L-Kynurenine | CAS#2922-83-0 | intermediate

MedKoo Cat#: 597402 | Name: L-Kynurenine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Kynurenine is a key intermediate in the breakdown of L-tryptophan and the formation of nicotinamide adenine dinucleotide (NAD+) via the kynurenine pathway. It is involved in a variety of neurological processes and diseases. L-Kynurenine is a substrate for kynureninase/kynurenine hydrolase; kynurenine 3-monooxygenase and kynurenine-oxoglutarate transaminase.

Chemical Structure

L-Kynurenine

CAS#2922-83-0

Theoretical Analysis

MedKoo Cat#: 597402

Name: L-Kynurenine

CAS#: 2922-83-0

Chemical Formula: C10H12N2O3

Exact Mass: 208.0848

Molecular Weight: 208.22

Elemental Analysis: C, 57.69; H, 5.81; N, 13.45; O, 23.05

Price and Availability

Size	Price	Availability
100mg	USD 250.00
250mg	USD 450.00	2 Weeks
1g	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Kynurenine; Kynurenine, L-; CCRIS 4425; L-Kynurenine;

IUPAC/Chemical Name

(S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

InChi Key

YGPSJZOEDVAXAB-QMMMGPOBSA-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-/m0/s1

SMILES Code

N[C@@H](CC(C1=CC=CC=C1N)=O)C(O)=O

Appearance

Solid powder

Purity

>95% (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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-Kynurenine is an aryl hydrocarbon receptor agonist.

In vitro activity:

This study identifies the tryptophan (Trp) catabolite kynurenine (Kyn) as an endogenous ligand of the human AHR that is constitutively generated by human tumour cells via tryptophan-2,3-dioxygenase (TDO), a liver- and neuron-derived Trp-degrading enzyme not yet implicated in cancer biology. TDO-derived Kyn suppresses antitumour immune responses and promotes tumour-cell survival and motility through the AHR in an autocrine/paracrine fashion. Reference: Nature. 2011 Oct 5;478(7368):197-203. https://pubmed.ncbi.nlm.nih.gov/21976023/

In vivo activity:

Wistar rats received l-kynurenine (1 mM) iv and subsequent linopirdine (10 μM) iv under 3% sevoflurane inhalation. l-Kynurenine iv caused hypotension, whereas linopirdine iv partially reversed it. In conclusion, kynurenine dilates arteries from rats as well as humans via Kv7 channels in the vascular smooth muscle. Reference: J Pharmacol Sci. 2015 Sep;129(1):31-7. https://pubmed.ncbi.nlm.nih.gov/26318674/

	Solvent	mg/mL	mM
Solubility
	DMSO	18.9	90.58
	Water	8.4	40.15

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. Ma W, Ye L, Zhong C, Li J, Ye F, Lv L, Yu Y, Jiang S, Zhou P. Kynurenine produced by tryptophan 2,3-dioxygenase metabolism promotes glioma progression through an aryl hydrocarbon receptor-dependent signaling pathway. Cell Biol Int. 2022 Oct;46(10):1577-1587. doi: 10.1002/cbin.11833. Epub 2022 Jun 14. PMID: 35702760. 2. Opitz CA, Litzenburger UM, Sahm F, Ott M, Tritschler I, Trump S, Schumacher T, Jestaedt L, Schrenk D, Weller M, Jugold M, Guillemin GJ, Miller CL, Lutz C, Radlwimmer B, Lehmann I, von Deimling A, Wick W, Platten M. An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor. Nature. 2011 Oct 5;478(7368):197-203. doi: 10.1038/nature10491. PMID: 21976023. 3. Sakakibara K, Feng GG, Li J, Akahori T, Yasuda Y, Nakamura E, Hatakeyama N, Fujiwara Y, Kinoshita H. Kynurenine causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels. J Pharmacol Sci. 2015 Sep;129(1):31-7. doi: 10.1016/j.jphs.2015.07.042. Epub 2015 Aug 10. PMID: 26318674. 4. Nozaki K, Beal MF. Neuroprotective effects of L-kynurenine on hypoxia-ischemia and NMDA lesions in neonatal rats. J Cereb Blood Flow Metab. 1992 May;12(3):400-7. doi: 10.1038/jcbfm.1992.57. PMID: 1569135.

In vitro protocol:

In vivo protocol:

1. Sakakibara K, Feng GG, Li J, Akahori T, Yasuda Y, Nakamura E, Hatakeyama N, Fujiwara Y, Kinoshita H. Kynurenine causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels. J Pharmacol Sci. 2015 Sep;129(1):31-7. doi: 10.1016/j.jphs.2015.07.042. Epub 2015 Aug 10. PMID: 26318674. 2. Nozaki K, Beal MF. Neuroprotective effects of L-kynurenine on hypoxia-ischemia and NMDA lesions in neonatal rats. J Cereb Blood Flow Metab. 1992 May;12(3):400-7. doi: 10.1038/jcbfm.1992.57. PMID: 1569135.

