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Allethrin

(Synonyms: 丙烯菊酯) 目录号 : GC40476

A pyrethroid insecticide

Allethrin Chemical Structure

Cas No.:584-79-2

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50mg
¥428.00
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100mg
¥823.00
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产品描述

Allethrin is a pyrethroid insecticide and modulator of voltage-gated sodium channels (NaV). It delays channel deactivation in cockroach giant axons when used at a concentration of 1 μM. Allethrin is 100-fold more potent at insect than rat NaV1.8 channels expressed in Xenopus oocytes. It decreases egg production by and is lethal to mosquitoes (LC50 = 0.01%). Allethrin induces production of reactive oxygen species (ROS), lipid peroxidation, and apoptosis in rat primary Leydig cells. In vivo, the smoke of an allethrin-based mosquito coil increases levels of the hepatic enzymes ALT and AST and induces hepatocyte apoptosis as well as emphysema and lung hyperplasia in mice.

Chemical Properties

Cas No. 584-79-2 SDF
别名 丙烯菊酯
Canonical SMILES C/C(C)=C/C1C(C)(C)C1C(OC2C(C)=C(CC=C)C(C2)=O)=O
分子式 C19H26O3 分子量 302.4
溶解度 Chloroform: Slightly Soluble 储存条件 Store at -20°C
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1 mM 3.3069 mL 16.5344 mL 33.0688 mL
5 mM 0.6614 mL 3.3069 mL 6.6138 mL
10 mM 0.3307 mL 1.6534 mL 3.3069 mL
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Research Update

Allethrin Promotes Apoptosis and Autophagy Associated with the Oxidative Stress-Related PI3K/AKT/mTOR Signaling Pathway in Developing Rat Ovaries

Int J Mol Sci 2022 Jun 7;23(12):6397.PMID:35742842DOI:10.3390/ijms23126397.

The increased concern regarding the reduction in female fertility and the impressive numbers of women undergoing fertility treatment support the existence of environmental factors beyond inappropriate programming of developing ovaries. Among these factors are pyrethroids, which are currently some of the most commonly used pesticides worldwide. The present study was performed to investigate the developmental effects of the pyrethroid-based insecticide Allethrin on ovarian function in rat offspring in adulthood. We mainly focused on the roles of oxidative stress, apoptosis, autophagy and the related pathways in ovarian injury. Thirty-day-old Wistar albino female rats were intragastrically administered 0 (control), 34.2 or 68.5 mg/kg body weight Allethrin after breeding from Day 6 of pregnancy until delivery. We found that allethrin-induced ovarian histopathological damage was accompanied by elevations in oxidative stress and apoptosis. Interestingly, the number of autophagosomes in allethrin-treated ovaries was higher, and this increase was correlated with the upregulated expression of genes and proteins related to the autophagic marker LC-3. Furthermore, Allethrin downregulated the expression of PI3K, AKT and mTOR in allethrin-treated ovaries compared with control ovaries. Taken together, the findings of this study suggest that exposure to the pyrethroid-based insecticide Allethrin adversely affects both the follicle structure and function in rat offspring during adulthood. Specifically, Allethrin can induce excessive oxidative stress and defective autophagy-related apoptosis, probably through inactivation of the PI3K/AKT/mTOR signaling pathway, and these effects may contribute to ovarian dysfunction and impaired fertility in female offspring.

Allethrin and prallethrin stimulates MUC5AC expression through oxidative stress in human airway epithelial cells

Biochem Biophys Res Commun 2018 Sep 3;503(1):316-322.PMID:29885834DOI:10.1016/j.bbrc.2018.06.022.

Pyrethroids, including Allethrin and prallethrin, have been widely used as major components of the common commercial insecticides. The toxicity of Allethrin and prallethrin were well established that it interfered with the way that the nerves and brain function. However, limited information was available regarding respiratory effects in humans following inhalation exposure to Allethrin and prallethrin. Therefore, we demonstrated effect of Allethrin and prallethrin, and the mechanism involved, on the mucin expressions in human airway epithelial cells. In human airway NCI-H292 epithelial cells, the effects of Allethrin and prallethrin and its signaling pathway for airway mucin, especially MUC5AC, were investigated by reverse transcriptase-polymerase chain reaction (RT-PCR), real-time PCR, and enzyme-linked immunosorbent assay (ELISA). The mechanism of Allethrin and prallethrin-induced MUC5AC expression in airway epithelial cells was studied in terms of reactive oxygen species (ROS) by flow cytometry analysis. Allethrin and prallethrin significant increased MUC5AC expression in human airway NCI-H292 epithelial cells. We also demonstrated Allethrin and prallethrin induced a marked rise of ROS production. In addition, NAC (ROS scavenger) and DPI (NADPH oxidase inhibitor) inhibited Allethrin and prallethrin-induced MUC5AC expression. These results are first to describe that Allethrin and prallethrin-induced MUC5AC expression through ROS in human airway epithelial cells.

