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β-Anthraniloyl-L-Alanine; AhR Agonist
5 x 10 mg
Tryptophan-derived agonist of AhR
L-Kynurenine (Beta-Anthraniloyl-L-Alanine) is an endogenous agonist for the cytosolic aryl hydrocarbon receptor (AhR) transcription factor .
L-Kynurenine is the first byproduct of tryptophan metabolism generated via the enzymatic “kynurenine pathway”, which produces other kynunerine derivatives . L-Kynurenine is implicated in the production of TGF-β and expansion of regulatory T cells through the AhR-Src-IDO1 pathway . 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) .
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.
Read our review on AhR's key role in the intestinal microbiota and immunity.
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.
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.
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
Molecular weight: 208.22 g/mol
- 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.
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.Back to the top
Chemical strucure of L-Kynurenine
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