

Biodegradation, Environmental↗
PubMed2002

Portal absorption of 14C after ingestion of spiked milk with 14C-phenanthrene, 14C-benzo[a]pyrene or 14C-TCDD in growing pigs.

Polycyclic aromatic hydrocarbons (PAHs) and dioxins are lipophilic organic pollutants occurring widely in the terrestrial environment. In order to study the PAHs and 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) transfer in the food chain, pigs have been fed with milk mixed either with 14C-phenanthrene, with 14C-benzo[a]pyrene or with 14C-TCDD. The analysis of portal and arterial blood radioactivity showed that both PAHs and TCDD were absorbed with a maximum concentration at 4-6 h after milk ingestion. Then, the blood radioactivity decreased to reach background levels 24 h after milk ingestion. Furthermore, the portal and arterial blood radioactivities were higher for phenanthrene (even if the injected load was the lowest) than these of benzo[a]pyrene or these of TCDD, in agreement with their lipophilicity and water solubility difference. Main 14C absorption occurred during the 1-3 h time period after ingestion for 14C-phenanthrene and during the 3-6 h time period for 14C-benzo[a]pyrene and for 14C-TCDD. 14C portal absorption rate was high for 14C-phenanthrene (95%), it was close to 33% for 14C-benzo[a]pyrene and very low for 14C-TCDD (9%). These results indicate that the three studied molecules have a quite different behaviour during digestion and absorption. Phenanthrene is greatly absorbed and its absorption occurs via the blood system, whereas benzo[a]pyrene and TCDD are partly and weakly absorbed respectively. However these two molecules are mainly absorbed via the portal vein.

Absorption↗
PubMed2002

Metabolism of pyrene by two clam species, Mya arenaria and Protothaca staminea.

Two species of marine clam, Mya arenaria and Protothaca staminea, were exposed to pyrene and 1-hydroxypyrene in small glass aquaria. After 10 days of exposure the clams were sacrificed, and both clam tissue and seawater were assayed for pyrene metabolites by using HPLC, fluorescence spectroscopy, HPLC-ESI-MS, GC-MS and 1H-NMR spectrometry. 1-Pyrenol-1-hydrogensulfate (pyrene-1-sulfate) was identified as the major water soluble metabolite formed from both pyrene and 1-hydroxypyrene by both species of clam. 1-Hydroxypyrene was identified as a minor metabolite of pyrene, and pyrenediol-hydrogen sulfate was identified as a minor metabolite of 1-hydroxypyrene.

Animals↗
PubMed1998

Pyrene degradation by Mycobacterium sp. strain KR2.

A Mycobacterium sp., strain KR2 which was able to utilise pyrene as sole source of carbon and energy was isolated from a polycyclic aromatic hydrocarbon (PAH) contaminated soil originating from the area of a former gaswork plant. The isolate metabolised up to 60% of the pyrene added (0.5 mg/mL) within 8 days at 20 degrees C. Cis-4,5-pyrene dihydrodiol, 4,5-phenanthrene dicarboxylic acid, 1-hydroxy-2-naphthoic acid, 2-carboxybenzaldehyde, phthalic acid, and protocatechuic acid were identified as degradation products. Based on these findings a degradation pathway for pyrene is suggested which is in good accordance with the data published so far on bacterial pyrene metabolism.

Biodegradation, Environmental↗
PubMed1998

Correlation between urinary 1-hydroxypyrene and ambient air pyrene measured with an inhalable aerosol sampler and a total dust sampler in an electrode paste plant.

