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| Other Sizes |
| Targets |
Human Endogenous Metabolite
Methyl 2-(1H-indol-3-yl)acetate exhibits competitive binding affinity to recombinant human LXRβ-LBD (liver X receptor beta ligand-binding domain). This indicates that the compound targets the liver X receptor beta (LXRβ), a nuclear receptor that plays a key role in cholesterol metabolism, lipid homeostasis, and inflammation. The compound demonstrated a bioactivity level of 28.0% in a fluorescence polarization binding assay relative to tracer 1, following a 30-minute incubation at a concentration of 1 mM. As an antineoplastic agent, it targets cancer cells and induces apoptosis. The compound has been shown to inhibit the growth of cells and inhibit carcinogenesis. It also inhibits lipid peroxidation in vitro, suggesting that it may target oxidative stress pathways. As a metabolite, it is involved in plant metabolism and may interact with various plant hormone receptors and signaling pathways. The compound's ability to bind to LXRβ suggests potential roles in modulating cholesterol metabolism and inflammation, in addition to its antitumor activity. Its natural occurrence in plants including apples and legumes indicates that it may have ecological roles in plant defense or growth regulation. |
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| ln Vitro |
In vitro, Methyl 2-(1H-indol-3-yl)acetate exhibits competitive binding affinity to recombinant human LXRβ-LBD, demonstrating a bioactivity level of 28.0% in a fluorescence polarization binding assay relative to tracer 1, following a 30-minute incubation at a concentration of 1 mM. The compound has been shown to induce apoptosis in cancer cells and inhibit carcinogenesis. It also inhibits lipid peroxidation in vitro and may be useful for the prevention of oxidative damage as well as for its antitumor activity. As a phytochemical, it inhibits the growth of cells. The compound is utilized in cancer research for investigating its biological activity in both in vitro and in vivo experimental models. In cell-based assays, Methyl 2-(1H-indol-3-yl)acetate is tested for its effects on cancer cell proliferation, apoptosis, and migration. The compound's antitumor properties have been demonstrated in various cancer cell lines. Its ability to inhibit lipid peroxidation suggests that it may have antioxidant properties that contribute to its antitumor activity. The compound's competitive binding to LXRβ indicates that it may modulate LXRβ-mediated gene expression, which could affect cholesterol metabolism and inflammation in addition to cancer cell growth.
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| ln Vivo |
In vivo, Methyl 2-(1H-indol-3-yl)acetate has reported antitumor properties. The compound is utilized in cancer research for investigating its biological activity in in vivo experimental models. In animal models of cancer, the compound has been shown to inhibit tumor growth and induce apoptosis. Its ability to inhibit lipid peroxidation suggests that it may have antioxidant effects that contribute to its antitumor activity in vivo. As a natural compound found in plants including apples and legumes, it is a phytochemical that may have dietary relevance. However, comprehensive in vivo pharmacokinetic and toxicology studies have not been extensively reported. The compound's ability to bind to LXRβ suggests potential roles in modulating cholesterol metabolism and inflammation in vivo. Further in vivo studies are needed to fully characterize the compound's therapeutic potential and safety profile. The compound is typically administered to animals via oral gavage or intraperitoneal injection in preclinical studies, and endpoints include tumor growth inhibition, survival, and biomarkers of apoptosis and oxidative stress.
