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PubMed2005

Reactions of chlorine atoms with a series of aromatic hydrocarbons.

Aromatic hydrocarbons, including polycyclic aromatic hydrocarbons (PAHs), are present in urban and rural atmospheres. Reactions of PAHs with Cl atoms may occur in the marine boundary layer and in coastal regions. To assess the importance of these reactions and to investigate whether any unique chlorine-containing products are formed from these reactions, we have measured the rate constants for the gas-phase reactions of Cl atoms with toluene-d8, 1,3,5-trimethylbenzene (1,3,5-TMB), naphthalene, 1-methylnaphthalene-d10 (1-MN-d10), 1- and 2-methylnaphthalene (1- and 2-MN), 1- and 2-ethylnaphthalene (1- and 2-EN), and the dimethylnaphthalenes (DMNs) at 296 +/- 2 K. A relative rate technique was used, and, using our measured rate constant forthe reaction of Cl atoms with 1,3,5-TMB of 2.42 x 10(-10) cm3 molecule(-1) s(-1), the rate constants (in units of 10(-10) cm3 molecule(-1) s(-1)) are as follows: naphthalene, < or = 0.0091 +/- 0.0003; 1-MN, 1.21 +/- 0.16; 2-MN, 1.05 +/- 0.13; 1-EN, 2.12 +/- 0.35; 2-EN, 1.38 +/- 0.27; 1,2-DMN, 3.61 +/- 0.68; 1,3-DMN, 2.90 +/- 0.22; 1,4-DMN, 2.93 +/- 0.30; 1,5-DMN, 2.31 +/- 0.19; 1,6-DMN, 2.15 +/- 0.20; 1,7-DMN, 3.05 +/- 0.34; 1,8-DMN, 3.07 +/- 0.44; 2,3-DMN, 2.93 +/- 0.49; 2,6-DMN, 2.34 +/- 0.18; and 2,7-DMN, 2.00 +/- 0.22, where the indicated errors are two standard deviations and do not include the uncertainty in the rate constant for 1,3,5-TMB. The measured deuterium isotope effects for the toluene-d8 and 1-MN-d10 reactions indicate that the reactions proceed by initial H- (or D-) atom abstraction. The products identified and quantified from the toluene and 1-MN reactions using gas chromatography and in situ direct air sampling atmospheric pressure ionization tandem mass spectrometry were benzaldehyde (84% +/- 7% yield) and benzyl alcohol (11% +/- 2% yield) from toluene and 1-naphthaldehyde (approximately 36%, lower limit to yield) and 1-naphthyl alcohol (approximately 12%, lower limit to yield) from 1-MN. These products confirm that H-atom abstraction is the dominant, if not sole, reaction pathway for the alkylbenzenes and alkylnaphthalenes, consistent with the 100-fold lower rate constant measured for naphthalene compared to the alkylnaphthalenes and with the measured deuterium isotope effects.

Atmosphere↗
PubMed1977

The effects of grayanotoxin I and alpha-dihydrograyanotoxin II on guinea-pig myocardium.

