3-Hydroxykynurenine: An intriguing molecule exerting dual actions in the Central Nervous System

NeuroToxicology

Volumn 34, Issue 1, 2013, Pages 189-204

  Colín González, Ana Laura ^a,b   Maldonado, Perla D ^a   Santamaría, Abel ^a  

^a NATIONAL INSTITUTE OF NEUROLOGY AND NEUROSURGERY   (Mexico)

^b Program in Biomedical Sciences   (Mexico)

Author keywords

3 Hydroxykynurenine; Brain damage; Kynurenine pathway; Neurological diseases; Oxidative stress; Redox modulation

Indexed keywords

3 HYDROXYANTHRANILIC ACID; 3 HYDROXYKYNURENINE; ACETYLCYSTEINE; ADENOSINE TRIPHOSPHATE; ALLOPURINOL; ALPHA TOCOPHEROL; ANTHRANILIC ACID; ANTIOXIDANT; ASCORBIC ACID; CATALASE; CREATINE KINASE; CYTOCHROME C; DOPAMINE; GAMMA INTERFERON; GLUTARIC ACID; GLUTATHIONE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDOLEAMINE 2,3 DIOXYGENASE; INTERLEUKIN 1; KYNURENINASE; KYNURENINE; KYNURENINE 3 MONOOXYGENASE; MITOGEN ACTIVATED PROTEIN KINASE; NITRIC OXIDE SYNTHASE; REACTIVE OXYGEN METABOLITE; TROLOX C; TRYPTOPHAN; TRYPTOPHAN 2,3 DIOXYGENASE; UNINDEXED DRUG; XANTHURENIC ACID;

ALZHEIMER DISEASE; ANTIOXIDANT ACTIVITY; BACTERIAL MENINGITIS; BRAIN ISCHEMIA; CELL DEATH; CENTRAL NERVOUS SYSTEM DISEASE; CONVULSION; CYTOKINE RELEASE; DEPRESSION; DISORDERS OF MITOCHONDRIAL FUNCTIONS; DNA DAMAGE; DNA STRAND BREAKAGE; DRUG MECHANISM; DRUG UPTAKE; ENZYME ACTIVITY; EXCITOTOXICITY; GENE; HUMAN; HUNTINGTON CHOREA; KYNURENINE 3 MONOOXYGENASE GENE; METABOLITE; MITOCHONDRIAL MEMBRANE POTENTIAL; MULTIPLE SCLEROSIS; NEUROMODULATION; NEUROPATHOLOGY; NONHUMAN; NUCLEOTIDE METABOLISM; OXIDATION; OXIDATION REDUCTION STATE; OXIDATIVE STRESS; PARKINSON DISEASE; PRIORITY JOURNAL; PROTEIN BINDING; REVIEW; STRUCTURE ANALYSIS; SYNAPTIC TRANSMISSION; TRYPTOPHAN METABOLISM;

ANIMALS; ANTIOXIDANTS; BIOTRANSFORMATION; CENTRAL NERVOUS SYSTEM; HUMANS; KYNURENINE; NEURODEGENERATIVE DISEASES; NEURONS; NEUROPROTECTIVE AGENTS; OXIDATION-REDUCTION; OXIDATIVE STRESS; SIGNAL TRANSDUCTION;

EID: 84871641982     PISSN: 0161813X     EISSN: 18729711     Source Type: Journal    
DOI: 10.1016/j.neuro.2012.11.007     Document Type: Review

References (152)

1. Aguilera P., Chánez-Cárdenas M.E., Floriano-Sánchez E., Barrera D., Santamaría A., Sánchez-González D.J., et al. Time-related changes in constitutive and inducible nitric oxide synthases in the rat striatum in a model of Huntington's disease. Neurotoxicology 2007, 28:1200-1207.
2. Aquilina J.A., Carver J.A., Truscott R.J. Oxidation products of 3-hydroxykynurenine bind to lens proteins: relevance for nuclear cataract. Exp Eye Res 1997, 64:235-727.
3. Aquilina J.A., Carver J.A., Truscott R.J.W. Elucidation of a novel polypeptide cross-link involving 3-hydroxykynurenine. Biochemistry 1999, 38:11455-11464.
4. Aquilina J.A., Truscott R.J.W. Identifying sites of attachment of UV filters to proteins in older human lenses. Biochim Biophys Acta 2002, 1596:6-15.
5. Backhaus C., Rahman H., Scheffler S., Laatsch H., Hardeland R. NO scavenging by 3-hydroxyanthranilic acid and 3-hydroxykynurenine: N-nitrosation leads via oxadiazoles to o-quinone diazides. Nitric oxide 2008, 19:237-244.