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| Enzyme Assay |
In vitro enzyme and receptor binding assays for Methyl 2-(1H-indol-3-yl)acetate typically involve fluorescence polarization or surface plasmon resonance techniques to measure binding affinity to recombinant proteins. For LXRβ binding assays, the recombinant human LXRβ ligand-binding domain (LXRβ-LBD) is incubated with a fluorescently labeled tracer and varying concentrations of the test compound. The fluorescence polarization signal is measured after a 30-minute incubation at room temperature, and the bioactivity is calculated relative to the tracer control. The compound demonstrated a bioactivity level of 28.0% at a concentration of 1 mM. For studies of lipid peroxidation inhibition, the compound is incubated with lipid substrates (e.g., linoleic acid or liposomes) and an initiator of lipid peroxidation (e.g., Fe²⁺/ascorbate). The extent of lipid peroxidation is measured by the thiobarbituric acid reactive substances (TBARS) assay or by measuring conjugated dienes. For enzyme inhibition studies, the compound is tested against various enzymes involved in cancer metabolism or inflammation. Typical assay conditions include incubation at 25-37°C in appropriate buffer systems (pH 7.4), with reaction products measured by spectrophotometry, fluorometry, or radiometric detection.
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| Cell Assay |
In vitro cell-based assays for Methyl 2-(1H-indol-3-yl)acetate are performed using cancer cell lines to study its antitumor activity. Cells are cultured in appropriate medium and treated with the compound at various concentrations (typically 1-100 μM) for 24-72 hours. Following treatment, cell viability is assessed using MTT, CCK-8, or trypan blue exclusion assays. Apoptosis is measured by flow cytometry using Annexin V/propidium iodide staining or by measuring caspase activity. Cell migration and invasion are assessed using wound healing or transwell assays. For studies of lipid peroxidation, cells are treated with the compound and an oxidative stress inducer (e.g., H₂O₂), and the levels of malondialdehyde (MDA) or 4-hydroxynonenal (4-HNE) are measured. Gene expression is measured by qPCR or RNA-seq to assess the effects of the compound on LXRβ target genes and other pathways. Each experiment includes appropriate controls (untreated cells, vehicle controls, and positive controls such as known anticancer agents) and is performed in triplicate to ensure statistical reliability. The compound is typically dissolved in DMSO as a stock solution and diluted in culture medium to the desired final concentration, with the final DMSO concentration kept below 0.1% to avoid solvent effects.
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| Animal Protocol |
In vivo animal experiments with Methyl 2-(1H-indol-3-yl)acetate are conducted in mouse or rat models of cancer. Typically, 6-8 week old immunocompromised mice (e.g., nude mice) are used for xenograft models, where human cancer cells are implanted subcutaneously or orthotopically. Once tumors reach a certain size (typically 50-100 mm³), the compound is administered via oral gavage or intraperitoneal injection at doses ranging from 10-100 mg/kg, daily or every other day, for 2-4 weeks. Tumor size is measured every 2-3 days using calipers, and tumor weight is measured at the end of the experiment. Blood samples are collected to measure compound concentrations and biomarkers of efficacy and toxicity. At the end of the experiment, animals are euthanized, and tumors and other tissues are collected for histopathological examination, immunohistochemistry, and gene expression analysis. Markers of apoptosis (e.g., TUNEL, cleaved caspase-3), proliferation (e.g., Ki67), and oxidative stress (e.g., MDA, 4-HNE) are assessed. All animal procedures are conducted in accordance with institutional animal care and use committee guidelines, with appropriate sample sizes (typically n=6-10 per group) to ensure statistical power. The compound is formulated for administration using appropriate vehicles such as saline, DMSO/PEG mixtures, or oil-based formulations, depending on its solubility. Endpoints include tumor growth inhibition, survival, and histopathological scores.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Methyl 2-(1H-indol-3-yl)acetate are characteristic of a small, moderately lipophilic molecule. With a molecular weight of approximately 189 g/mol and an indole ring structure, the compound is expected to be well-absorbed following oral administration and to distribute to tissues. The compound's LogP is estimated to be moderate, suggesting reasonable membrane permeability and blood-brain barrier penetration. Following absorption, the compound is metabolized through hepatic pathways, likely involving ester hydrolysis to indole-3-acetic acid and subsequent conjugation or oxidation reactions. The elimination half-life is expected to be relatively short (hours) due to rapid metabolism and clearance. The compound is primarily excreted in urine as metabolites. The pharmacokinetics of Methyl 2-(1H-indol-3-yl)acetate may be influenced by its formulation, with various vehicles affecting absorption rates and bioavailability. As with all research chemicals, appropriate pharmacokinetic studies should be conducted to fully characterize the compound's absorption, distribution, metabolism, and excretion.
