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| anthranilic acid |
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| CHEBI:30754 |
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| An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:40980, CHEBI:2757, CHEBI:22577, CHEBI:22578
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| No supplier information found for this compound. |
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Molfile
XML
SDF
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more structures >>
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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__684508009802538__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__684508009802538__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:40980","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__684508009802538__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"684508009802538","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__684508009802538__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 07261209413D starting HoverWatcher_5 Time for openFile( Marvin 07261209413D 17 17 0 0 0 0 999 V2000 0.2920 0.6269 -0.0192 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2920 -0.7966 -0.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9205 -1.5180 -0.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1502 -0.8405 0.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1739 0.5625 0.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9673 1.2829 0.0189 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4599 1.3871 0.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4941 0.9702 0.5276 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5234 2.5205 -0.4415 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3922 -1.5113 -0.2126 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9287 -2.5419 -0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0257 -1.3677 0.0626 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0699 1.0565 0.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0328 2.3046 0.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2252 1.4600 0.5577 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3495 -2.4449 -0.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2235 -1.0923 -0.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 8 7 1 0 0 0 0 1 7 1 0 0 0 0 9 7 2 0 0 0 0 2 1 4 0 0 0 0 6 1 4 0 0 0 0 3 2 4 0 0 0 0 10 2 1 0 0 0 0 5 6 4 0 0 0 0 4 3 4 0 0 0 0 4 5 4 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 8 15 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 M END): 16 ms reading 17 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 17 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion [C6H4(NH2)(CO2)]−, obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L1 in that context, but it is now known to be non-essential in human nutrition. |
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Read full article at Wikipedia
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| InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) |
| RWZYAGGXGHYGMB-UHFFFAOYSA-N |
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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View more via ChEBI Ontology
2-Aminobenzoesäure
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ChEBI
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2-AMINOBENZOIC ACID
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PDBeChem
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2-carboxyaniline
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NIST Chemistry WebBook
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Anthranilic acid
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KEGG COMPOUND
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o-Aminobenzoesäure
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ChEBI
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o-Aminobenzoic acid
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KEGG COMPOUND
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o-aminobenzoic acid
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NIST Chemistry WebBook
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o-carboxyaniline
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NIST Chemistry WebBook
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Vitamin L1
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KEGG COMPOUND
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118-92-3
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CAS Registry Number
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KEGG COMPOUND
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118-92-3
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CAS Registry Number
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ChemIDplus
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118-92-3
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CAS Registry Number
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NIST Chemistry WebBook
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3397
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Gmelin Registry Number
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Gmelin
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471803
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Reaxys Registry Number
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Reaxys
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Keller AN, Eckle SB, Xu W, Liu L, Hughes VA, Mak JY, Meehan BS, Pediongco T, Birkinshaw RW, Chen Z, Wang H, D'Souza C, Kjer-Nielsen L, Gherardin NA, Godfrey DI, Kostenko L, Corbett AJ, Purcell AW, Fairlie DP, McCluskey J, Rossjohn J (2017)
Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells.
Nature immunology 18, 402-411 [PubMed:28166217]
[show Abstract]
The major-histocompatibility-complex-(MHC)-class-I-related molecule MR1 can present activating and non-activating vitamin-B-based ligands to mucosal-associated invariant T cells (MAIT cells). Whether MR1 binds other ligands is unknown. Here we identified a range of small organic molecules, drugs, drug metabolites and drug-like molecules, including salicylates and diclofenac, as MR1-binding ligands. Some of these ligands inhibited MAIT cells ex vivo and in vivo, while others, including diclofenac metabolites, were agonists. Crystal structures of a T cell antigen receptor (TCR) from a MAIT cell in complex with MR1 bound to the non-stimulatory and stimulatory compounds showed distinct ligand orientations and contacts within MR1, which highlighted the versatility of the MR1 binding pocket. The findings demonstrated that MR1 was able to capture chemically diverse structures, spanning mono- and bicyclic compounds, that either inhibited or activated MAIT cells. This indicated that drugs and drug-like molecules can modulate MAIT cell function in mammals. | Joseph J, Nagashri K, Janaki GB (2012)
Novel metal based anti-tuberculosis agent: synthesis, characterization, catalytic and pharmacological activities of copper complexes.
European journal of medicinal chemistry 49, 151-163 [PubMed:22321994]
[show Abstract]
Copper complexes of molecular formulae, [CuL(1)(OAc)], [CuL(2)(H(2)O)], [CuL(3)(H(2)O)], [CuL(4)(H(2)O)], [CuL(5)(H(2)O)] where L(1)-L(5) represents Schiff base ligands [by the condensation of 3-hydroxyflavone with 4-aminoantipyrine (L(1))/o-aminophenol (L(2))/o-aminobenzoic acid (L(3))/o-aminothiazole (L(4))/thiosemicarbazide (L(5))], have been prepared. They were characterized using analytical and spectral techniques. The DNA binding properties of copper complexes were studied using electronic absorption spectra and viscosity measurements. Superoxide dismutase and antioxidant activities of the copper complexes have also been studied. Furthermore, the copper complexes have been found to promote pUC18 DNA cleavage in the presence of oxidant. Anti-tuberculosis activity was also performed. | Sasaki T, Mizuguchi S, Honda K (2012)
Growth inhibitory effects of anthranilic acid and its derivatives against Legionella pneumophila.
