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SML3499

Sigma-Aldrich

LM10

≥98% (HPLC)

Synonym(s):

(E)-3-(2-(1H-tetrazol-5-yl)vinyl)-6-fluoro-1H-indole, 6-Fluoro-3-[(1E)-2-(2H-tetrazol-5-yl)ethenyl]-1H-indole, LM 10, trans-6-Fluoro-3-(2-(1H-tetrazol-5-yl)vinyl)-1H-indole

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About This Item

Empirical Formula (Hill Notation):
C11H8FN5
CAS Number:
1316695-35-8
Molecular Weight:
229.21
MDL number:
MFCD26097257
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

FC1=CC2=C(C=C1)C(/C=C/C3=NN=NN3)=CN2

InChI

1S/C11H8FN5/c12-8-2-3-9-7(6-13-10(9)5-8)1-4-11-14-16-17-15-11/h1-6,13H,(H,14,15,16,17)/b4-1+

InChI key

JDBSZVDIUIRSDG-DAFODLJHSA-N

Biochem/physiol Actions

LM10 is an orally available, aqueous soluble, potent, selective and non-toxic tryptophan 2,3-dioxygenase (TDO) inhibitor. LM10 diminishes tryptophan degradation and effectively prevents the growth of TDO-expressing P815 tumor cells by reversing immune resistance in immune competent but not in immunodeficient mice (at a dose of 4 mg/day, 1 mg/ml in water, pH 9.0). LM10 suppresses autoimmune reactions induced by mouse hepatitis virus in mice.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Luc Pilotte et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(7), 2497-2502 (2012-02-07)
Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO1) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance, and IDO1 inhibition is an active area of drug development. Tryptophan 2,3-dioxygenase (TDO) is an unrelated hepatic enzyme that also
Abdulla A-B Badawy
Medical hypotheses, 131, 109314-109314 (2019-08-25)
Metabolic targeting of liver 5-aminolevulinate synthase (5-ALAS) by inhibition of heme utilisation by tryptophan (Trp) 2,3-dioxygenase (TDO) or the use of tryptophan is proposed as a therapy of acute hepatic porphyrias. 5-ALAS, the rate-limiting enzyme of heme biosynthesis, is under
Maite Duhalde Vega et al.
Immunology letters, 217, 25-30 (2019-11-15)
In a previous work we demonstrated that inhibition of mouse indoleamine 2,3-dioxygenase (IDO) by methyltryptophan (MT) exacerbated the pathological actions of mouse hepatitis virus (MHV-A59) infection, suggesting that tryptophan (TRP) catabolism was involved in viral effects. Since there is a

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