1-METHYL-D-TRYPTOPHAN

Bezeichnung:1-METHYL-D-TRYPTOPHAN

CAS-Nr110117-83-4

Englisch Name:1-METHYL-D-TRYPTOPHAN

CBNumberCB0467553

SummenformelC12H14N2O2

Molgewicht218.25

MOL-Datei110117-83-4.mol

1-METHYL-D-TRYPTOPHAN physikalisch-chemischer Eigenschaften

Schmelzpunkt	242-245 °C(lit.)
alpha	12.4o (C = 2 IN ACETIC ACID)
Siedepunkt	429.3±35.0 °C(Predicted)
Dichte	1.28
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Soluble in DMSO (greater than 25 mg/ml).
pka	2.26±0.10(Predicted)
Aggregatzustand	White to light brown crystalline powder.
Farbe	White
Optische Aktivität	[α]22/D +12.4°, c = 2 in acetic acid
Wasserlöslichkeit	Soluble to 5 mM in water with gentle warming
Stabilität	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

Sicherheit

WGK Germany

Gefahreninformationscode (GHS)

1-METHYL-D-TRYPTOPHAN Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Verwenden
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
Verwenden
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.
Lager
Store at -20°C
Einzelnachweise
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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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