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MedKoo Cat#: 558530 | Name: Kynurenic acid
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Description:

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

Kynurenic acid is a broad-spectrum amino acid antagonist used in research purposes. In particular it is a endogenous glutamate receptor antagonists, and exerts inhibitory action on the α7-nicotinic acetylcholine receptors.

Chemical Structure

Kynurenic acid
Kynurenic acid
CAS#492-27-3

Theoretical Analysis

MedKoo Cat#: 558530

Name: Kynurenic acid

CAS#: 492-27-3

Chemical Formula: C10H7NO3

Exact Mass: 189.0426

Molecular Weight: 189.17

Elemental Analysis: C, 63.49; H, 3.73; N, 7.40; O, 25.37

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 450.00 2 Weeks
25g USD 950.00 2 Weeks
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Synonym
Kynurenic acid; Kynurenic acid; Kynuronic acid; Quinurenic acid;
IUPAC/Chemical Name
2-Quinolinecarboxylic acid, 4-hydroxy-
InChi Key
HCZHHEIFKROPDY-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
SMILES Code
O=C(C1=NC2=CC=CC=C2C(O)=C1)O
Appearance
Solid powder
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Kynurenic acid is a broad-spectrum antagonist targeting NMDA, glutamate, α7 nicotinic acetylcholine receptor. Kynurenic acid is also an agonist of GPR35/CXCR8.
In vitro activity:
KA (kynurenic acid) suppressed caspase-1 activation and IL-1β production in macrophages by specifically inhibiting canonical and noncanonical activation of the NLRP3 inflammasome. Mechanistically, KA reduced calcium mobilization through G-protein receptor 35 (GPR35), resulting in reduced mitochondrial damage and decreased mtROS production, thus blocking NLRP3 inflammasome assembly and activation. Reference: Front Immunol. 2022 Oct 13;13:1019365. https://pubmed.ncbi.nlm.nih.gov/36311752/
In vivo activity:
Both lower (20 μg in total) and higher (100 μg in total) doses of KYNA (kynurenic acid) infused into the third brain ventricle differentially increased the abundance of BDNF and TrkB mRNA in the CA1 field; additionally, the higher dose increased BDNF tissue concentration. The lower dose of KYNA increased mRNA expression for 8-oxoguanine glycosylase (OGG1), N-methylpurine DNA glycosylase (MPG), and thymine DNA glycosylase and stimulated the repair of 1,N6-ethenodeoxyadenosine and 3,N4-ethenodeoxy-cytosine as determined by the excision efficiency of lesioned nucleobases. Reference: Int J Mol Sci. 2022 Dec 21;24(1):136. https://pubmed.ncbi.nlm.nih.gov/36613581/
Solvent mg/mL mM
Solubility
DMSO 9.5 50.15
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 189.17 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. Sun T, Xie R, He H, Xie Q, Zhao X, Kang G, Cheng C, Yin W, Cong J, Li J, Wang X. Kynurenic acid ameliorates NLRP3 inflammasome activation by blocking calcium mobilization via GPR35. Front Immunol. 2022 Oct 13;13:1019365. doi: 10.3389/fimmu.2022.1019365. PMID: 36311752; PMCID: PMC9606686. 2. Wang J, Simonavicius N, Wu X, Swaminath G, Reagan J, Tian H, Ling L. Kynurenic acid as a ligand for orphan G protein-coupled receptor GPR35. J Biol Chem. 2006 Aug 4;281(31):22021-22028. doi: 10.1074/jbc.M603503200. Epub 2006 Jun 5. PMID: 16754668. 3. Roszkowicz-Ostrowska K, Młotkowska P, Kowalczyk P, Marciniak E, Barszcz M, Misztal T. Central Stimulatory Effect of Kynurenic Acid on BDNF-TrkB Signaling and BER Enzymatic Activity in the Hippocampal CA1 Field in Sheep. Int J Mol Sci. 2022 Dec 21;24(1):136. doi: 10.3390/ijms24010136. PMID: 36613581; PMCID: PMC9820639. 4. Wang Z, Yin L, Qi Y, Zhang J, Zhu H, Tang J. Intestinal Flora-Derived Kynurenic Acid Protects Against Intestinal Damage Caused by Candida albicans Infection via Activation of Aryl Hydrocarbon Receptor. Front Microbiol. 2022 Jul 18;13:934786. doi: 10.3389/fmicb.2022.934786. PMID: 35923391; PMCID: PMC9339982.