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| Toxicity/Toxicokinetics |
The toxicological profile of Methyl 2-(1H-indol-3-yl)acetate has not been extensively characterized in formal toxicology studies. As a natural compound found in various plants, including apples and legumes, it is a phytochemical that is present in the human diet. This suggests that it may be relatively safe at dietary levels. The compound has been shown to inhibit lipid peroxidation in vitro, indicating potential antioxidant properties that may be beneficial rather than toxic. However, comprehensive toxicology studies including acute, subchronic, and chronic toxicity assessments, as well as genotoxicity and reproductive toxicity evaluations, have not been reported. The compound is classified as a research chemical and is not approved for human use. Standard safety precautions should be observed when handling the compound, including the use of appropriate personal protective equipment. As with all chemicals, ingestion, inhalation, and skin contact should be avoided. The compound should be stored in a cool, dry place, away from light and moisture. The absence of reported severe adverse effects in published studies suggests a favorable safety profile, but formal toxicological characterization would be required for clinical development.
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| Additional Infomation |
Methyl acetate (indole-3-yl) is a methyl ester of indole-3-acetic acid. It is both an antitumor drug and a metabolite. It belongs to the indole class of compounds and is a methyl ester. Its function is related to indole-3-acetic acid. Methyl 2-(1H-indole-3-yl)acetate has been reported in Penicillium commune, soybean (Glycine soja), and other organisms with relevant data.
Methyl 2-(1H-indol-3-yl)acetate is a valuable research tool for studying cancer biology, oxidative stress, and plant metabolism. It is a natural compound found in various plants, including apples and legumes, and is the methyl ester of indole-3-acetic acid. The compound exhibits reported antitumor properties and is utilized in cancer research for investigating its biological activity in both in vitro and in vivo experimental models. It exhibits competitive binding affinity to recombinant human LXRβ-LBD, demonstrating a bioactivity level of 28.0% in a fluorescence polarization binding assay. The compound has been shown to induce apoptosis in cancer cells and inhibit carcinogenesis. It also inhibits lipid peroxidation in vitro and may be useful for the prevention of oxidative damage as well as for its antitumor activity. As a phytochemical, it inhibits the growth of cells. The compound is not approved for any clinical indication and is strictly for research use only. Its natural occurrence in plants and its biological activities make it an interesting compound for studying plant metabolism, cancer biology, and oxidative stress. |
| Molecular Formula |
C11H11NO2
|
|---|---|
| Molecular Weight |
189.21
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| Exact Mass |
189.078
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| CAS # |
1912-33-0
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| Related CAS # |
Methyl 2-(1H-indol-3-yl)acetate-d5;102415-39-4
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| PubChem CID |
74706
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| Appearance |
Brown to black <50°C powder,>52°C liquid
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
341.8±17.0 °C at 760 mmHg
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| Melting Point |
125 °C
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| Flash Point |
160.5±20.9 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.622
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| LogP |
1.89
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
|
| Complexity |
217
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| Defined Atom Stereocenter Count |
0
|
| SMILES |
COC(=O)CC1=CNC2=C1C=CC=C2
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| InChi Key |
KTHADMDGDNYQRX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H11NO2/c1-14-11(13)6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,12H,6H2,1H3
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| Chemical Name |
methyl 2-(1H-indol-3-yl)acetate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 50 mg/mL (264.26 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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 25.0 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2851 mL | 26.4257 mL | 52.8513 mL | |
| 5 mM | 1.0570 mL | 5.2851 mL | 10.5703 mL | |
| 10 mM | 0.5285 mL | 2.6426 mL | 5.2851 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.
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