1-METHYL-D-TRYPTOPHAN
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1-METHYL-D-TRYPTOPHAN
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CAS No:
110117-83-4
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Formula:
C12H14N2O2
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Chemical Name:
1-METHYL-D-TRYPTOPHAN
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Synonyms:
1-METHYL-D-TRYPTOPHAN;1-Methyl-D-tryptophane;1-METHYL-D-TRYPTOPHAN 95%;(R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid;IndoxiMod;Indoximod (NLG-8189);NLG-8189;1-Me-D-Trp
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CAS No:
Description
Indoximod (D-1MT, NLG8189) is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor with a Ki of 19 μM.
Indoximod has been used in trials studying the treatment of Glioma, Melanoma, Ependymoma, Gliosarcoma, and Lung Cancer, among others.|Indoximod is a methylated tryptophan with immune checkpoint inhibitory activity. Indoximod inhibits the enzyme indoleamine 2,3-dioxygenase (IDO), which degrades the essential amino acid tryptophan, and may increase or maintain tryptophan levels important to T cell function. Tryptophan depletion is associated with immunosuppression involving T cell arrest and anergy.
Characteristics
68.2
-1.3
1.28
242-245 °C(lit.)
429.3±35.0 °C(Predicted)
213.4±25.9 °C
1.625
12.4o (C = 2 IN ACETIC ACID)
1-METHYL-D-TRYPTOPHAN Use and Manufacturing
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.
Computed Properties
Molecular Weight:218.25
XLogP3:-1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:218.105527694
Monoisotopic Mass:218.105527694
Topological Polar Surface Area:68.2
Heavy Atom Count:16
Complexity:270
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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