Appendix 2-5: Rejected ecotox bibliography for Chlorpyrifos

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we employed a three-phase partitioning system where silicone (polydimethylsiloxane, PDMS) serves as a third phase to determine partitioning between water and colloids and acts at the same time as a dosing device for hydrophobic chemicals. The applicability of this method was demonstrated with bovine serum albumin (BSA). Measured binding constants (KBSAw) for chlorpyrifos, methoxychlor, nonylphenol, and pyrene were in good agreement with an established quantitative structure--activity relationship (QSAR). A fifth compound, fluoxypyr-methyl-heptyl ester, was excluded from the analysis because of apparent abiotic degradation. The PDMS depletion method was then used to determine partition coefficients for test chemicals in rainbow trout (Oncorhynchus mykiss) liver S9 fractions (KS9w) and blood plasma (Kbloodw). Measured KS9w and Kbloodw values were consistent with predictions obtained using a mass-balance model that employs the octanol--water partition coefficient (Kow) as a surrogate for lipid partitioning and KBSAw to represent protein binding. For each compound, Kbloodw was substantially greater than KS9w, primarily because blood contains more lipid than liver S9 fractions (1.84% of wet weight vs 0.051%). Measured liver S9 and blood plasma binding parameters were subsequently implemented in an in vitro to in vivo extrapolation model to link the in vitro liver S9 metabolic degradation assay to in vivo metabolism in fish. Apparent volumes of distribution (Vd) calculated from the experimental data were similar to literature estimates. However, the calculated binding ratios (fu) used to relate in vitro metabolic clearance to clearance by the intact liver were 10 to 100 times lower than values used in previous modeling efforts. Bioconcentration factors (BCF) predicted using the experimental binding data were substantially higher than the predicted values obtained in earlier studies and correlated poorly with measured BCF values in fish. One possible explanation for this finding is that chemicals bound to proteins can desorb rapidly and thus contribute to metabolic turnover of the chemicals. This hypothesis remains to be investigated in future studies, ideally with chemicals of higher hydrophobicity.
Keywords: Dialysis
Keywords: Data processing
Keywords: Silicones
Keywords: Colloids
Keywords: Lipids
Keywords: Oncorhynchus mykiss
Keywords: Hydrophobicity
Keywords: Pyrene
Keywords: Esters
Keywords: Models
Keywords: Chlorpyrifos
Keywords: Microdialysis
Keywords: Blood
Keywords: polydimethylsiloxane
Keywords: Bioaccumulation
Keywords: Bovine serum albumin
Keywords: Kinetics
Keywords: Nonylphenol
Keywords: Liver
Keywords: Methoxychlor
Keywords: X 24330:Agrochemicals
Keywords: Toxicology Abstracts
Date revised - 2011-10-01
Language of summary - English
Pages - 1134-1143
ProQuest ID - 899167048
SubjectsTermNotLitGenreText - Dialysis; Data processing; Colloids; Silicones; Lipids; Hydrophobicity; Pyrene; Esters; Models; Microdialysis; Chlorpyrifos; Blood; polydimethylsiloxane; Bioaccumulation; Bovine serum albumin; Kinetics; Nonylphenol; Liver; Methoxychlor; Oncorhynchus mykiss
Last updated - 2012-12-03
British nursing index edition - Chemical Research in Toxicology [Chem. Res. Toxicol.]. Vol. 24, no. 7, pp. 1134-1143. 23 May 2011.
Corporate institution author - Escher, Beate I; Dyer, Scott; Embry, Michelle R; Halder, Marlies; Kwon, Jung-Hwan; Johanning, Karla; Oosterwijk, Mattheus T T; Rutishauser, Sibylle
DOI - 08591a38-354c-4465-b50ecsaobj201; 15629114; 0893-228X English

389. Espinal, A. ; Quijano, J.; Hunt, C.; Lorenzo, R.; Mulligan, C.; Sampson, M.; Sauchelli, M., and Patnaik, P. K. A 10 Base-Pair Sequence Within Domain Iii of the Gpeet Procyclin Promoter Is Essential for the Autonomous Replication of a Plasmid in Procyclic Trypanosoma Brucei.

