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PubMed1999

Purification and characterization of a benzo[a]pyrene hydroxylase from Pleurotus pulmonarius.

Cytochrome P450 has been implicated in the process of biotransformation of polycyclic aromatic hydrocarbons and of other organic pollutants by white-rot fungi. We have purified and reconstituted a benzo[a]pyrene hydroxylating cytochrome P450 (P450) from microsomal fractions of the white rot fungus Pleurotus pulmonarius. The microsomal P450 was recovered using a combination of n-aminooctyl agarose and hydroxyapatite chromatography and had an apparent molecular mass of 55 kDa. The purified protein exhibited moderate affinity for benzo[a]pyrene with a K(s) of 66 microM calculated from the Type I substrate binding spectra produced. Reconstitution of activity was achieved and a turnover of 0.75 nmol 3-hydroxybenzo[a]pyrene product/min/nmol P450 was observed, comparable to levels of metabolism observed by animal cytochromes P450 involved in xenobiotic detoxification.

Benzo(a)pyrene↗
PubMed1995

In vivo metabolism of benzo(a)pyrene in a lower vertebrate, the newt Pleurodeles walt.

The capacity of the newt to metabolize benzo(a)pyrene in vivo was investigated qualitatively and quantitatively: metabolism was found to be rapid. Treatment of bile with beta-glucuronidase and aryl-sulfatase released high proportions of diols and quinones. 3-Methylcholanthrene treatment shortened the elimination half-life of benzo(a)pyrene which was about three times shorter than the half-life found for non-3-methylcholanthrene-pretreated animals. Thus, a greater proportion of benzo(a)pyrene was converted into water-soluble products.

Animals↗
PubMed1997

Probing RNA-protein interactions using pyrene-labeled oligodeoxynucleotides: Qbeta replicase efficiently binds small RNAs by recognizing pyrimidine residues.

Binding of small RNAs by the RNA-dependent RNA polymerase of coliphage Qbeta was studied utilizing a fluorometric assay. A DNA oligonucleotide probe of sequence 5'-d(TTTTTCC) was 5'-end-labeled with pyrene. In this construct, the proximal thymine residues efficiently quench the fluorophore emission in solution. Upon stoichiometric binding of one probe per polymerase molecule, the pyrene steady-state fluorescence increases by two orders of magnitude, the fluorescence anisotropy increases, and a long fluorescence lifetime component of 140 ns appears. With addition of replicable RNA, steady-state fluorescence decreases in a concentration dependent manner and the long lifetime component is lost. This observation most likely reflects displacement of the pyrene-labeled probe from the proposed nucleic acid binding site II of Qbeta replicase. The effect was utilized to access binding affinities of different RNAs to this site in a reverse titration assay format. In 10 mM sodium phosphate (pH 7.0), 100 mM NaCl, at 16 degrees C, equilibrium dissociation constants for different template midi- and minivariant RNAs were calculated to be in the nanomolar range. In general, the minus and plus strands, concomitantly synthesized by Qbeta replicase during replication, exhibited discriminative affinities, while their hybrid bound less efficiently than either of the single strands. Different non-replicable tRNAs also bound to the polymerase with comparable dissociation constants. By titration with DNA homo-oligonucleotides it was shown that the probed site on Qbeta replicase does not require a 2' hydroxyl group for binding nucleic acids, but recognizes pyrimidine residues. Its interaction with thymine is lost in an A.T base-pair, while that with cytosine is retained after Watson-Crick base-pairing. These findings can explain the affinities of RNA-Qbeta replicase interactions reported here and in earlier investigations. The sensitivity of the described fluorometric assay allows detection of RNA amplification by Qbeta replicase in real-time.

Base Sequence↗
PubMed1998

Induction of peroxisomal oxidases in mussels: comparison of effects of lubricant oil and benzo(a)pyrene with two typical peroxisome proliferators on peroxisome structure and function in Mytilus galloprovincialis.

