| Identification | Back Directory | [Name]
1-METHYL-D-TRYPTOPHAN | [CAS]
110117-83-4 | [Synonyms]
NLG-8189
Me-D-Trp
IndoxiMod
1-Me-D-Trp
D-Trp(Me)-OH
H-D-Trp(1-Me)-OH
Indoximod (NLG-8189）
1-METHYL-D-TRYPTOPHAN
1-Methyl-D-tryptophane
D-Tryptophan, 1-methyl-
1-METHYL-D-TRYPTOPHAN 95%
1-METHYL-D-TRYPTOPHAN USP/EP/BP
(R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
(2R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
INDOXIMOD;1-METHYL-D-TRYPTOPHAN;1-METHYL-D-TRYPTOPHANE | [Molecular Formula]
C12H14N2O2 | [MDL Number]
MFCD00274271 | [MOL File]
110117-83-4.mol | [Molecular Weight]
218.25 |
| Chemical Properties | Back Directory | [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). | [form ]
White to light brown crystalline powder. | [pka]
2.26±0.10(Predicted) | [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. | [InChI]
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-/m1/s1 | [InChIKey]
ZADWXFSZEAPBJS-SNVBAGLBSA-N | [SMILES]
C(O)(=O)[C@@H](CC1C2=C(C=CC=C2)N(C)C=1)N |
| Hazard Information | Back Directory | [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.1,2 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo.3,4 In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO.4 It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO.1,2 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival.1,5 Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.5 | [Uses]
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. | [reaction suitability]
reaction type: solution phase peptide synthesis | [in vivo]
The D isomer is more efficacious as an anticancer agent in chemo-immunotherapy regimens using NSC-26271, NSC 125973, or LY 188011, 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 NSC 125973 can elicit regression of autochthonous breast tumors[1]. | [IC 50]
IDO: 19 μM (Ki) | [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 |
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