Rec #: 51509
Notes: Chemical of Concern: CPY
Abstract: COMMENTS: Cites: EMBO J. 1991 Nov;10(11):3379-86 (medline /1840521)
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MESH HEADINGS: Base Sequence
MESH HEADINGS: Life Cycle Stages
MESH HEADINGS: Membrane Glycoproteins/*genetics
MESH HEADINGS: Mutagenesis, Insertional
MESH HEADINGS: Plasmids/*genetics
MESH HEADINGS: *Promoter Regions, Genetic
MESH HEADINGS: Protozoan Proteins/*genetics
MESH HEADINGS: Trypanosoma brucei brucei/*genetics/growth &
MESH HEADINGS: development eng

390. Esralew, Rachel a; Andrews, William J; Smith, Sjerrod, and Esralew, Rachel A. Evaluation and Trends of Land Cover, Streamflow, and Water Quality in the North Canadian River Basin Near Oklahoma City, Oklahoma, 1968-2009. 2011.

Rec #: 47529
Keywords: FATE
Notes: Chemical of Concern: CPY
Abstract: Abstract: The U.S. Geological Survey, in cooperation with the city of Oklahoma City, collected water-quality samples from the North Canadian River at the streamflow-gaging station near Harrah, Oklahoma (Harrah station), since 1968, and at an upstream streamflow-gaging station at Britton Road at Oklahoma City, Oklahoma (Britton Road station), since 1988. Statistical summaries and frequencies of detection of water-quality constituent data from water samples, and summaries of water-quality constituent data from continuous water-quality monitors are described from the start of monitoring at those stations through 2009. Differences in concentrations between stations and time trends for selected constituents were evaluated to determine the effects of: (1) wastewater effluent discharges, (2) changes in land-cover, (3) changes in streamflow, (4) increases in urban development, and (5) other anthropogenic sources of contamination on water quality in the North Canadian River downstream from Oklahoma City. Land-cover changes between 1992 and 2001 in the basin between the Harrah station and Lake Overholser upstream included an increase in developed/barren land-cover and a decrease in pasture/hay land cover. There were no significant trends in median and greater streamflows at either streamflow-gaging station, but there were significant downward trends in lesser streamflows, especially after 1999, which may have been associated with decreases in precipitation between 1999 and 2009 or construction of low-water dams on the river upstream from Oklahoma City in 1999. Concentrations of dissolved chloride, lead, cadmium, and chlordane most frequently exceeded the Criterion Continuous Concentration (a water-quality standard for protection of aquatic life) in water-quality samples collected at both streamflow-gaging stations. Visual trends in annual frequencies of detection were investigated for selected pesticides with frequencies of detection greater than 10 percent in all water samples collected at both streamflow-gaging stations. Annual frequencies of detection of 2,4-dichlorophenoxyacetic acid and bromacil increased with time. Annual frequencies of detection of atrazine, chlorpyrifos, diazinon, dichlorprop, and lindane decreased with time. Dissolved nitrogen and phosphorus concentrations were significantly greater in water samples collected at the Harrah station than at the Britton Road station, whereas specific conductance was greater at the Britton Road station. Concentrations of dissolved oxygen, biochemical oxygen demand, and fecal coliform bacteria were not significantly different between stations.
Start Page: 76
End Page: 76
Keywords: Chlorophylls
Keywords: water quality
Keywords: USA, New Mexico, Canadian R.
Keywords: SW 3040:Wastewater treatment processes
Keywords: AQ 00006:Sewage
Keywords: Water sampling
Keywords: Heavy metals
Keywords: Water Analysis
Keywords: Water Sampling
Keywords: Q5 01502:Methods and instruments
Keywords: Water quality
Keywords: Freshwater
Keywords: Streams
Keywords: Dissolved oxygen
Keywords: Flow rates
Keywords: USA, Oklahoma, Oklahoma City
Keywords: USA, Oklahoma
Keywords: upstream
Keywords: Roads
Keywords: Urban areas
Keywords: Rivers
Keywords: Diurnal variations
Keywords: Coliforms
Keywords: Conductance
Keywords: Dissolved Oxygen
Keywords: Water Quality
Keywords: Streamflow
Keywords: River basins
Keywords: Fecal Coliforms
Keywords: Land use
Keywords: Stream flow
Keywords: Pollution Abstracts; Aqualine Abstracts; ASFA 3: Aquatic Pollution & Environmental Quality; Water Resources Abstracts
Keywords: Pesticides
Keywords: Biochemical oxygen demand
Date revised - 2011-11-01
Language of summary - English
Location - USA, Oklahoma; USA, New Mexico, Canadian R.; USA, Oklahoma, Oklahoma City
Pages - 76
ProQuest ID - 907193741
SubjectsTermNotLitGenreText - Chlorophylls; Heavy metals; Pesticides; River basins; Biochemical oxygen demand; Fecal Coliforms; Water quality; Dissolved oxygen; Stream flow; Diurnal variations; water quality; upstream; Water sampling; Streams; Land use; Flow rates; Urban areas; Rivers; Coliforms; Roads; Conductance; Water Analysis; Water Sampling; Water Quality; Dissolved Oxygen; Streamflow; USA, Oklahoma; USA, New Mexico, Canadian R.; USA, Oklahoma, Oklahoma City; Freshwater
Last updated - 2012-12-14
British nursing index edition - Scientific Investigations Report. U.S. Geological Survey. no. 2011-5117, 76 p. 2011.
Corporate institution author - Esralew, Rachel A; Andrews, William J; Smith, SJerrod
DOI - 470d7d45-38d7-45ec-8681csaobj201; 16041889; NO1103118 English

