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PubMed2004

Identification of recalcitrant hydrocarbons present in a drilling waste-polluted soil.

During spills of hydrocarbons in soil, it has been observed that aliphatic and the slightly aromatic hydrocarbons are first to be removed, however, branched aliphatic and aromatic compounds, polycyclic aromatic hydrocarbons (PAHs) and their similar heteroatoms with sulfur (PAS) remain strongly absorbed to soil particles. It is important to point out that studies of biodegradation of alkyl-substituted PAHs and PAS are scarce and most of them have been carried out using only available standard compounds. The aim of this investigation was to identify and to quantify the aliphatic, alkyl polycyclic aromatic, and sulfured recalcitrant fractions present in a contaminated soil with drilling wastes. A modified method of shaking-centrifugation extraction was implemented for the extraction of compounds from contaminated soil. The organic extract obtained was purified and fractionated using aluminum oxide. Gas Chromatograph with flame ionization detector (GC-FID) and Gas Chromatograph with mass spectrometer detector (GC-MS) identified the aliphatic, PAHs and PAS fractions. Hydrocarbon composition in the soil contaminated with 140,000 mg TPHs/Kg soil, consisted in 80% of branched aliphatic compounds of C10 to C22, 15% of alkyl PAHs, and 5% of PAS compounds. Lineal, lineal branched, and cyclic branched aliphatic hydrocarbons, as well as their alkyl naphthalene, anthracene and phenantrene, methyldibenzothiophene, dimethyldibenzothiophene, and dimethylnaphto[2,3-b]thiophene compounds were identified by CG-MS. The identification of compounds in soil P31, allowed us to speculate on the origin of the contamination and the natural attenuation that had occurred at this site.

Adsorption↗

PubMed2004

The study on the synthesis and the effects on the intracellular calcium of some 9-substituted-phenanthrene derivatives.

Some 9-(substituted with heteroaryl)-phenanthrene compounds, polycyclic aromatic hydrocarbons (PAH), were obtained by two different methods. In the first method, 9-phenanthraldehyde was reacted with some dion compounds such as benzil, toluil, anisil, etc in the presence of ammonium acetate and glacial acetic acid. In the second method, 9-phenanthraldehyde was reacted with 5-substituted-1,2-phenylenediamine derivatives in the presence of NaHSO3 and ethanol. All of synthesized compounds by us were original and these compounds have not been studied in literature so far. The structures of compounds were confirmed by spectral data and elemental analyses results. The effects of compounds were studied on intracellular calcium level. All of the compounds were examined between the concentrations of 1 and 0.5 microg/mL.

Animals↗

PubMed1979

[Measurement of fluorescence decay of substances absorbed by an isolated living cell: an experimental device and early results].

A microfluorometric system allowing the mesurements of fluorescence decay (i.e. fluorescence lifetime) has been built. It will complete the microspectrofluorometric studies of absorbed compounds-polycyclic aromatic hydrocarbons, metabolites of benzo (a) pyrene-by single living cells and allows a better understanding of the intake and metabolisation of these compounds. The preliminary results with benzo (a) pyrene, dibenzocarbazole, pyrene are shown.

Benzopyrenes↗

PubMed1986

[Chemical carcinogens and DNA, covalent binding and chemical modifications].

Chemical carcinogenic agents are usually metabolized into final metabolites susceptible to be DNA bound to form adducts. They may also modify DNA bases. Binding may be studied in vitro in the presence of an enzyme system causing the formation of final metabolites or in vivo. Because of the small amount of adducts formed in vivo, they can only be visualized with radioactive compounds or with a 32P marking technique after DNA hydrolysis. A limit of detection of adduct for 10(8) nucleotides has thus been reached for polycyclic compounds. The covalent binding index enables to quantify this binding. The consequences of DNA alterations vary according to the substitutes. In the case of acetyl-aminofluorene, they lead to mutations by shifting of the reading frame (frameshift). Alkylations lead to inaccurate pairing causing pin point mutations or depurinations.

Carcinogens↗

PubMed2001

Uptake of polycyclic aromatic hydrocarbon compounds by the gills of the bivalve mollusk Elliptio complanata.

