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1-METHYL-D-TRYPTOPHAN

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Products Intro: Product Name:1-methyl-D-tryptophan
CAS:110117-83-4
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CAS:110117-83-4
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1-METHYL-D-TRYPTOPHAN manufacturers

  • 1-Methyl-D-tryptophan
  • 1-Methyl-D-tryptophan pictures
  • $0.00 / 25Kg/Drum
  • 2025-05-09
  • CAS:110117-83-4
  • Min. Order: 1KG
  • Purity: 98%min
  • Supply Ability: 500kg
  • Indoximod
  • Indoximod pictures
  • $64.00 / 500mg
  • 2024-11-19
  • CAS:110117-83-4
  • Min. Order:
  • Purity: 99.5%
  • Supply Ability: 10g
  • 1-Methyl-D-tryptophan 95%
  • 1-Methyl-D-tryptophan 95% pictures
  • $15.00 / 1KG
  • 2021-07-02
  • CAS:110117-83-4
  • Min. Order: 1KG
  • Purity: 99%+ HPLC
  • Supply Ability: Monthly supply of 1 ton
1-METHYL-D-TRYPTOPHAN Basic information
Product Name:1-METHYL-D-TRYPTOPHAN
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
CAS:110117-83-4
MF:C12H14N2O2
MW:218.25
EINECS:
Product Categories:Inhibitors;Amino Acid Derivatives;Peptide Synthesis;Tryptophan
Mol File:110117-83-4.mol
1-METHYL-D-TRYPTOPHAN Structure
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).
pka2.26±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.
InChIKeyZADWXFSZEAPBJS-SNVBAGLBSA-N
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
SigmaAldrich English
1-METHYL-D-TRYPTOPHAN Usage And Synthesis
DescriptionIndoleamine 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.
Uses1-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
UsesIndoleamine 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 suitabilityreaction 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 50IDO: 19 μM (Ki)
storageStore at -20°C
References1) 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
1-METHYL-D-TRYPTOPHAN Preparation Products And Raw materials
Tag:1-METHYL-D-TRYPTOPHAN(110117-83-4) Related Product Information
5-METHYL-DL-TRYPTOPHAN 1-METHYL-D-TRYPTOPHAN 1-METHYL-DL-TRYPTOPHAN Fmoc-D-Trp(Boc)-OH 5-METHYL-DL-TRYPTOPHAN HYDRATE α-Methyl-(S)-tryptophan,ALPHA-METHYL-L-TRYPTOPHAN 1-METHYL-L-TRYPTOPHAN D(+)-Tryptophan L-Abrine BOC-D-TPI(FOR)-OH Z-D-TRP(BOC)-OH FMOC-D-TRP(ME)-OH H-D-TRP(BOC)-OH 7-METHOXY-1-METHYL-D-TRYPTOPHAN ETHYL ESTER BOC-D-TRP(FOR)-OH H-D-TRP(FOR)-OH HCL BOC-N-ALPHA-METHYL-DL-TRYPTOPHAN 4-METHYL-DL-TRYPTOPHAN

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