IUPAC/Chemical Name
(R)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
InChi Key
YGPSJZOEDVAXAB-MRVPVSSYSA-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-/m1/s1
SMILES Code
NC1=C(C(C[C@@H](N)C(O)=O)=O)C=CC=C1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
D-Kynurenine is an agonist for G protein-coupled receptor, GPR109B.
In vitro activity:
This study firstly confirmed that D-Kyn (10, 40, 60, and 100 µM) positively regulated the metastasis of 95D cells, a lung cancer cell line, which was reduced upon siRNAAhr treatment. Moreover, significant enhancement VIM expression was detected in the presence of D-Kyn (10 and 40 µM).
Reference: Mol Cell Biochem. 2018 Nov;448(1-2):165-173. https://pubmed.ncbi.nlm.nih.gov/29442266/
In vivo activity:
In conclusion, 300 mg/kg/d D-kynurenine treatment could impair T cell proliferation in vivo and alleviate Rag1–/– autoimmune colitis, but it failed to mitigate DSS-induced colitis and fully mismatched cardiac allograft rejection.
Reference: EBioMedicine. 2021 Dec;74:103734. https://pubmed.ncbi.nlm.nih.gov/34875457/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
5.0 |
24.01 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
208.22
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Duan Z, Li Y, Li L. Promoting epithelial-to-mesenchymal transition by D-kynurenine via activating aryl hydrocarbon receptor. Mol Cell Biochem. 2018 Nov;448(1-2):165-173. doi: 10.1007/s11010-018-3323-y. Epub 2018 Feb 13. PMID: 29442266.
2. Irukayama-Tomobe Y, Tanaka H, Yokomizo T, Hashidate-Yoshida T, Yanagisawa M, Sakurai T. Aromatic D-amino acids act as chemoattractant factors for human leukocytes through a G protein-coupled receptor, GPR109B. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3930-4. doi: 10.1073/pnas.0811844106. Epub 2009 Feb 23. PMID: 19237584; PMCID: PMC2656182.
3. Siska PJ, Jiao J, Matos C, Singer K, Berger RS, Dettmer K, Oefner PJ, Cully MD, Wang Z, QuinnIII WJ, Oliff KN, Wilkins BJ, Christensen LM, Wang L, Hancock WW, Baur JA, Levine MH, Ugele I, Mayr R, Renner K, Zhou L, Kreutz M, Beier UH. Kynurenine induces T cell fat catabolism and has limited suppressive effects in vivo. EBioMedicine. 2021 Dec;74:103734. doi: 10.1016/j.ebiom.2021.103734. Epub 2021 Dec 4. PMID: 34875457; PMCID: PMC8652007.
4. Notarangelo FM, Wang XD, Horning KJ, Schwarcz R. Role of d-amino acid oxidase in the production of kynurenine pathway metabolites from d-tryptophan in mice. J Neurochem. 2016 Feb;136(4):804-814. doi: 10.1111/jnc.13455. Epub 2016 Jan 13. PMID: 26661897; PMCID: PMC4902784.
In vitro protocol:
1. Duan Z, Li Y, Li L. Promoting epithelial-to-mesenchymal transition by D-kynurenine via activating aryl hydrocarbon receptor. Mol Cell Biochem. 2018 Nov;448(1-2):165-173. doi: 10.1007/s11010-018-3323-y. Epub 2018 Feb 13. PMID: 29442266.
2. Irukayama-Tomobe Y, Tanaka H, Yokomizo T, Hashidate-Yoshida T, Yanagisawa M, Sakurai T. Aromatic D-amino acids act as chemoattractant factors for human leukocytes through a G protein-coupled receptor, GPR109B. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3930-4. doi: 10.1073/pnas.0811844106. Epub 2009 Feb 23. PMID: 19237584; PMCID: PMC2656182.
In vivo protocol:
1. Siska PJ, Jiao J, Matos C, Singer K, Berger RS, Dettmer K, Oefner PJ, Cully MD, Wang Z, QuinnIII WJ, Oliff KN, Wilkins BJ, Christensen LM, Wang L, Hancock WW, Baur JA, Levine MH, Ugele I, Mayr R, Renner K, Zhou L, Kreutz M, Beier UH. Kynurenine induces T cell fat catabolism and has limited suppressive effects in vivo. EBioMedicine. 2021 Dec;74:103734. doi: 10.1016/j.ebiom.2021.103734. Epub 2021 Dec 4. PMID: 34875457; PMCID: PMC8652007.
2. Notarangelo FM, Wang XD, Horning KJ, Schwarcz R. Role of d-amino acid oxidase in the production of kynurenine pathway metabolites from d-tryptophan in mice. J Neurochem. 2016 Feb;136(4):804-814. doi: 10.1111/jnc.13455. Epub 2016 Jan 13. PMID: 26661897; PMCID: PMC4902784.
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).
