Cyprodinil
(Synonyms: 嘧菌环胺) 目录号 : GC47159
An anilinopyrimidine fungicide
Cas No.:121552-61-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cyprodinil is an anilinopyrimidine broad-spectrum fungicide that inhibits the biosynthesis of methionine in phytopathogenic fungi.1 It inhibits mycelial cell growth of B. cinerea, P. herpotrichoides, and H. oryzae on amino acid-free media (IC50s = 0.44, 4.8, and 0.03 µM, respectively), an effect that is reversed by addition of methionine or homocysteine. In an MDA-kb2 assay, cyprodinil acts as an androgen receptor (AR) agonist (EC20 = 1.91 µM) in the absence of the AR agonist DHT and inhibits the androgenic effect of DHT (IC20 = 15.1 µM).2 It is cytotoxic in a yeast antiandrogen screen (YAS; EC20 = 27.8 µM) but not in an MDA-kb2 assay (EC20 = >50 µM). Cyprodinil increases proliferation of estrogen receptor-expressing BG-1 ovarian cancer cells when used at low micromolar concentrations in combination with 17β-estradiol.3 It also increases tumor mass in a BG-1 ovariectomized mouse xenograft model after 70 days when administered at a dose of 3 mg/kg every three days. Formulations containing cyprodinil have been used in the control of fungi in agriculture.
1.Masner, P., Muster, P., and Schmid, J.Possible methionine biosynthesis inhibition by pyrimidinamine fungicidesPestic. Sci.42(3)163-166(1994) 2.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) 3.Go, R.-E., Kim, C.-W., and Choi, K.-C.Effect of fenhexamid and cyprodinil on the expression of cell cycle- and metastasis-related genes via an estrogen receptor-dependent pathway in cellular and xenografted ovarian cancer modelsToxicol. Appl. Pharmacol.289(1)48-57(2015)
| Cas No. | 121552-61-2 | SDF | |
| 别名 | 嘧菌环胺 | ||
| Canonical SMILES | CC1=CC(C2CC2)=NC(NC3=CC=CC=C3)=N1 | ||
| 分子式 | C14H15N3 | 分子量 | 225.3 |
| 溶解度 | Chloroform: Slightly Soluble | 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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.4385 mL | 22.1926 mL | 44.3853 mL |
| 5 mM | 0.8877 mL | 4.4385 mL | 8.8771 mL |
| 10 mM | 0.4439 mL | 2.2193 mL | 4.4385 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。
Cyprodinil as an activator of aryl hydrocarbon receptor
Toxicology 2013 Feb 8;304:32-40.PMID:23228475DOI:10.1016/j.tox.2012.11.018.
Cyprodinil is a pyrimidinamine fungicide, used worldwide by agriculture. It is used to protect fruit plants and vegetables from a wide range of pathogens. Benzo[a]pyrene (BaP) and 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) are toxic environmental pollutants and are prototypes of aryl hydrocarbon receptor (AHR) ligands. Although the structure of Cyprodinil distinctly differs from those of BaP and TCDD, our results show that Cyprodinil induced nuclear translocation of the AHR, and induced the transcriptional activity of aryl hydrocarbon response element (AHRE). Cyprodinil induced the expression of cytochrome P450 (CYP) 1A1, a well-known AHR-targeted gene, in ovarian granulosa cells, HO23, and hepatoma cells, Hepa-1c1c7. Its induction did not appear in AHR signal-deficient cells, and was blocked by the AHR antagonist, CH-223191. Cyprodinil decreased AHR expression in HO23 cells, resulting in CYP1A1 expression decreasing after it peaked at 9h of treatment in HO23 cells. Dexamethasone is a synthetic agonist of glucocorticoids. Cyprodinil enhanced dexamethasone-induced gene expression, and conversely, its induction of CYP1A1 expression was decreased by dexamethasone in HO23 cells, indicating its induction of crosstalk between the AHR and glucocorticoid receptor and its role as a potential endocrine disrupter. In addition to BaP, TCDD, and an AHR agonist, β-NF, Cyprodinil also phosphorylated extracellular signal-regulated kinase (ERK) in HO23 and Hepa-1c1c7 cells, indicating its deregulation of ERK activity. In summary, our results demonstrate that Cyprodinil, similar to BaP, acts as an AHR activator, a potential endocrine disrupter, and an ERK disrupter.
DNA damage effect of Cyprodinil and thiacloprid in adult zebrafish gills
Environ Sci Pollut Res Int 2021 Mar;28(12):14482-14487.PMID:33211291DOI:10.1007/s11356-020-11668-1.
