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| Targets |
3-Indoleacetic acid (IAA) is a plant hormone that acts as an auxin, targeting auxin signaling pathways in plants. Auxin binds to the TIR1/AFB family of F-box proteins, which are part of the SCF ubiquitin ligase complex, leading to the degradation of Aux/IAA transcriptional repressors and the activation of auxin-responsive gene expression. This regulates cell elongation, division, differentiation, tropisms, and other developmental processes. In addition, IAA is a metabolite in animals (endogenous metabolite) and exhibits antioxidant activity. The 13C-labeled version shares the same target but is used as a tracer and internal standard, not for activity studies.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
As a stable isotope tracer, 3-Indoleacetic acid-13C6 is not used to measure biological activity in the traditional sense. Instead, it is added to plant cell culture media or administered to plants to track auxin biosynthesis, transport, and metabolism. In plant cell culture, IAA (unlabeled) at concentrations of 0.1-10 uM induces cell elongation and division. The 13C-labeled version allows quantification of IAA biosynthesis rates from tryptophan via the indole-3-pyruvic acid (IPA) pathway or other routes. In addition, IAA exhibits antioxidant activity in plant and animal systems. The labeled version is also used as an analytical standard for quantifying IAA levels in plant tissues by LC-MS. |
| ln Vivo |
In vivo (in plants), 3-Indoleacetic acid (IAA) is the primary auxin that regulates growth and development. 3-Indoleacetic acid-13C6 is administered to plants (e.g., by leaf infiltration, root uptake, or injection into tissues) to trace the movement and metabolism of IAA in vivo. The compound can be used to study auxin polar transport, which is mediated by PIN and ABCB efflux carriers, and to quantify IAA conjugation and degradation (e.g., to oxIAA via the GH3 pathway). In plant research, 3-Indoleacetic acid is used to induce cell elongation and division in explants. In animal research, IAA is an endogenous metabolite found in urine and is a biomarker for certain diseases; however, the labeled version is not used in animal studies for activity testing.
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| Enzyme Assay |
For non-cellular assays (analytical quantification), 3-Indoleacetic acid-13C6 is prepared as a stock solution in methanol or 0.1 M HCl (1 mg/mL). For LC-MS/MS analysis, a calibration curve for IAA is prepared in plant extract, plasma, or urine (0.1-1000 ng/mL) with a fixed concentration of the 13C6 internal standard (e.g., 50 ng/mL). Sample preparation: plant tissue (50 mg) is homogenized in 1 mL of 70% methanol containing internal standard. After centrifugation, the supernatant is evaporated, reconstituted in mobile phase (0.1% formic acid in water and methanol, 60:40, v/v), and injected onto a C18 column (2.1×50 mm, 1.8 um). MRM transitions: IAA 176→130 (and 176→103), IAA-13C6 182→136 (and 182→109). For non-cellular auxin receptor binding assays (e.g., TIR1 binding), SPR (surface plasmon resonance) or fluorescence polarization assays can be used.
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| Cell Assay |
For cell-based assays, plant cell cultures (e.g., Arabidopsis thaliana cell suspension cultures, tobacco BY-2 cells) are used. Cells are seeded in flasks containing MS (Murashige and Skoog) medium with sucrose and appropriate hormones. Cells are treated with 3-Indoleacetic acid-13C6 (0.1-10 uM) for 1-24 hours. Cell elongation is measured by microscopic analysis of cell length. Cell division is assessed by counting cell number or by measuring DNA content (by flow cytometry). For auxin signaling studies, Arabidopsis protoplasts or transgenic plants expressing auxin-responsive reporters (e.g., DR5::GUS or DR5::GFP) are treated with IAA-13C6, and reporter activity is measured. For metabolite tracing, cells are harvested, and labeled IAA and its metabolites (e.g., IAA-aspartate, oxIAA) are analyzed by LC-MS/MS. For animal cells, IAA-13C6 can be used as an internal standard for quantifying IAA levels in biological fluids.
