1-METHYL-D-TRYPTOPHAN
- CAS NO.:110117-83-4
- Empirical Formula: C12H14N2O2
- Molecular Weight: 218.25
- MDL number: MFCD00274271
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is 1-METHYL-D-TRYPTOPHAN?
Description
Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.
The Uses of 1-METHYL-D-TRYPTOPHAN
Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.
The Uses of 1-METHYL-D-TRYPTOPHAN
1-Methyl-D-tryptophan is used in biological studies to determine the effect of IDO2 enzyme (indoleamine-(2,3)-dioxygenase) activity and IDO2-mediated arrest of human T cell proliferation. It reverses IDO-mediated immune suppression
What are the applications of Application
1-Methyl-D-tryptophan is an inhibitor of IDO and INDOL1 (IDO2)
storage
Store at -20°C
References
1) Hou?et al. (2007),?Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophan correlates with antitumor responses; Cancer Res.,?67?792 2) Soliman?et al. (2010),?Indoleamine 2,3-dioxygenase: is it an immune suppressor?; Cancer J.,?16?354 3) Friberg?et al. (2002),?Indoleamine 2,3-dioxygenase contributes to tumor cell evasion of T-cell mediated rejection; Int. J. Cancer,?101?151 4) Metz?et al. (2012),?IDO inhibits a tryptophan sufficiency signal that stimulates mTOR; Oncoimmunol.,?1?1460
Properties of 1-METHYL-D-TRYPTOPHAN
Melting point: | 242-245 °C(lit.) |
alpha | 12.4o (C = 2 IN ACETIC ACID) |
Boiling point: | 429.3±35.0 °C(Predicted) |
Density | 1.28 |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | Soluble in DMSO (greater than 25 mg/ml). |
pka | 2.26±0.10(Predicted) |
form | White to light brown crystalline powder. |
color | White |
optical activity | [α]22/D +12.4°, c = 2 in acetic acid |
Water Solubility | Soluble to 5 mM in water with gentle warming |
Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. |
Safety information for 1-METHYL-D-TRYPTOPHAN
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 1-METHYL-D-TRYPTOPHAN
InChIKey | ZADWXFSZEAPBJS-SNVBAGLBSA-N |
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