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Toxicology Letters Oct 2019Organophosphates are chemical pollutants that are existed widely in the environment, but the reactions of these agents with blood proteins are still not fully clarified....
Organophosphates are chemical pollutants that are existed widely in the environment, but the reactions of these agents with blood proteins are still not fully clarified. The current story was to analyze the static and dynamic interactions between human serum albumin (HSA) and phenthoate and then uncover the impact of the conjugations on the acetylcholinesterase (AChE) activity at the microscopic scale. Experimental results revealed clearly that the bioconjugate of the HSA-phenthoate was yielded and the conformation of HSA can produce autoregulation during the reaction. Dynamic reaction processes suggested that the conformational flexibility of the specific protein domain was changed significantly in equilibrium, and the electrostatic interaction energy played a major role in total energy of the biosystems, which matches the results of wet experiment and molecular docking. We also found that the modes of homologous proteins-phenthoate have obvious distinctions, and this point is related closely to the local dynamic flexibility of biomolecular structures. Additionally, the degree of bioconjugation of the HSA-phenthoate is positively associated with the enzymatic activity of target AChE, which may be attributed to the competitive reactions between HSA and AChE. Evidently, this scenario could provide useful molecular information for the systematic exploration of the toxicokinetics of organophosphorus compounds.
Topics: Acetylcholinesterase; Binding Sites; Binding, Competitive; Cholinesterase Inhibitors; Humans; Insecticides; Models, Biological; Molecular Docking Simulation; Organothiophosphorus Compounds; Protein Binding; Protein Conformation; Protein Domains; Serum Albumin, Human
PubMed: 31362050
DOI: 10.1016/j.toxlet.2019.07.025 -
Ecotoxicology and Environmental Safety Oct 1985The toxic potencies of carbaryl and phenthoate were studied on a freshwater fish, Channa punctatus, by evaluating the percentage kill at different concentrations of... (Comparative Study)
Comparative Study
The toxic potencies of carbaryl and phenthoate were studied on a freshwater fish, Channa punctatus, by evaluating the percentage kill at different concentrations of exposure. To determine the combined action of these compounds, LC studies were performed by using carbaryl (C) and phenthoate (P) mixtures in the 1:3, 1:1, and 3:1 ratios. The 48-hr LC50 values obtained by calculating the data with probit method were 8.71 ppm for carbaryl and 0.473 ppm for phenthoate. Similar values on the mixtures were 0.717, 0.741, and 0.750 ppm for 1:3, 1:1, and 3:1, carbaryl:phenthoate mixtures. The toxicities of carbaryl and phenthoate have been discussed in relation to sensitivity of the species and their interaction with the target enzyme. Effectiveness of the joint action of carbaryl and phenthoate was determined by measuring three different parameters: the CTC value, the V value, and the CI value. This analysis showed that 3C:1P combination exerted marked synergism, 1C:1P exerted moderate synergism, and 1C:3P showed moderate antagonism.
Topics: Animals; Carbaryl; Dose-Response Relationship, Drug; Drug Synergism; Fishes; Lethal Dose 50; Organothiophosphorus Compounds
PubMed: 3936694
DOI: 10.1016/0147-6513(85)90068-5 -
Environmental Science and Pollution... Oct 2020The risks of the health-associated problems of pesticide-exposed non-target organisms are ubiquitous, therefore an emerging concern to strike the balance between benefit...
The risks of the health-associated problems of pesticide-exposed non-target organisms are ubiquitous, therefore an emerging concern to strike the balance between benefit and risk factors. In the present study, by elucidating multiple biomarkers, the effects of Phenthoate 50 EC on the acute toxicity tests and different pathophysiological changes of common carp (Cyprinus carpio) fingerlings were studied in time- and concentration-dependent manners. The LC of Phenthoate 50 EC for the fish was 7.39 (6.716-8.076) ppm at 96 h. As an indicator of neurotoxicity, compared to the control group, significant (P < 0.01) reduction in brain acetylcholinesterase (AChE) activity was observed, whereas plasma glutamate-oxalacetate transaminase (PGOT) and plasma glutamate pyruvate transaminase (PGPT) activities were increased significantly (P < 0.01) at the doses of 2.22 and 3.69 ppm of Phenthoate 50 EC, respectively. Histopathological changes in the insecticide-treated fish liver suggested the hepatic tissue damages, while alteration of the blood, gills and kidney morphology; progressive decrease (P < 0.05) in the serum calcium levels; and significantly (P < 0.01) decreased blood glucose level at 2.22 and 3.69 or 5.17 ppm of Phenthoate 50 EC demonstrated the oxidative stress and requirement of the up-surging energy demands due to the exposure of this organophosphate chemical. These results advice the modulation caused by this widely used agrochemical on the physiology of aquatic fauna by changing the enzymatic and biochemical indices at cellular level.
