| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
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| Other Sizes |
Purity: =99.92%
| Targets |
Endogenous Metabolite; Microbial Metabolite
Indole-3-propionic acid targets multiple receptors and proteins. It binds to the pregnane X receptor (PXR) in intestinal cells. It also partially activates the aryl hydrocarbon receptor (AhR). Additionally, IPA is used as a ligand for melanocortin receptors and as an inhibitor of TGF-β receptor binding. It is also studied as an NR2B/NMDA receptor antagonist. |
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| ln Vitro |
3-Indolepropionic acid has been demonstrated to be an effective antioxidant that may be used to treat Alzheimer's [1]. 3. Compared to melatonin, indolepropionic acid is a more effective hydroxyl radical scavenger. 3-indolepropionic acid scavenges free radicals without causing the subsequent generation of reactive and pro-oxidant intermediate molecules, which is similar to melatonin but different from other antioxidants [2]. Research has additionally demonstrated that the metabolite indolepropionic acid, which is generated by gut microorganisms, may serve as a preventive factor against type 2 diabetes (T2D) by maintaining β-cell activity and acting as a possible biomarker for the disease's onset [3].
Indole-3-propionic acid exhibits potent antioxidant activity as a free radical scavenger. It inhibits the growth of E. coli. It is used as a reactant for the preparation of various bioactive compounds, including anti-tumor agents and melanocortin receptor ligands. Its activity as a TGF-β receptor binding inhibitor has also been reported. |
| ln Vivo |
Wide-scale profiling technologies including metabolomics broaden the possibility of novel discoveries related to the pathogenesis of type 2 diabetes (T2D). By applying non-targeted metabolomics approach, we investigated here whether serum metabolite profile predicts T2D in a well-characterized study population with impaired glucose tolerance by examining two groups of individuals who took part in the Finnish Diabetes Prevention Study (DPS); those who either early developed T2D (n = 96) or did not convert to T2D within the 15-year follow-up (n = 104). Several novel metabolites were associated with lower likelihood of developing T2D, including indole and lipid related metabolites. Higher indolepropionic acid was associated with reduced likelihood of T2D in the DPS. Interestingly, in those who remained free of T2D, indolepropionic acid and various lipid species were associated with better insulin secretion and sensitivity, respectively. Furthermore, these metabolites were negatively correlated with low-grade inflammation. We replicated the association between indolepropionic acid and T2D risk in one Finnish and one Swedish population. We suggest that indolepropionic acid, a gut microbiota-produced metabolite, is a potential biomarker for the development of T2D that may mediate its protective effect by preservation of β-cell function. Novel lipid metabolites associated with T2D may exert their effects partly through enhancing insulin sensitivity.[3]
Indole-3-propionic acid has been studied as an adjunct to improve perfusion after liver transplant. Its role as a gut microbiota-derived metabolite suggests it may have systemic effects on host physiology. By binding to PXR in intestinal cells, it facilitates mucosal homeostasis and protects against intestinal epithelial barrier damage. Its antioxidant properties may contribute to its protective effects in various tissues. |
| Enzyme Assay |
Although it has long been recognized that the enteric community of bacteria that inhabit the human distal intestinal track broadly impacts human health, the biochemical details that underlie these effects remain largely undefined. Here, we report a broad MS-based metabolomics study that demonstrates a surprisingly large effect of the gut "microbiome" on mammalian blood metabolites. Plasma extracts from germ-free mice were compared with samples from conventional (conv) animals by using various MS-based methods. Hundreds of features were detected in only 1 sample set, with the majority of these being unique to the conv animals, whereas approximately 10% of all features observed in both sample sets showed significant changes in their relative signal intensity. Amino acid metabolites were particularly affected. For example, the bacterial-mediated production of bioactive indole-containing metabolites derived from tryptophan such as indoxyl sulfate and the antioxidant indole-3-propionic acid (IPA) was impacted. Production of IPA was shown to be completely dependent on the presence of gut microflora and could be established by colonization with the bacterium Clostridium sporogenes. Multiple organic acids containing phenyl groups were also greatly increased in the presence of gut microbes. A broad, drug-like phase II metabolic response of the host to metabolites generated by the microbiome was observed, suggesting that the gut microflora has a direct impact on the drug metabolism capacity of the host. Together, these results suggest a significant interplay between bacterial and mammalian metabolism.[1]
The in vitro activity of Indole-3-propionic acid is assessed in various binding and functional assays. For PXR binding, radioligand binding assays can be used to measure its affinity for the receptor. For TGF-β receptor binding inhibition, competitive binding assays are employed. Its antioxidant activity is measured using standard free radical scavenging assays such as DPPH or ABTS. |
| Cell Assay |
In vitro cellular experiments involve treating intestinal epithelial cells with Indole-3-propionic acid and measuring its effects on PXR activation and downstream target gene expression. The compound's ability to protect against intestinal epithelial barrier damage can be assessed by measuring transepithelial electrical resistance (TEER) or permeability to macromolecules. Its effects on bacterial growth can be assessed in culture.
