Azoxystrobin
(Synonyms: 嘧菌酯) 目录号 : GC46904
A broad-spectrum fungicide
Cas No.:131860-33-8
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Azoxystrobin is a broad-spectrum β-methoxyacrylate fungicide (LC95s = <1 mg/L for ascomycete, basidiomycete, deuteromycete, and oomycete plant pathogens).1 It inhibits mitochondrial respiration by binding to the Qo site of the cytochrome bc1 complex and inhibiting electron transfer.2 Azoxystrobin is cytotoxic to MDA-kb2 cells with an EC20 value of 2.9 µM but has no antiandrogenic activity.3 It disrupts mRNA expression of antioxidant-, stress response-, and innate immune-related genes and induces the production of reactive oxygen species (ROS) in zebrafish larva when used at doses ranging from 0.1 to 100 µg/L.4 Azoxystrobin inhibits proliferation of KYSE-150 human esophageal squamous cell carcinoma cells (IC50 = 2.42 µg/ml after 48 hours) and induces apoptosis in a time- and dose-dependent manner.5 In a KYSE-150 nude mouse xenograft model, azoxystrobin reduces tumor growth when administered at a dose of 40 mg/kg per day.
1.Godwin, J.R., Anthony, V.M., Clough, J.M., et al.ICI A5504: A novel, broad spectrum, systemic β-methoxyacrylate fungicideBrit. Crop Prot. Conf. - Pests and Dis., Proc.1435-442(1992) 2.Wiggins, T.E., and Jager, B.J.Mode of action of the new methoxyacrylate antifungal agent ICIA5504Biochem. Soc. Trans.22(1)68S(1994) 3.Orton, F., Rosivatz, E., Scholze, M., et al.Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogensEnviron. Health Perspect.119(6)794-800(2011) 4.Jiang, J., Shi, Y., Yu, R., et al.Biological response of zebrafish after short-term exposure to azoxystrobinChemosphere20256-64(2018) 5.Shi, X.K., Bian, X.B., Huang, T., et al.Azoxystrobin induces apoptosis of human esophageal squamous cell carcinoma KYSE-150 cells through triggering of the mitochondrial pathwayFront. Pharmacol.8277(2017)
| Cas No. | 131860-33-8 | SDF | |
| 别名 | 嘧菌酯 | ||
| Canonical SMILES | CO/C=C(C(OC)=O)\C(C=CC=C1)=C1OC2=NC=NC(OC3=C(C#N)C=CC=C3)=C2 | ||
| 分子式 | C22H17N3O5 | 分子量 | 403.4 |
| 溶解度 | DMSO : 100 mg/mL (247.90 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.4789 mL | 12.3946 mL | 24.7893 mL |
| 5 mM | 0.4958 mL | 2.4789 mL | 4.9579 mL |
| 10 mM | 0.2479 mL | 1.2395 mL | 2.4789 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Ecotoxicity evaluation of Azoxystrobin on Eisenia fetida in different soils
Environ Res 2021 Mar;194:110705.PMID:33400946DOI:10.1016/j.envres.2020.110705.
Azoxystrobin, a widely used broad-spectrum strobilurin fungicide, may pose a potential threat in agricultural ecosystems. To assess the ecological risk of Azoxystrobin in real soil environments, we performed a study on the toxic effects of Azoxystrobin on earthworms (Eisenia fetida) in three different natural soils (fluvo-aquic soil, black soil and red clay soil) and an artificial soil. Acute toxicity of Azoxystrobin was determined by filter paper test and soil test. Accordingly, exposure concentrations of chronic toxicity were set at 0, 0.1, 1.0 and 2.5 mg kg-1. For chronic toxicity test, reactive oxygen species, activity of antioxidant enzymes (superoxide dismutase, catalase and peroxidase), detoxifying enzyme (glutathione transferase), level of lipid peroxidation (malondialdehyde) and level of oxygen damage of DNA (8-hydroxydeoxyguanosine) in earthworms were determined on the 7th, 14th, 21st, 28th, 42nd and 56th days after treatment. Both acute and chronic toxic results showed Azoxystrobin exhibit higher toxicity in natural soil than in artificial soil, indicating that traditional artificial soil testing method underestimate ecotoxicity of Azoxystrobin in a real agricultural environment on the earthworm population. Combining with the analysis of soil physicochemical properties, the present experiment provided scientific guidance for rational application of Azoxystrobin in agricultural production systems.
Occurrence, fate and effects of Azoxystrobin in aquatic ecosystems: a review
Environ Int 2013 Mar;53:18-28.PMID:23314040DOI:10.1016/j.envint.2012.12.005.
