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2922-83-0,MFCD00069912
Catalog No.:AA002XOP

2922-83-0 | L-Kynurenine

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50mg
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100mg
98%
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250mg
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1g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002XOP
Chemical Name:
L-Kynurenine
CAS Number:
2922-83-0
Molecular Formula:
C10H12N2O3
Molecular Weight:
208.2139
MDL Number:
MFCD00069912
SMILES:
OC(=O)[C@H](CC(=O)c1ccccc1N)N
Properties
Properties
 
BP:
466.6°C at 760 mmHg  
Form:
Solid  
MP:
219℃ (decomposition) (ethanol )  
Refractive Index:
-33 ° (C=0.4, H2O)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
255  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
4  
XLogP3:
-2.2  

Literature

Title: Indoleamine 2,3-dioxygenase activity and expression in patients with chronic lymphocytic leukemia.

Journal: Clinical lymphoma, myeloma & leukemia 20121001

Title: Modulatory effects of acupuncture on murine depression-like behavior following chronic systemic inflammation.

Journal: Brain research 20120907

Title: Brain indoleamine 2,3-dioxygenase contributes to the comorbidity of pain and depression.

Journal: The Journal of clinical investigation 20120801

Title: Serum analysis of tryptophan catabolism pathway: correlation with Crohn's disease activity.

Journal: Inflammatory bowel diseases 20120701

Title: [Kynurenic acid--a new tool in the treatment of hiperhomocysteinemia and its consequences?].

Journal: Postepy higieny i medycyny doswiadczalnej (Online) 20120622

Title: Identification of novel kynurenine production-inhibiting benzenesulfonamide derivatives in cancer cells.

Journal: Biochemical and biophysical research communications 20120316

Title: The association of the kynurenine pathway of tryptophan metabolism with acute brain dysfunction during critical illness*.

Journal: Critical care medicine 20120301

Title: Tryptophan degradation and neopterin levels in treated rheumatoid arthritis patients.

Journal: Clinical rheumatology 20120101

Title: Slow solvent relaxation dynamics of nanometer sized reverse micellar systems through tryptophan metabolite, kynurenine.

Journal: Photochemistry and photobiology 20120101

Title: The role of indoleamine 2,3-dioxygenase in a mouse model of neuroinflammation-induced depression.

Journal: Journal of Alzheimer's disease : JAD 20120101

Title: Plasma cell-free DNA levels are elevated in acute Puumala hantavirus infection.

Journal: PloS one 20120101

Title: Neuroimmune endocrine effects of antidepressants.

Journal: Neuropsychiatric disease and treatment 20120101

Title: The tryptophan depletion theory in delirium: not confirmed in elderly hip fracture patients.

Journal: Psychosomatics 20120101

Title: A Distinct Profile of Tryptophan Metabolism along the Kynurenine Pathway Downstream of Toll-Like Receptor Activation in Irritable Bowel Syndrome.

Journal: Frontiers in pharmacology 20120101

Title: Immunity and tolerance to fungi in hematopoietic transplantation: principles and perspectives.

Journal: Frontiers in immunology 20120101

Title: Inflammation-related disorders in the tryptophan catabolite pathway in depression and somatization.

Journal: Advances in protein chemistry and structural biology 20120101

Title: Reversal of imbalance between kynurenic acid and 3-hydroxykynurenine by antipsychotics in medication-naïve and medication-free schizophrenic patients.

Journal: Brain, behavior, and immunity 20111101

Title: Changes in kynurenine pathway metabolism in the brain, liver and kidney of aged female Wistar rats.

Journal: The FEBS journal 20111101

Title: Research on an in vitro cell system for testing the neurotoxicity of kynurenine pathway metabolites.

Journal: Die Pharmazie 20111101

Title: Kynurenine metabolism predicts cognitive function in patients following cardiac bypass and thoracic surgery.

