An internal standard for the quantification of kynurenine
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Unlabeled Version(s)
11305L-Kynurenine
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L-Kynurenine-d4

Item No. 36307

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(S)-2-amino-4-(2-aminophenyl-3,5-d2)-4-oxobutanoic-3,3-d2 acid
CAS Number
2672568-86-2
Synonyms
  • 3-anthraniloyl-Alanine-d4
  • L-KYN-d4
Molecular Formula
C10H8D4N2O3
Formula Weight
212.2
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 1 mg/mlEthanol: 2 mg/ml
SMILES
[2H]C1=CC([2H])=C(N)C(C(C([2H])([C@@H](C(O)=O)N)[2H])=O)=C1
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/i1D,4D,5D2
InChi Key
YGPSJZOEDVAXAB-LVQMRTGASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    L-Kynurenine-d4 is intended for use as an internal standard for the quantification of kynurenine by GC- or LC-MS. L-Kynurenine is an active metabolite of tryptophan (Item Nos. 29600 | 31210).1 It is formed from tryptophan via tryptophan 2,3-dioxygenase (TDO) or indoleamine 2,3-dioxygenase (IDO). L-Kynurenine binds to the aryl hydrocarbon receptor (AhR; Kd = ~4 µM) and increases the activity of ethoxyresorufin-O-deethylase (EROD) in H-4-II-E rat hepatoma cells (EC50 = 12.3 µM).2 It decreases intracellular concentrations of NAD+ (Item No. 16077) in, and increases lactate dehydrogenase (LDH) activity in the supernatant of, primary human astrocytes and neurons in a concentration-dependent manner.3 L-Kynurenine in combination with IFN-γ reduces lung injury induced by A. fumigatus infection in the p47phox-/- mouse model of chronic granulomatous disease.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stone, T.W., Forrest, C.M., and Darlington, L.G. Kynurenine pathway inhibition as a therapeutic strategy for neuroprotection. FEBS J. 279(8), 1386-1397 (2012).

    2. Opitz, C.A., Litzenburger, U.M., Sahm, F., et al. An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor. Nature 478(7368), 197-203 (2011).

    3. 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. 2, 61-69 (2009).

    4. Romani, L., Fallarino, F., De Luca, A., et al. Defective tryptophan catabolism underlies inflammation in mouse chronic granulomatous disease. Nature 451(7175), 211-215 (2008).