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PubMed1998

Use of 13C nuclear magnetic resonance to assess fossil fuel biodegradation: fate of [1-13C]acenaphthene in creosote polycyclic aromatic compound mixtures degraded by bacteria.

[1-13C]acenaphthene, a tracer compound with a nuclear magnetic resonance (NMR)-active nucleus at the C-1 position, has been employed in conjunction with a standard broad-band-decoupled 13C-NMR spectroscopy technique to study the biodegradation of acenaphthene by various bacterial cultures degrading aromatic hydrocarbons of creosote. Site-specific labeling at the benzylic position of acenaphthene allows 13C-NMR detection of chemical changes due to initial oxidations catalyzed by bacterial enzymes of aromatic hydrocarbon catabolism. Biodegradation of [1-13C]acenaphthene in the presence of naphthalene or creosote polycyclic aromatic compounds (PACs) was examined with an undefined mixed bacterial culture (established by enrichment on creosote PACs) and with isolates of individual naphthalene- and phenanthrene-degrading strains from this culture. From 13C-NMR spectra of extractable materials obtained in time course biodegradation experiments under optimized conditions, a number of signals were assigned to accumulated products such as 1-acenaphthenol, 1-acenaphthenone, acenaphthene-1,2-diol and naphthalene 1,8-dicarboxylic acid, formed by benzylic oxidation of acenaphthene and subsequent reactions. Limited degradation of acenaphthene could be attributed to its oxidation by naphthalene 1,2-dioxygenase or related dioxygenases, indicative of certain limitations of the undefined mixed culture with respect to acenaphthene catabolism. Coinoculation of the mixed culture with cells of acenaphthene-grown strain Pseudomonas sp. strain A2279 mitigated the accumulation of partial transformation products and resulted in more complete degradation of acenaphthene. This study demonstrates the value of the stable isotope labeling approach and its ability to reveal incomplete mineralization even when as little as 2 to 3% of the substrate is incompletely oxidized, yielding products of partial transformation. The approach outlined may prove useful in assessing bioremediation performance.

Acenaphthenes↗
PubMed1999

Fluorescence quenching of polycyclic aromatic compounds by humic substances. Part 1. Methodology for the determination of sorption coefficients.

An introduction to the methodology of fluorescence quenching measurements as an experimental tool for investigating the sorption of hydrophobic organic substances by dissolved organic matter (OM) is given. Special attention is paid to the implications of inner-filter effects (IFEs) on the determination of sorption coefficients. The essential aspects of the theoretical description of IFEs are outlined and various procedures for the IFE correction of fluorescence quenching measurements in the presence of dissolved OM are presented. Geometric parameters relevant for the quantitative description of IFE applying a 90 degrees arrangement between fluorescence excitation and detection are determined by different methods, newly developed or adapted from the literature, for the fluorescence spectrometer used in this work. Moreover, an experimental validation of the applicability of different IFE correction procedures is performed. In order to evaluate the variations of sorption coefficients that result from the use of different IFE correction procedures, the quenching of the fluorescence of the well-known polycyclic aromatic compound pyrene by a commercially available humic substance in aqueous solution is investigated. Compared to the apparent sorption coefficient, which is obtained without any IFE correction, the sorption coefficients determined with the correction of primary IFE or with the correction of primary and secondary IFE are on average ca. 40 or 60% lower. The application of different IFE correction procedures allows the determination of sorption coefficients with appropriate precision of +/- 15%.

Adsorption↗
PubMed1987

Polycyclic aromatic compounds as phototoxic mosquito larvicides.

The phototoxicity of 2-acetylnaphthalene, 1-acetylnaphthalene, 1-naphthalenecarboxaldehyde, 9-xanthenone, 9-thioxanthenone, 9-methylanthracene, anthracene, alpha-terthienyl, pyrene and fluoranthene was tested with larvae of Aedes aegypti, Ae. taeniorhynchus and Culex quinquefasciatus. The larvae were exposed to the chemicals in the presence of sunlight for intervals from 1 to 6 hr and the corresponding LC50 values calculated. The LC50 values determined when the 6-hr exposure was followed by 18 hr in the dark range from over 10 ppm to below 0.001 ppm. Naphthalene derivatives were the least active while alpha-terthienyl, anthracene, 9-methylanthracene, pyrene and fluoranthene were the most phototoxic.

