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L-Kynurenine is a key intermediate and metabolite during the breakdown of amino acid L-tryptophan and the biosynthesis of nicotinamide adenine dinucleotide (NAD+) via the kynurenine pathway. It acts as an AHR/aryl hydrocarbon receptor agonist and is involved in a variety of neurological processes and diseases. L-Kynurenine is also a substrate for multple enzymes such as kynureninase/kynurenine hydrolase; kynurenine 3-monooxygenase and kynurenine-oxoglutarate transaminase.
| ln Vitro |
Among the many biological roles of kynurenine and its breakdown products are the dilation of blood vessels and the regulation of immunological responses in cancer patients. Certain cancers produce more kynurenine, which promotes the growth of tumors. An aryl hydrocarbon receptor (AHR) agonist called L-Kynurenine (Kyn) stimulates naive T cells directed by the AHR to a phenotype of anti-inflammatory Tregs locally. 24 hours after being introduced, kynurenine works as an AHR agonist by activating the AHR-regulated luciferase gene in H1L7.5c3 mouse hepatocytes, and it stimulates the AHR signaling pathway in H1L7.5c3 cells at physiological doses [1].
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| ln Vivo |
Through Kv7 channels in the smooth muscle of blood vessels and the arteries in the body, kynurenic acid is circulated. This color channel in the channel induces hypotension, which is mediated in a specific flow diagram by Kv7 channel vascular transport [2]. One hour prior to hypoxia, L-kynurenine demonstrated a dose-dependent substantial effect. At 300 mg/kg, it is fully protective and has a notable neuroprotective impact. At such dosage, there was also a surge in L-kynurenine. C-fos immunoreactivity is induced in the cerebral cortex [3].
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| References |
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| Additional Infomation |
L-Kyrenurine is a kyrenurine with an L-configuration. It is found in humans, Saccharomyces cerevisiae, and mice as a metabolite. It is a non-protein L-α-amino acid and a type of kyrenurine. It is the conjugate acid of L-kyrenin and the enantiomer of D-kyrenurine. It is a zwitterion tautomer of L-kyrenurine. L-kyrenurine has been reported in Daphnia pulex, Bombyx mori, and other organisms with relevant data. Kyrenurine is a ketone and amino acid derivative synthesized from tryptophan via an oxidation reaction mediated by tryptophan 2,3-dioxygenase (TDO) or indoleamine 2,3-dioxygenase (IDO). It possesses various biological functions, including vasodilatory, immunomodulatory, and neuromodulatory activities. Kyrenurine is a precursor to niacin. Furthermore, kynurenine can be further metabolized into anthranilic acid, kynurenic acid, and 3-hydroxykynurenine; abnormal kynurenine production is associated with cognitive deficits and depressive symptoms related to neurological disorders. Kynurenine is overexpressed in certain cancer cell types and therefore has the potential to be used as a biomarker for assessing cancer risk.
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| Molecular Formula |
C10H12N2O3
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|---|---|
| Molecular Weight |
208.21
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| Exact Mass |
208.084
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| CAS # |
2922-83-0
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| Related CAS # |
L-Kynurenine-d4;2672568-86-2;L-Kynurenine-d4-1 hydrochloride;L-Kynurenine sulfate;16055-80-4;L-Kynurenine-d4-1;194546-33-3;L-Kynurenine-13C4,15N-1
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| PubChem CID |
161166
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| Appearance |
White to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
466.6±45.0 °C at 760 mmHg
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| Melting Point |
302.49° C
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| Flash Point |
236.0±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.626
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| LogP |
1.09
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
15
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| Complexity |
255
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)N
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| InChi Key |
YGPSJZOEDVAXAB-QMMMGPOBSA-N
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| InChi Code |
InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
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| Chemical Name |
(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
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| Synonyms |
CCRIS 4425 Kynurenine, L- Kynurenine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~20 mg/mL (~96.06 mM)
DMSO : ~12.5 mg/mL (~60.04 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (9.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 0.83 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 0.83 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 7.14 mg/mL (34.29 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). |
| Preparing Stock Solutions | 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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