Topics: Animals; Carps; Insecticides; Organothiophosphorus Compounds; Water Pollutants, Chemical
PubMed: 32607992
DOI: 10.1007/s11356-020-09697-x -
Journal of Chromatography. A Nov 2002A fast and precise method was developed for the determination of phenthoate and its enantiomeric ratio (ER) in three soil samples. A recently developed sample...
A fast and precise method was developed for the determination of phenthoate and its enantiomeric ratio (ER) in three soil samples. A recently developed sample pretreatment technology--matrix solid-phase dispersion (MSPD) was used to extract phenthoate simply and effectively. MSPD conditions, i.e. solid-phase Florisil amount, water content of Florisil-soil mixture, the constituent and volume of the eluting solvent, were optimized stepwise. The MSPD extract was directly used for quantitative determination of phenthoate by silica-based high-performance liquid chromatography (HPLC) with UV detection. The recoveries of phenthoate from three different types of soils fortified at three levels of 0.1, 1, 10 microg/g ranged from 75 to 94% with RSDs of 1.5-6.5%. On this basis, phenthoate was further isolated from the remainder of MSPD extract by silica-based HPLC and then ER determined on HPLC with cellulose tris-3, 5-dimethylphenylcarbamate as chiral stationary phase. The ERs determined in the soils spiked with racemic or enantiomer-enriched phenthoate agreed sufficiently well with those in the corresponding standard solutions. Finally, the proposed method was successfully applied to the study of enantioselective degradation of phenthoate in the three soils under laboratory conditions. High enantioselectivity was observed in the two alkaline soils with (+)-enantiomer degrading faster than the (-)-enantiomer, while there was little to no enantioselectivity in the acidic soil. The methodology can be used to study the enantioselective environmental behavior of chiral pollutants.
Topics: Chromatography, High Pressure Liquid; Organothiophosphorus Compounds; Soil Pollutants; Spectrophotometry, Ultraviolet; Stereoisomerism
PubMed: 12456092
DOI: 10.1016/s0021-9673(02)01342-0 -
Archives of Environmental Contamination... 1976The fate of 32P- and 14C-labeled O,O-dimethyl S-[alpha-(carboethoxy)benzyl] phosphorodithioate (phenthoate) was determined in citrus, water, and upon exposure to air and...
The fate of 32P- and 14C-labeled O,O-dimethyl S-[alpha-(carboethoxy)benzyl] phosphorodithioate (phenthoate) was determined in citrus, water, and upon exposure to air and sunlight. The products recovered from citrus and glass plates exposed to sunlight were unchanged phenthoate, phenthoate oxon, demethyl phenthoate, mandelic acid, bis-[alpha-(carboethoxy)benzyl] disulfide, O,O-dimethyl phosphorothioic and phosphorodithioic acid. Similar products generally were found in citrus leaf and fruit extracts. Phenthoate was fairly stable in phosphate buffered water with a half-life of approximately 12 days at pH 8.0. The major hydrolysis products were phenthoate acid, demethyl phenthoate and demethyl phenthoate oxon.
Topics: Air; Biodegradation, Environmental; Carbon Radioisotopes; Chemical Phenomena; Chemistry; Chromatography, Thin Layer; Citrus; Fresh Water; Hydrolysis; Insecticides; Organothiophosphorus Compounds; Phosphorus Radioisotopes; Photochemistry; Plants; Sunlight; Time Factors
PubMed: 1015864
DOI: 10.1007/BF02220891 -
Journal of Agricultural and Food... Jun 2000Residual malathion in wheat was estimated at a lower value when analysis was performed by extraction with acetone after addition of water to swell the wheat, according... (Comparative Study)
Comparative Study
Residual malathion in wheat was estimated at a lower value when analysis was performed by extraction with acetone after addition of water to swell the wheat, according to the Japanese Bulletin Method. The supernatant of the wheat homogenate showed degradation not only of malathion but also of phenthoate. Malathion and phenthoate were not degraded by the boiled supernatant of the wheat homogenate. It was presumed for this reason that glutathione reductase (GR; EC 1.6. 4.2) in the wheat degraded malathion. The following results were obtained: (1) GR originating in wheat could degrade malathion and phenthoate. (2) The degradation of malathion by the GR was inhibited by excessive GSSG. (3) There was a high correlation between GR activity and malathion degradation activity of the supernatant of wheat homogenates. It is likely that GR acted on the specific structure of malathion and phenthoate, the S=P-S bond, and the blanch structure bonding with the sulfur atom. Following the above, extraction with acetone after addition of water (the Japanese Bulletin Method) should be replaced by extraction with pure organic solvent and without addition of water for swelling.