Animals↗
PubMed1983

Experimental studies on the carcinogenicity of five nitrogen containing polycyclic aromatic compounds directly injected into rat lungs.

Using a beeswax/tricaprylin mixture as vehicle, three doses each of acridine, benz[a]acridine (BaAC), benz[c]acridine (BcAC), dibenz[a,h]-acridine (DBa,hAC) and dibenz[a,j]acridine (DBa,jAC) were injected into the lungs of 35 female Osborne-Mendel rats per group. To compare the carcinogenic potency of the heterocycles, benzo[a]pyrene (BaP) was taken as reference substance. Dose-response relationships were obtained for DBa,hAC as well as for BaP. DBa,jAC and BcAC exhibited no carcinogenic effects in the dose range from 0.1 mg to 1 mg tested in the lung implantation model. From the results presented here, it cannot be excluded that tumor development may occur when testing higher doses. BaP, however, must be considered much more potent since it revealed, by far, higher tumor incidences and diminished life times.

Acridines↗
PubMed1992

The formation of proximate carcinogens from three polycyclic aromatic compounds by human liver microsomes.

1. The metabolism of 3H-benzo[a]pyrene (BP), 3H-7-methylbenz[c]acridine (7MBAC) and 3H-dibenz[a,j]acridine (DBAJAC) have been studied in human liver microsomes from 13 subjects. 2. When the metabolism of these carcinogens to more polar ethyl acetate-soluble metabolites were compared, the activities towards the nitrogenous carcinogens were twice that determined for BP. 3. The specific rates of formation of the three proximate carcinogens, BP-7,8-dihydrodiol, 7MBAC-3,4-dihydrodiol and DBAJAC-3,4-dihydrodiol per nmol cytochrome P-450 for 12 subjects were positively correlated. 4. These dihydrodiols constituted 5.9 +/- 0.7% (mean +/- SEM), 57.8 +/- 2.6% and 3.0 +/- 0.4% of the total metabolites identified by cochromatography with standards, 7MBAC, DBAJAC and BP respectively.

Acridines↗
PubMed1983

Mixtures of polycyclic aromatic compounds inhibit mutagenesis in the Salmonella/microsome assay by inhibition of metabolic activation.

We observed that complex mixtures of aromatic compounds isolated from a coal-derived oil suppressed the mutagenic activity of the indirect mutagens benzo[a]pyrene, 7,12-dimethylbenz[a]anthracene, 2-aminofluorene, and 2-acetylaminofluorene as measured in the Salmonella/microsome mutagenicity assay, using strain TA98 and metabolic activation with Aroclor-induced rat-liver S9 or microsomes. The mixture also inhibited S9-dependent benzo[a]pyrene metabolism and covalent binding to DNA in a cell-free system. The mixture did not suppress the activity of either the direct acting mutagens 2-nitrofluorene and benzo[a]pyrene diol-epoxide, or of the indirect mutagen N-hydroxy-2-acetylaminofluorene which requires a microsomal deacetylase for metabolic activation. Spectrophotometric measurements showed that components of the mixture bound to microsomal cytochrome P-450. The mixture did not inhibit microsomal NADPH-cytochrome c (P-450) reductase. These observations show that the mixtures inhibited metabolic activation by the microsomal monooxygenase system, probably by binding of unidentified components to cytochrome P-450. The resulting inhibition of mutagenesis may have implications for risk estimates for the mixtures we examined as well as for other types of complex mixtures for which similar inhibitory effects have been observed.

Animals↗
PubMed1994

Prediction and monitoring of the carcinogenicity of polycyclic aromatic compounds (PACs).