Journal: Journal of neurochemistry 20111001

Title: Labeling of mesenchymal stromal cells with iron oxide-poly(L-lactide) nanoparticles for magnetic resonance imaging: uptake, persistence, effects on cellular function and magnetic resonance imaging properties.

Journal: Cytotherapy 20110901

Title: Neurodegenerative disease: the kynurenine pathway--promising new targets and therapies for neurodegenerative disease.

Journal: Nature reviews. Neurology 20110726

Title: Epigenetic and inflammatory marker profiles associated with depression in a community-based epidemiologic sample.

Journal: Psychological medicine 20110501

Title: Pathobiological targets of depression.

Journal: Expert opinion on therapeutic targets 20110401

Title: Systemic markers of interferon-γ-mediated immune activation and long-term prognosis in patients with stable coronary artery disease.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20110301

Title: The relationship between indoleamine 2,3-dioxygenase activity and post-stroke cognitive impairment.

Journal: Journal of neuroinflammation 20110101

Title: Neopterin production and tryptophan degradation during 24-months therapy with interferon beta-1a in multiple sclerosis patients.

Journal: Journal of translational medicine 20110101

Title: Toward an anti-inflammatory strategy for depression.

Journal: Frontiers in behavioral neuroscience 20110101

Title: Tryptophan degradation in women with breast cancer: a pilot study.

Journal: BMC research notes 20110101

Title: An observational cohort study of the kynurenine to tryptophan ratio in sepsis: association with impaired immune and microvascular function.

Journal: PloS one 20110101

Title: Vascular endothelial expression of indoleamine 2,3-dioxygenase 1 forms a positive gradient towards the feto-maternal interface.

Journal: PloS one 20110101

Title: On the antioxidant properties of kynurenic acid: free radical scavenging activity and inhibition of oxidative stress.

Journal: Neurotoxicology and teratology 20110101

Title: Crinum latifolium leave extracts suppress immune activation cascades in peripheral blood mononuclear cells and proliferation of prostate tumor cells.

Journal: Scientia pharmaceutica 20110101

Title: A biological pathway linking inflammation and depression: activation of indoleamine 2,3-dioxygenase.

Journal: Neuropsychiatric disease and treatment 20110101

Title: Peripheral anti-inflammatory effects explain the ginsenosides paradox between poor brain distribution and anti-depression efficacy.

Journal: Journal of neuroinflammation 20110101

Title: Identification of a variable number of tandem repeats polymorphism and characterization of LEF-1 response elements in the promoter of the IDO1 gene.

Journal: PloS one 20110101

Title: Stochastic resonance activity influences serum tryptophan metabolism in healthy human subjects.

Journal: International journal of tryptophan research : IJTR 20110101

Title: Insulin-like growth factor-I peptides act centrally to decrease depression-like behavior of mice treated intraperitoneally with lipopolysaccharide.

Journal: Journal of neuroinflammation 20110101

Title: Cytokine production by leukocytes of military personnel with depressive symptoms after deployment to a combat-zone: a prospective, longitudinal study.

Journal: PloS one 20110101

Title: Indole compounds in some culinary-medicinal higher basidiomycetes from Poland.

Journal: International journal of medicinal mushrooms 20110101

Title: Chronic gastrointestinal inflammation induces anxiety-like behavior and alters central nervous system biochemistry in mice.

Journal: Gastroenterology 20101201

Title: Relationship between an increased serum kynurenine/tryptophan ratio and atherosclerotic parameters in hemodialysis patients.

Journal: Hemodialysis international. International Symposium on Home Hemodialysis 20101001

Title: Indoleamine 2,3-dioxygenase (IDO) activity influence tumor growth in the TRAMP prostate cancer model.

Journal: The Prostate 20100915

Title: 3-hydroxyanthranilic acid is independently associated with monocyte chemoattractant protein-1 (CCL2) and macrophage inflammatory protein-1beta (CCL4) in patients with chronic kidney disease.

Journal: Clinical biochemistry 20100901

Title: Reminiscence of 40-year research on nitrogen metabolism.

