Kynurenine
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MedKoo CAT#: 592619

CAS#: 343-65-7

Description: Kynurenine is a metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway. It causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels..

Chemical Structure

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Kynurenine
CAS# 343-65-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 592619
Name: Kynurenine
CAS#: 343-65-7
Chemical Formula: C10H12N2O3
Exact Mass: 208.08
Molecular Weight: 208.217
Elemental Analysis: C, 57.69; H, 5.81; N, 13.45; O, 23.05

Price and Availability

Size Price Availability Quantity
100mg USD 285 2 Weeks
250mg USD 550 2 Weeks
1g USD 850 2 Weeks
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Synonym: Kynurenine; DL-Kynurenine

IUPAC/Chemical Name: alpha-2-Diamino-gamma-oxobenzenebutyric acid

InChi Key: YGPSJZOEDVAXAB-UHFFFAOYSA-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)

SMILES Code: O=C(O)C(N)CC(C1=CC=CC=C1N)=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:
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Biological target: 2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid is an endogenous metabolite.
In vitro activity: Kyn (kynurenine) is the main metabolite of Trp degradation by TDO in HepG2 cells. The accumulation of Kyn in HepG2 cells could be a key mechanism for tumor immune resistance. Reference: J Clin Med. 2022 Aug 16;11(16):4794. https://pubmed.ncbi.nlm.nih.gov/36013032/
In vivo activity: Mechanistically, elevated kynurenine triggers cardiomyocyte proliferation in mice by activating the cytoplasmic aryl hydrocarbon receptor-SRC-YAP/ERK pathway. In addition, cardiomyocyte-derived kynurenine transports to endothelial cells and stimulates cardiac angiogenesis by promoting aryl hydrocarbon receptor nuclear translocation and enhancing vascular endothelial growth factor A expression. Reference: Nat Commun. 2022 Oct 26;13(1):6371. https://pubmed.ncbi.nlm.nih.gov/36289221/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
1M HCl 20.0 96.05

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.

Recalculate based on batch purity %
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. Oweira H, Lahdou I, Mehrle S, Khajeh E, Nikbakhsh R, Ghamarnejad O, Terness P, Reißfelder C, Sadeghi M, Ramouz A. Kynurenine Is the Main Metabolite of Tryptophan Degradation by Tryptophan 2,3-Dioxygenase in HepG2 Tumor Cells. J Clin Med. 2022 Aug 16;11(16):4794. doi: 10.3390/jcm11164794. PMID: 36013032; PMCID: PMC9410271. 2. 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. 3. Zhang D, Ning J, Ramprasath T, Yu C, Zheng X, Song P, Xie Z, Zou MH. Kynurenine promotes neonatal heart regeneration by stimulating cardiomyocyte proliferation and cardiac angiogenesis. Nat Commun. 2022 Oct 26;13(1):6371. doi: 10.1038/s41467-022-33734-7. PMID: 36289221; PMCID: PMC9606021. 4. Huang T, Song J, Gao J, Cheng J, Xie H, Zhang L, Wang YH, Gao Z, Wang Y, Wang X, He J, Liu S, Yu Q, Zhang S, Xiong F, Zhou Q, Wang CY. Adipocyte-derived kynurenine promotes obesity and insulin resistance by activating the AhR/STAT3/IL-6 signaling. Nat Commun. 2022 Jun 17;13(1):3489. doi: 10.1038/s41467-022-31126-5. PMID: 35715443; PMCID: PMC9205899.
In vitro protocol: 1. Oweira H, Lahdou I, Mehrle S, Khajeh E, Nikbakhsh R, Ghamarnejad O, Terness P, Reißfelder C, Sadeghi M, Ramouz A. Kynurenine Is the Main Metabolite of Tryptophan Degradation by Tryptophan 2,3-Dioxygenase in HepG2 Tumor Cells. J Clin Med. 2022 Aug 16;11(16):4794. doi: 10.3390/jcm11164794. PMID: 36013032; PMCID: PMC9410271. 2. 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.
In vivo protocol: 1. Zhang D, Ning J, Ramprasath T, Yu C, Zheng X, Song P, Xie Z, Zou MH. Kynurenine promotes neonatal heart regeneration by stimulating cardiomyocyte proliferation and cardiac angiogenesis. Nat Commun. 2022 Oct 26;13(1):6371. doi: 10.1038/s41467-022-33734-7. PMID: 36289221; PMCID: PMC9606021. 2. Huang T, Song J, Gao J, Cheng J, Xie H, Zhang L, Wang YH, Gao Z, Wang Y, Wang X, He J, Liu S, Yu Q, Zhang S, Xiong F, Zhou Q, Wang CY. Adipocyte-derived kynurenine promotes obesity and insulin resistance by activating the AhR/STAT3/IL-6 signaling. Nat Commun. 2022 Jun 17;13(1):3489. doi: 10.1038/s41467-022-31126-5. PMID: 35715443; PMCID: PMC9205899.

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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. PubMed PMID: 26318674.

2: 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.

3: 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.

4: Savitz J, Dantzer R, Wurfel BE, Victor TA, Ford BN, Bodurka J, Bellgowan PS, Teague TK, Drevets WC. Neuroprotective kynurenine metabolite indices are abnormally reduced and positively associated with hippocampal and amygdalar volume in bipolar disorder. Psychoneuroendocrinology. 2015 Feb;52:200-11. doi: 10.1016/j.psyneuen.2014.11.015. Epub 2014 Nov 24. PubMed PMID: 25486577; PubMed Central PMCID: PMC4297593.

5: 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.