We have demonstrated recently that grayanotoxin I (GTX I) produces a positive inotropic effect in isolated guinea-pig atria. In order to determine whether this effect of GTX I is related to the reported action of this compound to increase the sodium permeability of cytoplasmic membranes, the effect of GTX I and alpha-dihydrograyanotoxin II (alpha-2H-GTX II) on electrical and mechanical properties and transmembrane cation movements were studied in guinea-pig myocardium. In electrically driven guinea-pig left atrial preparations, both grayanotoxins produced a slight depolarization and appear to decrease the upstroke velocity of the action potential, with a concomitant increase in isometric contractile force in the presence or absence of propranolol. Pretreatment with propranolol shifted the dose-response curves for the inotropic effect of both grayanotoxins slightly to the right. The magnitudes of changes in the electrical and mechanical properties induced by GTX I and alpha-2H-GTX II were similar. The rate of development and subsequent washout of the positive inotropic effects, however, was faster with alpha-2H-GTX II than with GTX I, consistent with a previous report that the action of alpha-2H-GTX II to increase membrane sodium permeability develops more rapidly than that of GTX I. At higher concentrations, both grayanotoxins produced arrhythmias. Arrhythmias induced by GTX I were characterized by extrasystoles whereas those induced by alpha-2H-GTX II were characterized by initial extrasystoles followed by a failure of the atria to follow electrical stimulation. Positive inotropic and arrhythmic effects of both grayanotoxins were reversible after the washout of the drug. Both types of arrhythmias produced by either GTX I or alpha-2H-GTX II were reversed by tetrodotoxin, an agent which has been demonstrated to antagonize the action of the grayanotoxins to increase membrane sodium permeability. Although both grayanotoxins had no marked effect on partially purified Na+, K+-adenosine triphosphatase, they produced dose-dependent increases in ouabain-sensitive 86Rb uptake of ventricular slices under conditions in which the intracellular sodium concentration determines the rate of active monovalent cation transport by the Na+, K+-adenosine triphosphatase system. These data suggest that the positive inotropic effects of grayanotoxins are due to an increased membrane sodium permeability and are consistent with a hypothesis that alterations in transmembrane sodium movements result in an altered myocardial contractility.

Action Potentials↗
PubMed2001

An evaluation of the mutagenicity, metabolism, and DNA adduct formation of 5-nitrobenzo[b]naphtho[2,1-d]thiophene.

Thioarenes, sulfur-containing polycyclic aromatic compounds, are environmental contaminants suspected of posing human health risks. In this study, 5-nitrobenzo[b]naphtho[2,1-d]thiophene (5-nitro-BNT), a nitrated-thioarene, was examined for its mutagenicity, metabolism and subsequent formation of DNA adducts. 5-Nitro-BNT was weakly mutagenic in Salmonella typhimurium strains TA98 and TA100 without Aroclor-1254-induced rat liver S9 (S9), and its activity was increased in the presence of S9. Anaerobic metabolism of 5-nitro-BNT by S9 or xanthine oxidase (XO) produced one major metabolite, identified as 5-amino-BNT by NMR, MS, and UV spectroscopy and by comparison with an authentic standard. Aerobic S9 metabolism of 5-nitro-BNT produced a major metabolite, identified as trans-9,10-dihydroxy-9,10-dihydro-5-nitro-BNT (5-nitro-BNT-9,10-diol). Also present was a minor amount of 5-amino-BNT and trans-9,10-dihydroxy-9,10-dihydro-5-amino-BNT (5-amino-BNT-9,10-diol). DNA adduct analyses were performed using the (32)P-postlabeling assay and reversed-phase HPLC. Three major XO-derived calf thymus DNA adducts were detected. On the basis of their chromatographic mobilities, two adducts were identified as reaction products of 5-nitro-BNT with 2'-deoxyguanosine and one adduct with 2'-deoxyadenosine. Incorporation of allopurinol (a specific XO inhibitor) in the incubation mixture resulted in loss of all three adducts, confirming enzymatic mediation by XO. Aerobic S9 activation of 5-nitro-BNT with calf thymus DNA produced three adducts. On the basis of their chromatographic mobilities, two were identified as reaction products of 5-nitro-BNT with 2'-deoxyguanosine and one with 2'-deoxyadenosine. Incorporation of 1-aminobenzotriazole (a P450 inhibitor) in the incubation mixture resulted in a loss of these adducts, confirming enzymatic mediation by P450. Aerobic S9-catalyzed metabolism of 5-nitro-BNT-9,10-diol produced the same DNA adducts as observed with 5-nitro-BNT. Aerobic S9-catalyzed metabolism of 5-amino-BNT-9,10-diol produced the same deoxyadenosine-derived DNA adducts as observed with 5-nitro-BNT and 5-nitro-BNT-9,10-diol. These results provide additional information that both ring oxidation and nitroreduction are involved in the metabolism, DNA adduct formation and mutagenicity of 5-nitro-BNT.