Journal: Proceedings of the Japan Academy. Series B, Physical and biological sciences 20100721

Title: Selective inhibition of IDO1 effectively regulates mediators of antitumor immunity.

Journal: Blood 20100429

Title: Evaluation of chloroform/methanol extraction to facilitate the study of membrane proteins of non-model plants.

Journal: Planta 20100401

Title: Increased serum kynurenine/tryptophan ratio correlates with disease progression in lung cancer.

Journal: Lung cancer (Amsterdam, Netherlands) 20100301

Title: Identification of crystallin modifications in the human lens cortex and nucleus using laser capture microdissection and CyDye labeling.

Journal: Molecular vision 20100101

Title: Immunosuppression by mesenchymal stem cells: mechanisms and clinical applications.

Journal: Stem cell research & therapy 20100101

Title: Attention-deficit hyperactivity disorder (ADHD) and glial integrity: S100B, cytokines and kynurenine metabolism--effects of medication.

Journal: Behavioral and brain functions : BBF 20100101

Title: Attention-deficit hyperactivity disorder (ADHD) and glial integrity: an exploration of associations of cytokines and kynurenine metabolites with symptoms and attention.

Journal: Behavioral and brain functions : BBF 20100101

Title: Central administration of lipopolysaccharide induces depressive-like behavior in vivo and activates brain indoleamine 2,3 dioxygenase in murine organotypic hippocampal slice cultures.

Journal: Journal of neuroinflammation 20100101

Title: Psychological stress-induced, IDO1-dependent tryptophan catabolism: implications on immunosuppression in mice and humans.

Journal: PloS one 20100101

Title: Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women.

Journal: PloS one 20100101

Title: On the Biological Importance of the 3-hydroxyanthranilic Acid: Anthranilic Acid Ratio.

Journal: International journal of tryptophan research : IJTR 20100101

Title: Accelerated tryptophan degradation predicts poor survival in trauma and sepsis patients.

Journal: International journal of tryptophan research : IJTR 20100101

Title: IDO-Mediated Tryptophan Degradation in the Pathogenesis of Malignant Tumor Disease.

Journal: International journal of tryptophan research : IJTR 20100101

Title: Tryptophan, Neurodegeneration and HIV-Associated Neurocognitive Disorder.

Journal: International journal of tryptophan research : IJTR 20100101

Title: The impact of neuroimmune dysregulation on neuroprotection and neurotoxicity in psychiatric disorders--relation to drug treatment.

Journal: Dialogues in clinical neuroscience 20090901

Title: Use of quinoline alkaloids as markers of the floral origin of chestnut honey.

Journal: Journal of agricultural and food chemistry 20090708

Title: Increased plasma kynurenine values and kynurenine-tryptophan ratios after major trauma are early indicators for the development of sepsis.

Journal: Shock (Augusta, Ga.) 20090701

Title: Increased indoleamine 2,3-dioxygenase (IDO) activity and elevated serum levels of tryptophan catabolites in patients with chronic kidney disease: a possible link between chronic inflammation and uraemic symptoms.

Journal: Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090601

Title: Lipopolysaccharide-induced depressive-like behavior is mediated by indoleamine 2,3-dioxygenase activation in mice.

Journal: Molecular psychiatry 20090501

Title: Kynurenine pathway in psychosis: evidence of increased tryptophan degradation.

Journal: Journal of psychopharmacology (Oxford, England) 20090501

Title: Inhibition of indoleamine 2, 3-dioxygenase-mediated tryptophan catabolism accelerates crescentic glomerulonephritis.

Journal: Clinical and experimental immunology 20090501

Title: Influence of bevacizumab, sunitinib and sorafenib as single agents or in combination on the inhibitory effects of VEGF on human dendritic cell differentiation from monocytes.

Journal: British journal of cancer 20090407

Title: Interferon-gamma and tumor necrosis factor-alpha mediate the upregulation of indoleamine 2,3-dioxygenase and the induction of depressive-like behavior in mice in response to bacillus Calmette-Guerin.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20090401

Title: Indoleamine 2,3-dioxygenase activity of acute myeloid leukemia cells can be measured from patients' sera by HPLC and is inducible by IFN-gamma.