6: Karakuła-Juchnowicz H, Flis M, Szymona K, Kuczyńska M, Stelmach E, Kowal-Popczak A. [New prospects for antipsychotic treatment - the role of the kynurenine pathway]. Psychiatr Pol. 2014 Nov-Dec;48(6):1167-77. doi: 10.12740/PP/25520. Review. Polish. PubMed PMID: 25717486.

7: de Bie J, Guest J, Guillemin GJ, Grant R. Central kynurenine pathway shift with age in women. J Neurochem. 2016 Mar;136(5):995-1003. doi: 10.1111/jnc.13496. Epub 2016 Jan 20. PubMed PMID: 26670548.

8: Giorgini F, Huang SY, Sathyasaikumar KV, Notarangelo FM, Thomas MA, Tararina M, Wu HQ, Schwarcz R, Muchowski PJ. Targeted deletion of kynurenine 3-monooxygenase in mice: a new tool for studying kynurenine pathway metabolism in periphery and brain. J Biol Chem. 2013 Dec 20;288(51):36554-66. doi: 10.1074/jbc.M113.503813. Epub 2013 Nov 4. PubMed PMID: 24189070; PubMed Central PMCID: PMC3868768.

9: 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.

10: Tomek P, Palmer BD, Kendall JD, Flanagan JU, Ching LM. Formation of fluorophores from the kynurenine pathway metabolite N-formylkynurenine and cyclic amines involves transamidation and carbon-carbon bond formation at the 2-position of the amine. Biochim Biophys Acta. 2015 Sep;1850(9):1772-80. doi: 10.1016/j.bbagen.2015.04.007. Epub 2015 Apr 20. PubMed PMID: 25907332.

11: Notarangelo FM, Wilson EH, Horning KJ, Thomas MA, Harris TH, Fang Q, Hunter CA, Schwarcz R. Evaluation of kynurenine pathway metabolism in Toxoplasma gondii-infected mice: implications for schizophrenia. Schizophr Res. 2014 Jan;152(1):261-7. doi: 10.1016/j.schres.2013.11.011. Epub 2013 Dec 15. PubMed PMID: 24345671; PubMed Central PMCID: PMC3922412.

12: 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.

13: Okada K, Angkawidjaja C, Koga Y, Kanaya S. Structural and mechanistic insights into the kynurenine aminotransferase-mediated excretion of kynurenic acid. J Struct Biol. 2014 Mar;185(3):257-66. doi: 10.1016/j.jsb.2014.01.009. Epub 2014 Jan 25. PubMed PMID: 24473062.

14: Dantzer R, O'Connor JC, Lawson MA, Kelley KW. Inflammation-associated depression: from serotonin to kynurenine. Psychoneuroendocrinology. 2011 Apr;36(3):426-36. doi: 10.1016/j.psyneuen.2010.09.012. Epub 2010 Oct 30. Review. PubMed PMID: 21041030; PubMed Central PMCID: PMC3053088.

15: Wang Y, Liu H, McKenzie G, Witting PK, Stasch JP, Hahn M, Changsirivathanathamrong D, Wu BJ, Ball HJ, Thomas SR, Kapoor V, Celermajer DS, Mellor AL, Keaney JF Jr, Hunt NH, Stocker R. Kynurenine is an endothelium-derived relaxing factor produced during inflammation. Nat Med. 2010 Mar;16(3):279-85. doi: 10.1038/nm.2092. Epub 2010 Feb 28. Erratum in: Nat Med. 2010 May;16(5):607. PubMed PMID: 20190767; PubMed Central PMCID: PMC3556275.

16: Guloksuz S, Arts B, Walter S, Drukker M, Rodriguez L, Myint AM, Schwarz MJ, Ponds R, van Os J, Kenis G, Rutten BP. The impact of electroconvulsive therapy on the tryptophan-kynurenine metabolic pathway. Brain Behav Immun. 2015 Aug;48:48-52. doi: 10.1016/j.bbi.2015.02.029. Epub 2015 Mar 9. PubMed PMID: 25765557.

17: Orhan F, Bhat M, Sandberg K, Ståhl S, Piehl F; Karolinska Schizophrenia Project (KaSP) consortium, Svensson C, Erhardt S, Schwieler L. Tryptophan Metabolism Along the Kynurenine Pathway Downstream of Toll-like Receptor Stimulation in Peripheral Monocytes. Scand J Immunol. 2016 Nov;84(5):262-271. doi: 10.1111/sji.12479. PubMed PMID: 27607184.

18: Duan Z, Duan Y, Lei H, Hu N, Shi J, Shen D, Wang X, Hu Y. Attenuation of antigenic immunogenicity by kynurenine, a novel suppressive adjuvant. Hum Vaccin Immunother. 2014;10(5):1295-305. doi: 10.4161/hv.28099. Epub 2014 Feb 28. PubMed PMID: 24583631; PubMed Central PMCID: PMC4896568.

19: Meier TB, Drevets WC, Wurfel BE, Ford BN, Morris HM, Victor TA, Bodurka J, Teague TK, Dantzer R, Savitz J. Relationship between neurotoxic kynurenine metabolites and reductions in right medial prefrontal cortical thickness in major depressive disorder. Brain Behav Immun. 2016 Mar;53:39-48. doi: 10.1016/j.bbi.2015.11.003. Epub 2015 Nov 4. PubMed PMID: 26546831; PubMed Central PMCID: PMC4783304.

20: Kolodziej L. Investigation of the kynurenine pathway in Indoleamine 2, 3 dioxygenase deficient mice with inflammatory arthritis. Transgenic Res. 2013 Oct;22(5):1049-54. doi: 10.1007/s11248-013-9696-5. Epub 2013 Feb 17. PubMed PMID: 23417792; PubMed Central PMCID: PMC3781305.