Oryzalin
(Synonyms: 氨磺乐灵) 目录号 : GC64626
Oryzalin 是一种二硝基苯胺除草剂，能在体外与植物微管蛋白结合，抑制微管(MT)聚合。Oryzalin 可在有丝分裂周期的各个阶段解聚微管并阻止新微管的聚合。
Cas No.:19044-88-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oryzalin is a dinitroaniline herbicide, binding to plant tubulin and inhibits microtubule (MT) polymerization in vitro. Oryzalin depolymerizes MTs and prevented the polymerization of new MTs at all stages of the mitotic cycle[1].
[1]. Morejohn LC, et al. Oryzalin, a dinitroaniline herbicide, binds to plant tubulin and inhibits microtubule polymerization in vitro. Planta. 1987 Oct;172(2):252-64.
| Cas No. | 19044-88-3 | SDF | Download SDF |
| 别名 | 氨磺乐灵 | ||
| 分子式 | C12H18N4O6S | 分子量 | 346.36 |
| 溶解度 | DMSO : 250 mg/mL (721.79 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。 |
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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 | 2.8872 mL | 14.4358 mL | 28.8717 mL |
| 5 mM | 0.5774 mL | 2.8872 mL | 5.7743 mL |
| 10 mM | 0.2887 mL | 1.4436 mL | 2.8872 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。
Crystal structure of Oryzalin
Acta Crystallogr E Crystallogr Commun 2015 May 30;71(Pt 6):o429.PMID:26090208DOI:10.1107/S205698901500955X.
The title compound, C12H18N4O6S (systematic name: 4-di-propyl-amino-3,5-di-nitro-benzene-sulfonamide), is a sulfonamide with herbicidal properties marketed as Oryzalin. The dihedral angles between the benzene ring and the mean planes of the nitro groups are 26.15 (11) and 54.80 (9)°. The propyl arms of the di-propyl-amino substituent lie on opposite sides of this ring plane. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds generate a three-dimensional network.
Unveiling the Possible Oryzalin-Binding Site in the α-Tubulin of Toxoplasma gondii
ACS Omega 2022 May 24;7(22):18434-18442.PMID:35694483DOI:10.1021/acsomega.2c00729.
Dinitroaniline derivatives have been widely used as herbicidal agents to control weeds and grass. Previous studies demonstrated that these compounds also exhibit good antiparasitic activity against some protozoan parasites. Oryzalin (ORY), a representative dinitroaniline derivative, exerts its antiprotozoal activity against Toxoplasma gondii by inhibiting the microtubule polymerization process. Moreover, the identification of ORY-resistant T. gondii lines obtained by chemical mutagenesis confirmed that this compound binds selectively to α-tubulin. Based on experimental information reported so far and a multiple sequence analysis carried out in this work, we propose that the pironetin (PIR) site is the potential ORY-binding site. Therefore, we employed state-of-the-art computational approaches to characterize the interaction profile of ORY at the proposed site in the α-tubulin of T. gondii. An exhaustive search for other possible binding sites was performed using the Wrap "N" Shake method, which showed that ORY exhibits highest stability and affinity for the PIR site. Moreover, our molecular dynamics simulations revealed that the dipropylamine substituent of ORY interacts with a hydrophobic pocket, while the sulfonamide group formed hydrogen bonds with water molecules at the site entrance. Overall, our results suggest that ORY binds to the PIR site on the α-tubulin of the protozoan parasite T. gondii. This information will be very useful for designing less toxic and more potent antiprotozoal agents.
Herbicide Oryzalin inhibits human carbonic anhydrases in vitro
J Biochem Mol Toxicol 2017 Jun;31(6).PMID:28251759DOI:10.1002/jbt.21894.
Herbicides of the dinitroaniline chemical class, widely used Oryzalin and trifluralin, and also nitralin were tested as inhibitors of recombinant human carbonic anhydrases (CAs). Oryzalin bound and inhibited 11 out of 12 catalytically active CA isoforms present in the human body with the affinities in the same range as clinically used CA drugs, while no effect was detected for the other two compounds. Binding of all three herbicides was examined by fluorescence-based thermal shift assay, isothermal titration calorimetry, and the inhibition of carbon dioxide hydratase activity. During the last decade, dinitroaniline compound-based therapies against protozoan diseases are being developed. Therefore, it is important to investigate their potential off-target effects, including human CAs.
