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110117-83-4

110117-83-4 structure
110117-83-4 structure
Name 1-Methyl-D-tryptophan
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
Description Indoximod (D-1MT, NLG8189) is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor with a Ki of 19 μM.
Related Catalog
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.
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
Hazard Codes Xn
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2933990090
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%

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title: CAS No. 110117-83-4 | Chemsrc address: https://m.chemsrc.com/en/baike/1113909.html

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