The aim of this study was to investigate whether the use of an inhalable aerosol sampler would improve the correlation between urinary 1-hydroxypyrene and occupational pyrene exposure compared to measurements with a total dust sampler in an electrode paste plant. PAHs were collected on a filter and adsorbent by a 37-mm closed-face total aerosol sampler and an open-face sampler for inhalable aerosol from the Institute of Occupational Medicine (IOM). 1-Hydroxypyrene in pre- and post-shift urine samples was quantitated by high performance liquid chromatography (HPLC). In this study, the use of the IOM sampler resulted in approximately four times higher concentrations of particulate PAH and pyrene than the total dust sampler. The correlation between pyrene levels measured with the two samplers was good with a correlation coefficient of 0.83. The correlation between workplace air pyrene and 1-hydroxypyrene in post-shift urine was poor (r = -0.12), but a small non-significant improvement was found with the IOM sampler (r = 0.11). In this factory the use of an inhalable aerosol sampler had only marginal effect on the correlation between 1-hydroxypyrene in urine and breathing zone pyrene. These results indicate that skin exposure is an important route of PAH uptake in this plant.

Adult↗
PubMed2003

Biotransformation and bioconcentration of pyrene in Daphnia magna.

Water fleas (Daphnia magna) were exposed to [14C]pyrene in the presence and absence of piperonyl butoxide (PBO), a general cytochrome P450 (CYP) inhibitor, in organic carbon-free artificial freshwater (AFW, DOC<0.2 mg l(-1)) and in natural lake water (DOC=19.9 mg l(-1)) for 24 h. The bioconcentration of total radioactivity after 24 h exposure was 50% lower in the natural lake water, indicating decreased bioavailability of pyrene by the dissolved organic matter. However, the proportions of parent compound were only ca. 12 and 19% of the total body burden in daphnids exposed in AFW and natural lake water, respectively. Therefore, the tissue concentration of the parent pyrene was not significantly different in the daphnids exposed in the two different waters. Due to extensive biotransformation the bioconcentration factor (BCF) of parent pyrene was only 16 and 23% of the BCF calculated on the basis of total radioactivity in the daphnids in AFW and natural lake water, respectively. The proportion of parent pyrene was significantly higher (over 60%) in the daphnids exposed simultaneously to PBO, which indicates the involvement of CYP monooxygenases in the biotransformation. Furthermore, increasing PBO concentration decreased the accumulation of total radioactivity in AFW but not in the natural lake water. The data demonstrate capability and importance of CYP monooxygenases in biotransformation of polycyclic aromatic hydrocarbons in D. magna.

Animals↗
PubMed1998

Urinary and biliary excretion kinetics of 1-hydroxypyrene following intravenous and oral administration of pyrene in rats.

The urinary and biliary excretion kinetics of 1-hydroxypyrene (1-OHP) were compared in male Sprague-Dawley rats exposed intravenously and orally to 1.5, 5, 15, 50 and 100 micromol/kg pyrene. Urine and bile samples were collected at 6-h intervals for up to 24 h. Results showed that the kinetics of 1-OHP were similar for both biliary and urinary excretion whatever the administered dose or exposure route. Furthermore, the time course of 1-OHP excretion in either bile or urine following intravenous dosing resembled that observed after oral administration. In addition, the exposure route and dose had no significant effect on the fraction of dose recovered in urine and bile as 1-OHP after 6, 12, 18 and 24 h post-dosing. Following intravenous injection of 1.5, 5, 15, 50 and 100 micromol/kg pyrene, the mean cumulative percent of dose excreted as 1-OHP in urine over 24 h ranged from 1.7 to 3.2%, while biliary values ranged from 6.5 to 9.5%. Correspondingly, after oral administration, on average, 2.6-3.3% of dose was excreted as 1-OHP in urine and 7.9-10.9% was recovered in bile. Overall, the linear dose-excretion relationship following either exposure routes supports the usefulness of 1-OHP in urine as a bioindicator of polycyclic aromatic hydrocarbon (PAH) exposure. Results further suggest that tissue uptake and distribution of intravenously and orally administered pyrene proceeds similarly. By comparing these data with predicted values from a previously published physiologically based pharmacokinetic model for pyrene in the rat, it also appears that a small fraction of pyrene dose (12%) remains in the body after 24 h and that metabolites other than 1-OHP as measured in the current study are present in significant proportions in urine and feces.

Administration, Oral↗