6. Bando M., Nakajima A., Satoh K. Spectrophotometric estimation of 3-OH L-kynurenine O-beta-glucoside in the human lens. J Biochem 1981, 89:103-109.
7. Baran H., Staniek K., Kepplinger B., Stur J., Draxler M., Nohl H. Kynurenines and the respiratory parameters on rat heart mitochondria. Life Sci 2003, 72:1103-1115.
8. Beal M.F. Mitochondrial dysfunction and oxidative damage in Alzheimer's and Parkinson's diseases and coenzyme Q10 as a potential treatment. J Bioenerg Biomembr 2004, 36:381-386.
9. Bellac C.L., Coimbra R.S., Christen S., Leib S.L. Pneumococcal meningitis causes accumulation of neurotoxic kynurenine metabolites in brain regions prone to injury. Neurobiol Dis 2006, 24:395-402.
10. Bender D.A., Njagi E.N., Danielian P.S. Tryptophan metabolism in vitamin B6-deficient mice. Br J Nutr 1990, 63:27-36.
11. Berger F., Ramírez-Hernández M.H., Ziegler M. The new life of a centenarian: signaling functions of NAD(P). Trends Biochem Sci 2004, 29:111-118.
12. Berry Y., Truscott R.J. The presence of a human UV filter within the lens represents an oxidative stress. Exp Eye Res 2001, 72:411-421.
13. Bindoli A., Rigobello M.P., Deeble D.J. Biochemical and toxicological properties of the oxidation products of catecholamines. Free Radic Biol Med 1992, 13:391-405.
14. Bonda D.J., Mailankot M., Stone J.G., Garrett M.R., Castellani R.J., Siedlak S.L., et al. Indoleamine 2,3-dioxygenase and 3-hydroxykynurenine modifications are found in the neuropathology of Alzheimer's disease. Redox Rep 2010, 15:161-168.
15. Brandy N., Grant R., Brew B.J., Adams S., Jayasena T., Guillemin G.J. Effects of kynurenine pathway metabolites on intracellular NAD synthesis and cell death in human primary astrocytes and neurons. Int J Tryptophan Res 2009, 2:61-69.
16. Brouillet E., Condé F., Beal M.F., Hantraye P. Replicating Huntington's disease phenotype in experimental animals. Prog Neurobiol 1999, 59:427-468.
17. Campesan S., Green E.W., Breda C., Sathyasaikumar K.V., Muchowski P.J., Schwarcz R., et al. The kynurenine pathway modulates neurodegeneration in a Drosophila model of Huntington's disease. Curr Biol 2011, 21:961-966.
18. Carpenedo R., Meli E., Peruginelli F., Pellegrini-giampietro D.E. Kynurenine 3-mono-oxygenase inhibitors attenuate post-ischemic neuronal death in organotypic hippocampal slice cultures. J Neurochem 2002, 82:1465-1471.
19. Ceresoli G., Guidetti P., Schwarcz R. Metabolism of [5-(3)H]kynurenine in the developing rat brain in vivo: effect of intrastriatal ibotenate injections. Brain Res 1997, 100:73-81.
20. Ceresoli-Borroni G., Schwarcz R. Perinatal kynurenine pathway metabolism in the normal and asphyctic rat brain. Amino Acids 2000, 19:311-323.
21. Chiarugi A., Carpenedo R., Moroni F. Kynurenine disposition in blood and brain of mice: effects of selective inhibitors of kynurenine hydroxylase and of kynureninase. J Neurochem 1996, 67:692-698.
22. Chiarugi A., Cozzi A., Ballerini C., Massacesi L., Moroni F. Kynurenine 3-mono-oxygenase activity and neurotoxic kynurenine metabolites increase in the spinal cord of rats with experimental allergic encephalomyelitis. Neuroscience 2001, 102:687-695.
23. Chiarugi A., Meli E., Moroni F. Similarities and differences in the neuronal death processes activated by 3OH-kynurenine and quinolinic acid. J Neurochem 2001, 77:1310-1318.
24. Christen S., Peterhans E., Stocker R. Antioxidant activities of some tryptophan metabolites: possible implication for inflammatory diseases. Proc Natl Acad Sci U S A 1990, 87:2506-2510.
25. Cornelio A.R., Rodrigues-Junior V.D., Rech V.C., de Souza W.A.T., Dutra-Filho C.S., Wajner M., et al. Inhibition of creatine kinase activity from rat cerebral cortex by 3-hydroxykynurenine. Brain Res 2006, 1124:188-196.
26. Corona A.W., Norden D.M., Skendelas J.P., Huang Y., O'Connor J.C., Lawson M., et al. Indoleamine 2,3-dioxygenase inhibition attenuates lipopolysaccharide induced persistent microglial activation and depressive-like complications in fractalkine receptor (CX(3)CR1)-deficient mice. Brain Behav Immun 2012, [Epub ahead].
