GLPBio

Indole-3-acetamide

Catalog No.: GC38268Purity:>98.00%Synonyms: IAM, NSC 1969
COASDSData Sheet
Indole-3-acetamide is a biosynthesis intermediate of indole-3-acetic acid.

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Indole-3-acetamide
Cas No.: 879-37-8
10mM (in 1mL DMSO)In Stock
$46.00
1
50mgIn Stock
$29.00
1
100mgIn Stock
$41.00
1
500mgIn Stock
$93.00
1
1gIn Stock
$137.00
1
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Description

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 (0-600米M) 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每905.
[2]?P谷rez-Alonso, M. M., Ortiz-Garc赤a, P., Moya-Cuevas, J., Lehmann, T., S芍nchez-Parra, B., Bj?rk, 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每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每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每8619.
[5]?Ortiz-Garc赤a, P., P谷rez-Alonso, M. M., Gonz芍lez Ortega-Villaiz芍n, A., S芍nchez-Parra, B., Ludwig-M邦ller, 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每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每609.

Protocol

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 600?M 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 400?M) 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

0-600米M; 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:
[1] 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每10548.

Product Documents

Purity:>98.00%Appearance:A solid
COASDSData Sheet

Chemical Properties

CAS No.
879-37-8
Synonyms
IAM, NSC 1969
SMILES
C1=CC=CC2=C1C(=C[NH]2)CC(N)=O
Molecular Formula
C10H10N2O
Molecular Weight
174.2
Solubility
DMSO : 100 mg/mL (574.05 mM; Need ultrasonic); H2O : 1.3 mg/mL (7.46 mM; Need ultrasonic)
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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