Marine mussels are used as bioindicators of water pollution in marine and estuarine environments in the so-called "Mussel Watch" programs because of their capacity to accumulate numerous organic xenobiotics including aromatic hydrocarbons. In this study, we have analyzed the effects of two xenobiotics [benzo(a)pyrene and the water accommodated fraction of a lubricant oil] and two typical (rodent) peroxisome proliferators (clofibrate and dioctyl phthalate) on structure and function of peroxisomes in digestive glands of mussels Mytilus galloprovincialis, either following water exposure (for 1, 7, and 21 days) or after direct injection through the adductor muscle (for 1 and 7 days). The activities of catalase (CAT), acyl-CoA oxidase (AOX), and D-amino acid oxidase were determined in whole homogenates of digestive glands. In addition, stereological methods were applied on sections stained histochemically for demonstration of catalase activity in order to quantify the morphological changes of peroxisomes. The peroxisomal acyl-CoA oxidase and D-amino acid oxidase were increased in mussels injected for 7 days with benzo(a)pyrene, phthalate, and clofibrate and a similar trend was noted for benzo(a)pyrene and lubricant oil in water exposure experiments (21 days). The catalase activity was reduced or unchanged depending on the mode of exposure of animals. By stereology, significant increases of numerical and volume densities of peroxisomes were found in animals injected for 7 days with lubricant oil or clofibrate. These observations indicate that peroxisomal oxidases in mussels are induced at moderate rates in response to different xenobiotics and that their determination could provide a (sensitive) marker for detection of effects of some toxic pollutants, particularly the lubricant oils which in addition induce significant structural alterations of mussel peroxisomes.

Animals↗
PubMed1994

Metabolism of the polycyclic aromatic hydrocarbon pyrene by Aspergillus niger SK 9317.

The metabolism of pyrene, a polycyclic aromatic hydrocarbon consisting of four rings, by Aspergillus niger SK 9317 was investigated. The metabolites formed were isolated and identified as 1-hydroxypyrene, 1,6- and 1,8-pyrenequinone, 1,6- and 1,8-dihydroxypyrene, 1-pyrenyl sulphate and 1-hydroxy-8-pyrenyl sulphate. This is the first report of 1-hydroxy-8-pyrenyl as a metabolite in the microbial metabolism of pyrene. The results suggest that A. niger metabolizes pyrene by cytochrome P-450 monooxygenase enzyme systems.

Aspergillus niger↗
PubMed1992

Binding of benzo(a)pyrene, ellipticine, and cis-parinaric acid to beta-lactoglobulin: influence of protein modifications.

The binding of benzo(a)pyrene, ellipticine, and cis-parinaric acid to native, esterified, and alkylated beta-lactoglobulin was followed by enhancement of the ligand fluorescence. Three studied ligands bind to native or modified beta-lactoglobulin in apparent molar ratios varying between 1/8 and 2/1, with apparent dissociation constants in the range of 10(-8) M for ligand/beta-lactoglobulin complexes. The studied, chemically modified beta-lactoglobulin derivatives display higher binding affinities for all studied ligands, cis-parinaric acid excluded. The reductive alkylation of epsilon-NH2 lysyl residues of beta-lactoglobulin increases the apparent molar ratios of benzo(a)pyrene and cis-parinaric acid, and decreases it for ellipticine. The esterified and native beta-lactoglobulin complexed to the investigated ligands display similar stoichiometries. Dynamic light scattering study of ligand-beta-lactoglobulin complexes in solution shows the formation of aggregates: the apparent hydrodynamic radius value of beta-lactoglobulin dimer (3.4 nm) reaches 49, 46, and 74 nm upon addition and binding of benzo(a)pyrene, ellipticine, and cis-parinaric acid, respectively.

Alkylation↗
PubMed1992

Protective role of aqueous turmeric extract against mutagenicity of direct-acting carcinogens as well as benzo [alpha] pyrene-induced genotoxicity and carcinogenicity.

Turmeric (Curcuma longa Linn.) has been shown to inhibit chemical carcinogenesis. In this study, we compared the chemopreventive efficacy of an aqueous turmeric extract (AqTE) and its constituents, curcumin-free aqueous turmeric extract (CFAqTE) and curcumin, using the Salmonella typhimurium mutagenicity assay and the bone marrow micronucleus test in female Swiss mice. AqTE exhibited antimutagenic activity against direct-acting mutagens, 4-nitro-O-phenylenediamine and 1-methyl-3-nitro-1-nitrosoguanidine, in strains TA 98 and TA 100 respectively. Both AqTE and CFAqTE inhibited the mutagenicity of benzo [alpha]pyrene in the two strains in the presence of Aroclor-1254-induced rat liver homogenate. The inhibition in both studies was dose-dependent. Administration of AqTE, CFAqTE and curcumin at a dose of 3 mg/animal 18 h prior to i.p. benzo [alpha]pyrene injection (250 mg/kg) significantly inhibited bone marrow micronuclei formation in female Swiss mice by 43%, 76%, and 65% respectively. Furthermore, the incidence and multiplicity of forestomach tumours induced by benzo [alpha]pyrene (1 mg/animal, twice weekly, p.o. for 4 weeks) in female Swiss mice were significantly inhibited by AqTE, CFAqTE and curcumin given 2 weeks before, during and after the carcinogen treatment. These data indicate that the protection against genomic damage by turmeric extract and its components tested could be necessary for some aspects of its cancer chemoprevention.