391. Essumang, D K; Dodoo, D K; Adokoh, C K; Fumador, E a, and Essumang, D K. Analysis of Some Pesticide Residues in Tomatoes in Ghana. 2008 Jul; 14, (4): 796-806.

Rec #: 42079
Keywords: SURVEY
Notes: Chemical of Concern: CPY
Abstract: Abstract: Pesticide residues, both natural and synthetic, can be found in most of the things we eat, for example, fruits, vegetables, bread, meat, poultry, fish, and the processed foods made from them. Some of this pesticide contamination is legal, but does this mean it is safe? Much of it is illegal, with residues found in excess of regulatory safe levels. Identifying and determining the level of trace contaminants in our food and environment is critical in protecting and improving human health and the environment. This study evaluates the residue levels of select pesticides used on tomato crops in Ghana that are likely to have accumulated in the tomatoes during application. The results obtained confirm that pesticide residues were indeed present in the tomatoes and further analysis quantified the amount present. Analysis of some organochlorine and organophosphorus residue levels in the fruits indicated that chlorpyrifos, which is an active ingredient of pesticides registered in Ghana under the trade name dursban 4E or terminus 480 EC for use on vegetables, has the greatest residue level of 10.76 mg/kg. The lowest residue level observed was that of pirimiphos-methyl with 0.03 mg/kg. Human health risk assessment was performed on the results obtained from the analysis using Human Health Evaluation computerized software-RISC 4.02. The risk assessment showed cancer risk for adults and children due to the presence of endosulfan and chlopyrifos. Endosulfan is not registered in Ghana as a pesticide for use on vegetables, therefore the detection of endosulfan in several samples indicates misuse of agrochemicals among Ghanaian farmers.
Keywords: Risk assessment
Keywords: Fruits
Keywords: Ghana
Keywords: Poultry
Keywords: Organochlorine compounds
Keywords: tomato
Keywords: poultry
Keywords: Pesticide residues
Keywords: fruits
Keywords: Food contamination
Keywords: Pollution Abstracts; Risk Abstracts; Health & Safety Science Abstracts
Keywords: Children
Keywords: Cancer
Keywords: Crops
Keywords: Endosulfan
Keywords: Chlorpyrifos
Keywords: Lycopersicon esculentum
Keywords: H 5000:Pesticides
Keywords: Pesticides
Keywords: R2 23060:Medical and environmental health
Keywords: Fish
Date revised - 2009-08-01
Language of summary - English
Location - Ghana
Pages - 796-806
ProQuest ID - 20793415
SubjectsTermNotLitGenreText - Risk assessment; Fruits; Poultry; Organochlorine compounds; poultry; Pesticide residues; fruits; Food contamination; Children; Cancer; Crops; Endosulfan; Chlorpyrifos; Pesticides; Fish; Lycopersicon esculentum; Ghana
Last updated - 2011-12-14
British nursing index edition - Human and Ecological Risk Assessment [Hum. Ecol. Risk Assess.]. Vol. 14, no. 4, pp. 796-806. Jul 2008.
Corporate institution author - Essumang, D K; Dodoo, D K; Adokoh, C K; Fumador, E A
DOI - MD-0010232855; 10310275; 1080-7039 English

392. Est+_vez, Esmeralda; Cabrera, Mar+ a del Carmen; Molina-D+ˇaz, Antonio; Robles-Molina, Jos+, and Palacios-D+ˇaz, Mar+ a del Pino. Screening of emerging contaminants and priority substances (2008/105/EC) in reclaimed water for irrigation and groundwater in a volcanic aquifer (Gran Canaria, Canary Islands, Spain). 2012 Sep 1-; 433, (0): 538-546.

