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Chemical Structure| 2922-83-0 Chemical Structure| 2922-83-0

Structure of Kynurenine
CAS No.: 2922-83-0

Chemical Structure| 2922-83-0

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L-Kynurenine is a metabolite of the amino acid L-tryptophan. L-Kynurenine is an aryl hydrocarbon receptor agonist.

Synonyms: 3-anthraniloyl-Alanine; (S)-Kynurenine; CCRIS 4425

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Product Details of Kynurenine

CAS No. :2922-83-0
Formula : C10H12N2O3
M.W : 208.21
SMILES Code : O=C(O)[C@@H](N)CC(C1=CC=CC=C1N)=O
Synonyms :
3-anthraniloyl-Alanine; (S)-Kynurenine; CCRIS 4425
MDL No. :MFCD00069912
InChI Key :YGPSJZOEDVAXAB-QMMMGPOBSA-N
Pubchem ID :161166

Safety of Kynurenine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Human monocyte-derived macrophages (MDMs) 25 μM 20 hours To investigate the effect of KYN on NAD+ levels, results showed that KYN supplementation prevented FK866-induced depletion of NAD+. Nat Immunol. 2019 Jan;20(1):50-63.
K562 human chronic myeloid leukemia cells 50 µM 16 h To study the effect of LKU on T cell cytotoxicity, it was found that LKU reduced the cytotoxic activity of T cells. Oncoimmunology. 2023 Aug 10;12(1):2244330.
Primary human CD3-positive T cells 50 µM 16 h To study the effect of LKU on HIF-1 activity, it was found that VEGF mRNA levels were significantly upregulated in the presence of IDO1 inhibitors. Oncoimmunology. 2023 Aug 10;12(1):2244330.
Jurkat T cells 50 µM 16 h To study the effect of LKU on HIF-1 activity, it was found that VEGF mRNA levels were significantly increased in Jurkat T cells. Oncoimmunology. 2023 Aug 10;12(1):2244330.
WT-3ab Wilms’ tumor cells 50 µM 4 h To study the effect of LKU on intracellular LKU levels, it was found that LKU levels were significantly increased in WT-3ab cells. Oncoimmunology. 2023 Aug 10;12(1):2244330.
LN18 human glioblastoma cells 50 µM 4 h To study the effect of LKU on intracellular LKU levels, it was found that LKU levels were not significantly increased in LN18 cells. Oncoimmunology. 2023 Aug 10;12(1):2244330.
MCF-7 human breast cancer cells 50 µM 4 h To study the effect of LKU on HIF-1α nuclear translocation, it was found that LKU downregulated HIF-1α nuclear levels under hypoxic conditions. Oncoimmunology. 2023 Aug 10;12(1):2244330.
Murine CD4+ T cells 1 mM 3 h To investigate the effect of D-kynurenine on murine T cell metabolism, found it increased fatty acid β-oxidation leading to fatty acid depletion. EBioMedicine. 2021 Dec;74:103734.
Human CD4+ T cells 1 mM 3 days To evaluate the effect of D-kynurenine on T cell proliferation and apoptosis, results showed 1 mM D-kynurenine inhibits T cell proliferation through apoptosis. EBioMedicine. 2021 Dec;74:103734.
Primary human NK cells 200 μM 48 h To investigate the effect of L-KYN on primary human NK cell viability, it was found that L-KYN significantly increased the proportion of primary human NK cell death J Exp Clin Cancer Res. 2023 Mar 1;42(1):52.
NK-92 cells 200 μM 24 or 48 h To investigate the effect of L-KYN on NK-92 cell viability, it was found that L-KYN significantly increased the proportion of NK-92 cell death J Exp Clin Cancer Res. 2023 Mar 1;42(1):52.
Arabidopsis thaliana seedlings 0.01 μM -1 mM 3 days To evaluate the inhibitory effect of Kyn on root growth in Arabidopsis thaliana seedlings. The results showed that Kyn significantly inhibited root growth in a concentration-dependent manner Plant Cell. 2011 Nov;23(11):3944-60.
conventional dendritic cells (cDCs) 50 μM 24 h To evaluate the ability of L-Kynurenine to induce IDO1 expression and TGF-β production in LPS-primed cDCs. Results showed that L-Kynurenine significantly enhanced IDO1 expression and TGF-β production, an effect dependent on AhR activation. Front Immunol. 2020 Mar 11;11:292.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice B6/Rag1-/- colitis model Dietary supplementation 300 mg/kg 10 days To evaluate the protective effect of D-kynurenine on autoimmune colitis, results showed D-kynurenine protected mice from colitis in an AhR-dependent manner. EBioMedicine. 2021 Dec;74:103734.
HIL-15 NOG mice Humanized CDX tumor model Subcutaneous injection 4 μg Every other day for 14 days To investigate the effect of L-KYN on NK cells in the tumor microenvironment, it was found that L-KYN significantly reduced the number of NK cells in tumor tissues and increased their death rate J Exp Clin Cancer Res. 2023 Mar 1;42(1):52.
Mice Tauopathy mouse model Intraperitoneal injection 33 mg/10 ml/kg Single injection, sacrificed after 3 hours To investigate the effects of Kynurenine on neuroinflammation and neurodegeneration in a tauopathy mouse model. Results showed that Kynurenine levels were elevated in the brains of tauopathy model mice, and Amino LP7 treatment significantly reduced these levels, suppressing neuroinflammation and brain atrophy. Sci Adv. 2021 Oct 22;7(43):eabd5046
Mice Cardiac arrest model Intravenous injection 20 mg/kg Single dose, observed for 7 days To evaluate the effects of the kynurenine pathway on brain injury after cardiac arrest. Results showed that IDO?/? mice had significantly higher survival rates and better neurological function compared to wild-type mice, and kynurenine pathway activation was associated with brain injury. Anesthesiology. 2023 Nov 1;139(5):628-645

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

4.80mL

0.96mL

0.48mL

24.01mL

4.80mL

2.40mL

48.03mL

9.61mL

4.80mL

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