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| Animal Protocol |
For in vivo animal experiments, 3-Indoleacetic acid-13C6 is not typically administered to animals as a drug. For plant studies, Arabidopsis thaliana or other plant species (e.g., rice, maize) are used. Plants are grown in growth chambers under controlled conditions. 3-Indoleacetic acid-13C6 (1-10 uM) is applied to roots (in hydroponic solution), leaves (by spraying), or to cut stems. Tissues are harvested at multiple time points (0, 1, 2, 4, 8, 24 hours) and extracted for LC-MS analysis of IAA-13C6 and its metabolites. For auxin transport studies, radiolabeled (3H or 14C) IAA is typically used, but 13C-labeled IAA can be used with high-resolution MS to study transport without radioactivity. For plant growth studies, IAA (unlabeled) is applied to stimulate root initiation, shoot elongation, and fruit development. The labeled version is used to measure the uptake, transport, and metabolism of applied IAA.
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| ADME/Pharmacokinetics |
3-Indoleacetic acid-13C6 has a molecular weight of 181.14, with six carbon-13 atoms (mass shift +6) relative to unlabeled IAA (MW 175.18). The compound is a white to off-white crystalline powder with a melting point of 165-169degC. It is soluble in organic solvents such as ethanol, methanol, DMSO, and acetone, and moderately soluble in water (approximately 1 mg/mL). The 13C label is stable and non-radioactive. It should be stored as a powder at -20degC, protected from light, for up to 3 years, and in solution at -80degC for up to 6 months or at -20degC for up to 1 month. IAA is light-sensitive and may degrade upon prolonged exposure to light.
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| Toxicity/Toxicokinetics |
3-Indoleacetic acid-13C6 is a stable isotope-labeled compound with low toxicity. The non-deuterated parent compound, 3-Indoleacetic acid (IAA), is a naturally occurring plant hormone that is present in many plants and foods. IAA has low acute toxicity (oral LD₅0 in rats: >2000 mg/kg). At high doses, it may cause mild eye and skin irritation. The compound is not considered hazardous at typical research concentrations (ug-mg per sample). Standard laboratory safety precautions for handling organic compounds should be followed. The compound is non-radioactive and safe for research use. No specific toxicity studies have been reported for the 13C-labeled version.
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| References | |
| Additional Infomation |
3-Indoleacetic acid-13C6 is a research compound and stable isotope tracer, not an approved drug. It has not undergone clinical trials for therapeutic use. Its primary applications are in plant science research: studying auxin biosynthesis, transport (polar auxin transport), signaling, and metabolism. The compound is used to quantify IAA levels in plant tissues by LC-MS/MS and to trace the fate of applied auxin in plants. It is also used as an internal standard in food safety testing to measure IAA residues in agricultural products. In animal research, IAA is an endogenous metabolite and a potential biomarker for certain diseases (e.g., colorectal cancer, metabolic disorders), but the labeled version is used only as an analytical standard. Available for research use only.
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| Molecular Formula |
C413C6H9NO2
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| Molecular Weight |
181.14
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| Exact Mass |
181.083
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| CAS # |
100849-36-3
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| Related CAS # |
3-Indoleacetic acid;87-51-4
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| PubChem CID |
170990918
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Index of Refraction |
1.694
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| LogP |
1.6
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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 |
2
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| Heavy Atom Count |
13
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| Complexity |
205
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C2[13C](=[13CH][13CH]=[13CH]1)[13CH]=[13C](N2)CC(=O)O
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| InChi Key |
QOPBEBWGSGFROG-LPGWLKFQSA-N
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| InChi Code |
InChI=1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13)/i1+1,2+1,3+1,5+1,7+1,8+1
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| Chemical Name |
2-(1H-indol-2-yl)acetic 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 5.5206 mL | 27.6030 mL | 55.2059 mL | |
| 5 mM | 1.1041 mL | 5.5206 mL | 11.0412 mL | |
| 10 mM | 0.5521 mL | 2.7603 mL | 5.5206 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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