In vitro protocol:
1. Sun T, Xie R, He H, Xie Q, Zhao X, Kang G, Cheng C, Yin W, Cong J, Li J, Wang X. Kynurenic acid ameliorates NLRP3 inflammasome activation by blocking calcium mobilization via GPR35. Front Immunol. 2022 Oct 13;13:1019365. doi: 10.3389/fimmu.2022.1019365. PMID: 36311752; PMCID: PMC9606686. 2. Wang J, Simonavicius N, Wu X, Swaminath G, Reagan J, Tian H, Ling L. Kynurenic acid as a ligand for orphan G protein-coupled receptor GPR35. J Biol Chem. 2006 Aug 4;281(31):22021-22028. doi: 10.1074/jbc.M603503200. Epub 2006 Jun 5. PMID: 16754668.
In vivo protocol:
1. Roszkowicz-Ostrowska K, Młotkowska P, Kowalczyk P, Marciniak E, Barszcz M, Misztal T. Central Stimulatory Effect of Kynurenic Acid on BDNF-TrkB Signaling and BER Enzymatic Activity in the Hippocampal CA1 Field in Sheep. Int J Mol Sci. 2022 Dec 21;24(1):136. doi: 10.3390/ijms24010136. PMID: 36613581; PMCID: PMC9820639. 2. Wang Z, Yin L, Qi Y, Zhang J, Zhu H, Tang J. Intestinal Flora-Derived Kynurenic Acid Protects Against Intestinal Damage Caused by Candida albicans Infection via Activation of Aryl Hydrocarbon Receptor. Front Microbiol. 2022 Jul 18;13:934786. doi: 10.3389/fmicb.2022.934786. PMID: 35923391; PMCID: PMC9339982.
1: Fejes-Szabó A, Bohár Z, Vámos E, Nagy-Grócz G, Tar L, Veres G, Zádori D, Szentirmai M, Tajti J, Szatmári I, Fülöp F, Toldi J, Párdutz Á, Vécsei L. Pre-treatment with new kynurenic acid amide dose-dependently prevents the nitroglycerine-induced neuronal activation and sensitization in cervical part of trigemino-cervical complex. J Neural Transm (Vienna). 2014 Jul;121(7):725-38. doi: 10.1007/s00702-013-1146-2. Epub 2014 Jan 3. PubMed PMID: 24385076. 2: Steiner L, Gold M, Mengel D, Dodel R, Bach JP. The endogenous α7 nicotinic acetylcholine receptor antagonist kynurenic acid modulates amyloid-β-induced inflammation in BV-2 microglial cells. J Neurol Sci. 2014 Sep 15;344(1-2):94-9. doi: 10.1016/j.jns.2014.06.032. Epub 2014 Jun 23. PubMed PMID: 25064444. 3: Turski WA, Małaczewska J, Marciniak S, Bednarski J, Turski MP, Jabłoński M, Siwicki AK. On the toxicity of kynurenic acid in vivo and in vitro. Pharmacol Rep. 2014 Dec;66(6):1127-33. doi: 10.1016/j.pharep.2014.07.013. Epub 2014 Aug 8. PubMed PMID: 25443745. 4: Małaczewska J, Siwicki AK, Wójcik R, Turski WA, Kaczorek E. The in vitro effect of kynurenic acid on the rainbow trout (Oncorhynchus mykiss) leukocyte and splenocyte activity. Pol J Vet Sci. 2014;17(3):453-8. PubMed PMID: 25286653. 5: Tajti J, Majlath Z, Szok D, Csati A, Toldi J, Fulop F, Vecsei L. Novel kynurenic acid analogues in the treatment of migraine and neurodegenerative disorders: preclinical studies and pharmaceutical design. Curr Pharm Des. 2015;21(17):2250-8. Review. PubMed PMID: 25557633. 6: Beggiato S, Tanganelli S, Fuxe K, Antonelli T, Schwarcz R, Ferraro L. Endogenous kynurenic acid regulates extracellular GABA levels in the rat prefrontal cortex. Neuropharmacology. 2014 Jul;82:11-8. doi: 10.1016/j.neuropharm.2014.02.019. Epub 2014 Mar 7. PubMed PMID: 24607890. 7: Walczak K, Deneka-Hannemann S, Jarosz B, Zgrajka W, Stoma F, Trojanowski T, Turski WA, Rzeski W. Kynurenic acid inhibits proliferation and migration of human glioblastoma T98G cells. Pharmacol Rep. 2014 Feb;66(1):130-6. doi: 10.1016/j.pharep.2013.06.007. Epub 2014 Feb 1. PubMed PMID: 24905318. 8: Tuboly G, Tar L, Bohar Z, Safrany-Fark A, Petrovszki Z, Kekesi G, Vecsei L, Pardutz A, Horvath G. The inimitable kynurenic acid: the roles of different ionotropic receptors in the action of kynurenic acid at a spinal level. Brain Res Bull. 2015 Mar;112:52-60. doi: 10.1016/j.brainresbull.2015.02.001. Epub 2015 Feb 9. PubMed PMID: 25677204. 