L-Kynurenine (Synonyms: 3-anthraniloyl-Alanine, L-KYN) |
| Catalog No.GC12040 |
L-Kynurenine is a metabolite of L-tryptophan and an aryl hydrocarbon receptor (AhR) agonist.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 2922-83-0
Sample solution is provided at 25 µL, 10mM.
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L-Kynurenine is a metabolite of L-tryptophan and an aryl hydrocarbon receptor (AhR) agonist. L-Kynurenine can also cause NK cell death through the reactive oxygen species (ROS) pathway[1][2].
L-Kynurenine triggers competition between aryl hydrocarbon receptor and hypoxia-inducible factor 1 alpha (HIF-1α) for ARNT (Aryl Hydrocarbon Receptor Nuclear Translocator) in MCF-7 cells under hypoxic conditions [1]. L-Kynurenine (0-1mM; 48h) specifically affects the expression of NKp46, NKG2D, and CD69 in the phenotype of NK cells cultured in IL-2, without altering the surface density of other triggering or coreceptors, including CD16, 2B4, NTB-A, DNAM-1, and CD59, or the surface density of inhibitory receptors[2]. After adding L-Kynurenine (10-40µM) to the supernatant of HCEC cells, cell apoptosis increased slightly and had a certain dose-dependent toxicity [3]. Treatment with L-Kynurenine (0–800μM; 72h) dose-dependently induced growth inhibition and apoptosis in NK92 MI cells[4].
L-Kynurenine (30mg/kg) inhibited ischemia-induced hyperlocomotion in the mouse MCAO model and reduced ischemia-induced deterioration of spontaneous alternation (a measure of spatial memory) without changing rectal temperature[5]. In the rat L5/L6 spinal nerve ligation model, L-Kynurenine (50-200mg/kg; ip) did not affect allodynia in neuropathic rats, while the combination of L-Kynurenine and the organic anion transport inhibitor probenecid (100mg/kg; ip) reversed allodynia[6].
References:
[1]. Cuartero M I, Ballesteros I, de la Parra J, et al. L-kynurenine/aryl hydrocarbon receptor pathway mediates brain damage after experimental stroke[J]. Circulation, 2014, 130(23): 2040-2051.
[2]. Schlichtner S, Yasinska I M, Klenova E, et al. L-Kynurenine participates in cancer immune evasion by downregulating hypoxic signaling in T lymphocytes[J]. OncoImmunology, 2023, 12(1): 2244330.
[3]. Chiesa M D, Carlomagno S, Frumento G, et al. The tryptophan catabolite L-kynurenine inhibits the surface expression of NKp46-and NKG2D-activating receptors and regulates NK-cell function[J]. Blood, 2006, 108(13): 4118-4125.
[4]. Serbecic N, Lahdou I, Scheuerle A, et al. Function of the tryptophan metabolite, L-kynurenine, in human corneal endothelial cells[J]. Molecular vision, 2009, 15: 1312.
[5]. Gigler G, Szénási G, Simó A, et al. Neuroprotective effect of L-kynurenine sulfate administered before focal cerebral ischemia in mice and global cerebral ischemia in gerbils[J]. European journal of pharmacology, 2007, 564(1-3): 116-122.
[6]. Pineda‐Farias J B, Pérez‐Severiano F, González‐Esquivel D F, et al. The l‐kynurenine–probenecid combination reduces neuropathic pain in rats[J]. European journal of pain, 2013, 17(9): 1365-1373.
| Cell experiment [1]: | |
Cell lines | MCF-7 human breast cancer cells |
Preparation Method | MCF-7 human breast cancer cells were exposed to 50µM L-Kynurenine for 4h under normal (21%) or low (1%) oxygen supply conditions. |
Reaction Conditions | 50µM; 4h |
Applications | L-Kynurenine triggers competition between aryl hydrocarbon receptor (AhR) and hypoxia-inducible factor 1 alpha (HIF-1α) for ARNT in cells under hypoxic conditions. |
| Animal experiment [2]: | |
Animal models | Middle cerebral artery occlusion (MCAO) Modle |
Preparation Method | Mice were injected with L-Kynurenine (30mg/kg) 15min before MCAO surgery, and the neuroprotective effects of L-Kynurenine sulfate (a precursor of kynurenic acid) were measured 24 to 48h later. |
Dosage form | 30mg/kg; ip |
Applications | L-Kynurenine inhibited the ischemia-induced hypermotility, and decreased the ischemia-induced deterioration of spontaneous alternation, a measure of spatial memory, without altering the rectal temperature. |
References: | |
| Cas No. | 2922-83-0 | SDF | |
| Synonyms | 3-anthraniloyl-Alanine, L-KYN | ||
| Chemical Name | (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid | ||
| Canonical SMILES | C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N | ||
| Formula | C10H12N2O3 | M.Wt | 208.21 |
| Solubility | ≥ 10.85mg/mL in Water with gentle warming | Storage | Store at RT |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 4.8028 mL | 24.0142 mL | 48.0284 mL |
| 5 mM | 0.9606 mL | 4.8028 mL | 9.6057 mL |
| 10 mM | 0.4803 mL | 2.4014 mL | 4.8028 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
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Average Rating: 5 (Based on Reviews and 32 reference(s) in Google Scholar.)
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