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| Animal Protocol |
In vivo animal experiments for Indole-3-propionic acid would involve administering the compound to animal models of intestinal inflammation or liver injury to assess its protective effects. Its role as a gut microbiota-derived metabolite can be studied in gnotobiotic or germ-free mouse models. However, specific in vivo data is not detailed in the provided sources.
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| ADME/Pharmacokinetics |
Indole-3-propionic acid has a molecular weight of 189.21 g/mol and a molecular formula of C11H11NO2. It is a small molecule that is typically used as a research reagent. Its purity is typically ≥98%. The compound is a tryptophan metabolite that is naturally produced by gut microbiota.
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| Toxicity/Toxicokinetics |
Mice were administered LDLo 100 mg/kg via intraperitoneal injection.
Toxicological data for Indole-3-propionic acid is not extensively detailed in the provided sources. As a naturally occurring metabolite, it is generally considered to have low toxicity. However, as a research compound, it is not intended for human use. Standard safety precautions should be followed when handling. |
| References |
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| Additional Infomation |
3-(1H-indole-3-yl)propionic acid is an indole-3-yl carboxylic acid, formed by substituting 1H-indole-3-yl at the 3-position of propionic acid. It is an auxin and a metabolite in both humans and plants. Functionally, it is related to propionic acid. It is the conjugate acid of 3-(1H-indole-3-yl)propionic acid ester. 3-Indolepropionic acid has been reported in Scheffersomyces spartinae, Tetrastigma hemsleyanum, and several other organisms with relevant data.
Indole-3-propionic acid is a gut microbiota-derived tryptophan metabolite with potent antioxidant properties. It binds to the pregnane X receptor (PXR) in intestinal cells, facilitating mucosal homeostasis and protecting against intestinal epithelial barrier damage. It is used as a reactant for the preparation of various bioactive compounds, including anti-tumor agents and receptor ligands. It is available from various chemical suppliers for research purposes. |
| Molecular Formula |
C11H11NO2
|
|---|---|
| Molecular Weight |
189.214
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| Exact Mass |
189.078
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| Elemental Analysis |
C, 69.83; H, 5.86; N, 7.40; O, 16.91
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| CAS # |
830-96-6
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| Related CAS # |
3-Indolepropionic acid-d2;2469257-98-3
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| PubChem CID |
3744
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
417.6±20.0 °C at 760 mmHg
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| Melting Point |
134-135 °C(lit.)
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| Flash Point |
206.4±21.8 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.667
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| LogP |
1.76
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| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
217
|
| Defined Atom Stereocenter Count |
0
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| InChi Key |
GOLXRNDWAUTYKT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
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| Chemical Name |
3-(1H-indol-3-yl)propanoic acid
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| Synonyms |
IPA; Indole 3 propionic acid; 3-Indolepropionic acid; 830-96-6; Indole-3-propionic acid; 3-(1H-Indol-3-yl)propanoic acid; 1H-Indole-3-propanoic acid; Indolepropionic acid; 3-(3-Indolyl)propionic acid; Indolylpropionic Acid; Indole-3-propionic 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 (~528.51 mM)
H2O : ~1 mg/mL (~5.29 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% 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 (13.21 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. (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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