Oryzalin, a dinitroaniline herbicide, binds to plant tubulin and inhibits microtubule polymerization in vitro
Planta 1987 Oct;172(2):252-64.PMID:24225878DOI:10.1007/BF00394595.
The effects of Oryzalin, a dinitroaniline herbicide, on chromosome behavior and on cellular microtubules (MTs) were examined by light microscopy and immunogold staining, respectively, in endosperm cells from Haemanthus katherinae Bak. Brief treatments with 1.0·10(-8) M Oryzalin reduced markedly the migration rate of anaphase chromosomes and 1.0·10(-7) M Oryzalin stopped migration abruptly. Oryzalin (1.0·10(-7) M) depolymerized MTs and prevented the polymerization of new MTs at all stages of the mitotic cycle. The chromosome condensation cycle was unaffected by Oryzalin. Endothelial cells from the heart of Xenopus leavis showed no chromosomal or microtubular rearrangements after Oryzalin treatment. The inhibition by Oryzalin of the polymerization of tubulin isolated from cultured cells of Rosa sp. cv. Paul's scarlet was examined in vitro by turbidimetry, electron microscopy and polymer sedimentation analysis. Oryzalin inhibited the rapid phase of taxol-induced polymerization of rose MTs at 24°C with an apparent inhibition constant (K i ) of 2.59·10(6) M. Shorter and fewer MTs were formed with increasing Oryzalin concentrations, and maximum inhibition of taxol-induced polymerization occurred at approx. 1:1 molar ratios of Oryzalin and tubulin. Oryzalin partially depolymerized taxol-stabilized rose MTs. Ligand-binding experiments with [(14)C]Oryzalin demonstrated the formation of a tubulin-oryzalin complex that was time- and pH-dependent. The tubulin-oryzalin interaction (24°C, pH 7.1) had an apparent affinity constant (K app) of 1.19·10(5) M(-1). Oryzalin did not inhibit taxol-induced polymerization of bovinebrain MTs and no appreciable binding of Oryzalin to brain tubulin or other proteins was detected. The results demonstrate pharmacological differences between plant and animal tubulins and indicate that the most sensitive mode of action of the dinitroaniline herbicides is the direct poisoning of MT dynamics in cells of higher plants.
Oryzalin impairs maternal-fetal interaction during early pregnancy via ROS-mediated P38 MAPK/AKT and OXPHOS downregulation
Food Chem Toxicol 2023 Apr;174:113665.PMID:36775140DOI:10.1016/j.fct.2023.113665.
Oryzalin is a dinitroaniline pesticide for the control of weed growth via suppression of microtubule synthesis. There are studies about the deleterious effects of dinitroaniline pesticides on the reproductive system. Therefore, we attempted to demonstrate the toxic mechanisms of Oryzalin on early pregnancy using porcine uterine epithelial cells (pLE) and trophectoderm (pTr) cells. According to our results, the viability and proliferation of pLE and pTr cells were suppressed in response to Oryzalin exposure, and cell cycle progression was affected. Additionally, Oryzalin induced apoptotic cell death and impaired mitochondrial membrane polarity in pLE and pTr cells. Moreover, we confirmed that Oryzalin significantly downregulated adenosine triphosphate (ATP) production via the oxidative phosphorylation system and upregulated reactive oxygen species (ROS) generation in both pLE and pTr cells. The oryzalin-induced ROS generation was mitigated by N-acetylcysteine, a ROS scavenger, and further upregulation of phosphor-P38 MAPK/AKT/P70S6K protein expression was ameliorated in both pLE and pTr cells. We also confirmed that the suppression of migration and proliferation in oryzalin-treated pLE and pTr cells was restored upon oxidative stress mitigation. In summary, we revealed that the cytotoxic mechanisms of oryzalin-induced implantation failure were mediated by ROS-induced intracellular signaling regulation and migratory potential in pLE and pTr cells.