1-METHYL-D-TRYPTOPHAN

ChemicalBook > CAS DataBase List > 1-METHYL-D-TRYPTOPHAN

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

reaction suitability

reaction type: solution phase peptide synthesis

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

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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