ITE

AHR agonist CAS# 448906-42-1

ITE

Catalog No. BCC3902----Order now to get a substantial discount!

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Quality Control of ITE

Number of papers citing our products

Chemical structure

ITE

3D structure

Chemical Properties of ITE

Cas No. 448906-42-1 SDF Download SDF
PubChem ID 4668801 Appearance Powder
Formula C14H10N2O3S M.Wt 286.3
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 41 mg/mL (143.20 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name methyl 2-(1H-indole-3-carbonyl)-1,3-thiazole-4-carboxylate
SMILES COC(=O)C1=CSC(=N1)C(=O)C2=CNC3=CC=CC=C32
Standard InChIKey KDDXOGDIPZSCTM-UHFFFAOYSA-N
Standard InChI InChI=1S/C14H10N2O3S/c1-19-14(18)11-7-20-13(16-11)12(17)9-6-15-10-5-3-2-4-8(9)10/h2-7,15H,1H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of ITE

DescriptionEndogenous aryl hydrocarbon receptor (AhR) agonist (Ki = 3 nM). Decreases Oct4 levels in U87 glioblastoma cells. Induces stem-like cancer cell differentiation in U87 tumor spheres and inhibits ovarian cancer cell proliferation in vitro. Suppresses tumor growth in U87 and OVCAR-3 cell xenografts in mice. Also inhibits TGF-β-induced human myofibroblast differentiation.

ITE Dilution Calculator

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Preparing Stock Solutions of ITE

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4928 mL 17.4642 mL 34.9284 mL 69.8568 mL 87.321 mL
5 mM 0.6986 mL 3.4928 mL 6.9857 mL 13.9714 mL 17.4642 mL
10 mM 0.3493 mL 1.7464 mL 3.4928 mL 6.9857 mL 8.7321 mL
50 mM 0.0699 mL 0.3493 mL 0.6986 mL 1.3971 mL 1.7464 mL
100 mM 0.0349 mL 0.1746 mL 0.3493 mL 0.6986 mL 0.8732 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Calcutta University

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Background on ITE

2-(1′H-indole-3′-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE) is a nontoxic immunosuppressive endogenous aryl hydrocarbon receptor (AhR) ligand [1] [2]. Its EC50 identified via yeast AhR assay is 7.8×10−10 mol/l [3].
AhR is a transcription factor mediating toxic effects of environmental pollutants such as 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD), it is activated by ligand [2].
ITE inhibited TGFβ1-induced myofibroblast differentiation in TGFβ1-challenged cultures of primary human fibroblasts from several distinct tissue types. In primary human orbital fibroblasts, ITE inhibited TGFβ1-induced nuclear translocation of Smad2/3/4 and its subsequent binding to SBE, but it did not inhibit TGFβ1-induced phosphorylation of Smad2/3, Erk1/2, or Akt [4], it inhibited TGFβ1 (1 ng/mL)-induced α-smooth muscle actin (α-SMA) expression, extracellular matrix production [5]. The inhibition of ITE to TGFβ1-induced myofibroblast differentiation in primary human fibroblasts is AhR independent [5].
In Sprague-Dawley rats maintained under a 12 h light/12 h dark cycle and given free access to a solid diet and distilled water, ITE at 1.6 and 8.0 mg/kg bw, significantly increased the CYP1A1 mRNA levels by 5.59 and 68.55 fold, respectively. It indicated that ITE activated AhR activation in placentas. 8.0 mg/kg bw ITE elevated the level of HIF-1a mRNA, induced the levels of VEGF-A, VEGF-B and PIGF mRNA in a dose-dependent manner [6].
References:
[1]. Lindsey F. Nugent, Guangpu Shi, Barbara P. Vistica, et al. ITE, A Novel Endogenous Nontoxic Aryl Hydrocarbon Receptor Ligand, Efficiently Suppresses EAU and T-Cell–Mediated Immunity. Invest Ophthalmol Vis Sci., 2013, 54(12):7463-7469.
[2]. Jaishree Bankoti, Ben Rase, Tom Simones, et al. Functional and phenotypic effects of AhR activation in inflammatory dendritic cells. Toxicol Appl Pharmacol., 2010, 246(1-2):18-28.
[3]. S. Medjakovic and A. Jungbauer. Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor. Journal of Steroid Biochemistry & Molecular Biology, 2008, 108:171-177.
[4]. Geniece M. Lehmann, Xia Xi, Ajit A. Kulkarni, et al. The Aryl Hydrocarbon Receptor Ligand ITE Inhibits TGFβ1-Induced Human Myofibroblast Differentiation. American Journal of Pathology, 2011, 178(4):1556–1567.
[5]. Geniece M. Lehmann, Xia Xi, Ajit A. Kulkarni, et al. The Aryl Hydrocarbon Receptor Ligand ITE Inhibits TGF1-Induced Human Myofibroblast Differentiation. The American Journal of Pathology, 2011, 178(4):1556-1567.
[6]. Yanming Wu, Xiao Chen, Qian Zhou, et al. ITE and TCDD Differentially Regulate the Vascular Remodeling of Rat Placenta via the Activation of AhR. PLoS ONE, 2014, 9(1): e86549.