Mechanism of Allethrin biodegradation by a newly isolated Sphingomonas trueperi strain CW3 from wastewater sludge

Bioresour Technol 2020 Feb 24;305:123074.PMID:32146283DOI:10.1016/j.biortech.2020.123074.

The main aim of this study was to investigate and characterize the bacterial strain that has the potential to degrade Allethrin. The isolated strain, Sphingomonas trueperi CW3, degraded Allethrin (50 mg L-1) in batch experiments within seven days. The Box-Behnken design optimized Allethrin degradation and had a confirmation of 93% degradation at pH 7.0, at a temperature of 30 °C and an inocula concentration of 100 mg L-1. The results from gas chromatography and mass spectrometry analysis confirmed the existence of nine metabolites from the degradation of Allethrin with strain CW3. The cleavage of the ester bond, followed by the degradation of the five-carbon rings, was Allethrin's primary degradation pathway. The strain CW3 also degraded other widely applied synthetic pyrethroids such as cyphenothrin, bifenthrin, permethrin, tetramethrin, β-cypermethrin and chlorempenthrin. Furthermore, in experiments performed with sterilized soil, strain CW3 based bioaugmentation effectively removed Allethrin at a significantly reduced half-life.

Novel mechanism and degradation kinetics of Allethrin using Bacillus megaterium strain HLJ7 in contaminated soil/water environments

Environ Res 2022 Nov;214(Pt 3):113940.PMID:35952736DOI:10.1016/j.envres.2022.113940.

As a common pyrethroid insecticide, Allethrin is widely used for various purposes in agriculture and home applications. At present, Allethrin residues have been frequently detected worldwide, yet little is known about the kinetics and degradation mechanisms of this insecticide. In this study, a highly efficient allethrin-degrading bacterium, Bacillus megaterium strain HLJ7, was obtained through enrichment culture technology. Strain HLJ7 can remove 96.5% of 50 mg L-1 Allethrin in minimal medium within 11 days. The first-order kinetic analysis of degradation demonstrated that the half-life of Allethrin degradation by strain HLJ7 was 3.56 days, which was significantly shorter than the 55.89 days of the control. The Box-Behnken design of the response surface method optimized the degradation conditions for strain HLJ7: temperature 32.18 °C, pH value 7.52, and inoculation amount 1.31 × 107 CFU mL-1. Using Andrews equation, the optimal concentration of strain HLJ7 to metabolize Allethrin was determined to be 21.15 mg L-1, and the maximum specific degradation rate (qmax), half-rate constant (Ks) and inhibition coefficient (Ki) were calculated to be 1.80 d-1, 1.85 mg L-1 and 68.13 mg L-1, respectively. Gas chromatography-mass spectrometry identified five intermediate metabolites, suggesting that Allethrin could be degraded firstly by cleavage of its carboxylester bond, followed by degradation of the five-carbon ring and subsequent metabolism. The results of soil remediation experiments showed that strain HLJ7 has excellent bioremediation potential in the soils. After 15 days of treatment, about 70.8% of the initial Allethrin (50 mg kg-1) was removed and converted into nontoxic intermediate metabolites, and its half-life was significantly reduced in the soils. Taken together, these findings shed light on the degradation mechanisms of Allethrin and also highlight the promising potentials of B. megaterium HLJ7 in bioremediation of allethrin-comtaminated environment.

Allethrin-induced genotoxicity and oxidative stress in Swiss albino mice

Mutat Res 2012 Aug 30;747(1):22-28.PMID:22475934DOI:10.1016/j.mrgentox.2012.03.003.

Allethrin (C(19)H(26)O(3)) is non-cyano-containing pyrethroid insecticide that is used extensively for controlling flies and mosquitoes. Apart from its neurotoxic effects in non-target species, Allethrin is reported to be mutagenic in bacterial systems. In this study, we observed oxidative damage-mediated genotoxicity caused by Allethrin in Swiss albino mice. The genotoxic potential of Allethrin was evaluated using chromosome aberrations (CAs) and a micronuclei (MN) induction assay as genetic end-points. The oral intubation of Allethrin (25 and 50mg/kg b.wt.) significantly induces CAs and MN in mouse bone marrow cells. The DNA-damaging potential of Allethrin was estimated in mouse liver using the DNA alkaline unwinding assay (DAUA) and by measuring the levels of 8-hydroxy-2'-deoxy-guanosine (8-OH-dG). Furthermore, a dose-dependent increase in reactive oxygen species (ROS) generation and lipid peroxidation (LPO), with a concurrent decrease in superoxide dismutase (SOD) and catalase, confirm its pro-oxidant potential. The DNA-damaging potential of Allethrin was found to be mediated through the modulation of p53, p21, GADD45α and MDM-2. These results confirm the genotoxic and the pro-oxidant potential of Allethrin in Swiss albino mice.