| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
|
||
| Other Sizes |
| Targets |
Aryl hydrocarbon receptor (AhR). [2]
Nuclear factor erythroid 2-related factor 2 (Nrf2). [2] |
|---|---|
| ln Vitro |
In endothelial cells (HUVEC) treated with oxidized low-density lipoprotein (ox-LDL, 100 mg/mL), indole-3-carboxaldehyde (100 mM) did not affect RNA levels of ICAM and ET-1, but increased eNOS transcription levels. It reduced gene expression of VCAM, CCL2, and IL6. [2]
Indole-3-carboxaldehyde (100 mM) reduced total reactive oxygen species (ROS) level induced by ox-LDL (100 mg/mL) by 70% in HUVEC. [2] Indole-3-carboxaldehyde increased AhR gene expression and downstream genes (CYP1a1, Arnt, Ahrr) in HUVEC. [2] After AhR knockdown, gene expression of VCAM, CCL2, and IL6 increased, while eNOS transcription levels reduced; ICA no longer controlled ROS levels. [2] CUT&Tag analysis showed that AhR binds to the promoter region of Nrf2 in ICA-treated HUVEC. ChIP-PCR and luciferase reporter assay confirmed that ICA treatment increased transcription and expression of Nrf2 and heme oxygenase-1 (HO-1). [2] When Nrf2 was knocked down, ICA did not increase eNOS expression nor reduce VCAM expression; ROS level remained high even with ICA treatment. [2] When HO-1 was silenced, ICA failed to reduce ROS levels; eNOS and ET-1 increased. [2] In the presence of the antioxidant N-acetyl-L-cysteine (NAC), ICA showed similar RNA expression patterns as NAC alone, with decreased ROS and reduced inflammatory/adhesion factors. [2] |
| ln Vivo |
In ApoE-/- mice fed a high-fat diet (HFD), indole-3-carboxaldehyde administration (100 mmol/mL by gavage) raised plasma ICA level. Oil Red O staining showed that plaques in the HFD+ICA group were dramatically smaller in the whole aorta (plaque area decreased by 40%, p<0.0001) and at the aortic roots (20% smaller, p=0.0005) compared to HFD alone. ICA prevented plaque development with less necrotic cores and decreased plaque thickness, and fewer inflammatory cells were found in plaques. [2]
In vivo, ICA induced AhR activation in aortic tissues, increasing expression of CYP1a1, Nrf2, and HO-1. ROS levels in the aortic root and liver were decreased in the HFD+ICA group. Plasma concentration of CCL2 was lower in the HFD+ICA group. [2] |
| Enzyme Assay |
Indole-3-carboxaldehyde was not utilized as a substrate by the IAA oxidase obtained from Lupinus albus. [1]
The study did not describe detailed enzyme assay procedures for ICA as a direct enzyme substrate. [2] |
| Cell Assay |
Human umbilical vein endothelial cells (HUVEC) were plated and treated with ox-LDL (100 ng/mL) for 24 hours, and indole-3-carboxaldehyde (0.1 mM) was added for the second 12 hours. [2]
For ROS detection, after 12 hours of treatment, dihydroethidium was added to the culture medium (1:1000, v/v) for 30 minutes. Treated cells were then fixed in 4% formalin for 30 minutes and analyzed using an inverted optical microscope. [2] Total mRNA was extracted using a kit. cDNA was synthesized for qRT-PCR. qRT-PCR was performed using SYBR Green Master Mix. Relative expression of target genes was normalized to beta-actin using the 2-ΔΔCT method. [2] For western blot, cells were lysed in RIPA lysis buffer with protease inhibitor, phosphatase inhibitor, and PMSF. Protein concentrations were calculated using Bradford assay. Proteins were separated by electrophoresis, transferred to PVDF membrane, blocked with 5% BSA, and incubated with primary antibodies (AhR, Nrf2, HO-1) overnight at 4°C, then with secondary antibody for 1 hour at 4°C. Densitometry was analyzed with ImageJ. [2] For CUT&Tag, cells were incubated with ConA Beads, then with AhR antibodies (1:50) or IgG control overnight at 4°C, followed by transposase incubation and tagmentation buffer. DNA was extracted, PCR amplified, and sequenced. [2] For luciferase assay, 293T cells were co-transfected with Nrf2 promoter reporter plasmids and AhR overexpression or empty plasmid using Lipofectamine 3000 for 8 hours. After 24 hours, cells were treated with ox-LDL or ox-LDL+ICA for 24 hours. Luciferase activity was measured using a dual-luciferase reporter system and normalized to Renilla. [2] For chromatin immunoprecipitation (ChIP), cells were cross-linked with 1% paraformaldehyde, glycine added, cells lysed, and sheared by sonication. Supernatants were incubated with Protein A+G magnetic beads and 10 μg of antibody overnight at 4°C. Beads were washed, and DNA fragments were purified and analyzed by real-time PCR. [2] |
