Pyributicarb (TSH-888)
(Synonyms: 稗草畏,TSH-888) 目录号 : GC33862
Pyributicarb (TSH-888) 是一种氨基甲酸酯类除草剂，是 CYP3A4 基因和人孕烷 X 受体 (hPXR) 的有效激活剂。
Cas No.:88678-67-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cell experiment: | HepG2-derived cells stably expressing the CYP3A4 reporter gene (3-1-10 cells) are used in this experiment. The cells are treated with 0.3 to 30 μM Pyributicarb for 48 h. Then reporter activities are determined[1]. |
Animal experiment: | Male ICR mice (5 weeks old) are used and fed standard rodent chow. After 18-h fasting, mice are injected i.v. with adenovirus [4.0 ×109 50% titer culture infectious dose (TCID50)/mouse]. Three days after the infection, vehicle (0.5% methyl cellulose/saline) or Pyributicarb (100 mg/kg/day) is administered p.o. for 2 consecutive days. Animals are killed 20 h after the last dose[1]. |
References: [1]. Matsubara T, et al. Assessment of human pregnane X receptor involvement in pesticide-mediated activation of CYP3A4 gene. Drug Metab Dispos. 2007 May;35(5):728-33. | |
Pyributicarb, a carbamate-type herbicide, is a potent activator of both CYP3A4 gene and human pregnane X receptor (hPXR).
Pyributicarb, a carbamate-type herbicide, is a potent activator of both CYP3A4 gene and human pregnane X receptor (hPXR). Pyributicarb is found to increase the CYP3A4 reporter activity at 0.1 to 1 μM more strongly than typical CYP3A4 inducer rifampicin. Expression of hPXR-siRNA clearly diminishes the Pyributicarb-stimulated CYP3A4 reporter activity in 3-1-10 cells and decreases the endogenous CYP3A4 mRNA levels in HepG2 cells[1]. Pyributicarb induces luciferase transcription via hPXR at low concentrations in the order of 10 nM. The relative potency of Pyributicarb for hPXR is 8.6-fold that of rifampicin (RIF)[2].
Pyributicarb causes enhancement of CYP3A4-derived reporter activity in mouse livers introduced with hPXR by adenovirus[1].
[1]. Matsubara T, et al. Assessment of human pregnane X receptor involvement in pesticide-mediated activation of CYP3A4 gene. Drug Metab Dispos. 2007 May;35(5):728-33. [2]. Kojima H, et al. Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87.
| Cas No. | 88678-67-5 | SDF | |
| 别名 | 稗草畏,TSH-888 | ||
| Canonical SMILES | S=C(OC1=CC=CC(C(C)(C)C)=C1)N(C2=NC(OC)=CC=C2)C | ||
| 分子式 | C18H22N2O2S | 分子量 | 330.44 |
| 溶解度 | DMSO : 100 mg/mL (302.63 mM);Water : < 0.1 mg/mL (insoluble) | 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 | 3.0263 mL | 15.1313 mL | 30.2627 mL |
| 5 mM | 0.6053 mL | 3.0263 mL | 6.0525 mL |
| 10 mM | 0.3026 mL | 1.5131 mL | 3.0263 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。
Assessment of human pregnane X receptor involvement in pesticide-mediated activation of CYP3A4 gene
Drug Metab Dispos 2007 May;35(5):728-33.PMID:17293382DOI:10.1124/dmd.106.013144.
Assessment of foreign chemical inducibility on CYP3A4 is necessary to optimize drug therapies. The properties of chemicals such as pesticides, however, are not well investigated. In the present study, properties of various pesticides on human CYP3A4 induction have been tested using HepG2-derived cells stably expressing the CYP3A4 promoter/enhancer (3-1-10 cells) and the human pregnane X receptor (hPXR)-small interfering RNA (siRNA) system. Among the examined pesticides, 13 pesticides were observed to activate the CYP3A4 gene. Surprisingly, Pyributicarb was found to increase the CYP3A4 reporter activity at 0.1 to 1 microM more strongly than typical CYP3A4 inducer rifampicin. Expression of hPXR-siRNA clearly diminished the pyributicarb-stimulated CYP3A4 reporter activity in 3-1-10 cells and decreased the endogenous CYP3A4 mRNA levels in HepG2 cells. Pyributicarb caused enhancement of CYP3A4-derived reporter activity in mouse livers introduced with hPXR by adenovirus. These results indicate Pyributicarb as a potent activator of CYP3A4 gene, suggesting the existence of pesticides leading to CYP3A4 induction in our environment.
Pesticides in water, fish and shellfish from littoral area of Lake Biwa
Bull Environ Contam Toxicol 2009 Jun;82(6):716-21.PMID:19277442DOI:10.1007/s00128-009-9681-0.