Topics: Biodegradation, Environmental; Glutathione Reductase; Insecticides; Malathion; Organothiophosphorus Compounds; Pesticide Residues; Seeds; Triticum
PubMed: 10888576
DOI: 10.1021/jf990545g -
Environmental and Molecular Mutagenesis 1997Cidial, an organophosphorous insecticide (also known as phenthoate), was tested for its genotoxic effect on both maternal and fetal cells. Cidial was administered at...
Cidial, an organophosphorous insecticide (also known as phenthoate), was tested for its genotoxic effect on both maternal and fetal cells. Cidial was administered at three different dose levels (53.5, 106.9, and 171 mg/kg) to pregnant mice on day 16 of gestation. Maternal bone marrow and embryonic liver cells were examined for chromosomal aberrations and cellular proliferation. Cidial was found to increase the percentage of cells with chromosomal aberrations in both mothers and fetuses. It also significantly inhibited the rate of mitotic activity of both maternal and fetal cells, with the inhibitory effect being more appreciable in fetal cells than in maternal cells. The data indicate that cidial, which is widely used in rural areas, is hazardous to both mothers and their transplacentally exposed babies.
Topics: Animals; Bone Marrow; Bone Marrow Cells; Cell Division; Chromosome Aberrations; Chromosome Disorders; Dose-Response Relationship, Drug; Female; Fetus; Insecticides; Liver; Male; Mice; Mitotic Index; Mutagenicity Tests; Mutagens; Organothiophosphorus Compounds; Pregnancy
PubMed: 9020307
DOI: No ID Found -
Archives of Environmental Contamination... Jul 1981The metabolism and fate of phenyl ring-labeled 14C-phenthoate (0,0-dimethyl S-[alpha-(carboethoxy)benzyl] phosphorodithioate) was examined in the Valencia orange fruit...
The metabolism and fate of phenyl ring-labeled 14C-phenthoate (0,0-dimethyl S-[alpha-(carboethoxy)benzyl] phosphorodithioate) was examined in the Valencia orange fruit with emphasis on the characterization of bound phenthoate residues in the fruit peel. The products recovered from the citrus fruit wash were unchanged phenthoate, phenthoate oxon, demethyl phenthoate, phenthoate acid, ethyl mandelate, and mandelic acid. The same products, with the exception of phenthoate oxon, were found in the acetone extract of the fruit peel. Enzymatic hydrolysis of the bound residue in the peel with beta-glucosidase, followed by acidic and basic hydrolysis gave ethyl mandelate as the major product, followed by mandelic acid, demethyl phenthoate and phenthoate acid. Phenthoate was metabolized and conjugated in citrus fruits into detoxication products.
Topics: Citrus; Insecticides; Organothiophosphorus Compounds; Pesticide Residues
PubMed: 7259311
DOI: 10.1007/BF01055446 -
Journal of Agricultural and Food... 1981
Topics: Air Pollutants; Citrus; Insecticides; Organothiophosphorus Compounds; Pesticide Residues; Plants; Soil Pollutants
PubMed: 7204748
DOI: 10.1021/jf00103a034 -
Journal of Environmental Sciences... 2004Adsorption of phenthoate and acetochlor onto kaolin, montmorillonite, bentonite clays and respective organoclays prepared by the exchange of quaternary ammonium as... (Comparative Study)
Comparative Study
Adsorption of phenthoate and acetochlor onto kaolin, montmorillonite, bentonite clays and respective organoclays prepared by the exchange of quaternary ammonium as tetradecyltrimethyl ammonium bromide(TTAB), dodecyltrimethylammonium bromide (DTAB), and cetylpyridinium chloride (CPC) were studied. The adsorption equilibrium data points were fitted to Freundlich isotherm equations. The adsorption of phenthoate and acetochlor were significantly enhanced by surfactant treatment of the clays. The amount of both pesticides adsorbed per unit mass of organoclay followed the order of TTA-kaolin < TTA-montmorillonite < TTA-bentonite, which is inconsistent with the organic carbon content of the clays. The removal efficiency of organomontmorillonite to treat acetochlor is in the order of CP (C16)-montmorillonite > TTA (C14)-montmorillonite > DTA (C12)-montmorillonite. Phenthoate is adsorbed to greater extent than acetochlor by each adsorbent, which may be due to the higher hydrophobicity of phenthoate, indicating considerable hydrophobic interaction between adsorbent/adsorbate systems.
Topics: Adsorption; Aluminum Silicates; Bromides; China; Chromatography, High Pressure Liquid; Organothiophosphorus Compounds; Pesticides; Quaternary Ammonium Compounds; Surface-Active Agents; Toluidines; Water Pollution, Chemical
PubMed: 15559802
DOI: No ID Found