Polycyclic aromatic hydrocarbons (PAHs) and herbicides are important contaminants of world water systems with effects on aquatic organisms. The uptake of naphthalene, anthracene, and chrysene by gills of the bivalve mollusk Elliptio complanata was determined. Additionally, the effects of paraquat, atrazine, alachlor, 2,4-dichlorophenoxyacetic acid (2,4-D), and 2,4-dinitrophenol on the uptake of these compounds were also determined. The results indicate (1) the uptake of anthracene is approximately equivalent to that of chrysene and the uptake of either of these compounds is higher than that of naphthalene; (2) comparisons of uptakes with that of inulin, which occupies only extracellular space, show that all compounds studied are taken up; (3) the uptakes of naphthalene, anthracene, and chrysene are initially altered by the presence of herbicides such as paraquat, alachlor, 2,4-D, atrazine, and 2,4-dinitrophenol.

Animals↗

PubMed2003

Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer.

[reaction: see text] In the presence of rhodium catalyst, (2-furyl)carbenoids generated from conjugated ene-yne-carbonyl compounds 1 efficiently undergo carbene transfer reactions with allylic sulfides followed by [2,3]sigmatropic rearrangement of sulfur ylides to give furan-containing sulfides in good yields. When diallyl sulfide is employed, heteroatom-containing polycyclic compounds are obtained by sequential intramolecular Diels-Alder cyclization reaction with a constructed furan ring as an enophile.

Journal Article↗

PubMed1986

Carbonyl reductase provides the enzymatic basis of quinone detoxication in man.

Enzymes catalyzing the two-electron reduction of quinones to hydroquinones are thought to protect the cell against quinone-induced oxidative stress. Using menadione as a substrate, carbonyl reductase, a cytosolic, monomeric oxidoreductase of broad specificity for carbonyl compounds, was found to be the main NADPH-dependent quinone reductase in human liver, whereas DT-diaphorase, the principal two-electron transferring quinone reductase in rat liver, contributed a very minor part to the quinone reductase activity of human liver. Carbonyl reductase from liver was indistinguishable from carbonyl reductase previously isolated from brain (B. Wermuth, J. biol. Chem. 256, 1206 (1981] on the basis of molecular weight, isoelectric point, immunogenicity, substrate specificity and inhibitor sensitivity. The purified enzyme from liver catalyzed the reduction of a great variety of quinones. The best substrates were benzo- and naphthoquinones with short substituents, and the K-region orthoquinones of phenanthrene, benz(a)anthracene, pyrene and benzo(a)pyrene. A long hydrophobic side chain in the 3-position of the benzo- and naphthoquinones and the vicinity of a bay area or aliphatic substituent (pseudo bay area) to the oxo groups of the polycyclic compounds decreased or abolished the ability of the quinone to serve as a substrate. Non-k-region orthoquinones of polycyclic aromatic hydrocarbons were more slowly reduced than the corresponding K-region derivatives. The broad specificity of carbonyl reductase for quinones is in keeping with a role of the enzyme as a general quinone reductase in the catabolism of these compounds.

Alcohol Oxidoreductases↗

PubMed2003

Use of ionic liquids for liquid-phase microextraction of polycyclic aromatic hydrocarbons.

This paper demonstrates, for the first time, that ionic liquids (IL) such as 1-octyl-3-methylimidazolium hexafluorophosphate ([C(8)MIM][PF(6)]) are excellent extraction solvents in liquid-phase microextraction (LPME). The unique properties of nonvolatility and adequate viscosity allow IL to be conveniently adopted as extraction solvents in both direct-immersion and headspace LPME. Model compounds, polycyclic aromatic hydrocarbons (PAHs), are conveniently and rapidly enriched in a 3-microL drop of [C(8)MIM][PF(6)] suspended on the tip of a microsyringe followed by liquid chromatographic determination. Compared to 1-octanol, a larger volume drop of [C(8)MIM][PF(6)] can be formed and survive for a longer extraction time; therefore, a much higher enrichment factor for PAHs can be reached. For low-volatility PAHs, direct-immersion LPME provides higher enrichment factors than that of headspace LPME. However, the enrichment factor obtained by headspace LPME was almost 3-fold of that by direct-immersion LPME in a 30-min extraction of the most volatile PAH, naphthalene. For 30-min direction-immersion LPME of EPA priority PAHs, the enrichment factor, correlation coefficient (R(2)), and reproducibility (RSD, n = 5) were in the range of 42-166, 0.9169-0.9976, and 2.8-12%, respectively. Considering that IL can be easily prepared from relatively inexpensive materials and tuned by combination of different anions and cations for task-specific extraction of analytes from various solvent media, this proposed method should have great potentiality in sample preparation. Furthermore, the nonvolatility of IL makes it potentially useful for headspace LPME of volatile analytes.