The use of pesticides for crop protection may result in the presence of toxic residues in environmental matrices. In the aquatic environment, pesticides might freely dissolve in the water or bind to suspended matter and to the sediments, and might be transferred to the organisms' tissues during bioaccumulation processes, resulting in adverse consequences to non-target species. One such group of synthetic organic pesticides widely used worldwide to combat pathogenic fungi affecting plants is the strobilurin chemical group. Whereas they are designed to control fungal pathogens, their general modes of action are not specific to fungi. Consequently, they can be potentially toxic to a wide range of non-target organisms. The present work had the intent to conduct an extensive literature review to find relevant research on the occurrence, fate and effects of Azoxystrobin, the first patent of the strobilurin compounds, in aquatic ecosystems in order to identify strengths and gaps in the scientific database. Analytical procedures and existing legislation and regulations were also assessed. Data gathered in the present review revealed that analytical reference standards for the most relevant environmental metabolites of Azoxystrobin are needed. Validated confirmatory methods for complex matrices, like sediment and aquatic organisms' tissues, are very limited. Important knowledge of base-line values of Azoxystrobin and its metabolites in natural tropical and estuarine/marine ecosystems is lacking. Moreover, some environmental concentrations of Azoxystrobin found in the present review are above the Regulatory Acceptable Concentration (RAC) in what concerns risk to aquatic invertebrates and the No Observed Ecologically Adverse Effect Concentration (NOEAEC) reported for freshwater communities. The present review also showed that there are very few data on Azoxystrobin toxicity to different aquatic organisms, especially in what concerns estuarine/marine organisms. Besides, toxicity studies mostly address Azoxystrobin and usually neglect the more relevant environmental metabolites. Further work is also required in what concerns effects of exposure to multi-stressors, e.g. pesticide mixtures. Even though Log K(ow) for Azoxystrobin and R234886, the main metabolite of Azoxystrobin in water, are below 3, the bio-concentration factor and the bioaccumulation potential for Azoxystrobin are absent in the literature. Moreover, no single study on bioaccumulation and biomagnification processes was found in the present review.
Azoxystrobin exposure impairs meiotic maturation by disturbing spindle formation in mouse oocytes
Front Cell Dev Biol 2022 Dec 2;10:1053654.PMID:36531942DOI:10.3389/fcell.2022.1053654.
Fungicides are a type of pesticide used to protect plants and crops from pathogenic fungi. Azoxystrobin (AZO), a natural methoxyacrylate derived from strobilurin, is one of the most widely used fungicides in agriculture. AZO exerts its fungicidal activity by inhibiting mitochondrial respiration, but its cytotoxicity to mammalian oocytes has not been studied. In this study, we investigated the effect of AZO exposure on mouse oocyte maturation to elucidate the underlying mechanisms of its possible reproductive toxicity. We found that AZO exposure disturbed meiotic maturation by impairing spindle formation and chromosome alignment, which was associated with decreased microtubule organizing center (MTOC) integrity. Moreover, AZO exposure induced abnormal mitochondrial distribution and increased oxidative stress. The AZO-induced toxicity to oocytes was relieved by melatonin supplementation during meiotic maturation. Therefore, our results suggest that AZO exposure impairs oocyte maturation not only by increasing oxidative stress and mitochondrial dysfunction, but also by decreasing MTOC integrity and subsequent spindle formation and chromosome alignment.
Azoxystrobin amine: A novel Azoxystrobin degradation product from Bacillus licheniformis strain TAB7
Chemosphere 2021 Jun;273:129663.PMID:33515965DOI:10.1016/j.chemosphere.2021.129663.
Azoxystrobin (AZ) is a broad-spectrum synthetic fungicide widely used in agriculture globally. However, there are concerns about its fate and effects in the environment. It is reportedly transformed into Azoxystrobin acid as a major metabolite by environmental microorganisms. Bacillus licheniformis strain TAB7 is used as a compost deodorant in commercial compost and has been found to degrade some phenolic and agrochemicals compounds. In this article, we report its ability to degrade Azoxystrobin by novel degradation pathway. Biotransformation analysis followed by identification by electrospray ionization-mass spectrometry (MS), high-resolution MS, and nuclear magnetic resonance spectroscopy identified methyl (E)-3-amino-2-(2-((6-(2-cyanophenoxy)pyrimidin-4-yl)oxy)phenyl)acrylate, or (E)-azoxystrobin amine in short, and (Z) isomers of AZ and Azoxystrobin amine as the metabolites of (E)-AZ by TAB7. Bioassay testing using Magnaporthe oryzae showed that although 40 μg/mL of (E)-AZ inhibited 59.5 ± 3.5% of the electron transfer activity between mitochondrial Complexes I and III in M. oryzae, the same concentration of (E)-azoxystrobin amine inhibited only 36.7 ± 15.1% of the activity, and a concentration of 80 μg/mL was needed for an inhibition rate of 56.8 ± 7.4%, suggesting that (E)-azoxystrobin amine is less toxic than the parent compound. To our knowledge, this is the first study identifying Azoxystrobin amine as a less-toxic metabolite from bacterial AZ degradation and reporting on the enzymatic isomerization of (E)-AZ to (Z)-AZ, to some extent, by TAB7. Although the fate of AZ in the soil microcosm supplemented with TAB7 will be needed, our findings broaden our knowledge of possible AZ biotransformation products.
Azoxystrobin Induces Apoptosis and Cell Cycle Arrest in Human Leukemia Cells Independent of p53 Expression
Anticancer Res 2022 Mar;42(3):1307-1312.PMID:35220221DOI:10.21873/anticanres.15598.
Background/aim: Azoxystrobin (AZOX), a methoxyacrylate derivative, has potent antimicrobial and antitumor activities. Here, we report the anticancer effects of AZOX on the p53-negative human myelogenous leukemia cell line HL-60RG and the p53 positive human T-cell leukemia cell line MOLT-4F. Materials and methods: Using both leukemia cells, the anticancer effect of AZOX treatment was analyzed throughout the cell cycle. Results: AZOX damaged both cell lines dose-dependently, and the cell damage rates were almost the same in both lines. Cell cycle distribution analysis showed that the treated MOLT-4F cells arrested at the S phase, whereas HL-60RG cells increased during the subG1 phase, suggesting that cell death was occurring. AZOX-induced cell death in HL-60RG was inhibited with the addition of uridine, which is used as a substrate for the salvage pathway of pyrimidine nucleotides. Conclusion: AZOX has p53-independent anticancer effects in leukemia cells, but the mechanisms underlying the damage differ between cell lines.