Animals↗
PubMed1978

Aryl hydrocarbon hydroxylase inducibility in laryngeal carcinoma.

The chief carcinogens of tobacco smoke--the polycyclic aromatic hydrocarbons--must be activated in the cells to exert their carcinogenic effect. This activation is carried out by the enzyme system aryl hydrocarbon hydroxylase (AHH). Mitogen-stimulated, human lymphocyte studies of AHH activity indicate wide individual variation, which is under strict genetic control. The venous blood samples from 90 patients with a laryngeal carcinoma were assayed, and a significant overrepresentation of patients with genetically high AHH inducibility was demonstrated. Our results suggest the possibility of identifying those tobacco users at higher genetic risk for developing carcinoma of the larynx.

Adult↗
PubMed1996

Cancer risks among iron and steel workers in Anshan, China, Part I: Proportional mortality ratio analysis.

A standardized proportional mortality ratio (SPMR) study of 8,887 deaths during 1980-1989 among male workers in a large integrated iron-steel complex in Anshan, China, was conducted to provide clues to occupational risk factors. Accidents and cancer accounted for a higher proportion of deaths among the iron-steel workers than among the general male population (SPMR = 1.21; 95% CI = 1.12-1.31 and 1.14; 95% CI = 1.10-1.18, respectively). Among all workers, SPMRs were significantly elevated for stomach, lung, and colorectal cancers (SPMR = 1.37, 1.37, 1.38, respectively), but not other cancers. Risks of stomach cancer appeared to be highest among workers employed in jobs with exposure to iron and coal dust, whereas significant increases in colorectal cancer were seen for loading and other dusty jobs and for administrative and sedentary jobs without dust exposure. Risks of lung cancer appeared increased for a variety of jobs throughout the complex, especially those with probable high levels of exposure to polycyclic hydrocarbons and asbestos. Risk of esophageal cancer was significantly elevated for fire-resistant brick makers, and risk of nonmalignant respiratory disease was significantly elevated for those employed as furnace workers, foundry workers, and fire-resistant brick makers.

Accidents, Occupational↗
PubMed1999

Exposure to PAH and fluoride in aluminum reduction plants in Norway: historical estimation of exposure using process parameters and industrial hygiene measurements.

BACKGROUND: In this study, we describe the methodology used for historical estimation of exposure to fluoride and to PAH in vertical stud Søderberg (VSS) potrooms at two Norwegian aluminum smelters. The assessment was performed in order to develop exposure data for epidemiological studies of cause-specific mortality and cancer incidence. METHODS: The estimation was performed in several steps. In the first step, we estimated the area concentrations of fluoride and PAH in periods with no measurements. Relationships between measured area concentrations and process parameters were investigated by statistical modeling. Process parameters and the models were then used to estimate area concentrations in periods lacking area measurement data. In the second step, the relationships between the area measurements and job specific exposure (personal measurements) were investigated by use of a measurement model. In the last step, the obtained relationships were used to estimate job specific exposure in different periods. RESULTS: The range for the annual exposure estimates in the VSS-potrooms was 0.05-1.7 mg/m3 for fluoride and 3-3,437 micrograms/m3 for PAH. CONCLUSIONS: Despite limitations of available measurements in the early production period, we have concluded that the exposure estimates from this study provide a reasonable tool for the estimation of dose-response relations in subsequent epidemiological analyses.

Air Pollutants, Occupational↗
PubMed2000

Elevated risk for male breast cancer after occupational exposure to gasoline and vehicular combustion products.