Animals↗
PubMed2001

Enhancing pyrene mineralization in contaminated soil by the addition of humic acids or composted contaminated soil.

The addition of composted PAH-contaminated soil to PAH-contaminated soil spiked with 14C-labeled pyrene resulted in rapid mineralization of pyrene (more than 57% after 21 days compared with 3.4% in un-amended soil). The addition of the humic acid fraction of the composted soil also increased the mineralization potential of the soil significantly, but to a lesser extent (37.5% mineralization after 106 days compared with 20.6% in unamended soil). Increasing the humic acid concentration increased mineralization up to a maximum of more than three times the unamended rate, after which the rate of pyrene mineralization decreased, possibly due to inhibitory pH or concentrations of salts. The amendment of PAH-contaminated soil with materials containing humic acids or humic acid extracts is suggested as a method of bioremediation.

Bacteria↗
PubMed2005

Metabolism of fluoranthene by mycobacterial strains isolated by their ability to grow in fluoranthene or pyrene.

Mycobacterium sp. strains CP1, CP2, CFt2 and CFt6 were isolated from creosote-contaminated soil due to their ability to grow in pyrene (CP1 and CP2) or fluoranthene (CFt2 and CFt6). All these strains utilized fluoranthene as a sole source of carbon and energy. Strain CP1 exhibited the best growth, with a cellular assimilation of fluoranthene carbon of approximately 45%. Identification of the metabolites accumulated during growth in fluoranthene, the kinetics of metabolites, and metabolite feeding studies, indicated that all these isolates oxidized fluoranthene by the following two routes: the first involves dioxygenation at C-1 and C-2, meta cleavage, and a 2-carbon fragment excision to produce 9-fluorenone-1-carboxylic acid. An angular dioxygenation of the latter yields cis-1,9a-dihydroxy-1-hydrofluorene-9-one-8-carboxylic acid, which is further degraded via 8-hydroxy-3,4-benzocoumarin-1-carboxylic acid, benzene-1,2,3-tricarboxylic acid, and phthalate; the second route involves dioxygenation at C-2 and C-3 and ortho cleavage to give Z-9-carboxymethylenefluorene-1-carboxylic acid. In addition, the pyrene-degrading strains CP1 and CP2 possess a third route initiated by dioxygenation at positions C-7 and C-8, which--following meta cleavage, an aldolase reaction, and a C(1)-fragment excision--yields acenaphthenone. Monooxygenation of this ketone to the corresponding quinone, and its subsequent hydrolysis, produces naphthalene-1,8-dicarboxylic acid. The results obtained in this study not only complete and confirm the three fluoranthene degradation routes previously proposed for the pyrene-degrading strain Mycobacterium sp. AP1, but also suggest that such routes represent general microbial processes for environmental fluoranthene removal.

Biodegradation, Environmental↗
PubMed2006

Stabilization of membrane bound enzyme profiles and lipid peroxidation by Withania somnifera along with paclitaxel on benzo(a)pyrene induced experimental lung cancer.

The present study was aimed to evaluate the therapeutic effects of Withania somnifera along with paclitaxel on lung tumor induced by benzo(a)pyrene in male Swiss albino mice. The levels of ATPase enzymes and lipid peroxidation were evaluated in lung cancer bearing mice, in erythrocyte membrane and tissues. The extent of peroxidation was estimated by measuring the thiobarbituric acid-reactive substances. Simultaneously the activities of different ATPases (Na(+)/K(+)-ATPases, Mg(2+)-ATPases and Ca(2+)-ATPases) were determined. The alterations of these enzyme activities in membrane and tissues were indicative of the tumor formation caused by benzo(a)pyrene (50 mg/kg body weight, orally) in cancer bearing animals. The activities of these enzymes were reversed to near normal control values in animals treated with Withania somnifera (400 mg/kg b.wt, orally) along with paclitaxel (33 mg/kg b.wt, i.p). Treatment with Withania somnifera along with paclitaxel altered these damage mediated through free radicals, and the treatment displays the protective role of these drugs by inhibiting free radical mediated cellular damages. Over, based on the data providing a correlation Withania somnifera along with paclitaxel provide stabilization of membrane bound enzyme profiles and decreased lipid peroxidation against benzo(a)pyrene induced lung cancer in mice.