27. Cowan C.M., Raymond L.A. Selective neuronal degeneration in Huntington's disease. Curr Top Dev Biol 2006, 75:25-71.
28. Coyle J.T., Puttfarcken P. Oxidative stress, glutamate, and neurodegenerative disorders. Science 1993, 262:689-695.
29. Crabtree M.J., Channon K.M. Synthesis and recycling of tetrahydrobiopterin in endothelial function and vascular disease. Nitric oxide 2011, 25:81-88.
30. Darlington L.G., Forrest C.M., Mackay G.M., Smith R.A., Smith A.J., Stoy N., et al. On the biological importance of the 3-hydroxyanthranilic acid:anthranilic acid ratio. Int J Tryptophan Res 2010, 3:51-59.
31. Duleu S., Mangas A., Sevin F., Veyret B., Bessede A., Geffard M. Circulating antibodies to IDO/THO pathway metabolites in Alzheimer's disease. Int J Alzheimer Dis 2010, 501541.
32. Eastman C.L., Guilarte T.R. Cytotoxicity of 3-hydroxykynurenine in a neuronal hybrid cell line. Brain Res 1989, 495:225-231.
33. Eastman C.L., Guilarte T.R. The role of hydrogen peroxide in the in vitro cytotoxicity of 3-hydroxykynurenine. Neurochem Res 1990, 15:1101-1107.
34. Eastman C.L., Guilarte T.R., Lever J.R. Uptake of 3-hydroxykynurenine measured in rat brain slices and in a neuronal cell line. Brain Res 1992, 584:110-116.
35. Fatokun A.A., Stone T.W., Smith R.A. Hydrogen peroxide mediates damage by xanthine and xanthine oxidase in cerebellar granule neuronal cultures. Neurosci Lett 2007, 416:34-38.
36. Foye WO. In: Barton D, Ollis WD, editor. Comprehensive organic chemistry. England: Pergamon, Oxford; 1979.
37. Gál E.M., Sherman A.D. L-kynurenine: its synthesis and possible regulatory function in brain. Neurochem Res 1980, 5:223-239.
38. Gál E.M., Sherman A.D. Synthesis and metabolism of L-kynurenine in rat brain. J Neurochem 1978, 30:607-613.
39. Garner B., Shaw D.C., Lindner R.A., Carver J.A., Truscott R.J. Non-oxidative modification of lens crystallins by kynurenine: a novel post-translational protein modification with possible relevance to ageing and cataract. Vision Res 2000, 1476:265-278.
40. Garner B., Vazquez S., Griffith R., Lindner R.A., Carver J.A., Truscott R.J.W. Identification of glutathionyl-3-hydroxykynurenine glucoside as a novel fluorophore associated with aging of the human lens. J Biol Chem 1999, 274:20847-20854.
41. Giles G.I., Collins C.A., Stone T.W., Jacob C. Electrochemical and in vitro evaluation of the redox-properties of kynurenine species. Biochem Biophys Res Commun 2003, 300:719-724.
42. Giorgini F., Guidetti P., Nguyen Q., Bennett S.C., Paul J. A genomic screen in yeast implicates kynurenine 3-monooxygenase as a therapeutic target for Huntington's disease. Nat Genet 2005, 37:526-531.
43. Giorgini F., Möller T., Kwan W., Zwilling D., Wacker J.L., Hong S., et al. Histone deacetylase inhibition modulates kynurenine pathway activation in yeast, microglia, and mice expressing a mutant huntingtin fragment. J Biol Chem 2008, 283:7390-7400.
44. Gobaille S., Kemmel V., Brumaru D., Dugave C., Aunis D., Maitre M. Xanthurenic acid distribution, transport, accumulation and release in the rat brain. J Neurochem 2008, 105:982-993.
45. Goda K., Hamane Y., Kishimoto R., Ogishi Y. Radical scavenging properties of tryptophan metabolites. Estimation of their radical reactivity. Adv Exp Med Biol 1999, 467:397-402.
46. Goldstein L.E., Leopold M.C., Huang X., Atwood C.S., Saunders A.J., Hartshorn M., et al. 3-Hydroxykynurenine and 3-hydroxyanthranilic acid generate hydrogen peroxide and promote alpha-crystallin cross-linking by metal ion reduction. Biochemistry 2000, 39:7266-7275.
47. Goshima N., Wadano A., Miura K. 3-Hydroxykynurenine as O2-scavenger in the blowfly, Aldrichina grahami. Biochem Biophys Res Commun 1986, 139:666-672.
48. Guidetti P., Bates G.P., Graham R.K., Hayden M.R., Leavitt B.R., MacDonald M.E., et al. Elevated brain 3-hydroxykynurenine and quinolinate levels in Huntington disease mice. Neurobiol Dis 2006, 23:190-197.