Cyprodinil and thiacloprid are two of the most commonly used pesticides in Turkey. It is more likely to reach humans or animals due to their widespread use. This study aims to investigate whether there is a DNA damage risk due to Cyprodinil and thiacloprid exposure. Zebrafish, which is used as a model organism in health and environmental research, and comet assay were chosen to demonstrate this damage. Ten zebrafish per group were exposed to 2 different concentrations for each pesticides (0.31 and 0.155 mg/L for Cyprodinil and 1.64 and 0.82 mg/L for thiacloprid) for 21 days. After, gills were excised and comet assay was performed. Photos of an average of 50 cells per slide were taken and were analyzed with visual evaluation program. DNA damage was found to be increased in the 0.31 mg/L Cyprodinil, 0.82 mg/L thiacloprid, and 1.64 mg/L thiacloprid treatment groups when compared to the control group (p < 0.001). Average tail DNA percentage parameter values were 9.45 ± 0.51, 10.30 ± 0.34, 11.17 ± 0.33, and 2.47 ± 0.06 respectively. Cyprodinil and thiacloprid were identified as genotoxic agents that should be investigated further.
Reproductive toxicity of long-term exposure to environmental relevant concentrations of Cyprodinil in female zebrafish (Danio rerio)
Sci Total Environ 2022 Nov 10;846:157504.PMID:35870602DOI:10.1016/j.scitotenv.2022.157504.
In recent years, the widespread use of the pesticide Cyprodinil has attracted attention due to its harmful effects on aquatic organisms. The purpose of this study was to evaluate the adverse effects of long-term exposure to Cyprodinil on the reproductive system of female zebrafish. After the embryos had been treated with 0.1, 1 and 10 μg/L Cyprodinil for 180 days, we observed that female fish treated with 1 and 10 μg/L Cyprodinil showed decreased sexual attractiveness, a decreased proportion of primordial follicles in the ovary, an increased proportion of mature follicles, and increased egg production. Moreover, exposed females that mated with normal males produced offspring with increased rates of mortality and deformity (the F1 generation). In addition, the levels of gonadotropin and testosterone (T) were increased in females after Cyprodinil exposure, especially in the 10 μg/L treated group. After Cyprodinil treatment, some key genes in the hypothalamic-pituitary-gonad axis underwent significant changes. For example, gene expression of brain gonadotropin-releasing hormone receptors (gnrhr1, gnrhr2 and gnrhr4) was significantly downregulated after Cyprodinil treatment. The study found that expression of the aromatase (cytochrome P450 family 19 subfamily A polypeptide 1a, cyp19a1a) responsible for converting T into estradiol was significantly downregulated after Cyprodinil treatment, consistent with elevated T levels in the ovaries and muscles. In summary, these data provide a more comprehensive understanding of the toxicity of Cyprodinil and may inform evaluation of the ecotoxicity of Cyprodinil to female reproduction at environmentally relevant concentrations.
Complete genome sequence of the cyprodinil-degrading bacterium Acinetobacter johnsonii LXL_C1
Microb Pathog 2019 Feb;127:246-249.PMID:30496837DOI:10.1016/j.micpath.2018.11.016.
Acinetobacter johnsonii LXL_C1, a Cyprodinil degrader, was isolated and purified from cyprodinil-contaminated agricultural soil. Here, we report the complete genome sequence of LXL_C1. The genome comprises one 3,398,706 bp circular chromosome with 41.2% G + C content and one 44,866 bp plasmid. Annotation based on COG and KEGG database analyses revealed genes encoding a cytochrome P450 monooxygenase and hydrolase, which can effectively degrade Cyprodinil. The complete genome sequence of LXL_C1 can facilitate genetic engineering of a recombinant Cyprodinil degrader.
Crystal structure of Cyprodinil
Acta Crystallogr E Crystallogr Commun 2015 Jan 1;71(Pt 1):o5.PMID:25705503DOI:10.1107/S2056989014025742.
In the title compound, C14H15N3 (systematic name: 4-cyclo-propyl-6-methyl-N-phenyl-pyrimidin-2-amine), which is the anilino-pyrimidine fungicide Cyprodinil, the dihedral angles between the planes of the central pyrimidine ring and the terminal phenyl ring and the mean plane of the cyclo-propane ring system are 14.52 (11) and 88.79 (10)°, respectively. In the crystal, weak π-π inter-actions [3.8551 (11) Å] connect the dimers into chains along the b-axis direction.