Chemical carcinogenesis is a multistage process that includes initiation, promotion, and progression. Some carcinogenic PACs have been shown to activate proto-oncogenes and deactivate tumor-suppression genes in the carcinogenic process. The function of DNA repair processes appears to be changed in some cases by PACs. Many PACs are well known for their carcinogenic activity, but for this activity to be exerted, metabolic activation by microsomal enzymes must occur. The enzyme system responsible for PAC activation is the mixed-function oxidase system and, in particular, cytochrome P-450. In the case of PAHs, oxidation predominantly produces reactive diol-epoxides that can then be converted to carbonium ions as the reactive electrophiles that can then covalently bind to DNA. Regions of high activity exist in PAHs, namely, the "bay," "K," and "L" regions which are associated with pi electron distribution. The diol-epoxides can exist in either syn or anti forms, each of which has two enantiomers producing four stereoisomers in all. Energy considerations favor the formation of the anti form. Nitrogen-containing PACs can be metabolically activated in a manner similar to that for PAHs, or the nitrogen atom can be oxidized to form hydroxylamines. These reactive electrophiles can then form covalently bound DNA adducts. The monitoring of DNA adducts has been used in risk assessment for human exposure to PACs. This form of biomonitoring has advantages over the monitoring of external exposure or body levels of the chemicals in question. In the case of PACs, binding to DNA is an important step in the multistage carcinogenic process. The estimation of DNA adducts has been used in the monitoring of humans exposed to PAHs in a wide range of industrial situations. Recent research has shown a dose-response relationship between PAH adduct levels and human cancer, thus developing molecular epidemiology as a relevant science for the field of risk assessment. Techniques have been developed for the determination of DNA adducts and these include immunochemical, fluorescence spectroscopic, GC-MS, and 32P-postlabeling methods. The 32P-postlabeling assay is by far the most sensitive, with limits of detection being of the order of one adduct in 10(10) normal nucleotides. The use of HPLC for separation of adducted nucleotides in this postlabeling assay is becoming more common and gives better resolution of adducts than does the TLC technique used in the traditional assay. The detection of adducts on hemoglobin and other proteins has been used as a surrogate for DNA adduct estimation.(ABSTRACT TRUNCATED AT 400 WORDS)

Carcinogens, Environmental↗
PubMed1980

Covalent binding of polycyclic aromatic compounds to mitochondrial and nuclear DNA.

Since the pioneering work of the Millers it has become clear that most chemical carcinogens require metabolism to reactive electrophiles and then exhibit their carcinogenic potential by reacting chemically with, and modifying, cellular macromolecules. At first modification of proteins was considered most likely to be of importance in carcinogenesis. Later, Brookes and Lawley demonstrated that the extent of binding of several polycyclic hydrocarbons to DNA, but not to RNA or protein isolated from the skin of mice treated topically with these compounds, correlated with their known carcinogenic potency to this tissue. Mammalian cells, particularly mouse embryo cells, treated with chemical carcinogens have often been used, and DNA has been involved almost exclusively from whole cells. However, mitochondria possess unique DNA which accounts for 0.1-1% of the total DNA present in mammalian cells, and three studies have shown that carcinogenic alkylating agents modify the michondrial DNA by a factor about five times greater than the nuclear DNA from the same cells. We demonstrate here that with six polycyclic aromatic compounds, all of which require metabolic activation and bind to DNA to a much smaller extent than direct than direct-acting alkylating agents, the binding to mitochondrial relative to DNA is dramatically increased by a factor of nearly 50 to over 500.

Animals↗
PubMed1990

Benzo(a)pyrene inhibits epidermal growth factor binding and receptor autophosphorylation in human placental cell cultures.

Studies investigated the effects of benzo(a)pyrene (BP) treatment on epidermal growth factor (EGF) receptor binding and kinase activity in human placental cell cultures. Specific binding of 125I-EGF to cells from early gestation placentae was significantly decreased by 37 and 60% following exposure to 1 and 10 microM BP, respectively, for 24 hr. In contrast, cells cultured from term placentae showed no inhibitory effect of either concentration of BP. Specific binding of 125I-labeled insulin and insulin-like growth factors-I and -II to early gestation cells was decreased only 15-18% at 10 microM BP, which indicates that loss of membrane receptors appears to be selective for EGF. Scatchard analysis of early gestation cells revealed that BP was associated with a dose-dependent loss in the number of high affinity EGF binding sites. Evidence from cross-linking and autophosphorylation experiments confirmed that the Mr 170,000 binding protein was decreased in a dose-dependent manner following BP treatment. In comparison, term placental cells exhibit a 26% loss of EGF receptor autophosphorylation without alteration in binding following exposure to 10 microM BP. Thus, early gestation cells exhibit a BP-related down-regulation of EGF receptors, whereas term placental cells show receptor desensitization. No adverse effect of BP treatment was observed on the incorporation of [35S] methionine into proteins secreted by early gestation cells. Further experiments compared the effects of BP with the related poly-cyclic compounds beta-naphthoflavone, alpha-naphthoflavone, and 3-methylcholanthrene. In early gestation cells, EGF binding and receptor autophosphorylation were measurably decreased at 10 microM concentrations of these polycyclic compounds, but to a lesser extent than observed with BP. In term placental cells, however, EGF binding was unchanged or increased, whereas receptor autophosphorylation was decreased 10-26%. Thus, exposure of term placental cells to these polycyclic compounds leads to a dissociation between EGF binding and receptor protein kinase activity. Finally, aryl hydrocarbon hydroxylase activity was induced 20- to 200-fold in early placental cells exposed to BP, beta-naphthoflavone, and 3-methylcholanthrene. In summary, the direct effects of BP and related compounds observed on placental EGF receptors may indicate altered function of EGF in the regulation of cell growth and differentiation in the human placenta.

