L-Kynurenine

Names

[ Name ]:
L-Kynurenine

[Synonym ]:
(S)-α,2-diamino-γ-oxo-Benzenebutanoic acid
(S)-a,2-diamino-g-oxo-Benzenebutanoic acid
3-Anthraniloyl-L-alanine
Benzenebutanoic acid, α,2-diamino-γ-oxo-, (αS)-
L-3-(o-Aminobenzoyl)alanine
3-anthraniloyl-alanine
3-Anthraniloylalanine
Alanine, 3-anthraniloyl-, L-
Kynurenine, L-
L-KYNURENINE
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
(S)-a,2-diamino-γ-oxo-Benzenebutanoic acid
Kynurenine
Benzenebutanoic acid, α,2-diamino-γ-oxo-, (S)-
L-Kynurenin
(S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
MFCD00069912
(S)-α,2-Diamino-γ-oxobenzenebutanoic acid

Biological Activity

[Description]:

L-Kynurenine is a metabolite of the amino acid L-tryptophan. L-Kynurenine is an aryl hydrocarbon receptor agonist.

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Aryl Hydrocarbon Receptor

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Neurological Disease

Natural Products >> Others

Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite

[In Vitro]

Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation and regulating the immune response. Some cancers increase kynurenine production, which increases tumor growth. L-kynurenine (Kyn) is an aryl hydrocarbon receptor (AHR) agonist that activates AHR-directed, naive T cell polarization to the anti-inflammatory Treg phenotype. Kynurenine activates AHR signaling at physiological concentrations in H1L7.5c3 cells and acts as an AHR agonist after a 24-hr exposure by inducing the AHR-regulated luciferase gene in H1L7.5c3 mouse hepatocyte cells[1].

[In Vivo]

Kynurenine dilates arteries from rats as well as humans via Kv7 channels in the vascular smooth muscle. In rats, this tryptophan metabolite causes hypotension, which is partly counteracted by Kv7 channel inhibition[2]. L-kynurenine administered 1 h before the hypoxia-ischemia shows a dose-dependent significant neuroprotective effect, with complete protection at a dose of 300 mg/kg. The induction of c-fos immunoreactivity in cerebral cortex is also blocked by this dose of L-kynurenine[3].

[Cell Assay]

Luciferase assays are carried out using the H1L7.5c3 cells. At the indicated times (0.5, 2, 4, 6, 12, 18, 24 h) and concentrations (0.1, 1, 10, 100 μM) of exposures to Kynurenine, cells are removed from incubation and allowed to equilibrate to room temperature for 15min. After equilibration, the medium is removed and the cells are washed twice with at room temperature with DPBS. The cells are lysed with 20 µL/well 1× Passive Lysis Buffer and shaken for 20min at room temperature. Luciferase activity is recorded using an Luminometer Microplate Reader[1].

[Animal admin]

Rats[3] The effects of increasing doses of L-kynurenine with or without probenecid on concentrations of kynurenic acid in cerebral cortex are examined in 7-day-old rats. Six animals are examined in each group. Animals are treated with L-kynurenine at doses of 100, 200, 300, and 400 mg/kg or kynurenine, 200 mg/kg with probenecid, 50 mg/kg. Animals are killed at 1 h, the brains promptly removed, and the cerebral cortex is dissected and placed in 0.5 mL of chilled 0. 1 M HCl. Kynurenic acid measurements are made by high-performance liquid chromatography with fluorescence detection. Protein measurements are made using a fluorometric assay[3].

[References]

[1]. Moyer BJ, et al. Inhibition of the aryl hydrocarbon receptor prevents Western diet-induced obesity. Model for AHR activation by kynurenine via oxidized-LDL, TLR2/4, TGFβ, and IDO1. Toxicol Appl Pharmacol. 2016 Jun 1;300:13-24.

[2]. Sakakibara K, et al. Kynurenine causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels. J Pharmacol Sci. 2015 Sep;129(1):31-7.

[3]. Nozaki K, et al. Neuroprotective effects of L-kynurenine on hypoxia-ischemia and NMDA lesions in neonatal rats. J Cereb Blood Flow Metab. 1992 May;12(3):400-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
466.6±45.0 °C at 760 mmHg

[ Melting Point ]:
302.49° C

[ Molecular Formula ]:
C₁₀H₁₂N₂O₃

[ Molecular Weight ]:
208.214

[ Flash Point ]:
236.0±28.7 °C

[ Exact Mass ]:
208.084793

[ PSA ]:
106.41000

[ LogP ]:
1.09

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.626

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

[ RTECS ]:
CY9049700

[ HS Code ]:
2922509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Vitamin B1 deficiency inhibits the increased conversion of tryptophan to nicotinamide in severe food-restricted rats.

Biosci. Biotechnol. Biochem. 79(1) , 103-8, (2015)

The conversion of tryptophan (Trp) → nicotinamide (Nam) is an important pathway for supplying vitamin niacin. We reported the following two phenomena: (1) severe food restriction led to an increase in...

The urinary ratio of 3-hydroxykynurenine/3-hydroxyanthranilic acid is an index to predicting the adverse effects of D-tryptophan in rats.

J. Nutr. Sci. Vitaminol. 60(4) , 261-8, (2014)

The adverse effects of D-tryptophan and the possibility of it being a surrogate index for predicting adverse effects in rats were investigated. Male rats were fed one of several test diets (20% casein...

Organic anion transporting polypeptides 1B1 and 1B3 play an important role in uremic toxin handling and drug-uremic toxin interactions in the liver.

J. Pharm. Pharm. Sci. 17(4) , 475-84, (2015)

Organic anion-transporting polypeptide (OATP) 1B1 and OATP1B3 contribute to hepatic uptake of numerous drugs. Thus, reduced OATP1B1 and OATP1B3 activity in chronic kidney disease (CKD) may have a majo...