CAS 110117-83-4|Indoximod
Introduction：Basic information about CAS 110117-83-4|Indoximod, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Indoximod | ||
|---|---|---|---|
| CAS Number | 110117-83-4 | Molecular Weight | 218.252 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 429.3±35.0 °C at 760 mmHg |
| Molecular Formula | C12H14N2O2 | Melting Point | 242-245 ℃(lit.) |
| MSDS | ChineseUSA | Flash Point | 213.4±25.9 °C |
Names
| Name | 1-Methyl-D-tryptophan |
|---|---|
| Synonym | More Synonyms |
Indoximod BiologicalActivity
| Description | Indoximod (D-1MT, NLG8189) is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor with a Ki of 19 μM. |
|---|---|
| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>Indoleamine 2,3-Dioxygenase (IDO)Research Areas >>Cancer |
| Target | IDO:19 μM (Ki) |
| In Vitro | The IDO inhibitor 1-methyl-tryptophan exists in two stereoisomers with potentially different biological properties. The L isomer is the more potent inhibitor of IDO activity using the purified enzyme and in HeLa cell–based assays. However, the D isomer is significantly more effective in reversing the suppression of T cells created by IDO-expressing dendritic cells. The L isomer of 1-methyl-tryptophan functioned as a competitive inhibitor (Ki=19 μM), whereas the d isomer is much less effective. The DL mixture is intermediate, with a Ki of 35 μM[1]. |
| In Vivo | The D isomer is more efficacious as an anticancer agent in chemo-immunotherapy regimens using cyclophosphamide, paclitaxel, or gemcitabine, when tested in mouse models of transplantable melanoma and transplantable and autochthonous breast cancer. The D isomer of 1-methyl-tryptophan specifically targets the IDO gene because the antitumor effect of d-1-methyl-tryptophan is completely lost in mice with a disruption of the IDO gene (IDO-knockout mice). Oral administration of dl-1-methyl-tryptophan in combination with paclitaxel can elicit regression of autochthonous breast tumors[1]. |
| Kinase Assay | 1MT enantiomers are solubilized in DMSO containing 0.1N HCl and added at concentrations of 100, 50, and 0 µM to wells containing the reaction mixture with tryptophan (0-200 µM) followed by addition of IDO enzyme. Plates are sealed and incubated 1 hr in a humidified 37°C incubator, after which the reactions are terminated by addition of 12.5 µl 30% TCA per well. Plates are then resealed in plastic wrap, incubated 30 min at 50°C to hydrolyze the reaction product N-formylkynurenine to kynurenine, and centrifuged. Supernatants are transferred to a flat-bottom 96-well plate, mixed with 100 µl Ehrlich reagent and incubated 10 min at room temperature. Absorbance at 490 nm is read[1]. |
| Animal Admin | Mice: B16F10 melanoma are established in B6 mice. For administration in drinking water, D-1MT is prepared at 2 mg/mL in water supplemented with a small amount of aspartame (2 envelopes per liter) to improve acceptance by the mice, and filter sterilized. The solution is delivered in standard autoclaved drinking-water bottles. Mice drink 4.5-5.0 mL/day (similar to consumption of water without drug)[1]. |
| References | [1]. Hou DY, et al. Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophancorrelates with antitumor responses. Cancer Res. 2007 Jan 15;67(2):792-801. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 429.3±35.0 °C at 760 mmHg |
| Melting Point | 242-245 ℃(lit.) |
| Molecular Formula | C12H14N2O2 |
| Molecular Weight | 218.252 |
| Flash Point | 213.4±25.9 °C |
| Exact Mass | 218.105530 |
| PSA | 68.25000 |
| LogP | 1.43 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.625 |
| InChIKey | ZADWXFSZEAPBJS-SNVBAGLBSA-N |
| SMILES | Cn1cc(CC(N)C(=O)O)c2ccccc21 |
Safety Information
| Hazard Codes | Xn |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles16
More Articles| Tumor indoleamine 2,3-dioxygenase (IDO) inhibits CD19-CAR T cells and is downregulated by lymphodepleting drugs. Blood 125 , 3905-16, (2015) Although T cells expressing CD19-specific chimeric antigen receptors (CARs) are a promising new therapy for B-cell malignancies, objective responses are observed at lower frequencies in patients with ... | |
| Rational design of indoleamine 2,3-dioxygenase inhibitors. J. Med. Chem. 53 , 1172-89, (2010) Indoleamine 2,3-dioxygenase (IDO) is an important therapeutic target for the treatment of diseases such as cancer that involve pathological immune escape. We have used the evolutionary docking algorit... | |
| Amino acid metabolism inhibits antibody-driven kidney injury by inducing autophagy. J. Immunol. 194 , 5713-24, (2015) Inflammatory kidney disease is a major clinical problem that can result in end-stage renal failure. In this article, we show that Ab-mediated inflammatory kidney injury and renal disease in a mouse ne... |
Synonyms
| (2R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid |
| D-Tryptophan, 1-methyl- |
| MFCD00274271 |
| (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid |
| (R)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid |
| Indoximod |
| D-1MT |
| 1-Methyl-D-tryptophan |
| NLG-8189 |