Aryl Hydrocarbon Hydroxylases↗
PubMed1998

Levels of organochlorine and polycyclic aromatic compounds in harp seal beaters (Phoca groenlandica).

Chlorinated dibenzo-p-dioxins, dibenzofurans, chlorobiphenyls, organochlorine pesticides and polycyclic aromatic hydrocarbons were measured in blubber, liver, kidney and muscle of five male and five female, 8-month-old harp seals (Phoca groenlandica). Levels of organochlorine contaminants were lowest in muscle, nearly 100 times higher in blubber and intermediate in kidney and liver. Only 2,3,7,8-tetrachlorodibenzofuran was detected in all liver and blubber samples (0.45 and 3.15 pg/g wet wt., respectively). Concentrations of chlorobiphenyls expressed as Aroclor 1254 were 3.8 and 8.2, 8.6 and 21.5, 23 and 73, and 945 and 890 ng/g wet wt. in the muscle, kidney, liver and blubber of female and male seals, respectively. p,p'-DDE, trans-nonachlor, oxychlordane and alpha-HCH were the additional predominant organochlorine compounds at 460 and 460, 415 and 530, 300 and 390, and 190 and 230 ng/g wet in the blubber of female and male seals, respectively. Concentrations of chlorobiphenyls and pesticides in muscle, liver and kidney were two-three times higher in males compared to females, whether expressed on a wet weight or a lipid weight basis, and approximately equal in blubber, even though the blubber layer of females was 30% thicker than that of males. Naphthalene and its C1-C3 homologues were detected in all tissues, generally at concentrations below 10 ng/g wet wt. The concentrations of PCBs and DDTs in blubber are considerably lower than those reported for juvenile seals from the same area 20 years ago. PCB and organochlorine pesticide concentrations and profiles are discussed in relation to those reported from other areas, as well as to sex and age of the seals.

Adipose Tissue↗
PubMed1997

Determination of polycyclic aromatic compounds and heavy metals in sludges from biological sewage treatment plants.

The procedure of the analysis of polycyclic aromatic hydrocarbons (PAHs) and their derivatives in the sludges from biological sewage treatment plants has been worked out. The analysis included isolation of organic matter from sludges, separation of the extract into fractions of similar chemical character, qualitative-quantitative analysis of individual PAHs and their nitrogenated and oxygenated derivatives. Liquid-solid chromatography, solid-phase extraction and semipreparative band thin-layer chromatography techniques were used for the separation. Capillary gas chromatography-mass spectrometry analysis of the separated fractions enabled identification of more than 21 PAHs, including hydrocarbons which contained 2-6 aromatic rings as well as their alkyl derivatives, 10 oxygen derivatives, 9 nitroarenes, aminoarenes and over 20 azaarenes and carbazoles. Using the capillary gas chromatography-flame ionization detection technique the content of 17 dominant PAHs was determined. The content of heavy metals was determined in investigated sludges with the use of atomic absorption spectrometry. The concentrations of the respective metals could be ranked in the order Cd < Co < Ni < Pb < Cr < or = Cu < Mn < Zn < Fe. The sludges were analysed for the first time in Poland in view of their possible utilisation in agriculture and in cultivating dumps of coal mine wastes, taking into consideration the contents of toxic organic pollutants and heavy metals.