1: Pineda-Farias JB, Pérez-Severiano F, González-Esquivel DF, Barragán-Iglesias P, Bravo-Hernández M, Cervantes-Durán C, Aguilera P, Ríos C, Granados-Soto V. The L-kynurenine-probenecid combination reduces neuropathic pain in rats. Eur J Pain. 2013 Oct;17(9):1365-73. doi: 10.1002/j.1532-2149.2013.00305.x. Epub 2013 Mar 25. PubMed PMID: 23529950. 2: Sano M, Ferchaud-Roucher V, Nael C, Aguesse A, Poupeau G, Castellano B, Darmaun D. Simultaneous detection of stable isotope-labeled and unlabeled L-tryptophan and of its main metabolites, L-kynurenine, serotonin and quinolinic acid, by gas chromatography/negative ion chemical ionization mass spectrometry. J Mass Spectrom. 2014 Feb;49(2):128-35. doi: 10.1002/jms.3313. PubMed PMID: 24677305. 3: Mabuchi R, Hara T, Matsumoto T, Shibata Y, Nakamura N, Nakamura H, Kitagawa J, Kanemura N, Goto N, Shimizu M, Ito H, Yamamoto Y, Saito K, Moriwaki H, Tsurumi H. High serum concentration of L-kynurenine predicts unfavorable outcomes in patients with acute myeloid leukemia. Leuk Lymphoma. 2016;57(1):92-8. doi: 10.3109/10428194.2015.1041388. Epub 2015 Jun 18. PubMed PMID: 25907424. 4: Sakakibara K, Feng GG, Li J, Akahori T, Yasuda Y, Nakamura E, Hatakeyama N, Fujiwara Y, Kinoshita H. Kynurenine causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels. J Pharmacol Sci. 2015 Sep;129(1):31-7. doi: 10.1016/j.jphs.2015.07.042. Epub 2015 Aug 10. PubMed PMID: 26318674. 5: He W, Brumos J, Li H, Ji Y, Ke M, Gong X, Zeng Q, Li W, Zhang X, An F, Wen X, Li P, Chu J, Sun X, Yan C, Yan N, Xie DY, Raikhel N, Yang Z, Stepanova AN, Alonso JM, Guo H. A small-molecule screen identifies L-kynurenine as a competitive inhibitor of TAA1/TAR activity in ethylene-directed auxin biosynthesis and root growth in Arabidopsis. Plant Cell. 2011 Nov;23(11):3944-60. doi: 10.1105/tpc.111.089029. Epub 2011 Nov 22. PubMed PMID: 22108404; PubMed Central PMCID: PMC3246337. 6: Gellért L, Knapp L, Németh K, Herédi J, Varga D, Oláh G, Kocsis K, Menyhárt A, Kis Z, Farkas T, Vécsei L, Toldi J. Post-ischemic treatment with L-kynurenine sulfate exacerbates neuronal damage after transient middle cerebral artery occlusion. Neuroscience. 2013 Sep 5;247:95-101. doi: 10.1016/j.neuroscience.2013.04.063. Epub 2013 May 16. PubMed PMID: 23685169. 7: Mándi Y, Vécsei L. The kynurenine system and immunoregulation. J Neural Transm (Vienna). 2012 Feb;119(2):197-209. doi: 10.1007/s00702-011-0681-y. Epub 2011 Jul 9. Review. PubMed PMID: 21744051. 8: Koshy Cherian A, Gritton H, Johnson DE, Young D, Kozak R, Sarter M. A systemically-available kynurenine aminotransferase II (KAT II) inhibitor restores nicotine-evoked glutamatergic activity in the cortex of rats. Neuropharmacology. 2014 Jul;82:41-8. doi: 10.1016/j.neuropharm.2014.03.004. Epub 2014 Mar 16. PubMed PMID: 24647121; PubMed Central PMCID: PMC4372264. 9: Orsatti L, Speziale R, Orsale MV, Caretti F, Veneziano M, Zini M, Monteagudo E, Lyons K, Beconi M, Chan K, Herbst T, Toledo-Sherman L, Munoz-Sanjuan I, Bonelli F, Dominguez C. A single-run liquid chromatography mass spectrometry method to quantify neuroactive kynurenine pathway metabolites in rat plasma. J Pharm Biomed Anal. 2015 Mar 25;107:426-31. doi: 10.1016/j.jpba.2015.01.030. Epub 2015 Jan 24. PubMed PMID: 25668794. 