Trans Permethrin Research Articles

Bar Adsorbent Microextraction with Carbon-Based Sorbent Layers for the Identification of Pharmaceutic Substances

Thirteen carbon materials were tested as sorbent layers in bar adsorbent microextraction (BA μE) to monitor hint amounts of 10 common pharmaceutical compounds (PhCs) in surface and groundwater matrices such as surface and groundwater, saltwater, spring water, and sewage. The persistence of trace amounts of three organophosphate insect repellent and cis and trans permethrin (PERM) in water quality matrices is suggested using bar adsorptive microextraction in conjunction with microliquid dissolution accompanied by significant volume injection-gas chromatography-mass spectroscopic analysis able to operate in the particular ion monitoring acquisition mode. Using BA μE to compare several sorbent coatings (five porous carbon and six polymers), it was discovered that activated carbon (AC2) was the optimum compromise among specificity and effectiveness. 17-estradiol, estrone, sulfamethoxazole, diclofenac, triclosan, gemfibrozil, 17-ethinylestradiol, mefenamic acid, and clofibric acid were chosen as system drugs to represent different treatment groups. Despite their lower porosity, statistics revealed that low-T-activated hydrochars, made from carbohydrates and a eutectic salt mixture at constant temperature (e.g., 180°C) and autogenerated pressures, could compete at the top level commercially carbonaceous materials in this purpose. These L-T-activated hydrochars had the best overall recovery (between 21.8 and 83.5 percent) for the simultaneous analysis of ten targeted PhCs with very different physical and chemical possessions, utilizing higher-efficiency liquid chromatography diode array identification.

Health Risks associated with residual pesticide levels in fish reared in purified wastewater from slaughterhouse

The main objective of the present research was to determine the concentrations of the selected pesticides in muscle, liver and skin of common carp. Fish were sampled in two different seasons from fish pond which received previously treated slaughterhouse wastewater. Pesticides including etridiazole, chloroneb, trifluralin, propachlor, chlorothalonil, hexa-chlorocyclopentadiene, atrazine, simazine, alachlor, metribuzin, metolachlor, DCPA, cyanazine, chlorobenzilate, endrin aldehyde, cis permethrin and trans permethrin were determined by using a GS-MS method. Many of pesticides were not determined or determined in low concentrations. Propachlor was found in muscle, skin and liver. The recommended acceptable daily intake was higher in comparison with the estimated daily intake for examined pesticides via fish reared in treated slaughterhouse wastewater. It is very important to maintain the safety of the fresh fish produced in wastewater in order to ensure food safety and avoid health problems in humans.

Determination of Pesticide Residues in Most Commonly Consumed Leafy Vegetables in Riyadh Region (Al-Kharej Province)

A total of 81 samples of various leafy vegetables viz., Rocket (Eruca sativa), Lettuce (Lactuca sativa), Coriander (Coriandrum sativum), Corchorus (Corchorus olitorius), Parsley (Petroselinum crispum), Spinach (Spinacia oleracea), Radish (Raphanus sativus), Dill (Anethum graveolens), Mint (Mentha sachalinensis) and Green onions (Allium cepa) were collected from 20 different areas in Riyadh region of the Kingdom of Saudi Arabia. Liquid-Liquid Extraction of extraction partitioning method and confirmation by gas chromatograph-mass spectrometer for the presence of various pesticide residues was performed. Pesticide residues were detected in all the collected samples with varying concentrations. A variety of pesticides including organochlorines, organophosphates, pyrethroids, carbamates, herbicides, acaricides and insecticides have been identified in the samples. While the residue levels were low for most pesticides, higher levels of chlorpyrifos (0.123 mg/kg and resmethrin (0.1 mg/kg) were found in Rocket, carbaryl (0.92 mg/kg) in spinach and corchorus (0.116 mg/kg), permethrin (total cis + trans permethrin) inlettuce (0.103 mg/kg) and coriander (0.126 mg/kg), and cypermethrin in parsley (0.126 ppm). The highest maximum residue limit (MRL) values of pesticide residues on leafy vegetables of 0.10 mg/kg were observed for carbaryl in Spinach and Corchorus, whereas in Parsley an MRL of 0.5 mg/kg was found. The current research shows that in some leafy vegetables, higher doses of pesticides were found.