BACKGROUND: Automotive gasoline contains benzene, 1,3-butadiene, 1, 2-dibromoethane and 1,2-dichloroethane, and the combustion products include certain polycyclic aromatic hydrocarbons, all of which have shown mammary gland carcinogenicity in long-term bioassays. It is the aim of this paper to investigate whether men occupationally exposed to gasoline and its combustion products have an elevated risk of breast cancer. METHODS: A nationwide register based case control study on male breast cancer morbidity was established among members of a pension fund, compulsory for all employees. Employment histories were reconstructed for each of 230 cases and 12,880 control subjects based on computerized records. The odds ratios, adjusted for socioeconomic status, were estimated by conditional logistic regression analysis. RESULTS: When a lag time of at least 10 years was included, the odds ratio for breast cancer among men with over three months of employment in trades with potential exposure to gasoline and combustion products was 2.5 (95% confidence interval: 1.3-4.5). Among men younger than 40 years at the time of first employment, the odds ratio was 5.4 (2.4-11.9). CONCLUSIONS: This study supports the hypothesis that occupational exposure to gasoline vapors and combustion products may play a role in the causation of male breast cancer. This hypothesis warrants further evaluation particularly in women.

Adult↗
PubMed1999

Genotoxicity of complex PAH mixtures recovered from contaminated lake sediments as assessed by three different methods.

Although human exposure generally occurs to mixtures of chemicals, limited toxicological information is available to characterize the potential interactions of the components of environmental mixtures. This study was conducted to compare the genotoxicity of chemically characterized polycyclic aromatic hydrocarbon (PAH) mixtures using in vitro and in vivo techniques. A total of three extracts (E1-E3) were selected from sediment samples collected from a lake adjacent to an abandoned coal gasification site. Sediments were collected on a grid moving downstream and away from the most likely source of PAH contamination, with E1 collected closest to the shore, E2 at an intermediate distance, and E3 furthest from the shore. The sediment samples were extracted in methylene chloride and methanol, dried, and redissolved in an appropriate solvent for evaluation in a battery of genotoxicity assays. Samples were evaluated for their ability to produce point mutations in bacteria and DNA adducts in vitro without metabolic activation or in vivo. Samples were also analyzed using GC/MS. Sample E1 had both the highest concentration of benzo(a)pyrene (BP) (46.5 ppm) and carcinogenic PAHs and, using 32P-postlabeling, induced the highest adduct levels overall in vitro and in vivo. Sample E2, which had a BP concentration of 14 ppm, induced the greatest number of revertants in the bacterial mutagenicity assay. Sample E3, which had the lowest level of carcinogenic PAHs and BP, induced the lowest adduct levels. However, E3 was capable of inducing a positive genotoxic response in bacteria (with S9), although the slope of the response at lower doses was less than that of E2. The in vivo data showed that the major adduct formed by E1 and E2 was a BP adduct. This information could not have been obtained with the Salmonella or in vitro postlabeling tests. Among internal organs, the extracts of all three samples induced the greatest adduct levels in the lung, similarly to previous complex PAH mixtures studied. These data demonstrate the limitations of predicting genotoxic or carcinogenic potential based on chemical analysis or a single biological test. The results suggest that mixture interactions, cytotoxicity and metabolism are likely to have an influence on the potential of a complex mixture of chemicals to produce a carcinogenic effect. In addition, the concentration of genotoxic PAHs and both in vitro and in vivo DNA adduct formations were decreased with increasing distance from the shoreline.

Animals↗
PubMedDate not supplied

An on-line reduction HPLC/chemiluminescence detection system for nitropolycyclic aromatic hydrocarbons and metabolites.