Rec #: 2920
Keywords: FATE
Notes: Chemical of Concern: CPY
Abstract: In semiarid regions, reclaimed water can be an important source of emerging pollutants in groundwater. In Gran Canaria Island, reclaimed water irrigation has been practiced for over thirty years and currently represents 8% of water resources. The aim of this study was to monitor contaminants of emerging concern and priority substances (2008/105/EC) in a volcanic aquifer in the NE of Gran Canaria where the Bandama Golf Course has been sprinkled with reclaimed water since 1976. Reclaimed water and groundwater were monitoring quarterly from July 2009 to May 2010. Only 43% of the 183 pollutants analysed were detected: 42 pharmaceuticals, 20 pesticides, 12 polyaromatic hydrocarbons, 2 volatile organic compounds and 2 flame retardants. The most frequent compounds were caffeine, nicotine, chlorpyrifos ethyl, fluorene, phenanthrene and pyrene. Concentrations were always below 50 ng LęĆ 1, although some pharmaceuticals and one pesticide, cholrpyrifos ethyl, were occasionally detected at higher concentrations. This priority substance for surface water exceeded the maximum threshold (0.1 ++g LęĆ 1) for pesticide concentration in groundwater (2006/118/EC). Sorption and degradation processes in soil account for more compounds being detected in reclaimed water than in groundwater, and that some contaminants were always detected in reclaimed water, but never in groundwater (flufenamic acid, propyphenazone, terbutryn and diazinon). Furthermore, erythromycin was always detected in reclaimed water (exceeding occasionally 0.1 ++g LęĆ 1), and was detected only once in groundwater. In contrast, some compounds (phenylephrine, nifuroxazide and miconazole) never detected in reclaimed water, were always detected in groundwater. This fact and the same concentration range detected for the groups, regardless of the water origin, indicated alternative contaminant sources (septic tanks, agricultural practices and sewerage breaks). The widespread detection of high adsorption potential compounds, and the independence of concentration with origin and depths, indicates the existence of preferential flows phenomena as potential contamination route in volcanic fractured materials. Emerging contaminants/ Reclaimed water/ Groundwater/ Irrigation/ Volcanic zone/ Chlorpyrifos ethyl

393. Estevan, Carmen; Vilanova, Eugenio, and Sogorb, Miguel A. Chlorpyrifos and its metabolites alter gene expression at non-cytotoxic concentrations in D3 mouse embryonic stem cells under in vitro differentiation: Considerations for embryotoxic risk assessment. 2013 Feb 13-; 217, (1): 14-22.

Rec #: 560
Keywords: IN VITRO
Notes: Chemical of Concern: CPY
Abstract: The effects of organophosphate insecticide chlorpyrifos (CPF) on development are currently under discussion. CPF and its metabolites, chlorpyrifos-oxon (CPO) and 3,5,6-trichloro-2-pyridinol (TClP), were more cytotoxic for D3 mouse embryonic stem cells than for differentiated fibroblasts 3T3 cells. Exposure to 10 ++M CPF and TClP and 100 ++M CPO for 12 h significantly altered the in vitro expression of biomarkers of differentiation in D3 cells. Similarly, exposure to 20 ++M CPF and 25 ++M CPO and TClP for 3 days also altered the expression of the biomarkers in the same model. These exposures caused no significant reduction in D3 viability with mild inhibition of acetylcholinesterase and neuropathy target esterase by CPF and severe inhibition by CPO. We conclude that certain in vivo exposure scenarios are possible, which cause inhibition of acetylcholinesterase but without clinical symptoms that reach high enough systemic CPF concentrations able to alter the expression of genes involved in cellular differentiation with potentially hazard effects on development. Conversely, the risk for embryotoxicity by CPO and TClP was very low because the required exposure would induce severe cholinergic syndrome. Chlorpyrifos/ Chlorpyrifos-oxon/ Embryonic stem cell/ Differentiation/ Risk assessment

394. Estevez, J. and Vilanova, E. Model equations for the kinetics of covalent irreversible enzyme inhibition and spontaneous reactivation: Esterases and organophosphorus compounds . 2009; 39, (5): 427-448.