Plasma Protein and Lipoprotein Binding of Cis- and Trans-Permethrin and Deltamethrin in Adult Humans and Rats.

The majority of residents of the United States, Canada, and Europe are exposed to pyrethroids, the most commonly used class of insecticides. Surprisingly little is known about key aspects of their pharmacokinetics, including their mode of transport in the systemic circulation. This study tested the hypothesis that pyrethroids are transported by both plasma lipoproteins and proteins, similarly to other highly lipophilic environmental contaminants. Other aims were to characterize the binding of representative type I and II pyrethroids, and to compare their binding to rat versus human plasma. Binding of 14C-labeled cis-permethrin (CIS), trans-permethrin (TRANS) and deltamethrin (DLM) to proteins and lipoproteins was measured by sequential extraction of spiked plasma with isooctane, 2-octanol, and acetonitrile. Binding of DLM, CIS, and TRANS to plasma proteins and lipoproteins was linear from 250 to 750 nM; concentrations present in the plasma of orally dosed rats. Binding of DLM to high-density lipoprotein was twice that to low-density lipoprotein. Binding of DLM, CIS, and TRANS was ∼2-fold greater to proteins than to lipoproteins of rat and human plasma; albumin was primarily responsible for protein binding. Higher total binding of each pyrethroid to human (∼90%) than to rat (∼80%) plasma resulted from higher protein binding in human plasma. This was attributable in part to the higher albumin/protein content of human plasma. Rat albumin exhibited lower pyrethroid binding capacity than did human albumin. The results of this investigation indicate that albumin and lipoproteins play a major role in binding and transport of pyrethroids in the systemic circulation of both rats and humans.

Metabolism of deltamethrin and cis- and trans-permethrin by human expressed cytochrome P450 and carboxylesterase enzymes

The metabolism of the pyrethroids deltamethrin (DLM), cis-permethrin (CPM) and trans-permethrin (TPM) was studied in human expressed cytochrome P450 (CYP) and carboxylesterase (CES) enzymes.DLM, CPM and TPM were metabolised by human CYP2B6 and CYP2C19, with the highest apparent intrinsic clearance (CLint) values for pyrethroid metabolism being observed with CYP2C19. Other CYP enzymes contributing to the metabolism of one or more of the three pyrethroids were CYP1A2, CYP2C8, CYP2C9*1, CYP2D6*1, CYP3A4 and CYP3A5. None of the pyrethroids were metabolised by CYP2A6, CYP2E1, CYP3A7 or CYP4A11.DLM, CPM and TPM were metabolised by both human CES1 and CES2 enzymes.Apparent CLint values for pyrethroid metabolism by CYP and CES enzymes were scaled to per gram of adult human liver using abundance values for microsomal CYP enzymes and for CES enzymes in liver microsomes and cytosol. TPM had the highest and CPM the lowest apparent CLint values for total metabolism (CYP and CES enzymes) per gram of adult human liver.Due to their higher abundance, all three pyrethroids were extensively metabolised by CES enzymes in adult human liver, with CYP enzymes only accounting for 2%, 10% and 1% of total metabolism for DLM, CPM and TPM, respectively.

Metabolism of deltamethrin and cis- and trans-permethrin by rat and human liver microsomes, liver cytosol and plasma preparations

The metabolism of deltamethrin (DLM), cis-permethrin (CPM) and trans-permethrin (TPM) was studied in liver microsomes, liver cytosol and plasma from male Sprague–Dawley rats aged 15, 21 and 90 days and from adult humans.DLM and CPM were metabolised by rat hepatic microsomal cytochrome P450 (CYP) enzymes and to a lesser extent by microsomal and cytosolic carboxylesterase (CES) enzymes, whereas TPM was metabolised to a greater extent by CES enzymes.In human liver, DLM and TPM were mainly metabolised by CES enzymes, whereas CPM was metabolised by CYP and CES enzymes.The metabolism of pyrethroids by cytosolic CES enzymes contributes to the overall hepatic clearance of these compounds.DLM, CPM and TPM were metabolised by rat, but not human, plasma CES enzymes.This study demonstrates that the ability of male rats to metabolise DLM, CPM and TPM by hepatic CYP and CES enzymes and plasma CES enzymes increases with age. In all instances, apparent intrinsic clearance values were lower in 15 than in 90 day old rats. As pyrethroid-induced neurotoxicity is due to the parent compound, these results suggest that DLM, CPM and TPM may be more neurotoxic to juvenile than to adult rats.

