An inhibitor of indoleamine 2,3-dioxygenase
Related Products
Enantiomer(s)
333131-methyl-L-Tryptophan
Isomer(s)
34914L-Abrine
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1-methyl-D-Tryptophan

Item No. 16456

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-methyl-D-tryptophan
CAS Number
110117-83-4
Synonyms
  • D-1MT
  • Indoximod
Molecular Formula
C12H14N2O2
Formula Weight
218.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetic Acid (2%): 1 mg/mlMethanol: 0.1 mg/ml
λmax
223, 286 nm
SMILES
CN1C2=CC=CC=C2C(C[C@H](C(O)=O)N)=C1
InChi Code
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
InChi Key
ZADWXFSZEAPBJS-SNVBAGLBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

    $41

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    500 mg

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    1 g

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    5 g

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    Cayman Chemical
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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yoshida, N., Ino, K., Ishida, Y., et al. Overexpression of indoleamine 2,3-dioxygenase in human endometrial carcinoma cells induces rapid tumor growth in a mouse xenograft model. Clin. Cancer Res. 14(22), 7251-7259 (2008).

    2. Rytelewski, M., Meilleur, C.E., Yekta, M.A., et al. Suppression of immunodominant antitumor and antiviral CD8+ T cell responses by indoleamine 2,3-dioxygenase. PLoS One 9(2), 1-15 (2014).

    3. Dolusic, E., Larrieu, P., Blanc, S., et al. Discovery and preliminary SARs of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors. Eur. J. Med. Chem. 46(7), 3058-3065 (2011).

    4. Munn, D.H., Sharma, M.D., Hou, D., et al. Expression of indoleamine 2,3-dioxygenase by plasmacytoid dendritic cells in tumor-draining lymph nodes. J. Clin. Invest. 114(2), 280-290 (2004).

    5. Opitz, C.A., Litzenburger, U.M., Opitz, U., et al. The indoleamine-2,3-dioxygenase (IDO) inhibitor 1-methyl-D-tryptophan upregulates IDO1 in human cancer cells. PLoS One 6(5), 1-11 (2011).