49. Guidetti P., Luthi-Carter R.E., Augood S.J., Schwarcz R. Neostriatal and cortical quinolinate levels are increased in early grade Huntington's disease. Neurobiol Dis 2004, 17:455-461.
50. Guidetti P., Reddy P.H., Tagle D.A., Schwarcz R. Early kynurenergic impairment in Huntington's disease and in a transgenic animal model. Neurosci Lett 2000, 283:233-235.
51. Guidetti P., Schwarcz R. 3-Hydroxykynurenine potentiates quinolinate but not NMDA toxicity in the rat striatum. Eur J Neurosci 1999, 11:3857-3863.
52. Guidetti P., Schwarcz R. 3-Hydroxykynurenine and quinolinate: pathogenic synergism in early grade Huntington's disease?. Adv Exp Med Biol 2003, 527:137-145.
53. Guilarte T.R., Block L.D., Wagner H.N. The putative endogenous convulsant 3-hydroxykynurenine decreases benzodiazepine receptor binding affinity: implications to seizures associated with neonatal vitamin B-6 deficiency. Behav Pharmacol Biochem 1988, 30:665-668.
54. Guilarte T.R., Wagner H.N. Increased concentrations of 3-hydroxykynurenine in vitamin B6 deficient neonatal rat brain. J Neurochem 1987, 49:1918-1926.
55. Guilarte T.R., Wagner H.N. Effects of perinatal vitamin B6 deficiency on dopaminergic neurochemistry. J Neurochem 1987, 48:432-439.
56. Guillemin G.J., Brew B.J., Noonan C.E., Takikawa O., Cullen K.M. Indoleamine 2,3 dioxygenase and quinolinic acid immunoreactivity in Alzheimer's disease hippocampus. Neuropathol Appl Neurobiol 2005, 31:395-404.
57. Guillemin G.J., Cullen K.M., Lim C.K., Smythe G.A., Garner B., Kapoor V., et al. Characterization of the kynurenine pathway in human neurons. J Neurosci 2007, 27(47 Nov 21):12884-12892.
58. Halliwell B. Oxidative stress and neurodegeneration: where are we now?. J Neurochem 2006, 97:1634-1658.
59. Han Q., Beerntsen B.T., Li J. The tryptophan oxidation pathway in mosquitoes with emphasis on xanthurenic acid biosynthesis. J Insect Physiol 2007, 53:254-263.
60. Hardingham G.E., Bading H. Synaptic versus extrasynaptic NMDA receptor signalling: implications for neurodegenerative disorders. Nat Rev Neurosci 2001, 11:682-696.
61. Hervé C., Beyne P., Jamault H., Delacoux E. Determination of tryptophan and its kynurenine pathway metabolites in human serum by high-performance liquid chromatography with simultaneous ultraviolet and fluorimetric detection. J Chromatogr B Biomed Appl 1996, 675:157-161.
62. Heyes M.P., Quearry B.J., Markey S.P. Systemic endotoxin increases L-tryptophan, 5-hydroxyindoleacetic acid, 3-hydroxykynurenine and quinolinic acid content of mouse cerebral cortex. Brain Res 1989, 491:173-179.
63. Heyes M.P., Saito K., Devinsky O., Nadi N.S. Kynurenine pathway metabolites in cerebrospinal fluid and serum in complex partial seizures. Epilepsia 1994, 35:251-257.
64. Heyliger S.O., Goodman C.B., Ngong J.M., Soliman K.F. The analgesic effects of tryptophan and its metabolites in the rat. Pharmacol Res 1998, 38:243-250.
65. Hiraku Y., Inoue S., Oikawa S., Yamamoto K., Tada S., Nishino K., et al. Metal-mediated oxidative damage to cellular and isolated DNA by certain tryptophan metabolites. Carcinogenesis 1995, 16:349-356.
66. Ischiropoulos H., Beckman J.S. Oxidative stress and nitration in neurodegeneration: cause, effect, or association?. J Clin Invest 2003, 111:163-169.
67. Ishii T., Iwahashi H., Sugata R., Kido R. Formation of hydroxanthommatin-derived radical in the oxidation of 3-hydroxykynurenine. Arch Biochem Biophys 1992, 294:616-622.
68. Jeong J.H., Kim H.J., Lee T.J., Kim M.K., Park E.S., Choi B.S. Epigallocatechin 3-gallate attenuates neuronal damage induced by 3-hydroxykynurenine. Toxicology 2004, 195:53-60.
69. Jimenez-Del-Rio M., Velez-Pardo C. The bad, the good, and the ugly about oxidative stress. Oxid Med Cell Longev 2012, 2012:163913.