A survey of 29 pesticides were performed for water, fish and shellfish from two littoral areas of Lake Biwa and Yanamune River in 2007. Three insecticides, 5 fungicides and 13 herbicides were detected in the water from the sampling locations, but the insecticides and fungicides were not and the only 9 herbicides were detected in the fish and shellfish from the locations. Bioconcentration factors (BCF) of the 9 herbicides in the fish and shellfish were calculated by the field data obtained from the survey. The average field BCF values of the herbicides in the fish were 8 and 25 for molinate, 5-23 for bromobutide, 4 and 10 for simetryn, 100-214 for esprocarb, 15-41 for pretilachlor, 148 for anilofos, 14 and 79 for mefenacet and 78 for cafenstrole. Those in the shellfish were 6 and 13 for bromobutide, 4 and 8 for simetryn, 67 and 135 for esprocarb, 2 for pretilachlor, 117 for Pyributicarb and 57 and 139 for mefenacet. The field BCF data in the fish were evaluated by laboratory BCF data from literatures for molinate, bromobutide, pretilachlor, simetryn and mefenacet.
Purity determination of Pyributicarb by internal standard correction-high-performance liquid chromatography-quantitative nuclear magnetic resonance
Anal Bioanal Chem 2020 Oct;412(25):6983-6993.PMID:32754793DOI:10.1007/s00216-020-02832-0.
An internal standard correction-high-performance liquid chromatography-quantitative nuclear magnetic resonance (ISC-HPLC-qNMR) procedure was established as a reliable quantitative method for complex organic compounds with low purity in order to solve the risk of qNMR inaccuracy because of insufficient resolution of impurity peaks from the selected quantitative peak. This method collects a small quantity of target analyte from low-purity organics by LC. After drying and re-dissolving in deuterated solvent containing internal standard, the solution was analyzed by 1H NMR and HPLC. Another solution prepared by accurately weighing unpurified low-purity substance and internal standard was analyzed by HPLC. Based on the theoretical derivation derived from the Beer-Lambert law, using the ratio of the HPLC peak areas of two solutions as correction, the purity was then calculated without the same reference as target analyte. Compared to previous methods with similar selectivity and accuracy, it has advantages such as a less purified sample is required, time for lyophilization is reduced by half, and sample preparation is more controllable. The proposed method was verified by analysis of a suite of six commercially available, high-purity compounds, and the difference of results between it and direct qNMR was within 0.1%. The result of Pyributicarb using ISC-HPLC-qNMR was 97.6% (U = 0.5%; k = 2), and the reference value was 97.61% (U = 0.22%; k = 2). The results demonstrate that the proposed method provides a new way for reference material producers to calibrate lower-purity organics and has the potential advantage of accurate quantification of lower-purity organics.
Elongating responses to herbicides of heterotrophic and photoautotrophic hairy roots derived from pak-bung plant
J Biosci Bioeng 2002;93(5):505-8.PMID:16233240DOI:10.1016/s1389-1723(02)80100-1.
The heterotrophic (HT) and photoautotrophic (PT) hairy roots of pak-bung were found to exhibit different elongating responses depending on the modes of actions of test herbicides. Treatment with 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU), an inhibitor of photosynthesis, decreased the tip elongation rate of the PT hairy roots, while no adverse effect was observed in the case of the HT hairy roots when DCMU were used at concentrations of 0.001-10 micromol/dm3. The values of the median effective concentration (EC50), defined as the herbicide concentration at which the tip elongation rate is decreased to 50% that of the herbicide-free control, were calculated. For the HT hairy roots: EC50 =1.8 (paraquat) and 1.4 micromol/dm3 (Pyributicarb), and for the PT hairy roots: EC50 = 0.45 (DCMU), 0.37 (paraquat) and 1.2 micromol/dm3 (Pyributicarb).
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays
Toxicology 2011 Feb 27;280(3):77-87.PMID:21115097DOI:10.1016/j.tox.2010.11.008.
The nuclear receptor, pregnane X receptor (PXR), is a ligand-dependent transcription factor that regulates genes involved in xenobiotic metabolism. Recent studies have shown that PXR activation may affect energy metabolism as well as the endocrine and immune systems. In this study, we characterized and compared the agonistic activities of a variety of pesticides against human PXR (hPXR) and mouse PXR (mPXR). We tested the hPXR and mPXR agonistic activity of 200 pesticides (29 organochlorines, 11 diphenyl ethers, 56 organophosphorus pesticides, 12 pyrethroids, 22 carbamates, 12 acid amides, 7 triazines, 7 ureas, and 44 others) by reporter gene assays using COS-7 simian kidney cells. Of the 200 pesticides tested, 106 and 93 activated hPXR and mPXR, respectively, and a total of 111 had hPXR and/or mPXR agonistic activity with greater or lesser inter-species differences. Although all of the pyrethroids and most of the organochlorines and acid amides acted as PXR agonists, a wide range of pesticides with diverse structures also showed hPXR and/or mPXR agonistic activity. Among the 200 pesticides, Pyributicarb, pretilachlor, piperophos and butamifos for hPXR, and phosalone, prochloraz, pendimethalin, and butamifos for mPXR, acted as particularly potent activators at low concentrations in the order of 10⁻⁸-10⁻⁷ M. In addition, we found that several organophosphorus oxon- and Pyributicarb oxon-metabolites decreased PXR activation potency compared to their parent compounds. These results suggest that a large number of structurally diverse pesticides and their metabolites possess PXR-mediated transcriptional activity, and their ability to do so varies in a species-dependent manner in humans and mice.