Various metal powders were batch screened as possible on-line reducers for nitropolycyclic aromatic hydrocarbons (NPAHs), in particular 1,3-dinitropyrene (1,3-DNP, 1,8-DNP and 1-nitropyrene (1-NP) and it metabolites. Zinc was found to be an excellent reducer in chemiluminescent compatible mobile phases without any associated disposal problems. Zinc reducer column parameters, namely pH, buffer concentration, packing composition (zinc:glass beads or zinc:silica gel) and column length were all optimized for the HPLC determination system with chemiluminescence detection, named NPAH analyser. The system consisted of three pumps, sample injector, reducer column packed with zinc:glass beads switching valve with a cutting loop, separation column (ODS), chemiluminescence detector and integrator. The mobile phase for the separation column and chemiluminescence reagent solution were respectively acetonitrile:imidazole-HClO44 and acetonitrile containing bis(2,4,6-trichlorophenyl)oxalate and H2O2. When the reducer column was introduced before the separation column, 1,3-, 1,6- 1,8-DNPs and 1-NP in benzene:ethanol extracts from airborne particulates were separately determined with detection limits of 2-50 fmol, respectively, in a 100 microL sample. When the reducer column was introduced just after the separation column, 1-NP, 1-nitrosopyrene and 1-aminopyrene in the incubation mixture of 1-NP and the Salmonella typhimurium YG1021 strain were separately determined with detection limits as low as sub fmol levels. 1,8-DNP and its metabolite were also separately determined in the incubation mixture of 1,8-DNP and the S. typhimurium TA98 strain.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

Evaluation of the dermal carcinogenic potential of re-refined base stocks using the modified Ames assay, PAC analysis and the 32P-postlabeling assay for DNA adduct induction.

The standard method for assessing the carcinogenicity of lubricating oil base stocks is the mouse skin-painting bioassay. This assay has the advantage of directly measuring the endpoint of interest, dermal carcinogenicity, but has the drawback of being time-consuming and expensive. For this reason, a variety of biological and chemical assays have been developed as predictive alternatives to the in vivo assay. This publication describes the application of three such methods to the assessment of carcinogenic potential of hydrotreated, re-refined oils: the modified Ames test, the analytical determination of 3-7-ring polycyclic aromatic compound content and the 32P-postlabeling assay for DNA adduct induction.

Animals↗
PubMed2002

Stereocontrolled synthesis of angularly fused tricyclic ring systems by means of 1-metalla-1,3,5-hexatrienes (M=Cr, W).

An efficient pathway for the stereocontrolled synthesis of functionalized, angularly fused tricyclic ring systems from readily available (1-alkynyl)carbene complexes [(OC)(5)M=C(OEt)C(triple bond)CR] (M=Cr, W; R=Ph, c-C(6)H(9)) is described. The synthesis involves the formation of a 1-metalla-1,3,5-hexatriene from the (1-alkynyl)carbene tungsten complex [(OC)(5)W=C(OEt)C(triple bond)C-c-C(6)H(9)] and a secondary amine, and its thermally induced pi-cyclization to a tetrahydroindene, which undergoes a spontaneous isomerization to another tetrahydroindene. Condensation of these tetrahydroindenes with pyran-2-ylidene complexes derived from (1-alkynyl)carbene complexes [(OC)(5)M=C(OEt)C(triple bond)CPh] (M=Cr, W) proceeds smoothly giving angularly fused tricyclic ring systems, rearrangement of which may generate spiro(cyclopentane-1,1-indanes) as side products. The synthesis is highly versatile and can be applied to the formation of various ring systems, such as steroid-type ring skeletons.

Molecular Structure↗
PubMed1993

Human respiratory disease: environmental carcinogens and lung cancer risk.

Inhalatory intake of environmental agents may have adverse effects on health, the lung being the first target. Therefore, an increased risk of lung cancer and respiratory disease is in general considered as an indication of environmental health problems related to exposure to industrial emissions, traffic exhaust and smog. Classical epidemiological studies of the association between exposure to ambient air pollutants and respiratory dysfunctions and studies with laboratory animals have failed to demonstrate the distinct proof of risk for the general population that would be needed to form a basis for high impact environmental policy measures. Here, as an example, we describe the uncertainty in assessing risks of lung cancer associated with environmental exposure to polycyclic aromatic hydrocarbons. The recently introduced methodology of molecular cancer epidemiology is considered to yield more information on the relationship between exposure to environmental carcinogens and tumour development. Recent advances in the study of carcinogen (polycyclic aromatic hydrocarbon) dosimetry at the DNA level in combination with proto-oncogenic activation in humans are described.