Journal Article↗

PubMed2006

Polycyclic aromatic hydrocarbon contamination in coastal sediments of the Izmit Bay (Marmara Sea): case studies before and after the Izmit Earthquake.

Izmit Bay and its coastal environment was strongly affected by the August 17th, 1999 Izmit Earthquake. The changes in the Bay ecosystem and its chemical oceanography have been studied in detail previously [Okay, O.S., Tolun, L, Telli-Karakoç, F., Tüfekçi, V., Tüfekçi, H. And Morkoç, E. 2001. Yzmit Bay ecosystem after Marmara earthquake and subsequent fire: The long-term data. Marine Pollution Bulletin 42, 361-369; Balkýs, N. 2003. The effect of Marmara (Izmit ) Earthquake on the chemical oceanography of Izmit Bay, Turkey. Marine Pollution Bulletin 46, 865-878.]. In this study surface sediments collected from the Izmit Bay before and after the earthquake have been analysed for total and individual (14 compounds) polycyclic aromatic hydrocarbons (PAH). Analyses have been performed by high performance liquid chromatography with fluorescence detection (HPLC/FD). Before the earthquake, total PAH concentrations in the Bay sediments ranged from 120 to 8900 ng/g while after the earthquake PAH concentrations varied between 240 and 11,400 ng/g. Molecular indices based on isomeric PAH ratios used to differentiate the pollution sources, clearly indicate the differences in molecular distribution of PAHs before and after the earthquake. Sediment data obtained before the earthquake shows that most of the contamination originated from high temperature pyrolytic inputs while after the earthquake it originated from petrogenic sources. This difference emphasises the environmental impact of uncontrolled discharges from petroleum industries after the earthquake. The LMW/HMW ratio (sum of the low molecular weight PAHs / the sum of higher molecular weight PAHs) predominance also changed after the earthquake as a result of the strong water movements. According to the characteristics of aromatic rings distributed in the bay sediments, the soluble parts of the total PAH were probably transferred to the water column after the earthquake as a result of resuspension process. The TEL/PEL (Threshold Effect Level / Probable Effect Level) analysis suggests that the Izmit Bay sediments were likely contaminated by acutely toxic PAH compounds.

Disasters↗

PubMed1994

Dioxin-receptor ligands in urban air and vehicle exhaust.

The ability of extracts of urban air and vehicle exhaust particulates to bind to the dioxin receptor has been determined. It was shown that such extracts do contain significant amounts of dioxin-receptor binding activity. The level of dioxin-receptor binding found in ambient air reflects its pollution level as determined by mutagenic activity. Furthermore, it was shown that the extracts of both urban air and vehicle exhaust particulates could provoke the induction of cytochrome P450IA1 in cultured rat hepatoma cells. Chemical fractionation of the extracts revealed that the majority of the dioxin-receptor binding activity from urban air and gasoline vehicle samples fractionated with the polycyclic aromatic compounds. However, unknown polycyclic aromatic compounds were responsible for the majority of the binding activity measured. In the case of diesel vehicle exhausts, the majority of the dioxin-receptor binding activity was found to be associated with nitro-polycyclic aromatic compounds. Studies with a variety of diesel fuels showed that the amount of dioxin-receptor ligands present in exhaust emissions are fuel-dependent and that substantial amounts of dioxin-receptor ligands are present in the semivolatile phase of exhaust emissions.

Air Pollutants↗

PubMed2005

Predicting single and mixture toxicity of petrogenic polycyclic aromatic hydrocarbons to the copepod Oithona davisae.