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References on ITE

Genome-wide transcriptional profiling of human glioblastoma cells in response to ITE treatment.[Pubmed:26484269]

Genom Data. 2015 Jun 30;5:281-3.

A ligand-activated transcription factor aryl hydrocarbon receptor (AhR) is recently revealed to play a key role in embryogenesis and tumorigenesis (Feng et al. [1], Safe et al. [2]) and 2-(1'H-indole-3'-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE) (Song et al. [3]) is an endogenous AhR ligand that possesses anti-tumor activity. In order to gain insights into how ITE acts via the AhR in embryogenesis and tumorigenesis, we analyzed the genome-wide transcriptional profiles of the following three groups of cells: the human glioblastoma U87 parental cells, U87 tumor sphere cells treated with vehicle (DMSO) and U87 tumor sphere cells treated with ITE. Here, we provide the details of the sample gathering strategy and show the quality controls and the analyses associated with our gene array data deposITEd into the Gene Expression Omnibus (GEO) under the accession code of GSE67986.

A tryptophan derivative, ITE, enhances liver cell metabolic functions in vitro.[Pubmed:27959388]

Int J Mol Med. 2017 Jan;39(1):101-112.

Cell encapsulation provides a three-dimensional support by incorporating isolated cells into microcapsules with the goal of simultaneously maintaining cell survival and function, as well as providing active transport for a bioreactor in vitro similarly to that observed in vivo. However, the biotra-nsformation and metabolic functions of the encapsulated cells are not satisfactory for clinical applications. For this purpose, in this study, hepatoma-derived Huh7 cells/C3A cells were treated with 2-(1'H-indole-3'-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE), an endogenous non-toxic ligand for aryl hydrocarbon receptor, in monolayer cultures and on microspheres. The mRNA and protein levels, as well as the metabolic activities of drug metabolizing enzymes, albumin secretion and urea synthesis were determined. When the Huh7 and C3A cells cultured in a monolayer on twodimensional surfaces, ITE enhanced the protein levels and the metabolic activities of the major cytochrome P450 (CYP450) enzymes, CYP1A1, CYP1A2, CYP3A4 and CYP1B1, and slightly increased albumin secretion and urea synthesis. Moreover, when cultured on microspheres, ITE also substantially increased the protein levels and metabolic activities of CYP1A1, CYP1A2, CYP3A4 and CYP1B1 in both liver cell lines. On the whole, our findings indicate that ITE enhances the enzymatic activities of major CYP450 enzymes and the metabolic functions of liver cells cultured in monolayer or on microspheres, indicating that it may be utilized to improve the functions of hepatocytes. Thus, it may be used in the future for the treatment of liver diseases.

ITE and TCDD differentially regulate the vascular remodeling of rat placenta via the activation of AhR.[Pubmed:24475139]

PLoS One. 2014 Jan 24;9(1):e86549.

Vascular remodeling in the placenta is essential for normal fetal development. The previous studies have demonstrated that in utero exposure to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD, an environmental toxicant) induces the intrauterine fetal death in many species via the activation of aryl hydrocarbon receptor (AhR). In the current study, we compared the effects of 2-(1'H-indole-3'-carbonyl)-thiazole-4-carboxylic acid methyl ester (ITE) and TCDD on the vascular remodeling of rat placentas. Pregnant rats on gestational day (GD) 15 were randomly assigned into 5 groups, and were exposed to a single dose of 1.6 and 8.0 mg/kg body weight (bw) ITE, 1.6 and 8.0 microg/kg bw TCDD, or an equivalent volume of the vehicle, respectively. The dams were sacrificed on GD20 and the placental tissues were gathered. The intrauterine fetal death was observed only in 8.0 microg/kg bw TCDD-exposed group and no significant difference was seen in either the placental weight or the fetal weight among all these groups. The immunohistochemical and histological analyses revealed that as compared with the vehicle-control, TCDD, but not ITE, suppressed the placental vascular remodeling, including reduced the ratio of the placental labyrinth zone to the basal zone thickness (at least 0.71 fold of control), inhibITEd the maternal sinusoids dilation and thickened the trophoblastic septa. However, no marked difference was observed in the density of fetal capillaries in the labyrinth zone among these groups, although significant differences were detected in the expression of angiogenic growth factors between ITE and TCDD-exposed groups, especially Angiopoietin-2 (Ang-2), Endoglin, Interferon-gamma (IFN-gamma) and placenta growth factor (PIGF). These results suggest ITE and TCDD differentially regulate the vascular remodeling of rat placentas, as well as the expression of angiogenic factors and their receptors, which in turn may alter the blood flow in the late gestation and partially resulted in intrauterine fetal death.

Description

ITE is a potent endogenous agonist of aryl hydrocarbon receptor (AhR), binding directly to AHR, with a Ki of 3 nM. ITE also has immunosuppressive activity.

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