Chromatography, Gas↗
PubMed1986

Inhibitors and dipeptide substrates for a microsomal tyrosylsulfotransferase from rat brain.

The sulfotransferase associated with a microsomal fraction from rat brain was previously shown to transfer sulfate groups from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to peptides derived from the cholecystokinin (CCK) molecule. Three tyrosine-containing dipeptide derivatives, i.e., Cbz-Glu-Tyr, Cbz-Gly-Tyr and Ac-Phe-Tyr are shown here to accept the [35S] sulfate group from [35S] PAPS under the action of this sulfotransferase. The sulfotransferase activity evaluated with either any of these dipeptide derivatives or CCK-8 as acceptors is similarly inhibited by a series of compounds, i.e., lipophilic polycyclic compounds like fluphenazine, tyrosine derivatives like Boc-O-benzyl-tyrosine and phenolsulfotransferase inhibitors like 4,4-di-isothiocyano 2',2'-disulfonic acid stilbene.

Animals↗
PubMed1990

Multiple DNA-binding factors interact with overlapping specificities at the aryl hydrocarbon response element of the cytochrome P450IA1 gene.

Three nuclear factors, the Ah receptor, XF1, and XF2, bind sequence specifically to the Ah response elements or xenobiotic response elements (XREs) of the cytochrome P450IA1 (P450c) gene. The interactions of these factors with the Ah response element XRE1 were compared by three independent methods, methylation interference footprinting, orthophenanthroline-Cu+ footprinting, and mobility shift competition experiments, using a series of synthetic oligonucleotides with systematic alterations in the XRE core sequence. These studies established the following (i) all three factors interact sequence specifically with the core sequence of XRE1; (ii) the pattern of contacts made with this sequence by the Ah receptor are different from those made by XF1 and XF2; and (iii) although XF1 and XF2 can be distinguished by the mobility shift assay, the sequence specificities of their interactions with XRE1 are indistinguishable. Further characterization revealed the following additional differences among these three factors: (i) XF1 and XF2 could be extracted from nuclei under conditions quite different from those required for extraction of the Ah receptor; (ii) XF1 and XF2 were present in the nuclei of untreated cells and did not respond to polycyclic compounds, such as 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and beta-napthoflavone, while nuclear Ah receptor was undetectable in untreated cells and rapidly increased in response to TCDD; (iii) inhibition of protein synthesis did not affect the TCDD-induced appearance of the Ah receptor but substantially decreased the constitutive activities of XF1 and XF2, suggesting that the Ah receptor must be present in untreated cells in an inactive form that can be rapidly activated by polycyclic compounds, while the constitutive expression of XF1 and XF2 depends on the continued synthesis of a relatively unstable protein; (iv) the receptor-deficient and nuclear translocation-defective mutants of the hepatoma cell line Hepa1, which are known to lack nuclear Ah receptor, expressed normal levels of XF1 and XF2, suggesting that the former factor is genetically distinct from the latter two; and (v) a divalent metal ion, probably Zn2+, is known to be an essential cofactor for the Ah receptor but was not required for the DNA-binding activities of XF1 and XF2. Together, these findings indicate that the Ah receptor is distinct from XF1 and XF2, while the latter two activities may be related. Because the DNA-binding domains of these three factors overlap substantially, their binding to XREs is probably mutually exclusive, which suggests that the interplay of these factors at Ah response elements may be important to the regulation of CYP1A1 gene transcription. The results of preliminary transfection experiments with constructs harboring XREs upstream of the chloramphenicol acetyltransferase gene driven by a minimal simian virus 40 promoter are presented that are consistent with this hypothesis.

Base Sequence↗
PubMed2001

Monitoring of indoor volatile organic compounds and polycyclic aromatic hydrocarbons arising from kerosene cooking fuel.

Air samples, representing indoor environments of a kitchen in which a kerosene stove was used were collected and analysed for volatile organic compounds (VOCs) viz., n-hexane, benzene, heptane, toluene, p- and o-xylene and n-decane using a cryogenic preconcentration system and a gas chromatograph with a flame-ionisation detector. Simultaneous outdoor samples were also collected to determine indoor to outdoor (I/O) ratios for each compound. Reversed phase high performance liquid chromatography (HPLC) with ultra violet absorption detection was optimised for separation and quantification of polycyclic aromatic hydrocarbons (PAHs) in air particulate matter. Concentration of total suspended particulate matter (TSPM), benzene soluble organics and the PAHs in air samples collected in indoor environment of some tenements at Trombay, Mumbai where kerosene is used as cooking fuel are discussed in relation to the concentration of the same in outdoor environment in vicinity of the tenement. VOCs and PAHs results from samples collected in kitchens in Trombay are discussed in relation to indoor air pollution.

