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L-Kynurenine

L-Kynurenine Unit size Cat. code Docs Qty Price
β-Anthraniloyl-L-Alanine; AhR Agonist
10 mg
5 x 10 mg
tlrl-kyn
+-
$95.00

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Tryptophan-derived agonist of AhR

L-Kynurenine (Beta-Anthraniloyl-L-Alanine) is an endogenous agonist for the cytosolic aryl hydrocarbon receptor (AhR) transcription factor [1].
L-Kynurenine is the first byproduct of tryptophan metabolism generated via the enzymatic “kynurenine pathway”, which produces other kynunerine derivatives [2]. L-Kynurenine is implicated in the production of TGF-β and expansion of regulatory T cells through the AhR-Src-IDO1 pathway [1]. Yet, L-Kynurenine mode of action on AhR is still unclear. Indeed, it could be a low-affinity AhR pro-ligand that is slowly converted in high-affinity compounds acting as AhR agonists at subnanomolar concentrations. This conversion occurs independently of enzymes, when fresh crystalline L-Kynurenine is resuspended as a solution, and gives rise to trace-amounts of derivatives named TEACOPs (trace-extended aromatic condensation products) [3].

InvivogGen's L-Kynurenine is a high quality product (> 95% purity) and is guaranteed free of bacterial contamination. Each lot of L-Kynurenine is functionally tested in cellular assays using HepG2-Lucia™ AhR and HT29-Lucia™ AhR reporter cells.

Other AhR ligands, as well as an AhR antagonist are also available.

 

Learn more on AhR. Read our review on AhR's key role in the intestinal microbiota and immunity.

 

References:

1. Bessede A. et al., 2014. Aryl hydrocarbon receptor control of a disease tolerance defence pathway. Nature. 511:184-90.
2. Hubbard T.D. et al., 2015. Indole and tryptophan metabolism: endogenous and dietary routes to Ah receptor activation. Drug Metab. Dispos. 43:1522-35.
3. Seok, S.H. et al., 2018. Trace derivatives of kynurenine potently activate the aryl hydrocarbon receptor (AHR). J. Biol. Chem. 293:1994-2005.

Figures

Evaluation of cellular AhR activation by L-Kynurenine
Evaluation of cellular AhR activation by L-Kynurenine

L-Kynurenine induces a time-dependent response in HepG2-Lucia™ Ahr and HT29-Lucia™ Ahr cells. The cells were incubated with 33 µg/ml (160 µM) of L-Kynurenine that had been resuspended and incubated at room temperature for 1, 7 or 14 days. After overnight incubation, the AhR activation was assessed by determining Lucia luciferase activity in the supernatant using QUANTI-Luc™. Data are expressed as fold responses, as compared to non-induced cells. DMSO final concentration impacts cells viability and AhR activation. We recommend to include a control dilution of DMSO in your assay. Using our protocol, a 33 µg/ml (160 µM) L-Kynurenine concentration includes 1.7% DMSO.

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Specifications

CAS number: 2922-83-0

Synonyms: β-anthraniloyl-L-alanine, L-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

Solubility: 20 mg/ml (96 mM) in DMSO

Working concentration: 10 to 100 µg/ml for cell culture assays

Formula: C10H12N2O3

Molecular weight: 208.22 g/mol

Quality control:

  • Purity ≥ 95% (UHPLC).
  • The absence of bacterial contamination (e.g. lipoproteins and endotoxins) has been confirmed using HEK-Blue™ TLR2 and HEK‑Blue™ TLR4 cells.
  • The biological activity has been validated using cellular assays.
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Contents

L-Kynurenine is available in two pack sizes:

  • tlrl-kyn: 1 x 10 mg L-Kynurenine
  • tlrl-kyn-5: 5 x 10 mg L-Kynurenine
     

L-Kynurenine is shipped at room temperature.

Store at 15-25°C.

Resuspended product is stable at 15-25°C for 6 months when properly stored.

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Details

Chemical strucure of L-Kynurenine

Chemical strucure of L-Kynurenine

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