70. Kimoto M., Ogawa T., Sasaoka K. Accumulation of 3-hydroxy-L-kynurenine sulfate and ethanolamine in urine of the rat injected with 1-aminoproline. Tokushima J Exp Med 1991, 38:37-44.
71. Kocki T., Wnuk S., Kloc R., Kocki J., Owe-Larsson B., Urbanska E.M. New insight into the antidepressants action: modulation of kynurenine pathway by increasing the kynurenic acid/3-hydroxykynurenine ratio. J Neural Transm 2012, 119:235-243.
72. Korlimbinis A., Truscott R.J. Identification of 3-hydroxykynurenine bound to proteins in the human lens. A possible role in age-related nuclear cataract. Biochemistry 2006, 45:1950-1960.
73. Krause D., Suh H.S., Tarassishin L., Cui Q.L., Durafourt B.A., Choi N., et al. The tryptophan metabolite 3-hydroxyanthranilic acid plays anti-inflammatory and neuroprotective roles during inflammation: role of hemeoxygenase-1. Am J Pathol 2011, 179:1360-1372.
74. Laugeray A., Launay J.M., Callebert J., Surget A., Belzung C., Barone P.R. Peripheral and cerebral metabolic abnormalities of the tryptophan-kynurenine pathway in a murine model of major depression. Behav Brain Res 2010, 210:84-91.
75. Lee H.J., Bach J.H., Chae H.S., Lee S.H., Joo W.S., Choi S.H., et al. Mitogen-activated protein kinase/extracellular signal-regulated kinase attenuates 3-hydroxykynurenine-induced neuronal cell death. J Neurochem 2004, 88:647-656.
76. Lee J.M., Johnson J.A. An important role of Nrf2-ARE pathway in the cellular defense mechanism. J Biochem Mol Biol 2004, 37:139-143.
77. Lehrmann E., Guidetti P., Löve A., Williamson J., Bertram E.H., Schwarcz R. Glial activation precedes seizures and hippocampal neurodegeneration in measles virus-infected mice. Epilepsia 2008, 49:13-23.
78. Leipnitz G., Schumacher C., Dalcin K.B., Scussiato K., Solano A., Funchal C., et al. In vitro evidence for an antioxidant role of 3-hydroxykynurenine and 3-hydroxyanthranilic acid in the brain. Neurochem Int 2007, 50:83-94.
79. Leonard B.E., Myint A. Inflammation and depression: is there a causal connection with dementia?. Neurotox Res 2006, 10:149-160.
80. Lévay G., Ye Q., Bodell W.J. Formation of DNA adducts and oxidative base damage by copper mediated oxidation of dopamine and 6-hydroxydopamine. Exp Neurol 1997, 146:570-574.
81. Lin M.T., Beal M.F. Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases. Nature 2006, 443:787-795.
82. Loh K.P., Huang S.H., De Silva R., Tan B.K., Zhu Y.Z. Oxidative stress: apoptosis in neuronal injury EurekaSelect. Curr Alzheimer Res 2006, 81-88.
83. López-Burillo S., Tan D.X., Mayo J.C., Sainz R.M., Manchester L.C., Reiter R.J. Melatonin, xanthurenic acid, resveratrol, EGCG, vitamin C and alpha-lipoic acid differentially reduce oxidative DNA damage induced by Fenton reagents: a study of their individual and synergistic actions. J Pineal Res 2003, 34:269-277.
84. Lugo-Huitrón R., Blanco-Ayala T., Ugalde-Muñiz P., Carrillo-Mora P., Pedraza-Chaverrí J., Silva-Adaya D., et al. On the antioxidant properties of kynurenic acid: free radical scavenging activity and inhibition of oxidative stress. Neurotoxicol Teratol 2011, 33:538-547.
85. Luthra M., Balasubramanian D. 3-Hydroxykynurenine and 3-hydroxyanthranilic acid may act as endogenous antioxidants in the eye lens. Exp Eye Res 1992, 55:641-643.
86. Mailankot M., Nagaraj R.H. Induction of indoleamine 2,3-dioxygenase by interferon-gamma in human lens epithelial cells: Apoptosis through the formation of 3-hydroxykynurenine. Int J Biochem Cell Biol 2010, 42:1446-1454.
87. Maldonado P.D., Molina-Jijón E., Villeda-Hernández J., Galván-Arzate S., Santamaría A., Pedraza-Chaverrí J. NAD(P)H oxidase contributes to neurotoxicity in an excitotoxic/prooxidant model of Huntington's disease in rats: protective role of apocynin. J Neurosci Res 2010, 88:620-629.
88. Malina H.Z., Martin X.D. Deamination of 3-hydroxykynurenine in bovine lenses: a possible mechanism of cataract formation in general. Graefes Arch Clin Exp Ophthalmol 1995, 233:38-44.
