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| Other Sizes |
| Targets |
Indole-4-carboxaldehyde targets inflammatory signaling pathways, specifically the NF-κB pathway. The compound has been shown to activate NF-κB, a transcription factor that plays a central role in regulating immune and inflammatory responses. By activating NF-κB, the compound modulates the expression of pro-inflammatory cytokines and other mediators. Studies have demonstrated that Indole-4-carboxaldehyde reduces methylglyoxal-induced hepatic inflammation in HepG2 cells, decreasing the expression of AGEs (advanced glycation end-products), glyoxalase-1 mRNA, TNF-α (tumor necrosis factor-alpha), and IFN-γ (interferon-gamma). This suggests that the compound may target pathways involved in glycation stress and inflammatory signaling, potentially through interaction with pattern recognition receptors or other upstream regulators of NF-κB.
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| ln Vitro |
One synthetic intermediate that can be utilized in the synthesis of drugs is indole-4-carboxaldehyde.
In vitro studies have demonstrated that Indole-4-carboxaldehyde exhibits anti-inflammatory activity in HepG2 liver cells. The compound alleviates methylglyoxal (MGO)-induced hepatic inflammation by activating NF-κB signaling. Treatment with Indole-4-carboxaldehyde reduces the expression of AGEs (advanced glycation end-products), glyoxalase-1 mRNA, TNF-α, and IFN-γ. These findings indicate that the compound can modulate inflammatory responses at the cellular level, potentially through mechanisms involving the regulation of glycation stress and cytokine production. The compound's natural occurrence in algae suggests it may have evolved biological functions, though its precise mechanism of action and potency require further investigation. |
| ln Vivo |
In vivo activity data for Indole-4-carboxaldehyde are not well documented in the literature. The compound is primarily utilized as a chemical intermediate and research tool rather than as a drug candidate for in vivo pharmacological evaluation. However, given its in vitro anti-inflammatory activity, the compound may have potential for in vivo studies in models of inflammatory diseases or metabolic disorders involving glycation stress. Such studies would typically involve administration via oral gavage or intraperitoneal injection to rodents, with assessment of inflammatory markers, tissue histology, and metabolic parameters. Further research is needed to establish the compound's in vivo efficacy, bioavailability, and therapeutic potential.
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| Enzyme Assay |
For in vitro enzyme or receptor binding assays with Indole-4-carboxaldehyde, the following protocol can be employed: The compound is tested for its ability to modulate inflammatory signaling pathways in cell-free systems. For NF-κB activation studies, electrophoretic mobility shift assays (EMSA) or reporter gene assays can be used with nuclear extracts from treated cells. For binding studies to potential targets, surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC) may be employed. The compound is dissolved in DMSO and diluted in assay buffer to appropriate concentrations (typically 0.1–100 µM). Controls include vehicle-only samples and reference compounds. Each concentration is tested in triplicate, and experiments are repeated to ensure reproducibility.
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| Cell Assay |
For cell-based in vitro studies, Indole-4-carboxaldehyde is evaluated using HepG2 liver cells or other relevant cell lines. Cells are cultured in appropriate media (e.g., DMEM with 10% FBS) at 37°C in a 5% CO₂ atmosphere. Cells are pre-treated with Indole-4-carboxaldehyde at various concentrations (typically 1–100 µM) for a specified period (e.g., 1–24 hours), followed by stimulation with methylglyoxal (MGO) to induce inflammatory responses. After treatment, cells are harvested for analysis of inflammatory markers including AGEs, glyoxalase-1 mRNA, TNF-α, and IFN-γ using RT-PCR, ELISA, or Western blotting. Cell viability is assessed using MTT or similar assays to ensure compound concentrations are not cytotoxic.