Adenosine Triphosphatases↗
PubMed1987

A pyrene fluorescence technique and microchamber for measurement of oxygen consumption of single isolated axons.

Pyrene fluorescence is quenched by oxygen in an inverse and linear manner related to the partial pressure of O2 in solution. We have developed a microchamber for measuring QO2 of a single isolated axon, monitoring the change in fluorescence of a pyrene probe. The probe consists of a Spectra/Por dialysis hollow fiber filled with 2.5 mM pyrene in paraffin oil. The probe is inserted into a 1-mm-i.d. 2-cm-long quartz capillary tube with a freshly isolated crayfish medial giant axon. The capillary is mounted in an apparatus that forms an air- and water-tight seal except for a 0.2-mm-i.d. stainless steel tube at both ends permitting the exchange of solutions. An Olympus inverted microscope, equipped with epifluorescence optics and a 150-W xenon lamp, is used to view the preparation, generate the excitation light, and monitor the emitted fluorescence with a photomultiplier tube placed in the microscope TV port. A dichroic filter unit is utilized to select an excitation wavelength of 350 nm and collect emitted light above 420 nm. The signal is amplified with a Keithley 480 picoammeter and recorded on a strip chart. QO2 of isolated axons was 552 +/- 70 X 10(-6) mol O2/liter tissue X min. Following sequential treatment with 2 mM ouabain and 2 mM NaCN, QO2 decreased by 22 and 82%, respectively. These data are consistent with QO2 measurements of whole nerve cord made with a Clark electrode O2 monitor.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1989

High-performance liquid chromatographic analysis of acylated lipids containing pyrene fatty acids.

A high-performance liquid chromatographic method for the separation and quantification of acylated lipids containing pyrene fatty acids is described. The method is adapted from a procedure originally developed for the analysis of tissue lipids (Christie, W. W. (1985) J. Lipid Res. 26, 507-512). Pyrenyl lipid analogs ranging in polarity from cholesteryl ester to lysophosphatidylcholine are completely resolved on a silica column in 50 min by gradient elution with a ternary solvent system. Furthermore, pyrene-labeled triglycerides are resolved according to the number of pyrene fatty acid residues incorporated. Pyrenyl lipids are detected at levels of 10(-13) mol by high-sensitivity fluorescence detection. Accurate quantification of pyrenyl lipids is obtained by correcting peak areas for mobile-phase quenching effects. The close correspondence between chromatograms obtained for the separation of labeled lipids extracted from Hep-G2 cells incubated with either 12-(1-pyrenyl)dodecanoic acid (fluorescence detection) or [1-14C]oleic acid (radioactivity detection) indicates that this HPLC method is equally suitable for analysis of native lipids.

Carcinoma, Hepatocellular↗
PubMed1986

A change in the lipid fluidity of the porcine intestinal brush-border membranes by lipid peroxidation. Studies using pyrene and fluorescent stearic acid derivatives.

The effect of lipid peroxidation on the lipid fluidity of porcine intestinal brush-border membranes was examined by measuring the rotational mobility and the accessibility to fluorescence quenchers (CH3COOT1, CuSO4 and KI) of pyrene or n-(9-anthroyloxy)stearic acid (n = 2 or 12) in the membranes. The harmonic mean of the rotational relaxation times of pyrene increased and the rate constants, kq, of the quenching reaction of pyrene and 2-(9-anthroyloxy)stearic acid incorporated in the membrane lipids decreased upon lipid peroxidation, indicating reduction of the lipid fluidity of the membranes by lipid peroxidation. In addition, the kq value of the reaction of 2-(9-anthroyloxy)stearic acid in the membranes with Cu2+ decreased in proportion to the amount of the products of lipid peroxidation. On the other hand, the kq value of the reaction of 12-(9-anthroyloxy)stearic acid with Cu2+ or I- was unaffected by lipid peroxidation. Based on these results, a localized change in the lipid fluidity of the membranes in association with lipid peroxidation has been discussed.

Animals↗
PubMed1985

Identification of the 11,12-dihydro-11,12-dihydroxybenzo(a)pyrene as a major metabolite produced by the green alga, Selenastrum capricornutum.

Benzo(a)pyrene metabolites were isolated after incubation of [14C]-benzo(a)pyrene with the green alga, Selenastrum capricornutum. A significant amount of radioactivity chromatographed in the dihydrodiol region which did not coelute with any of the previously identified dihydrodiol metabolites isolated from this system. Following characterization by mass spectrometry, fluorescence spectroscopy, and high pressure liquid chromatography, this metabolite was identified as the cis-11,12-dihydro-11,12-dihydroxybenzo(a)pyrene. This metabolite has not been identified previously as a metabolite formed in a plant system.