Journal: Leukemia research 20090301

Title: Potato (Solanum tuberosum L.) tuber ageing induces changes in the proteome and antioxidants associated with the sprouting pattern.

Journal: Journal of experimental botany 20090301

Title: Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.

Journal: Journal of medicinal chemistry 20090122

Title: Tryptophan degradation in irritable bowel syndrome: evidence of indoleamine 2,3-dioxygenase activation in a male cohort.

Journal: BMC gastroenterology 20090101

Title: Plasma and urine biomarkers in acute viral hepatitis E.

Journal: Proteome science 20090101

Title: Kynurenine pathway metabolites in humans: disease and healthy States.

Journal: International journal of tryptophan research : IJTR 20090101

Title: Effects of Kynurenine Pathway Metabolites on Intracellular NAD Synthesis and Cell Death in Human Primary Astrocytes and Neurons.

Journal: International journal of tryptophan research : IJTR 20090101

Title: Epsilon-poly-L-lysine dispersity is controlled by a highly unusual nonribosomal peptide synthetase.

Journal: Nature chemical biology 20081201

Title: High expression of indoleamine 2,3-dioxygenase gene in prostate cancer.

Journal: European journal of cancer (Oxford, England : 1990) 20081001

Title: Immunomodulation by mesenchymal stem cells: a potential therapeutic strategy for type 1 diabetes.

Journal: Diabetes 20080701

Title: Urinary excretory ratio of anthranilic acid/kynurenic acid as an index of the tolerable amount of tryptophan.

Journal: Bioscience, biotechnology, and biochemistry 20080701

Title: A subset of dendritic cells express joining chain (J-chain) protein.

Journal: Immunology 20080401

Title: 4-pyridone-3-carboxamide ribonucleoside triphosphate accumulating in erythrocytes in end stage renal failure originates from tryptophan metabolism.

Journal: Clinical and experimental medicine 20071201

Title: Nanosensor detection of an immunoregulatory tryptophan influx/kynurenine efflux cycle.

Journal: PLoS biology 20071001

Title: [Mutations in structural genes of tryptophan metabolic enzymes of the kynurenine pathway modulate some units of the L-glutamate receptor--actin cytoskeleton signaling cascade].

Journal: Genetika 20071001

Title: Tryptophan metabolism and indoleamine 2,3-dioxygenase expression in coeliac disease.

Journal: Clinical and experimental immunology 20070601

Title: Temporal and mechanistic dissociation of ATP and adenosine release during ischaemia in the mammalian hippocampus.

Journal: Journal of neurochemistry 20070601

Title: Plasma kynurenine and related measures in tic disorder patients.

Journal: European child & adolescent psychiatry 20070601

Title: [Immunology in schizophrenic disorders].

Journal: Der Nervenarzt 20070301

Title: Antibacterial lysine analogs that target lysine riboswitches.

Journal: Nature chemical biology 20070101

Title: Inhibition of indoleamine 2,3-dioxygenase-mediated tryptophan catabolism accelerates collagen-induced arthritis in mice.

Journal: Arthritis research & therapy 20070101

Title: Gene expression analysis reveals early changes in several molecular pathways in cerebral malaria-susceptible mice versus cerebral malaria-resistant mice.

Journal: BMC genomics 20070101

Title: The effect of age on the enzyme activities of tryptophan metabolism along the kynurenine pathway in rats.

Journal: Clinica chimica acta; international journal of clinical chemistry 20051001

Title: Indolamine 2,3-dioxygenase is expressed in the CNS and down-regulates autoimmune inflammation.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050801

Title: Interferon-beta affects the tryptophan metabolism in multiple sclerosis patients.

Journal: European journal of neurology 20050801

Title: Enhanced enzymatic degradation of tryptophan by indoleamine 2,3-dioxygenase contributes to the tryptophan-deficient state seen after major trauma.