89. Massudi H., Grant R., Guillemin G.J., Braidy N. NAD+ metabolism and oxidative stress: the golden nucleotide on a crown of thorns. Redox Rep 2012, 17:28-46.
90. Miura H., Ozaki N., Sawada M., Isobe K., Ohta T., Nagatsu T. A link between stress and depression: shifts in the balance between the kynurenine and serotonin pathways of tryptophan metabolism and the etiology and pathophysiology of depression. Stress 2008, 11:198-209.
91. Mollica A., Stefanucci A., Costante R., Pinnen F. Role of formyl peptide receptors (FPR) in abnormal inflammation responses involved in neurodegenerative diseases. Anti-inflamm Anti-allergy Agents Med Chem 2012, [Epub ahead].
92. Mühl H., Pfeilschifter J. Anti-inflammatory properties of pro-inflammatory interferon-gamma. Int Immunopharmacol 2003, 3:1247-1255.
93. Murakami K., Haneda M., Yoshino M. Prooxidant action of xanthurenic acid and quinoline compounds: role of transition metals in the generation of reactive oxygen species and enhanced formation of 8-hydroxy-2'-deoxyguanosine in DNA. Biometals 2006, 19:429-435.
94. Murakami K., Ito M., Yoshino M. Xanthurenic acid inhibits metal ion-induced lipid peroxidation and protects NADP-isocitrate dehydrogenase from oxidative inactivation. J Nutr Sci Vitaminol (Tokyo) 2001, 47:306-310.
95. Nagaraj R.H., Padmanabha S., Mailankot M., Staniszewska M., Mun L.J., Glomb M.A., et al. Modulation of advanced glycation endproduct synthesis by kynurenines in human lens proteins. Biochim Biophys Acta 2010, 1804:829-838.
96. Nakagami Y., Saito H., Katsuki H. 3-Hydroxykynurenine toxicity on the rat striatum in vivo. Jpn J Pharmacol 1996, 71:183-186.
97. Nicholls D.G., Johnson-Cadwell L., Vesce S., Jekabsons M., Yadava N. Bioenergetics of mitochondria in cultured neurons and their role in glutamate excitotoxicity. J Neurosci Res 2007, 85:3206-3212.
98. Notarangelo F.M., Wu H.Q., Macherone A., Graham D.R., Schwarcz R. Gas chromatography/tandem mass spectrometry detection of extracellular kynurenine and related metabolites in normal and lesioned rat brain. Anal Biochem 2012, 421:573-581.
99. Ogawa T., Matson W.R., Beal M.F., Myers R.H., Bird E.D., Milbury P., et al. Kynurenine pathway abnormalities in Parkinson's disease. Neurology 1992, 42:1702-1706.
100. Okuda S., Nishiyama N., Saito H., Katsuki H. Hydrogen peroxide-mediated neuronal cell death induced by an endogenous neurotoxin, 3-hydroxykynurenine. Proc Natl Acad Sci U S A 1996, 93:12553-12558.
101. Okuda S., Nishiyama N., Saito H., Katsuki H. 3-Hydroxykynurenine, an endogenous oxidative stress generator, causes neuronal cell death with apoptotic features and region selectivity. J Neurochem 1998, 70:299-307.
102. Pawlak D., Takada Y., Urano T., Takada A. Serotonergic and kynurenic pathways in rats exposed to foot shock. Brain Res Bull 2000, 52:197-205.
103. Pearson S.J., Meldrum A., Reynolds G.P. An investigation of the activities of 3-hydroxykynureninase and kynurenine aminotransferase in the brain in Huntington's disease. J Neural Transm Gen Sect 1995, 102:67-73.
104. Pearson S.J., Reynolds G.P. Determination of 3-hydroxykynurenine in human brain and plasma by high-performance liquid chromatography with electrochemical detection. Increased concentrations in hepatic encephalopathy. J Chromatogr 1991, 565:436-440.
105. Pearson S.J., Reynolds G.P. Increased brain concentrations of a neurotoxin, 3-hydroxykynurenine, in Huntington's disease. Neurosci Lett 1992, 144:199-201.
106. Pinelli A., Ossi C., Colombo R., Tofanetti O., Spazzi L. Experimental convulsions in rats induced by intraventricular administration of kynurenine and structurally related compounds. Neuropharmacology 1984, 23:333-337.
107. Ramaswamy S., Mcbride J.L., Kordower J.H. Animal models of Huntington's disease. ILAR 2007, 48:356-373.
108. Reynolds G.P., Pearson S.J. Increased brain 3-hydroxykynurenine in Huntington's disease. Lancet 1989, 2:979-980.
109. Rios C., Santamaria A. Quinolinic acid is a potent lipid peroxidant in rat brain homogenates. Neurochem Res 1991, 16:1139-1143.
