1-METHYL-D-TRYPTOPHAN Chemical Properties

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.

InChIKey

ZADWXFSZEAPBJS-SNVBAGLBSA-N

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

1-METHYL-D-TRYPTOPHAN Usage And Synthesis

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.

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.

Uses

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

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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