In the present study, the acute toxicity of 10 polycyclic aromatic hydrocarbons (PAHs) associated with the Prestige fuel oil spill (Spain, 2002) were evaluated, either as single substances or in mixtures, in adults of the copepod Oithona davisae. All but dimethylphenanthrene had negative effects on O. davisae survival at concentrations below their water solubility, with 48-h median lethal concentrations for naphthalene and pyrene of 56.1 and 0.8 micromol/L, respectively, making these the least and most toxic compounds. Polycyclic aromatic hydrocarbons had narcotic effects on copepods, as evidenced by the lack of motility at lower concentrations than those causing death. Naphthalene showed the greatest narcotic effects, and phenanthrene showed minor effects. Acute toxicity of the tested PAHs was inversely related (r2 = 0.9) with their octanol-water partition coefficient, thereby confirming the validity of the baseline quantitative structure-activity regression models for predicting the toxicity of PAH compounds in copepod species. When supplied in mixtures, the toxic effect of PAHs was additive. These results indicate that the many PAHs in an oil spill can be considered unambiguous baseline toxicants (class 1) acting additively as nonpolar narcotics in copepods; hence, their individual and combined toxicity can be predicted using their octanol-water partition coefficient.

Animals↗

PubMed1978

Carcinogenicity and polarographic behavior of dibenz[a,h]anthracene, dibenz[a,h]acridine and dibenz[a,h]phenazine.

In a simultaneous test of carcinogenicity the authors have studied the activities of dibenz-[a,h]anthracene, dibenz[a,h]acridine and dibenz-[a,h]phenazine. These compounds were dispersed in paraffin disks and subcutaneously implanted in rats. Each experimental group consisted of 30 animals. The number of sarcomas induced by the above-mentioned compounds was 20, 5 and 3 respectively. Tumorigenicity of the aza analogues of dibenz[a,h]anthracene was proportional to their electron donation and inversely proportional to their electron acceptance in the performed polarographic test. The authors discuss the possibilities of using polarography as a screening test for the exclusion of carcinogenic polycyclic compounds.

Acridines↗

PubMed2003

[The chemistry of pericyclic reactions and their application to syntheses of heterocyclic compounds].

Diels-Alder reactions of benzylidenecyanomethyl-1,3-benzothiazoles 17 and -1,3-benzoxazoles 18 as 1-aza-1,3-butadienes are described. The dienes 17 and 18 featuring stabilized imine moieties in the form of heteroaromatic rings react with both electron-deficient and electron-rich dienophiles to give corresponding cycloadducts regioselectively. The cycloadditions of the intramolecular systems 34c,d and 35c,d proceeded smoothly via the exo-transition state, stereoselectively affording polycyclic compounds 36c,d and 37c,d in good to excellent yields. The diene systems of 17 and 18 were extended to dienes 19a-c with ester groups at diene-4-positions. Dienes 19a-c exhibited high Diels-Alder reactivities with electron-rich alkenes. Dienes 19a-c also reacted with allyl alcohols 55-58 in the presence of stanoxane catalyst 53 to give cycloadducts 59-62 via transesterification and intramolecular cycloaddition. Although alpha-alkoxycarbonylnitrones 64 have been very attractive nitrones for the syntheses of amino acids, the nitrones 64 exist as equilibrating mixtures of (E)-64 and (Z)-64. To solve this problem, three methods were explored: 1) sequential transesterification and intermolecular cycloaddition of nitrones 64 with allyl alcohols; 2) use of chiral and geometry-fixed nitrone 84; and 3) selective activation of (Z)-64 by Eu(fod)3. These methods were applied to syntheses of nikkomycins, clavalanine, and beta-substituted alpha-amino acids. The reactions of photoinduced carbonyl ylides from alpha,beta-unsaturated gamma,delta-epoxy nitriles were studied. Direct irradiation (lambda = 254 nm) of (E)-129 led selectively to products arising from the carbonyl ylide XXV or the carbene intermediate XXVI. The carbonyl ylides generated from (E)-129, (E)-139, and (Z)-143 were trapped with MeOH in the presence of amine, affording the corresponding acetals in moderate yields (Schemes 42 and 43). Photocyclization reactions of delta-hydroxyalkyl epoxy nitriles 148a-e led to spiro acetals arising from the carbonyl ylides (Scheme 45). The photoinduced carbonyl ylides from the epoxy dinitriles 158 and 160-163 underwent 1,3-dipolar cycloaddition with enol ethers, leading to a tetrahydrofuran system (Schemes 49 and 50, Table 14). Electrocyclization of 3-butadienylindoles 184 to intermediary dihydrocarbazoles XXXII followed by elimination of MeOH gave 3-oxyganated carbazoles 185, which were transformed to carbazole alkaloids hyellazole 168, 4-demethoxycarbazomycin B 170 and carazostatin 171, respectively. Claisen rearrangement of 3-(1-amino-1-vinyloxy) indolines derived from 3-hydroxyindolines 192 and amide acetal 193 gave indol-4-ylacetamides 194, which was reduced to afford 4-(2-aminoethyl) indoles 198, which has a framework of biologically active 4-substituted indole compounds. Claisen rearrangement of 3-allyloxyindoles produced in situ by condensation of indolin-3-ones 202 with allyl alcohols 203 and 206-211 gave 2-allylindolin-3-ones 204, 205 and 212-220. The domino reactions, Horner-Wadsworth-Emmons olefination of 2-allyloxyindole 233, isomerization, and Claisen rearrangement produced 3-allylindolin-2-one 234, which was derivatized to 3a-allylpyrrolo [2,3-b] indole alkaloid, flustramine C 221. Reverse aromatic Cope rearrangement of 2-allyl-3-indolidene acetonitriles 241-243, formed by Horner-Wadsworth-Emmons reaction of 2-allylindolin-3-ones 238-240, afforded indoles 244-246.

