2922-83-0

2922-83-0 structure

Name: L-Kynurenine
Chemical Name: L-kynurenine
CAS Number: 2922-83-0
Molecular Formula: C₁₀H₁₂N₂O₃
Molecular Weight: 208.214
Catalog: Biochemical Common amino acids and protein drugs
Create Date: 2018-02-13 08:00:00
Modify Date: 2024-01-01 23:00:06
L-Kynurenine is a metabolite of the amino acid L-tryptophan. L-Kynurenine is an aryl hydrocarbon receptor agonist.

Name	L-kynurenine
Synonyms	(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

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.

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

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

343-65-7

2922-83-0

13441-51-5

Literature: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; ARMSTRONG, Daniel, W.; PING, Sun; BREITBACH, Zachary, S.; WANG, Chunlei Patent: WO2010/148191 A2, 2010 ; Location in patent: Page/Page column 45-49; 61 ;

172479-59-3

~90%

2922-83-0

Literature: Jackson, Richard F. W.; Turner, Debra; Block, Michael H. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 6 p. 865 - 870

73-22-3

2922-83-0

Literature: Lu, Changyuan; Lin, Yu; Yeh, Syun-Ru Biochemistry, 2010 , vol. 49, # 24 p. 5028 - 5034

117269-81-5

2922-83-0

Literature: Jackson; Turner; Block Journal of the Chemical Society - Series Chemical Communications, 1995 , # 21 p. 2207 - 2208

615-43-0

2922-83-0

Literature: Jackson, Richard F. W.; Turner, Debra; Block, Michael H. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 6 p. 865 - 870

Precursor 4
343-65-7 172479-59-3 73-22-3 615-43-0
DownStream 7
492-27-3 56-41-7 118-92-3 609-85-8
363-36-0 33925-79-0 15462-45-0

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%

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