3-hydroxy-DL-Kynurenine (Synonyms: DL-3-Hydroxykynurenine) |
| Catalog No.GC45336 |
3-hydroxy-DL-Kynurenine is a potential endogenous neurotoxin which significantly inhibited CD4+ T-cell proliferation in a dose-dependent manner with IC50 value of approximately 70μM.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 2147-61-7
Sample solution is provided at 25 µL, 10mM.
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3-hydroxy-DL-Kynurenine is a potential endogenous neurotoxin which significantly inhibited CD4+ T-cell proliferation in a dose-dependent manner with IC50 value of approximately 70μM. 3-hydroxy-DL-Kynurenine is a metabolic intermediate of the kynurenine pathway, the major metabolic pathway of tryptophan (Trp). Increased levels of 3-hydroxy-DL-Kynurenine have been described in several neurodegenerative disorders[1][2].
In vitro, human colon cancer HCT116 cells treated with 3-hydroxy-DL-Kynurenine (0.008-2mM) for 6-48h disrupted TCA cycle metabolism, depleted glutathione levels and reduced cell viability in a dose-dependent manner[3]. Neuronally derived hybrid cell line (N18-RE-105) was treated with increasing concentration of 3-hydroxy-DL-Kynurenine for 24h. 3-hydroxy-DL-Kynurenine was toxic to greater than 85% of cultured cells at concentrations in excess of 100μM. N18-RE-105 exposed to 500μM 3-hydroxy-DL-Kynurenine for 2h did not induced significant cell lysis, yet marked cell death emerged 22h after harvest[4]. Human neurons and astrocytes treated with 3-hydroxy-DL-Kynurenine (0.1–1000μM) for 24h significantly increased intracellular NAD+ levels at a low concentration of 100nM but substantially decreased NAD+ levels at higher concentrations. Treatment with 3-hydroxy-DL-Kynurenine increased extracellular LDH activity at concentrations above 100nM in both cell types[5].
In vivo, kynurenine 3-monooxygenase (KMO) is a pivotal enzyme in the kynurenine pathway (KP) and normally oxidizes kynurenine (KYN) to 3-hydroxy-DL-Kynurenine in the presence of reduced NADPH and molecular oxygen. Endotoxic shock was induced in KMO-/- C57BL/6N mice with 15mg/kg LPS. KMO-/- mice given 10mg/kg 3-hydroxy-DL-Kynurenine i.p. every 12h after LPS survived significantly longer than PBS-treated KMO-/- mice by inhibiting inflammation via halving serum IL-6 and blocking ATF4 nuclear translocation[6]. Intrastriatal injection of 1μl of 3-hydroxy-DL-Kynurenine (50nmol) dissolved in DMSO into Wistar rats brain induced lesion at the injected area characterized by a dose-dependent, well-defined cavity surrounded by necrosis and reactive gliosis[7].
References:
[1] Okuda S, Nishiyama N, Saito N, and Katsuki H. 3-Hydroxykynurenine, an endogenous oxidative stress generator, causes neuronal cell death with apoptotic features and region selectivity. J Neurochem. 1998 Jan;70(1):299-307.
[2] Sarah S Zaher,Germain C, Fu H, et al. 3-hydroxykynurenine suppresses CD4+ T-cell proliferation, induces T-regulatory-cell development, and prolongs corneal allograft survival. Invest Ophthalmol Vis Sci. 2011 Apr 22;52(5):2640-8.
[3] Buchanan J L, Rauckhorst A J, Taylor E B. 3-hydroxykynurenine is a ROS-inducing cytotoxic tryptophan metabolite that disrupts the TCA cycle. bioRxiv. 2023 Jul 10:2023.07.10.548411.
[4] Eastman C L, Guilarte T R. Cytotoxicity of 3-hydroxykynurenine in a neuronal hybrid cell line. Brain Res. 1989 Aug 28;495(2):225-31.
[5] Braidy N, Grant R, Brew B J, et al. Effects of Kynurenine Pathway Metabolites on Intracellular NAD Synthesis and Cell Death in Human Primary Astrocytes and Neurons. Int J Tryptophan Res. 2009:2:61-9.
[6] Hoshi M, Kubo H, Ando T, et al. 3-Hydroxykynurenine Regulates Lipopolysaccharide-Stimulated IL-6 Production and Protects against Endotoxic Shock in Mice. Immunohorizons. 2021 Jun 28;5(6):523-534.
[7] Nakagami Y, Saito H, Katsuki H. 3-Hydroxykynurenine toxicity on the rat striatum in vivo. Jpn J Pharmacol. 1996 Jun;71(2):183-6.
| Cell experiment [1]: | |
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Cell lines |
Murine CD4+ T cells |
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Preparation Method |
CD3/CD28 bead-stimulated CD4+ T cells were incubated for 72 hours in the presence of 3-hydroxy-DL-Kynurenine at concentrations varying from 0 to 100µM. |
|
Reaction Conditions |
0-100µM; 72h |
|
Applications |
3-hydroxy-DL-Kynurenine significantly inhibited CD4+ T-cell proliferation in a dose-dependent manner with IC50 of approximately 70µM. |
| Animal experiment [2]: | |
|
Animal models |
Male Wistar rats |
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Preparation Method |
3-hydroxy-DL-Kynurenine was administered as a single 50nmol intrastriatal injection dissolved in 1µL DMSO into the rat striatum. |
|
Dosage form |
1µL of 50nmol; intrastriatal injection; a single administration |
|
Applications |
3-hydroxy-DL-Kynurenine induced lesion around the injected area characterized by a dose-dependent, well-defined cavity surrounded by necrosis and reactive gliosis. |
|
References: |
|
| Cas No. | 2147-61-7 | SDF | |
| Synonyms | DL-3-Hydroxykynurenine | ||
| Chemical Name | α,2-diamino-3-hydroxy-γ-oxo-benzenebutanoic acid | ||
| Canonical SMILES | OC1=CC=CC(C(CC(N)C(O)=O)=O)=C1N | ||
| Formula | C10H12N2O4 | M.Wt | 224.2 |
| Solubility | DMF: 0.5 mg/ml,DMSO: 1 mg/ml,Ethanol: 2 mg/ml,PBS (pH 7.2): 0.5 mg/ml | Storage | Store at -20°C |
| 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. |
||
| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.4603 mL | 22.3015 mL | 44.603 mL |
| 5 mM | 892.1 μL | 4.4603 mL | 8.9206 mL |
| 10 mM | 446 μL | 2.2302 mL | 4.4603 mL |
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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 20 reference(s) in Google Scholar.)
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