Downstream assessment of chlorinated organic compounds in the bed-sediment of Aiba Stream, Iwo, South-Western, Nigeria.

This study investigated levels and distribution pattern of chlorinated organic compounds (COCs) otherwise known as organochlorine pesticides in sediment samples at downstream of Aiba watercourse in Iwo, South-western Nigeria. Soxhlet extraction method followed by GC–ECD analysis were used to ascertain levels of COCs in the sediment samples collected from four different locations along the stream. Eighteen COCs were detected with trans permethrin and endosulfan sulfate having highest and lowest concentrations of 375.70 ± 689.41 and 0.03 ± 0.05 µg/g, respectively. The varying levels of COCs as obtained in this study were attributed to organochlorine pesticides contamination emanated from different agricultural practices and domestic sewage loads of the study area.

Measurement of plasma protein and lipoprotein binding of pyrethroids

IntroductionA simple, reliable procedure was developed to measure binding of pyrethroid insecticides to total proteins and lipoproteins of rat and human plasma. MethodsThe extent of binding of 14C-labeled deltamethrin (DLM), cis-permethrin (CIS) and trans-permethrin (TRANS) was quantified by a 3-step organic solvent extraction technique. Rat and human plasma samples, containing NaF to inhibit esterases, were spiked with a range of concentrations of each radiolabeled pyrethroid. Protein binding reached equilibrium within ~1h of incubation at 37°C. The samples were extracted in turn with: isooctane to collect the unbound fraction; 2-octanol to extract the lipoprotein-bound fraction; and acetonitrile to obtain the protein-bound fraction. ResultsAbsolute recoveries of DLM, CIS and TRANS ranged from 86 to 95%. Adherence of these very lipophilic chemicals to glass and plastic was minimized by using silanized glass vials and LoBind® plastic pipettes. The method's ability to distinguish lipoprotein from protein binding was confirmed by experiments with diazepam and cyclosporine, drugs that bind selectively to albumin and lipoproteins, respectively. DiscussionThis procedure was effectively utilized for studies of the species-dependence of plasma protein and lipoprotein binding of three pyrethroids for inclusion in physiologically-based pharmacokinetic models of pyrethroids for use in health risk assessments of the insecticides in children and adults.

Improvements on bar adsorptive microextraction (BAμE) technique–Application for the determination of insecticide repellents in environmental water matrices

Bar adsorptive microextraction combined with micro-liquid desorption followed by large volume injection-gas chromatography-mass spectrometry operating in the selected-ion monitoring acquisition mode (BAµE-µLD/LVI-GC-MS(SIM)), is proposed for the determination of trace levels of three insecticide repellents (N,N-diethyl-meta-toluamide (DEET), cis and trans permethrin (PERM)) in environmental water matrices. By comparing different sorbent coatings (five activated carbons and six polymers) through BAµE, an activated carbon (AC2) proved to be the best compromise between selectivity and efficiency, even against polydimethylsiloxane through stir bar sorptive extraction. The novel improvement proposed on the back-extraction stage performed in a single step, by reducing the desorption solvent volume at the microliter level, demonstrated remarkable performance turning possible to save time, making easier the practical manipulation and more environmentally friendly. Assays performed by BAµE(AC2)-µLD/LVI-GC-MS(SIM) on 25 mL of ultrapure water samples spiked at the 1.0 μg/L level, yielded recoveries ranging from 73.8±8.8% (trans-PERM) to 96.4±9.9% (DEET), under optimised experimental conditions. The analytical performance showed convenient detection limits (8-20 ng/L) and good linear dynamic ranges (0.04-4.0 µg/L) with suitable determination coefficients (r(2)>0.9963, DEET). Excellent repeatability were also achieved through intraday (RSD<14.9%) and interday (RSD<11.9%) experiments. The novel improvement on downsizing the BAµE device to half-size proved to be either a promising option in forthcoming to reduce still more the desorption solvent volume without losing microextraction efficiency. By using the standard addition methodology, the application of the present analytical approach on tap, ground, river, swimming-pool and estuary water samples revealed good sensitivity at trace level and absence of matrix effects.

