| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
||
| 250mg |
|
||
| 500mg | |||
| 1g | |||
| Other Sizes |
| Targets |
L-Kynurenine acts as an endogenous agonist of the aryl hydrocarbon receptor (AHR). It is also a substrate for multiple enzymes such as kynureninase (kynurenine hydrolase), kynurenine 3-monooxygenase, and kynurenine-oxoglutarate transaminase. By activating AHR, L-Kynurenine can modulate immune responses, specifically by promoting a shift in T cell differentiation towards an anti-inflammatory Treg phenotype.
|
|---|---|
| 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].
In vitro, L-Kynurenine acts as an AHR agonist, activating the AHR-regulated luciferase gene in H1L7.5c3 mouse hepatocytes. It inhibits the proliferation of allogeneic T cells. In cancer models, it increases the invasion of malignant U87 glioma cells into a collagen matrix. These activities highlight its role in immunosuppression and tumor progression. |
| 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].
In vivo, L-Kynurenine has demonstrated neuroprotective effects. One hour prior to hypoxia, L-kynurenine showed a dose-dependent protective effect, with 300 mg/kg providing full protection. Its metabolic products, such as kynurenic acid, can induce hypotension by acting on Kv7 channels in vascular smooth muscle. It is also a precursor to niacin. Its role in the immune system and as a signaling molecule has been studied in various disease contexts. |
| Enzyme Assay |
Cell-free assays for L-Kynurenine measure its interaction with the aryl hydrocarbon receptor (AHR). Receptor binding assays can be used to confirm its agonist activity. Enzymatic assays using purified enzymes like kynureninase, kynurenine 3-monooxygenase, and kynurenine-oxoglutarate transaminase can be used to measure its substrate activity. Its purity (>98%) can be confirmed by HPLC.
|
| Cell Assay |
Cellular assays for L-Kynurenine measure its effects on immune cells and cancer cells. In T cell assays, its ability to inhibit allogeneic T cell proliferation is measured. In cancer cell assays, its effect on increasing the invasion of malignant U87 glioma cells into a collagen matrix is evaluated. Its AHR agonist activity can be measured in reporter cell lines.
|
| Animal Protocol |
In vivo animal experiments for L-Kynurenine include models of hypoxia. In these studies, animals are administered L-Kynurenine prior to hypoxia exposure, and its neuroprotective effects are measured. The compound's effects on blood pressure and vascular tone are studied in models where kynurenic acid, a downstream metabolite, induces hypotension via Kv7 channels. Its role in cancer and immune modulation is also studied in disease models.
|
| ADME/Pharmacokinetics |
L-Kynurenine has a molecular weight of 208.21 and a molecular formula of C10H12N2O3. It is a metabolite of L-tryptophan. It is a white to off-white solid, soluble in water and organic solvents. It is stable under recommended storage conditions. It is rapidly absorbed and can cross the blood-brain barrier. Its levels are altered in various diseases, including cancer, inflammation, and neurological disorders.
|
| Toxicity/Toxicokinetics |
L-Kynurenine is generally considered safe at physiological concentrations. However, elevated levels of its downstream metabolites, such as quinolinic acid, are associated with neurotoxicity. In the context of cancer, tumor-derived kynurenine promotes tumor growth and suppresses antitumor immune responses. Its role as an AHR agonist can have both beneficial and detrimental effects depending on the context.
|
| References |
|
| 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.
L-Kynurenine is an endogenous metabolite of the amino acid L-tryptophan. It is a key intermediate in the kynurenine pathway, which is responsible for the biosynthesis of nicotinamide adenine dinucleotide (NAD+). Its role in various biological processes, including vasodilation, immunomodulation, and neuromodulation, makes it a significant research compound. Abnormal kynurenine production is associated with cognitive deficits and depressive symptoms. |
| Molecular Formula |
C10H12N2O3
|
|---|---|
| Molecular Weight |
208.21
|
| Exact Mass |
208.084
|
| CAS # |
2922-83-0
|
| 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
|
| PubChem CID |
161166
|
| Appearance |
White to yellow solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
466.6±45.0 °C at 760 mmHg
|
| Melting Point |
191 °C
|
| Flash Point |
236.0±28.7 °C
|
| Vapour Pressure |
0.0±1.2 mmHg at 25°C
|
| Index of Refraction |
1.626
|
| LogP |
1.09
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
15
|
| Complexity |
255
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)N
|
| InChi Key |
YGPSJZOEDVAXAB-QMMMGPOBSA-N
|
| 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
|
| Chemical Name |
(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
|
| Synonyms |
CCRIS 4425 Kynurenine, L- Kynurenine
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
H2O : ~20 mg/mL (~96.06 mM)
DMSO : ~12.5 mg/mL (~60.04 mM) |
|---|---|
| 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
