| Targets |
(S)-Indoximod targets indoleamine 2,3-dioxygenase (IDO), a heme-containing enzyme that catalyzes the oxidative cleavage of the pyrrole ring of L-tryptophan to N-formylkynurenine. This pathway is upregulated in many cancers and contributes to immune suppression by depleting tryptophan and producing immunosuppressive metabolites. By inhibiting IDO, (S)-Indoximod prevents this immunosuppression, thereby enhancing anti-tumor immunity. It has a Ki of 19 µM for IDO.
|
|---|---|
| ln Vitro |
In vitro, (S)-Indoximod is a competitive inhibitor of IDO with a Ki of 19 µM. It has been shown to reduce Foxp3 protein expression, which is a marker of regulatory T-cells (Tregs), suggesting a mechanism for its immunomodulatory effects. It is used to study the role of the kynurenine pathway in immune suppression and other cellular processes.
|
| ln Vivo |
In vivo, (S)-Indoximod has shown activity in preclinical models of cancer. By inhibiting IDO, it can relieve immune suppression and enhance the efficacy of other immunotherapies. It has also been investigated for its potential in neurological diseases.
|
| Enzyme Assay |
The inhibitory activity of (S)-Indoximod is assessed using in vitro enzyme assays. Recombinant IDO is incubated with its substrate L-tryptophan and varying concentrations of the compound. The production of kynurenine is measured, and the Ki is calculated. Its competitive mechanism is confirmed by varying the substrate concentration.
|
| Cell Assay |
The cellular activity of (S)-Indoximod is evaluated in cell lines and primary immune cells. Cells are treated with (S)-Indoximod, and its effect on IDO activity is measured by quantifying kynurenine levels in the culture medium. Its effect on T-cell proliferation and immune cell function is assessed.
|
| Animal Protocol |
In animal studies, (S)-Indoximod is typically administered via oral gavage or intraperitoneal (i.p.) injection. In tumor models, it is given to assess its effect on tumor growth and immune cell infiltration. In models of neurological disease, its effect on disease progression is evaluated.
|
| ADME/Pharmacokinetics |
As a small molecule (MW 218.25), (S)-Indoximod is orally bioavailable. Its pharmacokinetic properties, such as half-life and exposure, support its use in preclinical studies. Its solubility in DMSO facilitates formulation for in vivo administration.
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| Toxicity/Toxicokinetics |
Toxicology data for (S)-Indoximod is limited. As a modulator of tryptophan metabolism, its effects on the immune system and other physiological processes are the primary considerations. Its safety has been evaluated in clinical trials, with a manageable safety profile.
|
| References |
|
| Additional Infomation |
1-Methyl-L-tryptophan is an indole carboxylic acid.
(S)-Indoximod (CAS: 21339-55-9) is a well-characterized IDO inhibitor that has been extensively studied in cancer research. It is a key tool for investigating the role of the kynurenine pathway in immune suppression and for developing combination immunotherapies. Its development has contributed to the understanding of how tumors evade the immune system and has paved the way for new treatment strategies. |
| Molecular Formula |
C12H14N2O2
|
|---|---|
| Molecular Weight |
218.252
|
| Exact Mass |
218.105
|
| CAS # |
21339-55-9
|
| Related CAS # |
(Rac)-Indoximod;26988-72-7;Indoximod;110117-83-4;(S)-Indoximod-d3;1801851-87-5
|
| PubChem CID |
676159
|
| Appearance |
White to off-white solid powder
|
| Density |
1.28
|
| Boiling Point |
429.3±35.0 °C at 760 mmHg
|
| Melting Point |
223-226 ºC
|
| Flash Point |
213.4±25.9 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.625
|
| LogP |
1.43
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
16
|
| Complexity |
270
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
CN1C=C(C2=CC=CC=C21)C[C@@H](C(=O)O)N
|
| InChi Key |
ZADWXFSZEAPBJS-JTQLQIEISA-N
|
| InChi Code |
InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m0/s1
|
| Chemical Name |
(2S)-2-amino-3-(1-methylindol-3-yl)propanoic acid
|
| 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: 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)
|
| Solubility (In Vitro) |
DMSO : ~4.81 mg/mL (~22.0 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 5 mg/mL (22.91 mM) in 50% PEG300 +50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O 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 | 4.5819 mL | 22.9095 mL | 45.8190 mL | |
| 5 mM | 0.9164 mL | 4.5819 mL | 9.1638 mL | |
| 10 mM | 0.4582 mL | 2.2910 mL | 4.5819 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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