10: Pérez-de la Cruz V, Amori L, Sathyasaikumar KV, Wang XD, Notarangelo FM, Wu HQ, Schwarcz R. Enzymatic transamination of D-kynurenine generates kynurenic acid in rat and human brain. J Neurochem. 2012 Mar;120(6):1026-35. doi: 10.1111/j.1471-4159.2012.07653.x. Epub 2012 Feb 2. PubMed PMID: 22224417; PubMed Central PMCID: PMC3929305. 11: Tuna D, Došlić N, Mališ M, Sobolewski AL, Domcke W. Mechanisms of photostability in kynurenines: a joint electronic-structure and dynamics study. J Phys Chem B. 2015 Feb 12;119(6):2112-24. doi: 10.1021/jp501782v. Epub 2014 Aug 1. PubMed PMID: 25054917. 12: Song H, Park H, Kim YS, Kim KD, Lee HK, Cho DH, Yang JW, Hur DY. L-kynurenine-induced apoptosis in human NK cells is mediated by reactive oxygen species. Int Immunopharmacol. 2011 Aug;11(8):932-8. doi: 10.1016/j.intimp.2011.02.005. Epub 2011 Feb 23. PubMed PMID: 21352963. 13: Apalset EM, Gjesdal CG, Ueland PM, Midttun Ø, Ulvik A, Eide GE, Meyer K, Tell GS. Interferon (IFN)-γ-mediated inflammation and the kynurenine pathway in relation to bone mineral density: the Hordaland Health Study. Clin Exp Immunol. 2014 Jun;176(3):452-60. doi: 10.1111/cei.12288. PubMed PMID: 24528145; PubMed Central PMCID: PMC4008990. 14: Theofylaktopoulou D, Ulvik A, Midttun Ø, Ueland PM, Vollset SE, Nygård O, Hustad S, Tell GS, Eussen SJ. Vitamins B2 and B6 as determinants of kynurenines and related markers of interferon-γ-mediated immune activation in the community-based Hordaland Health Study. Br J Nutr. 2014 Oct 14;112(7):1065-72. doi: 10.1017/S0007114514001858. Epub 2014 Aug 8. PubMed PMID: 25105221. 15: Chauvel V, Vamos E, Pardutz A, Vecsei L, Schoenen J, Multon S. Effect of systemic kynurenine on cortical spreading depression and its modulation by sex hormones in rat. Exp Neurol. 2012 Aug;236(2):207-14. doi: 10.1016/j.expneurol.2012.05.002. Epub 2012 May 14. PubMed PMID: 22587906. 16: Guo S, Vecsei L, Ashina M. The L-kynurenine signalling pathway in trigeminal pain processing: a potential therapeutic target in migraine? Cephalalgia. 2011 Jul;31(9):1029-38. doi: 10.1177/0333102411404717. Epub 2011 May 18. Review. PubMed PMID: 21593189. 17: Wang XD, Notarangelo FM, Wang JZ, Schwarcz R. Kynurenic acid and 3-hydroxykynurenine production from D-kynurenine in mice. Brain Res. 2012 May 21;1455:1-9. doi: 10.1016/j.brainres.2012.03.026. Epub 2012 Mar 17. PubMed PMID: 22498176; PubMed Central PMCID: PMC3340494. 18: Klockow JL, Glass TE. Development of a fluorescent chemosensor for the detection of kynurenine. Org Lett. 2013 Jan 18;15(2):235-7. doi: 10.1021/ol303025m. Epub 2012 Dec 24. PubMed PMID: 23265271. 19: Liu XC, Holtze M, Powell SB, Terrando N, Larsson MK, Persson A, Olsson SK, Orhan F, Kegel M, Asp L, Goiny M, Schwieler L, Engberg G, Karlsson H, Erhardt S. Behavioral disturbances in adult mice following neonatal virus infection or kynurenine treatment--role of brain kynurenic acid. Brain Behav Immun. 2014 Feb;36:80-9. doi: 10.1016/j.bbi.2013.10.010. Epub 2013 Oct 17. PubMed PMID: 24140727; PubMed Central PMCID: PMC3947209. 20: Maitrani C, Heyes DJ, Hay S, Arumugam S, Popik VV, Phillips RS. Preparation and photophysical properties of a caged kynurenine. Bioorg Med Chem Lett. 2012 Apr 15;22(8):2734-7. doi: 10.1016/j.bmcl.2012.02.097. Epub 2012 Mar 6. PubMed PMID: 22444682.