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| Animal Protocol |
In vivo animal studies for Indole-4-carboxaldehyde are not standard, as the compound is primarily a synthetic intermediate and research tool. For evaluation of anti-inflammatory or anti-glycation effects, potential protocols would involve rodent models of metabolic or inflammatory diseases. For example, mice or rats could be administered Indole-4-carboxaldehyde via oral gavage or intraperitoneal injection at various dose levels (e.g., 5–50 mg/kg) daily for 1–4 weeks. Disease models might include high-fat diet-induced metabolic syndrome, streptozotocin-induced diabetes, or LPS-induced systemic inflammation. Endpoints would include serum levels of inflammatory cytokines, tissue histology, oxidative stress markers, and advanced glycation end-product measurements. All animal studies must be conducted in accordance with institutional guidelines.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Indole-4-carboxaldehyde have not been extensively characterized. As a small molecule with molecular weight 145.16 g/mol and an aldehyde functional group, the compound is expected to have moderate aqueous solubility and the potential for rapid metabolism via aldehyde dehydrogenase or aldehyde oxidase to the corresponding carboxylic acid. The indole moiety may undergo oxidative metabolism via cytochrome P450 enzymes. The compound's LogP is estimated to be around 1.5–2.0, indicating moderate lipophilicity. As a naturally occurring metabolite in algae, the compound may have a biological half-life and distribution profile consistent with endogenous metabolites. However, detailed pharmacokinetic studies have not been reported for this compound.
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| Toxicity/Toxicokinetics |
Toxicological data for Indole-4-carboxaldehyde are limited, as the compound is primarily handled as a research chemical in laboratory settings. Standard safety precautions should be observed when handling indole derivatives, including the use of personal protective equipment such as gloves, goggles, and lab coats. The compound may cause skin, eye, and respiratory tract irritation upon exposure. Inhalation of dust should be avoided, and adequate ventilation should be ensured. The aldehyde functionality may contribute to reactivity with biological nucleophiles, necessitating careful handling. In case of accidental exposure, affected areas should be rinsed thoroughly with water. The compound should be stored in a cool, dry place away from strong oxidizing agents and light. Comprehensive toxicological profiling has not been reported.
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| Additional Infomation |
Indole-4-carboxaldehyde is a heteroaromatic formaldehyde formed by replacing the hydrogen at the 4-position of indole with a formyl group. It is a metabolite of algae. It belongs to the indole class of compounds and is also a heteroaromatic formaldehyde. Indole-4-carboxaldehyde has been reported to have been found in the acidophilic algae Limonia acidissima, and relevant data are available for reference.
Indole-4-carboxaldehyde is a naturally occurring compound found in algae and serves as a valuable synthetic intermediate for the preparation of natural products, alkaloids, and biologically active molecules. Research has demonstrated that Indole-4-carboxaldehyde exhibits anti-inflammatory activity by activating NF-κB and reducing methylglyoxal-induced hepatic inflammation in HepG2 cells, with decreased expression of AGEs, glyoxalase-1 mRNA, TNF-α, and IFN-γ. This suggests potential therapeutic applications in inflammatory diseases and conditions involving glycation stress, though further research is needed. No clinical trials or regulatory approvals have been documented for this compound as a therapeutic agent. The compound is commercially available as a research-grade chemical, supplied for laboratory synthesis and biochemical research. |
| Molecular Formula |
C9H7NO
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|---|---|
| Molecular Weight |
145.16
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| Exact Mass |
145.052
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| CAS # |
1074-86-8
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| PubChem CID |
333703
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| Appearance |
Gray to brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
339.1±15.0 °C at 760 mmHg
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| Melting Point |
139-143 °C(lit.)
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| Flash Point |
166.8±27.8 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.729
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| LogP |
1.56
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
158
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C([H])C1C([H])=C([H])C([H])=C2C=1C([H])=C([H])N2[H]
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| InChi Key |
JFDDFGLNZWNJTK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H
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| Chemical Name |
1H-indole-4-carbaldehyde
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 (344.45 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.8890 mL | 34.4448 mL | 68.8895 mL | |
| 5 mM | 1.3778 mL | 6.8890 mL | 13.7779 mL | |
| 10 mM | 0.6889 mL | 3.4445 mL | 6.8890 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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