110. Ross C.A., Poirier M.A. Protein aggregation and neurodegenerative disease. Nat Med 2004, 10:S10-S17.
111. Saito K., Nowak T.S., Suyama K., Quearry B.J., Saito M., Crowley J.S., et al. Kynurenine pathway enzymes in brain: responses to ischemic brain injury versus systemic immune activation. J Neurochem 1993, 61:2061-2070.
112. Santamaria A., Jimenez M.E. Oxidative/nitrosative stress, a common factor in different neurotoxic paradigms: an overview. Cur Topic Neurochem Res Trends 2005, 4:1-20.
113. Sardar A.M., Bell J.E., Reynolds G.P. Increased concentrations of the neurotoxin 3-hydroxykynurenine in the frontal cortex of HIV-1-positive patients. J Neurochem 1995, 64:932-935.
114. Sardar A.M., Reynolds G.P. Frontal cortex indoleamine-2,3-dioxygenase activity is increased in HIV-1-associated dementia. Neurosci Lett 1995, 187:9-12.
115. Sas K., Robotka H., Toldi J., Vécsei L. Mitochondria, metabolic disturbances, oxidative stress and the kynurenine system, with focus on neurodegenerative disorders. J Neurol Sci 2007, 257:221-239.
116. Sathyasaikumar K.V., Stachowski E.K., Amori L., Guidetti P., Muchowski P.J., Schwarcz R. Dysfunctional kynurenine pathway metabolism in the R6/2 mouse model of Huntington's disease. J Neurochem 2010, 113:1416-1425.
117. Savvateeva E., Popov A., Kamyshev N., Bragina J., Heisenberg M., Senitz D., et al. Age-dependent memory loss, synaptic pathology and altered brain plasticity in the Drosophila mutant cardinal accumulating 3-hydroxykynurenine. J Neural Transm 2000, 107:581-601.
118. Schon E.A., Area-Gomez E. Mitochondria-associated ER membranes in Alzheimer disease. Mol Cell Neurosci 2012, [Epub ahead].
119. Schwarcz R., Bruno J.P., Muchowski P.J., Wu H. Kynurenines in the mammalian brain: when physiology meets pathology. Nat Rev Neurosci 2012, 13:465-477.
120. Schwarcz R., Foster A.C., French E.D., Whetsell W.O., Köhler C. Excitotoxic models for neurodegenerative disorders. Life Sci 1984, 35:19-32.
121. Schwarcz R., Guidetti P., Sathyasaikumar K.V., Muchowski P.J. Of mice, rats and men: revisiting the quinolinic acid hypothesis of Huntington's disease. Prog Neurobiol 2010, 90:230-245.
122. Schwarcz R., Scholz D., Coyle J.T. Structure-activity relations for the neurotoxicity of kainic acid derivatives and glutamate analogues. Neuropharmacology 1978, 17:145-151.
123. Schwarcz R., Whetsell W.O., Mangano R.M. Quinolinic acid: an endogenous metabolite that produces axon-sparing lesions in rat brain. Science 1983, 219:316-318.
124. Smith A.J., Smith R.A., Stone T.W. 5-Hydroxyanthranilic acid, a tryptophan metabolite, generates oxidative stress and neuronal death via p38 activation in cultured cerebellar granule neurones. Neurotox Res 2009, 15:303-310.
125. Snytnikova O.A., Fursova A.Z., Chernyak E.I., Vasiliev Vladimir G., Morozov S.V., Kolosova N.G., et al. Deaminated UV filter 3-hydroxykynurenine O-beta-D-glucoside is found in cataractous human lenses. Exp Eye Res 2008, 86:951-956.
126. Sorolla M.A., Rodríguez-Colman M.J., Vall-Llaura N., Tamarit J., Ros J., Cabiscol E. Protein oxidation in Huntington disease. BioFactors 2012, 38:173-185.
127. Speciale C., Schwarcz R. Uptake of kynurenine into rat brain slices. J Neurochem 1990, 54:156-163.
128. Stachowski E.K., Schwarcz R. Regulation of quinolinic acid neosynthesis in mouse, rat and human brain by iron and iron chelators in vitro. J Neural Transm 2012, 119:123-131.
129. Staniszewska M.M., Nagaraj R.H. 3-Hydroxykynurenine-mediated modification of human lens proteins. J Biol Chem 2005, 280:22154-22164.
130. Stone T.W. Neuropharmacology of quinolinic and kynurenic acids. Pharmacol Rev 1993, 5:309-379.
131. Stoy N., Mackay G.M., Forrest C.M., Christofides J., Egerton M., Stone T.W., et al. Tryptophan metabolism and oxidative stress in patients with Huntington's disease. J Neurochem 2005, 93:611-623.