| Animal Protocol |
Male ApoE-/- mice (8 weeks old) were fed a high-fat diet (1.25% cholesterol, D12108C) for four months to induce atherosclerosis. Indole-3-carboxaldehyde was administered via gavage (100 mmol/mL) for four months. Mice were anesthetized with chloral hydrate. Blood was collected after eye removal, and plasma was obtained by centrifugation at 3000 rpm for 10 min at 4°C. Fecal samples were collected under aseptic conditions. [2]
Whole aortas were isolated, opened longitudinally, and excess adventitial fat removed. Aortas were washed in 78% methanol for 5 seconds. Serial 5-mm-thick sections were obtained from the aortic root. Oil Red O staining was performed, and plaques were quantified by detecting positively stained areas (red) with ImageJ software. [2] |
| Toxicity/Toxicokinetics |
10256 mouse LDLo intraperitoneal 600 mg/kg AUTONOMIC NERVOUS SYSTEM: SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC); BEHAVIORAL: ANTICONVULSANT; BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Pharmaceutical Chemistry Journal, 6(33), 1972
|
| References | |
| Additional Infomation |
Indole-3-carboxaldehyde is a heteroaromatic formaldehyde with the structure indole, where the hydrogen at the 3-position is replaced by a formyl group. It can be used as a plant metabolite, a human heterologous metabolite, a bacterial metabolite, and a marine metabolite. It is a heteroaromatic formaldehyde, an indole alkaloid, and a member of the indole class of compounds. Indole-3-carboxaldehyde has been reported to be detected in Lactarius subplinthogalus, Arthrographis, and other organisms with available data.
Indole-3-carboxaldehyde is a gut microbe-derived tryptophan metabolite. The abundance of Bacteroidaceae and Lactobacillaceae (which produce tryptophanase metabolizing tryptophan into ICA) was lower in HFD group than control. ICA treatment probably prevents HFD-induced change in the absence of these bacteria. [2] ICA acts on endothelial cells to attenuate release of pro-inflammatory cytokines and ROS levels via AhR-dependent mechanism. Activated AhR triggers the Nrf2-HO-1 pathway, reducing pro-atherosclerosis factors and ROS. ICA is a systematic antioxidant in vivo. [2] In the 1957 study, indole-3-carboxaldehyde was identified as a major reaction product of IAA oxidation when IAA oxidase was coupled to cytochrome-cytochrome oxidase system. Indole-3-glycolic acid yielded ICA with equal efficiency both in absence and presence of cytochrome c. Substituted IAA experiments indicated that the ring system, not the side chain, is the primary site of oxidation. [1] |
| Molecular Formula |
C₉H₇NO
|
|---|---|
| Molecular Weight |
145.16
|
| Exact Mass |
145.052
|
| CAS # |
487-89-8
|
| Related CAS # |
Indole-3-carboxaldehyde-13C3;1093452-52-8
|
| PubChem CID |
10256
|
| Appearance |
Off-white to yellow solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
339.1±15.0 °C at 760 mmHg
|
| Melting Point |
193-198 °C(lit.)
|
| Flash Point |
166.8±27.8 °C
|
| Vapour Pressure |
0.0±0.7 mmHg at 25°C
|
| Index of Refraction |
1.729
|
| LogP |
1.68
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
11
|
| Complexity |
158
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1=CC=C2C(=C1)C(=CN2)C=O
|
| InChi Key |
OLNJUISKUQQNIM-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
|
| Chemical Name |
1H-indole-3-carbaldehyde
|
| Synonyms |
Indole3carboxaldehyde;
INDOLE-3-CARBOXALDEHYDE; 487-89-8; 3-Formylindole; 1H-Indole-3-carboxaldehyde; Indole-3-carbaldehyde; Indole 3 carboxaldehyde
|
| 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. |
| 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 : ~20 mg/mL (~137.78 mM)
H2O : < 0.1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2 mg/mL (13.78 mM) 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; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.0 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. Solubility in Formulation 2: ≥ 2 mg/mL (13.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (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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