| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| 250mg |
|
||
| 500mg |
|
||
| Other Sizes |
| Targets |
Indole-3-pyruvic acid targets the aryl hydrocarbon receptor (AHR), a ligand-activated transcription factor involved in the regulation of immune responses, cell proliferation, and xenobiotic metabolism. As an AHR agonist, IPA can modulate the expression of AHR target genes, influencing various physiological and pathological processes. The compound's activity as an AHR agonist is linked to its antioxidant properties and its potential therapeutic effects in inflammation and anxiety. IPA is also a key intermediate in tryptophan metabolism and auxin biosynthesis in plants.
|
|---|---|
| ln Vitro |
In HepG2 cells, indole-3-pyruvic acid (50 and 250 μM, 24 h) activates AHR[1]. Triole-3-pyruvic acid (50 μM, 4 days) stimulates Tr1 cells but does not prevent Th1 cell elimination [1]. Indole-3-pyruvic acid (1 mM, 24 h) lessens the cytotoxicity of UVB-induced HaCaT [1]. In HaCaT cells, indole-3-pyruvic acid (25 mM, 6 hours) lowers COX-2 levels [2].
In vitro, indole-3-pyruvic acid has demonstrated antioxidant properties and is used as a research tool to study AHR signaling. It has been shown to protect HR-1 hairless mice from UVB-induced skin damage when applied topically at a dose of 100 µM. In cell-based assays, IPA can modulate the expression of genes involved in inflammation and oxidative stress. It is also used as a precursor for the synthesis of chromopyrrolic acid and as a reactant in Biginelli-like scaffold syntheses. The compound's ability to activate AHR makes it a valuable tool for studying the role of this receptor in immune function and metabolism. |
| ln Vivo |
Mice BALB/c are given indole-3-pyruvic acid (face, 0.1% chow; 5 d) to activate their AHR [1]. Indole-3-pyruvic acid (100 μM, dose at skin) protects HR-1 hairless shell from UVB-induced skin damage. Indole-3-pyruvic acid (face, fed MF food (0.1%) for 5 weeks) eliminates T cells [ 2]. mediated long-term inflammation in vaginitis models [1]. -In the elevated plus maze, mice can open their arms for a longer period of time when given pyruvate (ip, 100–200 mg/kg) [3].
In vivo, indole-3-pyruvic acid is orally bioactive. It has been shown to eliminate T cells and mediate long-term inflammation in vaginitis models when administered in feed (0.1% for 5 weeks). Dietary administration of IPA (0.1%) has also been reported to reduce diarrhea. In an elevated plus maze test, IPA demonstrated anxiolytic-like effects. These in vivo findings suggest that IPA has potential therapeutic applications in treating inflammation, anxiety, and other conditions. However, further research is needed to fully characterize its in vivo pharmacology and therapeutic potential. |
| Enzyme Assay |
In vitro experiments with indole-3-pyruvic acid typically involve preparing stock solutions in DMSO or other suitable solvents and diluting them in assay buffers or cell culture media. For cell-based studies, cells are treated with IPA at concentrations ranging from 1-100 µM for various durations. The compound's effects on AHR activation are often measured using reporter gene assays, where cells are transfected with a luciferase construct containing AHR response elements. Antioxidant activity can be assessed using cell-based or cell-free assays measuring the scavenging of reactive oxygen species (ROS). IPA is also used as a substrate or reactant in enzymatic synthesis reactions.