Rec #: 59859
Keywords: MODELING
Notes: Chemical of Concern: CPY
Abstract: Abstract: Type B carboxylesterases (acetylcholinesterases, neuropathy target esterase, serine peptidases), catalyse the hydrolysis of carboxyl-ester substrates by formation of a covalent acyl-enzyme intermediate and subsequent cleavage and release of the acyl group. Organophosphorus compounds, carbamates, and others exert their mechanism of neurotoxicity by permanent covalent organophosphorylation or carbamylation at the catalytic site of carboxylesterases. Classical kinetic studies converted the exponential kinetic equation to a logarithmic equation for graphic analysis. This process, however, does not allow analysing complex situations. In this paper, kinetic model equations are reviewed and strategies developed for the following cases: (a) single enzyme, with classical linear equation; (b) multi-enzymatic system-discriminating several inhibitor-sensitive and inhibitor-resistant components; (c) 'ongoing inhibition'-high sensitive enzymes can be significantly inhibited during the substrate reaction time, the model equations need a correction; (d) spontaneous reactivation (de-phosphorylation)-one or several components can be simultaneously inhibited and spontaneously reactivated; (e) spontaneous reactivation from starting time with the enzyme being partly or totally inhibited; (f) aging-single enzyme can be inhibited, spontaneously reactivated and dealkylating reaction ('aging') simultaneously occurs; and (g) aging and spontaneous reactivation from starting time with the enzyme being partly or totally inhibited. Analysis of data using the suggested equations allows the deduction of inhibition kinetic constants and the proportions of each of the enzymatic components. Strategies for practical application of the models and for obtaining consistent kinetic parameters, using multi-steps approaches or 3D fitting, are presented.
Keywords: Acetylcholinesterase, aging reaction, carbamates, dephosphorylation,
ISI Document Delivery No.: 541BH

395. European Commission DG Environment. Endocrine Disrupters: Study on Gathering Information on 435 Substances with Insufficient Data. 2002: 279 p.

Rec #: 1830
Keywords: REVIEW
Notes: EcoReference No.: 110504

396. Eyer, Florian; Roberts, Darren M.; Buckley, Nicholas A.; Eddleston, Michael; Thiermann, Horst; Worek, Franz, and Eyer, Peter. Extreme variability in the formation of chlorpyrifos oxon (CPO) in patients poisoned by chlorpyrifos (CPF). 2009 Sep 1-; 78, (5): 531-537.

Rec #: 790
Notes: Chemical of Concern: CPY
Abstract: Chlorpyrifos (CPF) is a pesticide that causes tens of thousands of deaths per year worldwide. Chlorpyrifos oxon (CPO) is the active metabolite of CPF that inhibits acetylcholinesterase. However, this presumed metabolite has escaped detection in human samples by conventional methods (HPLC, GC-MS, LC-MS) until now. A recently developed enzyme-based assay allowed the determination of CPO in the nanomolar range and was successfully employed to detect this metabolite. CPO and CPF were analysed in consecutive plasma samples of 74 patients with intentional CPF poisoning. A wide concentration range of CPO and CPF was observed and the ratio of CPO/CPF varied considerably between individuals and over time. The ratio increased during the course of poisoning from a mean of 0.005 in the first few hours after ingestion up to an apparent steady-state mean of 0.03 between 30 and 72 h. There was a hundred-fold variation in the ratio between samples and the interquartile range (between individuals) indicated over half the samples had a 5-fold or greater variation from the mean. The ratio was independent of the CPF concentration and the pralidoxime regimen. CPO was present in sufficient quantities to explain any observed acetylcholinesterase inhibitory activity. The effectiveness of pralidoxime in reactivating the inhibited acetylcholinesterase is strongly dependent on the CPO concentration. Differences in clinical outcomes and the response to antidotes in patients with acute poisoning may occur due to inter-individual variability in metabolism. Organophosphorus/ Chlorpyrifos/ Poisoning/ Toxicokinetics/ Pralidoxime

397. Eyer, P.; Worek, F.; Thiermann, H., and Eddleston, M. Paradox findings may challenge orthodox reasoning in acute organophosphate poisoning. 2010; 187, (1-3): 270-278.

Rec #: 59879
Notes: Chemical of Concern: CPY
Abstract: Abstract: It is generally accepted that inhibition of acetylcholinesterase (AChE) is the most important acute toxic action of organophosphorus compounds, leading to accumulation of acetylcholine followed by a dysfunction of cholinergic signaling. However, the degree of AChE inhibition is not uniformly correlated with cholinergic dysfunction, probably because the excess of essential AChE varies among tissues. Moreover, the cholinergic system shows remarkable plasticity, allowing modulations to compensate for dysfunctions of the canonical pathway. A prominent example is the living (-/-)AChE knockout mouse. Clinical experience indicates that precipitous inhibition of AChE leads to more severe poisoning than more protracted yet finally complete inhibition. The former situation is seen in
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