An antagonist of GPR109B
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Isomer(s)
11305L-Kynurenine
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D-Kynurenine

Item No. 28254

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αR,2-diamino-γ-oxo-benzenebutanoic acid
CAS Number
13441-51-5
Molecular Formula
C10H12N2O3
Formula Weight
208.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
0.5M HCl: 50 mg/ml
λmax
228, 257, 370 nm
SMILES
NC1=C(C(C[C@@H](N)C(O)=O)=O)C=CC=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-/m1/s1
InChi Key
YGPSJZOEDVAXAB-MRVPVSSYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 mg

    $156

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    100 mg

    $294

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    250 mg

    $541

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    500 mg

    $922

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    Cayman Chemical
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    Product Description

    D-Kynurenine is an antagonist of hydroxycarboxylic acid receptor 3 HCA3/GPR109B (EC50 = 2.61 µM in a luciferase reporter assay) and a metabolite of D-tryptophan.1 It increases levels of intracellular calcium and decreases forskolin-stimulated production of cAMP in CHO cells expressing human HCA3/GPR109B when used at concentrations of 10 and 100, or 1,000 µM, respectively. D-Kynurenine (10 µM) increases expression of vimentin and decreases expression of E-cadherin in 95D lung cancer cells.2 It has been used as a substrate in fluorometric assays for D-amino acid oxidase activity.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Irukayama-Tomobe, Y., Tanaka, H., Yokomizo, T., et al. Aromatic D-amino acids act as chemoattractant factors for human leukocytes through a G protein-coupled receptor, GPR109B. Proc. Natl. Acad. Sci. USA 106(10), 3930-3934 (2009).

    2. Duan, Z., Li, Y., and Li, L. Promoting epithelial-to-mesenchymal transition by D-kynurenine via activating aryl hydrocarbon receptor. Mol. Cell. Biochem. 448(1-2), 165-173 (2018).

    3. Kozaki, A., Iwasa, S., Hosoda, S., et al. Fluorimetric assay for D-amino acid oxidase activity in rat brain homogenate by using D-kynurenine as a substrate. Biosci. Trends 6(5), 241-247 (2012).

    4. Song, Z., Ogaya, T., Ishii, K., et al. Utilization of kynurenic acid produced from D-kynurenine in an in vitro assay of D-amino acid oxidase activity. J. Health Sci. 56(3), 341-346 (2010).