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1-METHYL-D-TRYPTOPHAN

Product Name
1-METHYL-D-TRYPTOPHAN
CAS No.
110117-83-4
Chemical Name
1-METHYL-D-TRYPTOPHAN
Synonyms
Me-D-Trp;NLG-8189;IndoxiMod;1-Me-D-Trp;D-Trp(Me)-OH;H-D-Trp(1-Me)-OH;Indoximod (NLG-8189）;1-METHYL-D-TRYPTOPHAN;1-Methyl-D-tryptophane;D-Tryptophan, 1-methyl-
CBNumber
CB0467553
Molecular Formula
C12H14N2O2
Formula Weight
218.25
MOL File
110117-83-4.mol
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1-METHYL-D-TRYPTOPHAN Property

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
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
452483
Product name
1-Methyl-D-tryptophan
Purity
95%
Packaging
1g
Price
$146
Updated
2024/03/01
Sigma-Aldrich
Product number
452483
Product name
1-Methyl-D-tryptophan
Purity
95%
Packaging
10g
Price
$959
Updated
2024/03/01
Cayman Chemical
Product number
16456
Product name
1-methyl-D-Tryptophan
Purity
≥95%
Packaging
1g
Price
$115
Updated
2024/03/01
Cayman Chemical
Product number
16456
Product name
1-methyl-D-Tryptophan
Purity
≥95%
Packaging
5g
Price
$474
Updated
2024/03/01
Sigma-Aldrich
Product number
452483
Product name
1-Methyl-D-tryptophan
Purity
95%
Packaging
250mg
Price
$47
Updated
2024/03/01
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1-METHYL-D-TRYPTOPHAN Chemical Properties,Usage,Production

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

1-METHYL-D-TRYPTOPHAN Preparation Products And Raw materials

Raw materials

Preparation Products

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1-METHYL-D-TRYPTOPHAN Suppliers

China 175 Germany 1 India 4 Switzerland 1 United Kingdom 1 United States 20 Global 202
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View Lastest Price from 1-METHYL-D-TRYPTOPHAN manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
1-Methyl-D-tryptophan 110117-83-4
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kg
Release date
2021-08-24
Zhuozhou Wenxi import and Export Co., Ltd
Product
1-Methyl-D-tryptophan 95% 110117-83-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
1-METHYL-D-TRYPTOPHAN 110117-83-4
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000kg
Release date
2020-01-13

110117-83-4, 1-METHYL-D-TRYPTOPHANRelated Search:

5-METHYL-DL-TRYPTOPHAN 1-METHYL-D-TRYPTOPHAN 1-METHYL-DL-TRYPTOPHAN Fmoc-D-Trp(Boc)-OH 1-METHYL-L-TRYPTOPHAN 5-METHYL-DL-TRYPTOPHAN HYDRATE α-Methyl-(S)-tryptophan,ALPHA-METHYL-L-TRYPTOPHAN 1-METHYL-L-TRYPTOPHAN D(+)-Tryptophan 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

  • 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
  • Me-D-Trp
  • 1-Me-D-Trp
  • D-Trp(Me)-OH
  • H-D-Trp(1-Me)-OH
  • INDOXIMOD;1-METHYL-D-TRYPTOPHAN;1-METHYL-D-TRYPTOPHANE
  • (2R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
  • D-Tryptophan, 1-methyl-
  • 1-METHYL-D-TRYPTOPHAN USP/EP/BP
  • (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
  • Indoximod, Indoleamine 2,3-dioxygenase (IDO) inhibitor
  • 110117-83-4
  • Amino Acid Derivatives
  • Peptide Synthesis
  • Specialty Synthesis
  • Tryptophan
  • Inhibitors
  • Amino Acid Derivatives
  • Peptide Synthesis
  • Tryptophan