(Rac)-Indoximod

Names

[ Name ]:
(Rac)-Indoximod

[Synonym ]:
racemic N-methyl tryptophan
methyl tryptophan
1-methyl-D,L-tryptophan
DL-1-Methyltryptophan
1-MT
EINECS 248-157-6
racemic-1-methyl-D-tryptophan
MFCD00005803
2-amino-3-(1-methylindol-3-yl)propanoic acid
L-Tryptophan,1-methyl
2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
1-Methyl-tryptophan

Biological Activity

[Description]:

(Rac)-Indoximod (1-Methyl-DL-tryptophan) is an indoleamine 2,3-dioxygenase (IDO) inhibitor. Co-treatment with IFN-γ and (Rac)-Indoximod markedly reduces the activity of human cardiac myofibroblasts (hCMs) expressing α-SMA and induces apoptosis through up-regulating the IRF-1, Fas, and FasL genes[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Indoleamine 2,3-Dioxygenase (IDO)

Research Areas >> Inflammation/Immunology

[Target]

IDO

[In Vitro]

(Rac)-Indoximod (1-Methyl-DL-tryptophan; 0.5 mM; 3 days) inhibits tryptophan depletion, thereby partially reversing the growth-inhibitory activity of IFN-γ, but eventually induces cell death regardless of tryptophan depletion[1]. Cell Viability Assay[1] Cell Line: Human cardiac myofibroblasts (hCMs) Concentration: 0.5 mM Incubation Time: 3 days Result: Growth retardation by IFN-γ was partially reversed on day 2, but cell viability was further reduced on day 3.

[References]

[1]. Jun-Won Lee,et al. Co-treatment with interferon-γ and 1-methyl tryptophan ameliorates cardiac fibrosis through cardiac myofibroblasts apoptosis. Mol Cell Biochem. 2019 Aug;458(1-2):197-205.

Chemical & Physical Properties

[ Density]:
1.28g/cm3

[ Boiling Point ]:
429.3ºC at 760mmHg

[ Melting Point ]:
250ºC (dec.)(lit.)

[ Molecular Formula ]:
C₁₂H₁₄N₂O₂

[ Molecular Weight ]:
218.25200

[ Flash Point ]:
213.4ºC

[ Exact Mass ]:
218.10600

[ PSA ]:
68.25000

[ LogP ]:
1.83300

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus ( section sign).

J. Nat. Prod. 72 , 44-52, (2009)

This study reports that a series of tryptophan derivatives with modifications on the side chain or at the indole ring were accepted by two cyclic dipeptide prenyltransferases, CdpNPT and FtmPT1, and c...

Inhibition of indoleamine 2,3-dioxygenase promotes vascular inflammation and increases atherosclerosis in Apoe-/- mice.

Cardiovasc. Res. 106 , 295-302, (2015)

Atherosclerosis is a chronic inflammatory disease that is initiated by the retention and accumulation of low-density lipoprotein in the artery, leading to maladaptive response of cells from the immune...

Immunosuppressive properties of Wharton's jelly-derived mesenchymal stromal cells in vitro.

Int. J. Hematol. 102 , 368-78, (2015)

Recent studies have reported that mesenchymal stromal cells (MSCs) migrate to areas of inflammation and suppress adverse immune reactions. Bone marrow (BM)-derived MSCs have been successfully used in ...