132. Stutchbury G.M., Truscott R.J. The modification of proteins by 3-hydroxykynurenine. Exp Eye Res 1993, 57:149-155.
133. Szabó N., Kincses Z.T., Toldi J., Vécsei L. Altered tryptophan metabolism in Parkinson's disease: a possible novel therapeutic approach. J Neurol Sci 2011, 310:256-260.
134. Teismann P. COX-2 in the neurodegenerative process of Parkinson's disease. BioFactors 2012, [Epub ahead].
135. Tohgi H., Abe T., Takahashi S., Kimura M., Takahashi J., Kikuchi T. Concentrations of serotonin and its related substances in the cerebrospinal fluid in patients with Alzheimer type dementia. Neurosci Lett 1992, 141:9-12.
136. Tohgi H., Abe T., Takahashi S., Humitoshi H. Concentrations of serotonin and its related substances in the cerebrospinal fluid of Parkinsonian patients and their relations to the severity of symptoms. Neurosci Lett 1993, 150:71-74.
137. Tohgi H., Abe H., Takahashi T., Takahashi S., Hamato J. Alterations in the concentration of serotonergic and dopaminergic substances in the cerebrospinal fluid of patients with Parkinson's disease, and their changes after L-dopa administration. Neurosci Lett 1993, 159:135-138.
138. Truscott R.J., Carver J.A., Thorpe A., Douglas R.H. Identification of 3-hydroxykynurenine as the lens pigment in the gourami Trichogaster trichopterus. Exp Eye Res 1992, 54:1015-1017.
139. Truscott R.J., Wood A.M. Gourami lenses convert tryptophan into 3-hydroxykynurenine. Ophthalmic Res 1994, 26:214-2188.
140. Urenjak J., Obrenovitch T.P. Neuroprotective potency of kynurenic acid against excitotoxicity. Neuroreport 2000, 11:1341-1344.
141. Van Heyningen R. Fluorescent derivatives of 3-hydroxy-L-kynurenine in the lens of man, the baboon and the grey squirrel. Biochem J 1971, 123:30P-31P.
142. Vazquez S., Garner B., Sheil M.M., Truscott R.J. Characterisation of the major autoxidation products of 3-hydroxykynurenine under physiological conditions. Free Radic Res 2000, 32:11-23.
143. Viau K., Ernst S.L., Vanzo R.J., Botto L.D., Pasquali M., Longo N. Glutaric acidemia Type 1: outcomes before and after expanded newborn screening. Mol Genet Metab 2012, 106:430-438.
144. Wei H., Leeds P., Chen R.W., Wei W., Leng Y., Bredesen D.E., et al. Neuronal apoptosis induced by pharmacological concentrations of 3-hydroxykynurenine: characterization and protection by dantrolene and Bcl-2 overexpression. J Neurochem 2000, 75:81-90.
145. Wood A.M., Truscott R.J. Ultraviolet filter compounds in human lenses: 3-hydroxykynurenine glucoside formation. Vision Res 1994, 34:1369-1374.
146. Yamamoto H. Studies on CSF tryptophan metabolism in infantile spasms. Pediatr Neurol 1991, 7:411-414.
147. Yamamoto H., Shindo I., Egawa B., Horiguch K. Kynurenic acid is decreased in cerebrospinal fluid of patients with infantile spasms. Pediatr Neurol 1994, 10:9-12.
148. Yokoi N., Nishijima I., Uchida Y., Kabuto A., Yamamoto H. Effects of kynurenine metabolites on the electrocorticographic activity in the rat. J Neural Transm 1998, 105:2-3.
149. Yu P., Di Prospero N.A., Sapko M.T., Cai T., Chen A., Melendez-Ferro M., et al. Biochemical and phenotypic abnormalities in kynurenine aminotransferase II-deficient mice. Mol Cell Biol 2004, 24:6919-6930.
150. Zhang T., Berrocal J.G., Frizzell K.M., Gamble M.J., DuMond M.E., Krishnakumar R., et al. Enzymes in the NAD+ salvage pathway regulate SIRT1 activity at target gene promoters. J Biol Chem 2009, 284:20408-20417.
151. Zunszain P.A., Anacker C., Cattaneo A., Carvalho L.A., Pariante C.M. Glucocorticoids, cytokines and brain abnormalities in depression. Prog Neuropsychopharmacol Biol Psychiatry 2011, 35:722-729.
152. Zwilling D., Huang S.Y., Sathyasaikumar K.V., Francesca M., Guidetti P., Wu H.Q., et al. Kynurenine 3-monooxygenase inhibition in blood ameliorates neurodegeneration. Cell 2012, 145:863-874.