Benzo(a)pyrene↗
PubMed1985

Hormonal regulation of benzo[a]pyrene metabolism in human adrenocortical cell cultures.

In cultured fetal human adrenocortical cells, metabolism of the carcinogen benzo[a]pyrene was found to be unresponsive to the xenobiotic inducers 3-methylcholanthrene, benz[a]anthracene and 2,3,7,8-tetrachlorodibenzo-p-dioxin. However, exposure of cultures to the hormone adrenocorticotropin (ACTH) for 48 hours stimulated benzo[a]pyrene metabolism 3-fold. The major metabolite was the 7,8-diol. Other compounds which stimulate the production of adrenocortical cell cyclic AMP (forskolin and cholera toxin) as well as monobutyryl cyclic AMP also increased benzo[a]pyrene metabolism. Human adrenocortical cells thus provide an unusual example of hormonal regulation of the metabolism of a carcinogen.

Adrenal Cortex↗
PubMed1983

Metabolic activation of benzo[a]pyrene in human skin maintained in short-term organ culture.

The metabolic activation of benzo[a]pyrene (BP) was examined in six samples of human skin after topical application of the hydrocarbon to the skin in short-term organ culture. The results show that all of the samples were capable of metabolizing BP to water-soluble products and to ether-soluble products that included the 4,5-, 7,8- and 9,10-dihydrodiols and a product which had chromatographic properties identical with those of authentic trans-11,12-dihydro-11,12-dihydroxybenzo[a]pyrene (BP-11,12-diol). The major BP-deoxyribonucleoside adduct detected in each skin sample appeared to be formed from the reaction of r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BP-7,8-diol 9,10-oxide) with deoxyguanosine residues in DNA.

Benzo(a)pyrene↗
PubMed1983

Caffeine enhancement of the initiation of DNA replication in benzo[a]pyrene diol epoxide damaged cells.

We have used a newly developed pH stepwise alkaline elution method to show that caffeine enhances DNA initiation (DNA replication in sub-replicon size nascent strands) in (+/-)-7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene (BPDEI) damaged mouse primary epidermal cells. Caffeine alone caused a dose-dependent increase in DNA initiation without an effect on DNA elongation (joining of replicon-sized nascent DNA). BPDEI alone inhibited DNA elongation as shown by a relative increase in sub-replicon size nascent DNA. When BPDEI treated cells were incubated with caffeine, there was a dose-dependent increase in sub-replicon size nascent DNA without a significant effect on the proportion of joined replicons. Therefore, caffeine can enhance DNA initiation in mammalian cells damaged with a reactive form of the carcinogen benzo[a]pyrene and this may account for the biological interaction between caffeine and the ultimate carcinogenic form of benzo[a]pyrene.

7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide↗
PubMed1988

Stereoselective aspects of the metabolic activation of benzo[a]pyrene by human skin in vitro.

Benzo[a]pyrene (BP) is activated within tissues in both a regio- and a stereoselective manner and, since human skin is sensitive to tumour induction by polycyclic aromatic hydrocarbons (PAH), the steroselective metabolism of BP in this tissue has been investigated. Samples of skin from eleven individuals were treated with [3H]BP in short-term organ culture. Two samples were also treated with mixtures of [14C](+)- and (-)-trans-7,8-dihydro-7,8-dihydroxybenzo[a]pyrene (BP-7,8-dihydrodiol) in varying proportions. Following application of [3H] BP, more 7,8-dihydrodiol was recovered from the skin itself than from the culture fluid in ten cases; no 7.8-dihydrodiol was detected in extracts from the eleventh. The 7,8-dihydrodiol metabolite was extracted predominantly (range 74-greater than 99%) as the (-)-enantiomer in nine of these ten patients, although proportionately more (+)-enantiomer was recovered from the culture fluid than from the skin in each case. The relative proportions of [3H]BP tetrols derived from syn- and anti-7,8-dihydroxy-9,10-oxy-7,8,9,10-tetrahydroxybenzo[a]pyrene (BPDE) detected in these extracts was more variable. When skin samples were treated with [14C]BP-7,8-dihydrodiol, more anti- than syn-BPDE-derived tetrols were extracted, irrespective of the optical purity of the dihydrodiol applied. These findings provide evidence for interindividual variations in the stereoselective metabolism of BP, which may be of some importance in determining individual susceptibility to PAH-induced skin carcinogenesis.

Benzo(a)pyrene↗