9: 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. 10: Kassai F, Kedves R, Gyertyán I, Tuka B, Fülöp F, Toldi J, Lendvai B, Vécsei L. Effect of a kynurenic acid analog on home-cage activity and body temperature in rats. Pharmacol Rep. 2015 Dec;67(6):1188-92. doi: 10.1016/j.pharep.2015.04.015. Epub 2015 May 9. PubMed PMID: 26481540. 11: Albuquerque EX, Schwarcz R. Kynurenic acid as an antagonist of α7 nicotinic acetylcholine receptors in the brain: facts and challenges. Biochem Pharmacol. 2013 Apr 15;85(8):1027-32. doi: 10.1016/j.bcp.2012.12.014. Epub 2012 Dec 25. Review. PubMed PMID: 23270993; PubMed Central PMCID: PMC3721521. 12: Zador F, Samavati R, Szlavicz E, Tuka B, Bojnik E, Fulop F, Toldi J, Vecsei L, Borsodi A. Inhibition of opioid receptor mediated G-protein activity after chronic administration of kynurenic acid and its derivative without direct binding to opioid receptors. CNS Neurol Disord Drug Targets. 2014;13(9):1520-9. PubMed PMID: 25478797. 13: Wang J, Simonavicius N, Wu X, Swaminath G, Reagan J, Tian H, Ling L. Kynurenic acid as a ligand for orphan G protein-coupled receptor GPR35. J Biol Chem. 2006 Aug 4;281(31):22021-8. Epub 2006 Jun 5. PubMed PMID: 16754668. 14: Parada-Turska J, Zgrajka W, Majdan M. Kynurenic acid in synovial fluid and serum of patients with rheumatoid arthritis, spondyloarthropathy, and osteoarthritis. J Rheumatol. 2013 Jun;40(6):903-9. doi: 10.3899/jrheum.121035. Epub 2013 Apr 15. PubMed PMID: 23588943. 15: Klein C, Patte-Mensah C, Taleb O, Bourguignon JJ, Schmitt M, Bihel F, Maitre M, Mensah-Nyagan AG. The neuroprotector kynurenic acid increases neuronal cell survival through neprilysin induction. Neuropharmacology. 2013 Jul;70:254-60. doi: 10.1016/j.neuropharm.2013.02.006. Epub 2013 Feb 17. PubMed PMID: 23422298. 16: Hornok V, Bujdosó T, Toldi J, Nagy K, Demeter I, Fazakas C, Krizbai I, Vécsei L, Dékány I. Preparation and properties of nanoscale containers for biomedical application in drug delivery: preliminary studies with kynurenic acid. J Neural Transm (Vienna). 2012 Feb;119(2):115-21. doi: 10.1007/s00702-011-0726-2. Epub 2011 Nov 8. PubMed PMID: 22065206. 17: Uwai Y, Honjo H, Iwamoto K. Interaction and transport of kynurenic acid via human organic anion transporters hOAT1 and hOAT3. Pharmacol Res. 2012 Feb;65(2):254-60. doi: 10.1016/j.phrs.2011.11.003. Epub 2011 Nov 16. PubMed PMID: 22108572. 18: Oláh G, Herédi J, Menyhárt A, Czinege Z, Nagy D, Fuzik J, Kocsis K, Knapp L, Krucsó E, Gellért L, Kis Z, Farkas T, Fülöp F, Párdutz A, Tajti J, Vécsei L, Toldi J. Unexpected effects of peripherally administered kynurenic acid on cortical spreading depression and related blood-brain barrier permeability. Drug Des Devel Ther. 2013 Sep 16;7:981-7. doi: 10.2147/DDDT.S44496. eCollection 2013. PubMed PMID: 24068867; PubMed Central PMCID: PMC3782408. 19: DiNatale BC, Murray IA, Schroeder JC, Flaveny CA, Lahoti TS, Laurenzana EM, Omiecinski CJ, Perdew GH. Kynurenic acid is a potent endogenous aryl hydrocarbon receptor ligand that synergistically induces interleukin-6 in the presence of inflammatory signaling. Toxicol Sci. 2010 May;115(1):89-97. doi: 10.1093/toxsci/kfq024. Epub 2010 Jan 27. PubMed PMID: 20106948; PubMed Central PMCID: PMC2855350. 20: Marosi M, Nagy D, Farkas T, Kis Z, Rózsa E, Robotka H, Fülöp F, Vécsei L, Toldi J. A novel kynurenic acid analogue: a comparison with kynurenic acid. An in vitro electrophysiological study. J Neural Transm (Vienna). 2010 Feb;117(2):183-8. doi: 10.1007/s00702-009-0346-2. Epub 2009 Dec 2. PubMed PMID: 19953278.

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