|
| Cell Assay |
RT-PCR[2]
Cell Types: HaCaT cells Tested Concentrations: 5-25mM Incubation Duration: 6 hrs (hours) Experimental Results: Inhibition of UVB-stimulated mRNA expression of IL-1β, IL-6 and cyclooxygenase 2 (Cox-2). In vitro cell-based assays using indole-3-pyruvic acid are performed in various cell lines to study its effects on AHR signaling, inflammation, and oxidative stress. Cells are seeded in multi-well plates and treated with IPA at concentrations typically ranging from 1-100 µM for 24-48 hours. AHR activation is assessed by measuring the expression of AHR target genes (e.g., CYP1A1) using qPCR or by using reporter gene assays. Anti-inflammatory effects are evaluated by measuring the production of pro-inflammatory cytokines (e.g., TNF-α, IL-6) using ELISA. Antioxidant activity is assessed by measuring ROS levels using fluorescent probes such as DCFH-DA. The compound is typically dissolved in DMSO and diluted in cell culture medium. |
| Animal Protocol |
Animal/Disease Models: balb/c (Bagg ALBino) mouse [1]
Doses: Fed with MF feed. 0.1% for 5 days. Route of Administration: Oral. Experimental Results: Up-regulated the expression of Cyp1a1 (a biomarker of AHR activation) in the colon. Animal/Disease Models: SCID mouse T cell-mediated colitis model [1] Doses: fed with 0.1% MF feed for 5 consecutive weeks. Route of Administration: oral. Experimental Results: inhibited diarrhea and improved colon inflammation. Downregulates the expression of Th1 and pro-inflammatory cytokines and upregulates the expression of IL-10 in the colon. Animal/Disease Models: HR-1 hairless mice [2] Doses: 100 μM Route of Administration: Skin Dose Experimental Results: Increased epidermal thickness. Attenuation of UVB-induced necrosis was observed in the upper dermis. In vivo animal experiments with indole-3-pyruvic acid have been conducted in various models. In a study on UVB-induced skin damage, IPA was applied topically at a dose of 100 µM to the skin of HR-1 hairless mice. In a vaginitis model, IPA was administered in the diet (MF food containing 0.1% IPA) for 5 weeks to study its effects on T cell elimination and long-term inflammation. In another study, dietary administration of IPA (0.1%) was used to assess its effect on diarrhea. The elevated plus maze test was used to evaluate the anxiolytic effects of IPA in mice. These protocols demonstrate the compound's oral bioavailability and its potential for topical and dietary administration. |
| ADME/Pharmacokinetics |
Indole-3-pyruvic acid has a molecular weight of 203.19 g/mol and the formula C11H9NO3. It is a beige powder with a melting point of 215°C. For pharmacokinetic studies, IPA is typically administered orally or topically. It is absorbed and can reach target tissues to exert its biological effects. The compound is stable under normal storage conditions and should be stored at room temperature, protected from light and moisture. Its solubility in water is limited, but it is soluble in DMSO and other organic solvents.
|
| Toxicity/Toxicokinetics |
The toxicity of indole-3-pyruvic acid has not been extensively characterized in the available literature. As a naturally occurring metabolite of tryptophan, it is likely to have a relatively low toxicity profile. In animal studies, it has been administered orally in the diet at 0.1% for 5 weeks without reported severe adverse effects. However, as a research chemical, it is intended for laboratory use only and is not for human consumption. Standard laboratory safety precautions should be followed when handling IPA, including the use of appropriate personal protective equipment.
|
| References | |
| Additional Infomation |
Indole-3-pyruvic acid (IPA) is a naturally occurring α-keto analogue of tryptophan. It is an endogenous metabolite of tryptophan and a key intermediate in the biosynthesis of the plant hormone auxin, indole-3-acetic acid. IPA is an orally bioactive aryl hydrocarbon receptor (AHR) agonist with antioxidant properties. It has been studied for its potential to treat inflammation and anxiety. In animal models, IPA has demonstrated protective effects against UVB-induced skin damage, anxiolytic-like effects, and the ability to modulate immune responses. It is used as a research tool to study AHR signaling, tryptophan metabolism, and oxidative stress. IPA is intended for research use only and is not for human consumption.
|
| Molecular Formula |
C11H9NO3
|
|---|---|
| Molecular Weight |
203.19406
|
| Exact Mass |
203.058
|
| CAS # |
392-12-1
|
| PubChem CID |
803
|
| Appearance |
Light yellow to brown solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
445.2±28.0 °C at 760 mmHg
|
| Melting Point |
215 °C (dec.)(lit.)
|
| Flash Point |
223.0±24.0 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.685
|
| LogP |
0.46
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
15
|
| Complexity |
277
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
RSTKLPZEZYGQPY-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
|
| Chemical Name |
3-(1H-indol-3-yl)-2-oxopropanoic acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~166.67 mg/mL (~820.27 mM)
H2O : ~20 mg/mL (~98.43 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.9215 mL | 24.6075 mL | 49.2150 mL | |
| 5 mM | 0.9843 mL | 4.9215 mL | 9.8430 mL | |
| 10 mM | 0.4922 mL | 2.4608 mL | 4.9215 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