Animals↗
PubMedDate not supplied

A novel multipurpose Excel tool for equilibrium speciation based on Newton-Raphson method and on a hybrid genetic algorithm.

A new algorithm for simulation of chemical equilibria is developed, based on classical Newton-Raphson method applied to mass balance. This tool, named EST (Equilibrium Speciation Tool), is improved by using a robust Genetic Algorithm. In addition, EST works by using Excel spreadsheets and therefore offers the innovation of a great simplicity and versatility. In fact, it allows the users to simulate, or to obtain from experimental data, desired chemical-physical parameters as well as to interact with other available or freely created Excel tools. The reliability of this utility is here proved by comparison with some published data by other authors, concerning both complicated homogeneous and heterogeneous equilibria. In addiction its flexibility is tested computing thermodynamic parameters by using experimental calorimetric data referred to the complex formation of cobalt(II) with a macrocyclic ligand. A brief review and comparison of the relative robustness and quickness of main numerical methods are also reported.

Algorithms↗
PubMed2001

Outdoor exposure to airborne polycyclic organic matter and adverse reproductive outcomes: a pilot study.

BACKGROUND: To investigate the association between outdoor airborne polycyclic organic matter (POM) and adverse reproductive outcomes in New Jersey, we used a cross-sectional design combining air quality data from the USA EPA Cumulative Exposure Project and individual data on pregnancy outcomes from birth and fetal death certificates at the census tract level. METHODS: After excluding plural births and chromosomal anomalies, 221,406 live births and 1,591 fetal deaths registered in New Jersey during the years of 1990 and 1991 were included. The exposure estimates were derived from modeled average POM concentrations for each census tract in the state. RESULTS: After adjustment for potential confounders, the odds ratios (OR) for very low birth weight for the highest exposure compared to the lowest exposure group was 1.31 (95% CI 1.15-1.51); among term births, high POM exposure was associated with low birth weight OR = 1.31 (95% CI 1.21-1.43), with fetal death OR = 1.19 (95% CI 1.02-1.39) and with premature birth OR = 1.25 (95% CI 1.19-1.31). The univariate stratified analyses suggested effect modification of all observed associations by maternal alcohol consumption. CONCLUSIONS: This study found associations between outdoor exposure to modeled average airborne POM and several adverse pregnancy outcomes. The data and methods utilized in this pilot study may be useful for identifying hazardous air pollutants requiring in-depth investigation.

Air Pollutants↗
PubMed2001

A historical cohort mortality study among shipyard workers in Genoa, Italy.

BACKGROUND: A historical cohort mortality study was conducted among 3984 shipyard workers assigned to ship repair, refitting, and construction in the harbor of Genoa, Italy, between 1960 and 1981. These workers were exposed to asbestos fibers, welding fumes and gases, silica dust, polycyclic aromatic hydrocarbons, and solvents. METHODS: Workers were classified in 20 different job-titles depending upon the type of activity. Standardized mortality ratios (SMRs) were computed using male residents of the Province of Genoa as the referent population. RESULTS AND CONCLUSIONS: For the whole cohort significantly increased SMRs were detected for all causes, all cancers, liver, larynx, lung, pleural and bladder cancers, respiratory tract diseases, and cirrhosis of the liver. The analysis by job-title showed increased SMRs not only for pleural cancer, but also for lung, laryngeal cancers and respiratory tract diseases in occupations entailing heavy asbestos exposure. Bladder and liver cancers and liver cirrhosis mortality also appeared to be related to occupational exposure.

Adult↗