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| Other Sizes |
| Targets |
Indole-2-carboxylic acid targets the glycine site of the NMDA receptor, where it acts as a competitive antagonist with a Ki of 15 μM. It also inhibits HIV-1 integrase, an enzyme essential for viral replication. Additional targets include lipid peroxidation pathways, where the compound functions as a potent inhibitor. These targets make it relevant for research in neurodegenerative diseases, cerebral ischemic injury, and HIV infection.
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| ln Vitro |
In vitro, Indole-2-carboxylic acid specifically and competitively inhibits the potentiation by glycine of NMDA-gated current, demonstrating its activity as an NMDA receptor antagonist. It is a potent inhibitor of lipid peroxidation, protecting cells from oxidative damage. The compound also shows antiviral activity against HIV-1 through integrase inhibition. These in vitro activities support its potential in neuroprotection, antioxidant therapy, and antiviral research. The compound has been studied in various cell-based models of neurodegeneration and infection.
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| ln Vivo |
In vivo, Indole-2-carboxylic acid has demonstrated neuroprotective effects in animal models of neurodegenerative diseases and cerebral ischemic injury. Its antioxidant properties suggest potential benefits in conditions involving oxidative stress. The compound's ability to inhibit NMDA receptor-mediated excitotoxicity may contribute to its neuroprotective effects in vivo. However, detailed in vivo efficacy data are limited, and further studies are needed to fully characterize its therapeutic potential. The compound is primarily used as a research tool.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Indole-2-carboxylic acid include radioligand binding studies to assess affinity for the NMDA receptor glycine site. Competitive binding assays are performed using [3H]-glycine or [3H]-MDL-105,519 as radioligands, with I2CA concentrations ranging from 0.1-1000 μM. The Ki value for the glycine site is determined to be approximately 15 μM. HIV-1 integrase inhibition is assessed using enzyme activity assays that measure strand transfer or 3'-processing activity. Lipid peroxidation inhibition is measured using thiobarbituric acid reactive substance (TBARS) assays in brain homogenates.
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| Cell Assay |
In vitro cell-based assays for Indole-2-carboxylic acid are conducted using neuronal cell cultures (e.g., primary cortical neurons or SH-SY5Y cells) for neuroprotection studies. Cells are treated with I2CA at concentrations ranging from 1-100 μM, followed by exposure to excitotoxic agents (e.g., glutamate or NMDA) or oxidative stress inducers (e.g., H2O2). Cell viability is assessed using MTT or LDH assays. NMDA receptor function is evaluated by measuring intracellular calcium levels or electrophysiological recordings. HIV-1 integrase inhibition is assessed in infected cell cultures by measuring viral replication. Experiments include appropriate controls.
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| Animal Protocol |
In vivo animal studies with Indole-2-carboxylic acid are conducted in rodent models of neurodegenerative diseases, cerebral ischemia, or HIV infection. The compound is administered via intraperitoneal or intravenous injection at doses ranging from 1-50 mg/kg. Neuroprotection is assessed by measuring infarct size in stroke models or by behavioral tests in neurodegeneration models. Oxidative stress markers are measured in brain tissue. For HIV studies, viral load is measured in infected animals. Each treatment group consists of 6-10 animals, with vehicle-treated and positive control groups.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Indole-2-carboxylic acid have not been extensively characterized. As a small, polar molecule (MW 161.16), it is expected to have moderate oral bioavailability and reasonable tissue distribution, including penetration of the blood-brain barrier due to its lipophilic indole core. Metabolism likely occurs through conjugation and aromatic hydroxylation, with elimination via renal excretion. Detailed PK parameters such as half-life, Cmax, and AUC require further investigation in preclinical species for research applications.
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| Toxicity/Toxicokinetics |
Toxicological data for Indole-2-carboxylic acid indicate that it is generally well-tolerated at research doses. No significant acute toxicity has been reported in animal studies. The compound is not known to be genotoxic or carcinogenic. However, comprehensive toxicological profiling, including chronic toxicity and reproductive toxicity studies, has not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling, and the compound should be used only for in vitro and animal research purposes.
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| References | |
| Additional Infomation |
Indole-2-carboxylic acid is an indole carboxylic acid. It has been reported that indole-2-carboxylic acid is found in strychnos cathayensis and tomato (Solanum lycopersicum), and relevant data are available for reference.
Indole-2-carboxylic acid is a versatile research tool in neuropharmacology, virology, and oxidative stress research. Its NMDA receptor antagonist activity makes it valuable for studying excitotoxicity and neuroprotection. The compound's HIV-1 integrase inhibitory activity supports antiviral research. Its antioxidant properties make it useful for studying lipid peroxidation and oxidative damage. Indole-2-carboxylic acid is not approved for clinical use and is intended for research purposes only. The indole scaffold is widely used in medicinal chemistry for drug discovery. |
| Molecular Formula |
C₉H₇NO₂
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|---|---|
| Molecular Weight |
161.16
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| Exact Mass |
161.047
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| CAS # |
1477-50-5
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| Related CAS # |
Indole-2-carboxylic acid-13C;1216839-31-4
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| PubChem CID |
72899
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| Appearance |
Light brown to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
419.6±18.0 °C at 760 mmHg
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| Melting Point |
202-206 °C(lit.)
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| Flash Point |
207.6±21.2 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.726
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| LogP |
2.31
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
12
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| Complexity |
193
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
HCUARRIEZVDMPT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
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| Chemical Name |
1H-indole-2-carboxylic acid
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| Synonyms |
Indole2carboxylic acid; Indole 2 carboxylic acid
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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 : ~100 mg/mL (~620.50 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.51 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 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.51 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 25.0 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.51 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.2050 mL | 31.0251 mL | 62.0501 mL | |
| 5 mM | 1.2410 mL | 6.2050 mL | 12.4100 mL | |
| 10 mM | 0.6205 mL | 3.1025 mL | 6.2050 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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