Aza Compounds↗

PubMed2006

Rapid energy transfer in cascade-type bodipy dyes.

Three new molecular dyads, comprising a bora-3a,4a-diaza-s-indacene (Bodipy) dye linked to two aromatic polycycles via the boron center, have been synthesized and fully characterized. The polycyclic compounds are either pyrene or perylene, or a mixture of both. Whereas the absorption spectral profiles contain important contributions from each of the subunits, fluorescence occurs exclusively from the Bodipy fragment. Intramolecular excitation energy transfer is extremely efficient in each case, even though spectral overlap integrals for the pyrene-based system are modest. Although these polycycles are sterically congested, molecular dynamics simulations indicate that they are in dynamic motion, and this hinders proper computation of the orientation factors for Förster-type energy transfer. These new dyes, especially the mixed polycycle system, greatly extend the range of excitation wavelengths that can be used for fluorescence microscopy.

Journal Article↗

PubMed1993

Nurturing and breast-feeding: exposure to chemicals in breast milk.

All chemicals that are not normal constituents of human milk should be considered undesirable contaminants. In the present review, the following substances detected in human milk are considered: persistent organochlorine pesticides; polychlorinated biphenyls (PCB); polychlorinated dibenzodioxins (PCDD) and dibenzofurans (PCDF); polybrominated compounds; polycyclic aromatic hydrocarbons (PAH); trace elements; mycotoxins; nitrate, nitrite, nitrosamines; nicotine, caffeine, ethanol; and drugs. The levels of most of these substances found in human milk were within a range that would not constitute health hazards for breast-fed infants. For many of these, there is a comfortable safety margin. This applies also to organochlorine pesticides and PCB, particularly since, as a result of their discontinued use, the levels of these compounds have clearly declined in recent years. On the other hand, the aflatoxin burden mediated through breast milk, at least in certain tropical countries, appears to pose a definite health hazard. Detailed reference are given on the contamination of human milk with PCDD/PCDF which has to be considered as a matter of concern from the viewpoint of preventive public health. Although the low PCDD/PCDF levels found in the adipose tissue of infants indicate that there is no appreciable health risk emanating from these substances for breast-fed infants, appropriate measures to reduce the current rate of their emission into the environment have to be taken.

Body Burden↗

PubMed2003

Polycyclic aromatic musk compounds in sewage treatment plant effluents of Canada and Sweden--first results.