Air Pollution, Indoor↗
PubMed2000

Bridged silver(I) complexes of the polycyclic aromatic compounds tetraphenylethylene and 1,1,4,4-tetraphenyl-1,3-butadiene.

For the purpose of investigating the coordination behavior of the sterically congested alkenes and exploring the possibility of cofacial complexation in the polycyclic aromatic system for formation of extended polymeric networks, tetraphenylethylene (tphe) and 1,1,4,4-tetraphenyl-1,3-butadiene (tphb) have been studied with regard to their complexation with a silver(I) ion. The crystal structures of [Ag(tphe)(ClO4)(p-xylene)], [Ag2(tphe)(ClO4)2], [Ag4(tphe)(CF3SO3)4], [Ag2(tphb)(ClO4)2], and [Ag2(tphb)(CF3SO3)2], together with the metal-free ligands tphe and tphb, have been determined by single-crystal X-ray diffraction. The pi-electron-rich cleft in organic components is found to offer a potential site for complexation, which can be utilized to generate an interesting array of organometallic compounds with one- and two-dimensional frameworks.

Journal Article↗
PubMed2001

Polycyclic aromatic compounds as anticancer agents: structure-activity relationships of chrysene and pyrene derivatives.

A large number of diamides and diamines were synthesized using 6-amino chrysene and 1-amino pyrene as starting materials. A structure activity study with cis-platinum as internal control against animal and human tumor lines was carried out in vitro. This study indicated that the in vitro cytotoxicity toward these lines depends on the functionality present in the molecules. The diamino compounds were found to be more potent than the diamides, and these were equally active irrespective of the end heterocyclic group, whereas the activity of the diamides was strongly dependent on the terminal unit. In general, the diamides containing chrysene as the chromophore were more active than those with a pyrene ring. The size of the end heterocyclic ring, along with the nature of the spacer connecting the polycyclic ring to the heterocyclic ring, seemed to affect the biological activity in certain cell lines. Hemolysis experiments on a lead compound established that it had activities similar to those described for membrane-stabilizing agents. This agent also demonstrated the capacity to produce differentiation in leukemia cell lines.

Animals↗
PubMed2001

Bioaccumulation of polycyclic aromatic compounds: 1. Bioconcentration in two marine species and in semipermeable membrane devices during chronic exposure to dispersed crude oil.

Assessing the fate in marine biota of hydrocarbons derived from oil particles that are discharged during exploration and production is of relevant environmental concern. However, a rather complex experimental setup is required to carry out such investigations. In this study, a sophisticated tool, the continuous-flow system (CFS), was used to mimic dispersed oil exposure to marine biota. Polycyclic aromatic hydrocarbon (PAH) uptake was studied in two species, the blue mussel Mytilus edulis and juvenile of the turbot Scophthalmus maximus, and in semipermeable membrane devices (SPMD) exposed to crude oil dispersed in a flow-through system. After an exposure period of 8 to 21 d, elimination in organisms and devices was analyzed for 9 to 10 d following transfer to PAH-free seawater. Principal component analysis (PCA) revealed different PAH patterns. In mussel and SPMD, the PAH profiles were very close to that analyzed in seawater. Slight differences were, however, indicated for large molecules with log Kow above six. Nonachievement of steady-state concentration and bioavailability of PAH in oil droplets may account for these differences. The PAH composition in fish revealed only congeners with two to three aromatic rings. A combination of bioavailability and efficient metabolism of the larger PAH molecules may explain this pattern. The CFS made possible a better understanding of some critical factors governing bioconcentration in marine biota from dispersed oil. Yet the results illustrate that uptake of PAH from exposure to oil particles is complex and that different species may bioconcentrate different molecules depending on factors like life style and metabolic capability to degrade the potential harmful substances. Hence, risk assessment of the actual impact of discharges to marine biota should consider these essential biological and ecological factors.

Animals↗