Journal: Shock (Augusta, Ga.) 20050301

Title: Identification of kynurenine pathway enzyme mRNAs and metabolites in human placenta: up-regulation by inflammatory stimuli and with clinical infection.

Journal: American journal of obstetrics and gynecology 20050101

Title: Mass spectral evidence for carbonate-anion-radical-induced posttranslational modification of tryptophan to kynurenine in human Cu, Zn superoxide dismutase.

Journal: Free radical biology & medicine 20041215

Title: Overexpression of indoleamine 2,3-dioxygenase in human inflammatory bowel disease.

Journal: Clinical immunology (Orlando, Fla.) 20041001

Title: Plasma homocysteine and immune activation in patients with malignant melanoma undergoing treatment with IFN-alpha.

Journal: Journal of interferon & cytokine research : the official journal of the International Society for Interferon and Cytokine Research 20040501

Title: Protein-bound kynurenine decreases with the progression of age-related nuclear cataract.

Journal: Investigative ophthalmology & visual science 20040301

Title: Basic science behind the catastrophic epilepsies.

Journal: Epilepsia 20040101

Title: Increased degradation of tryptophan in blood of patients with rheumatoid arthritis.

Journal: The Journal of rheumatology 20030901

Title: Similar pattern of inhibition of tryptophan pyrrolase activity by fluoxetine hydrochloride in both sexes of rats.

Journal: Pakistan journal of pharmaceutical sciences 20030701

Title: HPLC profiling of Trp-related metabolites in humans.

Journal: Advances in experimental medicine and biology 20030101

Title: Depressive and anxiety symptoms in the early puerperium are related to increased degradation of tryptophan into kynurenine, a phenomenon which is related to immune activation.

Journal: Life sciences 20020906

Title: 'Untypical aging off-flavor' in wine: synthesis of potential degradation compounds of indole-3-acetic acid and kynurenine and their evaluation as precursors of 2-aminoacetophenone.

Journal: Journal of agricultural and food chemistry 20020717

Title: Serum tryptophan decrease correlates with immune activation and impaired quality of life in colorectal cancer.

Journal: British journal of cancer 20020605

Title: Effects of excitatory amino acid antagonists on the activity of inferior colliculus neurons during sleep and wakefulness.

Journal: Hearing research 20020601

Title: 2-Amino-4-[3'-hydroxyphenyl]-4-hydroxybutanoic acid; a potent inhibitor of rat and recombinant human kynureninase.

Journal: Bioorganic & medicinal chemistry letters 20020211

Title: Increased neopterin production and tryptophan degradation in advanced Parkinson's disease.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20020201

Title: Multiple rostral medullary nuclei can influence breathing in awake goats.

Journal: Journal of applied physiology (Bethesda, Md. : 1985) 20010801

Title: Treatment with interferon-alpha (IFN alpha) of hepatitis C patients induces lower serum dipeptidyl peptidase IV activity, which is related to IFN alpha-induced depressive and anxiety symptoms and immune activation.

Journal: Molecular psychiatry 20010701

Title: Kynurenic acid influences the respiratory parameters of rat heart mitochondria.

Journal: Pharmacology 20010201

Title: Pharmacological elevation of endogenous kynurenic acid levels activates nigral dopamine neurons.

Journal: Amino acids 20010101

Title: Moyer BJ, et al. Inhibition of the aryl hydrocarbon receptor prevents Western diet-induced obesity. Model for AHR activation by kynurenine via oxidized-LDL, TLR2/4, TGFβ, and IDO1. Toxicol Appl Pharmacol. 2016 Jun 1;300:13-24.

Title: Sakakibara K, et al. Kynurenine causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels. J Pharmacol Sci. 2015 Sep;129(1):31-7.

Title: Nozaki K, et al. 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.

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Tags:2922-83-0 Molecular Formula|2922-83-0 MDL|2922-83-0 SMILES|2922-83-0 L-Kynurenine