Polycyclic musk fragrances (PMF) are widely used fragrances for cosmetics and other personal and household care products. Quantitative data on PMF (HHCB-Galaxolide, AHTN-Tonalide, ATTI-Traseolide, AHMI-Phantolide, ADBI-Celestolide, and DPMI-Cashmeran) and the most prominent nitro musks (Musk Xylene-MX, and Musk Ketone-MK) in different wastewater treatment effluents in Canada and Sweden are presented to provide preliminary information on the variations within the emission pattern of these compounds. In all samples HHCB and AHTN were detected at concentrations of up to 1300 and 520 ngl(-1), respectively. ADBI, AHMI were also present, but close to the detection limit. The other PMF DPMI, ATTI, and more surprisingly musk ketone and musk xylene were not detected in any sample analysed. In comparison the samples from Canada were contaminated at a higher level than the Swedish samples, by a maximum factor of ca 10 for HHCB and AHTN.

Canada↗

PubMed2005

Analytical methods in environmental effects-directed investigations of effluents.

Effluent discharges are released into aquatic environments as complex mixtures for which there is commonly either no knowledge of the toxic components or a lack of understanding of how known toxicants interact with other effluent components. Effects-directed investigations consist of chemical extraction and iterative fractionation steps directed by a biological endpoint that is designed to permit the identification or characterization of the chemical classes or compounds in a complex mixture responsible for the observed biological activity. Our review of the literature on effects-directed analyses of effluents for non-mutagenic as well as mutagenic endpoints showed that common extraction and concentration methods have been used. Since the mid-1980s, the methods have evolved from the use of XAD resins to C18 solid-phase extraction (SPE). Blue cotton, blue rayon, and blue chitin have been used specifically for investigations of mutagenic activity where polycyclic compounds were involved or suspected. After isolation, subsequent fractionations have been accomplished using SPE or a high-pressure liquid chromatography (HPLC) system commonly fitted with a C18 reverse-phase column. Substances in active fractions are characterized by gas chromatography/mass spectrometry (GC-MS) and/or other spectrometric techniques for identification. LC-MS methods have been developed for difficult-to-analyze polar substances identified from effects-directed studies, but the potential for LC-MS to identify unknown polar compounds has yet to be fully realized. Salmonella-based assays (some miniaturized) have been coupled with fractionation methods for most studies aimed at identifying mutagenic fractions and chemical classes in mixtures. Effects-directed investigations of mutagens have focused mostly on drinking water and sewage, whereas extensive investigations of non-mutagenic effects have also included runoff, pesticides, and pulp mill effluents. The success of effects-directed investigations should be based on a realistic initial objective of each project. Identification of chemical classes associated with the measured biological endpoint is frequently achievable; however, confirmation of individual compounds is much more difficult and not always a necessary goal of effects-directed chemical analysis.

Animals↗

PubMed1991

Comparison of three forward mutation systems in Saccharomyces cerevisiae for sensitivity to polycyclic and heterocyclic compounds.

Forward mutation to cycloheximide resistance, L-canavanine resistance and DL-alpha-aminoadipic acid resistance in Saccharomyces cerevisiae wild-type strain S7a was tested for sensitivity to nine mutagens in treat-and-plate assays. Eight of these agents, 2-aminofluorene, 2-acetylaminofluorene, benzo[a]pyrene, benzidine, cyclophosphamide, acriflavine, 7,12-dimethylbenz[a]anthracene and 2-aminoanthracene were known or suspected to be difficult to detect whilst one, methyl methanesulphonate, was known to be very active in yeast. Forward mutation to cycloheximide resistance was, overall, the most sensitive system, detecting all nine agents under optimal conditions, although neither benzidine nor benzo[a]pyrene were consistently positive. Mutation to adipic acid resistance occasionally gave responses superior to those at the cycloheximide loci, but mutation to canavanine resistance was never more sensitive than the cycloheximide resistance system. We conclude that forward mutation in strain S7a using both cycloheximide and adipic acid resistance loci is capable of detecting the genetic effects of a range of polycyclic and heterocyclic compounds with greater sensitivity than is seen in other published gene mutation assays with yeast. Although sensitivity is much lower than in bacterial assays, such yeast assays provide a reasonable alternative to bacterial genotoxicity screening for agents such as potent bactericides.

2-Aminoadipic Acid↗