Lack of P-Glycoprotein-Mediated Efflux and the Potential Involvement of an Influx Transport Process Contributing to the Intestinal Uptake of Deltamethrin, cis-Permethrin, and trans-Permethrin

The effectiveness and widespread use of pyrethroid insecticides has lead to concerns regarding their safety. Human ingestion of these potentially neurotoxic compounds is typically through hand-to-mouth contact or consumption of contaminated foods. A substantial proportion of ingested pyrethroids are eliminated in feces, suggesting that absorption is limited, possibly by the action of the efflux transporter P-glycoprotein (P-gp). We utilized caco-2 cells as a model system for intestinal enterocytes and qualitatively and quantitatively assessed the transport of deltamethrin (DLM), cis-permethrin (CPM), and trans-permethrin (TPM). Caco-2 cell uptake of the P-gp substrate R6G was increased by the P-gp inhibitors cyclosporine A (CSA) and ritonavir but not by DLM, CPM, and TPM. Unexpectedly, CSA and ritonavir significantly reduced the uptake of DLM, CPM, and TPM. Permeability coefficients (P app) and directional flux of DLM, CPM, or TPM were greater in the absorptive than the secretory (efflux) direction when measured across caco-2 monolayers grown on Transwell inserts. When CSA was applied to the monolayers' apical (AP) side, the AP to basolateral (BL) P app was significantly reduced, with no change in the BL to AP P app. Kinetic analysis demonstrated saturable transport kinetics for all 3 pyrethroids. These findings indicate that the cellular uptake of DLM, CPM, and TPM is not limited by P-gp efflux but undergo absorptive influx transport as a contributing mechanism for cellular uptake. However, the overall P app values for DLM, CPM, and TPM are consistent with the low permeability/low absorption compound mannitol, suggesting limited gastrointestinal absorption potential.

Hydrolysis of pyrethroids by carboxylesterases from Lucilia cuprina and Drosophila melanogaster with active sites modified by in vitro mutagenesis

The cloned genes encoding carboxylesterase E3 in the blowfly Lucilia cuprina and its orthologue in Drosophila melanogaster were expressed in Sf9 cells transfected with recombinant baculovirus. Resistance of L. cuprina to organophosphorus insecticides is due to mutations in the E3 gene that enhance the enzyme's ability to hydrolyse insecticides. Previous in vitro mutagenesis and expression of these modifications (G137D, in the oxyanion hole and W251L, in the acyl pocket) have confirmed their functional significance. We have systematically substituted these and nearby amino acids by others expected to affect the hydrolysis of pyrethroid insecticides. Most mutations of G137 markedly decreased pyrethroid hydrolysis. W251L was the most effective of five substitutions at this position. It increased activity with trans permethrin 10-fold, and the more insecticidal cis permethrin >130-fold, thereby decreasing the trans: cis hydrolysis ratio to only 2, compared with >25 in the wild-type enzyme. Other mutations near the bottom of the catalytic cleft generally enhanced pyrethroid hydrolysis, the most effective being F309L, also in the presumptive acyl binding pocket, which enhanced trans permethrin hydrolysis even more than W251L. In these assays with racemic 1RS cis and 1RS trans permethrin, two phases were apparent, one being much faster suggesting preferential hydrolysis of one enantiomer in each pair as found previously with other esterases. Complementary assays with individual enantiomers of deltamethrin and the dibromo analogue of cis permethrin showed that the wild type and most mutants showed a marked preference for the least insecticidal 1S configuration, but this was reversed by the F309L substitution. The W251L/F309L double mutant was best overall in hydrolysing the most insecticidal 1R cis isomers. The results are discussed in relation to likely steric effects on enzyme–substrate interactions, cross-resistance between pyrethroids and malathion, and the potential for bioremediation of pyrethroid residues.

Aqueous chlorination of permethrin

Cis and trans permethrin were shown not to react with chlorine under conditions likely to be found during water treatment disinfection. Consequently, no products are likely to be formed should operators wish to maintain a chlorine residual whilst deinfesting mains water supply.