Indole-3-acetamide
(Synonyms: 3-吲哚乙酰胺) 目录号 : GC38268
Indole-3-acetamide是吲哚-3-乙酸的生物合成中间体。
Cas No.:879-37-8
Sample solution is provided at 25 µL, 10mM.
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Indole-3-acetamide is a biosynthesis intermediate of indole-3-acetic acid[1]. Indole-3-acetamide is formed directly from tryptophan by tryptophan monooxygenase or, indirectly, through indole-3-acetonitrile or indole-3-acetaldoxime intermediates, and converted to indole-3-acetic acid(IAA) by amidase[2]. IAA is the most common natural plant growth hormone of the auxin class, mainly regulating growth and development in plants and microorganisms by binding to the auxin receptor TIR1[3][4]. Indole-3-acetamide is usually used in the fileds of plant growth regulation, biochemistry, intestinal microbiota metabolism[5-7].
In vitro, treatment of HepG2 cells with Indole-3-acetamide (0-600μM) for 12 hours bolstered cell viability, decreased levels of ALT, AST, TC, and TG, reduced ROS production, attenuated EtOH-induced oxidative damage, activated AhR gene and protein expression, and significantly upregulated ADH and ALDH gene expression while downregulating inflammatory gene expression[6].
References:
[1] Lehmann, T., Hoffmann, M., Hentrich, M., & Pollmann, S. (2010). Indole-3-acetamide-dependent auxin biosynthesis: a widely distributed way of indole-3-acetic acid production?. European journal of cell biology, 89(12), 895–905.
[2] Pérez-Alonso, M. M., Ortiz-García, P., Moya-Cuevas, J., Lehmann, T., Sánchez-Parra, B., Björk, R. G., Karim, S., Amirjani, M. R., Aronsson, H., Wilkinson, M. D., & Pollmann, S. (2021). Endogenous indole-3-acetamide levels contribute to the crosstalk between auxin and abscisic acid, and trigger plant stress responses in Arabidopsis. Journal of experimental botany, 72(2), 459–475.
[3] Dimkpa, C. O., Zeng, J., McLean, J. E., Britt, D. W., Zhan, J., & Anderson, A. J. (2012). Production of indole-3-acetic acid via the indole-3-acetamide pathway in the plant-beneficial bacterium Pseudomonas chlororaphis O6 is inhibited by ZnO nanoparticles but enhanced by CuO nanoparticles. Applied and environmental microbiology, 78(5), 1404–1410.
[4] Duca, D. R., & Glick, B. R. (2020). Indole-3-acetic acid biosynthesis and its regulation in plant-associated bacteria. Applied microbiology and biotechnology, 104(20), 8607–8619.
[5] Ortiz-García, P., Pérez-Alonso, M. M., González Ortega-Villaizán, A., Sánchez-Parra, B., Ludwig-Müller, J., Wilkinson, M. D., & Pollmann, S. (2022). The Indole-3-Acetamide-Induced Arabidopsis Transcription Factor MYB74 Decreases Plant Growth and Contributes to the Control of Osmotic Stress Responses. Frontiers in plant science, 13, 928386.
[6] Wang, M., Feng, X., Zhao, Y., Lan, Y., & Xu, H. (2023). Indole-3-acetamide from gut microbiota activated hepatic AhR and mediated the remission effect of Lactiplantibacillus plantarum P101 on alcoholic liver injury in mice. Food & function, 14(23), 10535–10548.
[7] Eguchi, N., Watanabe, Y., Kawanishi, K., Hashimoto, Y., & Hayaishi, O. (1984). Inhibition of indoleamine 2,3-dioxygenase and tryptophan 2,3-dioxygenase by beta-carboline and indole derivatives. Archives of biochemistry and biophysics, 232(2), 602–609.
Indole-3-acetamide是吲哚-3-乙酸的生物合成中间体[1]。Indole-3-acetamide可以直接由色氨酸通过色氨酸单加氧酶形成，也可以通过吲哚-3-乙腈或吲哚-3-乙醛肟中间体间接形成，并且可以在酰胺酶的作用下转化为吲哚-3-乙酸（IAA）[2]。IAA是最常见的天然植物生长素类激素，主要通过与生长素受体TIR1结合来调节植物和微生物的生长和发育[3][4]。Indole-3-acetamide通常用于植物生长调节、生物化学以及肠道微生物群代谢等领域的研究[5-7]。
在体外实验中，用Indole-3-acetamide（0-600μM）处理HepG2细胞12小时，可以增强细胞活性，降低ALT、AST、TC和TG水平，减少活性氧（ROS）的产生，减轻乙醇诱导的氧化损伤，激活AhR基因和蛋白表达，并显著上调乙醇脱氢酶（ADH）和乙醛脱氢酶（ALDH）基因表达，同时下调炎症基因表达[6]。
| Cell experiment [1]: | |
Cell lines | HepG2 cell line |
Preparation Method | The HepG2 cells were cultured in a 25cm2 culture flask using DMEM that was supplemented with 10% fetal bovine serum, 100U/mL penicillin, and 0.1mg/mL streptomycin. The cells were maintained at 37°C and 5% CO2 and passaged every 2 days. HepG2 cells were seeded in a 96-well plate at a density of 3 × 105 cells per mL, when they reached 80% confluence, HepG2 cells were stimulated with Indole-3-acetamide dissolved in DMSO at the concentrations of 0, 50, 100, 200, 400 and 600µM for 12h. The cells were then treated with varying concentrations of ethanol (EtOH) at 0, 400, 600 and 800mM for 24h. After the treatment, the cells were washed with PBS and incubated with CCK-8 solution for 2h. The absorbance at 450nm was measured using a Varioskan. Finally, 4 groups including a control group without Indole-3-acetamide and EtOH treatment (Ctrl), a model group with 400mM EtOH only (EtOH), and two treatment groups with different doses of Indole-3-acetamide (200, and 400µM) before EtOH (L-IAM and H-IAM) were divided. Accordingly, HepG2 cells were seeded in 6-well plates at a density of 3 × 105 cells per mL and treated as description for the analysis of the protein and transcript levels. |
Reaction Conditions | 0-600μM; 12h |
Applications | Indole-3-acetamide bolstered cell viability, decreased levels of ALT, AST, TC, and TG, reduced ROS production, attenuated EtOH-induced oxidative damage, activated AhR gene and protein expression,and significantly upregulated ADH and ALDH gene expression while downregulating inflammatory gene expression. |
References: | |
| Cas No. | 879-37-8 | SDF | |
| 别名 | 3-吲哚乙酰胺 | ||
| Canonical SMILES | C1=CC=CC2=C1C(=C[NH]2)CC(N)=O | ||
| 分子式 | C10H10N2O | 分子量 | 174.2 |
| 溶解度 | DMSO : 100 mg/mL (574.05 mM; Need ultrasonic); H2O : 1.3 mg/mL (7.46 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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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.7405 mL | 28.7026 mL | 57.4053 mL |
| 5 mM | 1.1481 mL | 5.7405 mL | 11.4811 mL |
| 10 mM | 0.5741 mL | 2.8703 mL | 5.7405 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。
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Quality Control & SDS
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- Purity: >98.00%
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