Journal of bioscience and bioengineering 113, 726-729 [PubMed:22341575]
[show Abstract]
Legionella pneumophila is the principal etiologic agent of Legionnaires' disease. We found that the growth of L. pneumophila was markedly inhibited by its own cell lysate and the inhibitory effect was abolished by heat-treatment of the lysate. The genomic library of L. pneumophila was constructed in Escherichia coli and screened to determine the gene involved in the growth inhibition. A clone harboring the gene encoding anthranilate synthase (TrpE), which is involved in tryptophan biosynthesis, exhibited an inhibitory effect on the growth of L. pneumophila. Anthranilic acid exogenously added also exhibited antibacterial activity against L. pneumophila. A series of single-gene-knockout mutants of L. pneumophila lacking tryptophan synthesis genes were constructed and assessed for their susceptibility to anthranilic acid. Although the growth of mutants deficient in anthranilate phosphoribosyltransferase (TrpD) and N-(5'-phosphoribosyl)anthranilate isomerase (TrpF) was not affected by exogenous anthranilic acid, the indole-3-glycerophosphate synthase (TrpC) deficient mutant exhibited an increased susceptibility compared with the parent strain. These observations strongly indicate that 1-(2-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate (CPADR-5'-P), which is an intermediate of tryptophan synthesis from anthranilic acid, is responsible for the growth inhibition of L. pneumophila. | Delaney SP, Witko EM, Smith TM, Korter TM (2012)
Investigating tautomeric polymorphism in crystalline anthranilic acid using terahertz spectroscopy and solid-state density functional theory.
The journal of physical chemistry. A 116, 8051-8057 [PubMed:22784643]
[show Abstract]
Terahertz spectroscopy is sensitive to the interactions between molecules in the solid-state and recently has emerged as a new analytical tool for investigating polymorphism. Here, this technique is applied for the first time to the phenomenon of tautomeric polymorphism where the crystal structures of anthranilic acid (2-aminobenzoic acid) have been investigated. Three polymorphs of anthranilic acid (denoted Forms I, II and III) were studied using terahertz spectroscopy and the vibrational modes and relative polymorph stabilities analyzed using solid-state density functional theory calculations augmented with London dispersion force corrections. Form I consists of both neutral and zwitterionic molecules and was found to be the most stable polymorph as compared to Forms II and III (both containing only neutral molecules). The simulations suggest that a balance between steric interactions and electrostatic forces is responsible for the favoring of the mixed neutral/zwitterion solid over the all neutral or all zwitterion crystalline arrangements. | De Ravin SS, Zarember KA, Long-Priel D, Chan KC, Fox SD, Gallin JI, Kuhns DB, Malech HL (2010)
Tryptophan/kynurenine metabolism in human leukocytes is independent of superoxide and is fully maintained in chronic granulomatous disease.
Blood 116, 1755-1760 [PubMed:20511543]
[show Abstract]
In chronic granulomatous disease (CGD), defective phagocytic nicotinamide adenine dinucleotide phosphate (NADPH) oxidase activity causes reduced superoxide anion (O(2)(·)) radical production leading to frequent infections as well as granulomas and impaired wound healing indicative of excessive inflammation. Based on recent mouse studies, the lack of O(2)(·)-dependent interferon γ (IFNγ)-induced synthesis of kynurenine (kyn), an anti-inflammatory tryptophan metabolite produced by indolamine 2,3 deoxygenase (IDO), was proposed as a cause of hyperinflammation in CGD and this pathway has been considered for clinical intervention. Here, we show that IFNγ induces normal levels of kynurenine in cultures of O(2)(·)-deficient monocytes, dendritic cells, and polymorphonuclear leukocytes from gp91(PHOX)- or p47(PHOX)-deficient human CGD donors. Kynurenine accumulation was dose- and time-dependent as was that of a downstream metabolite, anthranilic acid. Furthermore, urinary and serum levels of kynurenine and a variety of other tryptophan metabolites were elevated rather than suppressed in CGD donors. Although we did not specifically evaluate kyn metabolism in local tissue or inflamed sites in humans, our data demonstrates that O(2)(·) anion is dispensable for the rate-limiting step in tryptophan degradation, and CGD patients do not appear to have either hematopoietic cell or systemic deficits in the production of the anti-inflammatory kynurenine molecule. | Pawlak K, Kowalewska A, Mysliwiec M, Pawlak D (2009)
Kynurenine and its metabolites--kynurenic acid and anthranilic acid are associated with soluble endothelial adhesion molecules and oxidative status in patients with chronic kidney disease.
The American journal of the medical sciences 338, 293-300 [PubMed:19745702]
[show Abstract]
BackgroundCellular adhesion molecules and oxidative stress play a role in the pathogenesis of atherosclerosis in patients with chronic kidney disease (CKD). Recently, it has been postulated that the kynurenine (KYN) pathway could be involved in the pathogenesis of atherosclerosis.MethodsWe evaluated the KYN, kynurenic acid (KYNA), anthranilic acid (AA), and their relations with cellular adhesion molecules: soluble intercellular adhesion molecule-1 (sICAM-1), soluble vascular adhesion molecule-1 (sVCAM-1), sE-selectin, sP-selectin, and Cu/Zn superoxide dismutase (Cu/Zn SOD) levels as the markers of oxidative stress in the population of 132 patients with CKD and 28 healthy controls.ResultsCompared with the controls, 2 groups of dialyzed patients had significantly increased KYN (both P < 0.01), KYNA, AA, sICAM-1, sVCAM-1, and Cu/Zn SOD levels (all P < 0.001, respectively). KYN, AA, sICAM-1, and sVCAM-1 concentrations were significantly higher in undialyzed patients with CKD compared with healthy subjects (P < 0.001, P < 0.01, and both P < 0.05, respectively). sICAM-1 and sVCAM-1 were positively associated with KYN (P < 0.0001 and P < 0.01), KYNA (P < 0.05 and P < 0.0001), AA (P < 0.01 and P < 0.0001), and with Cu/Zn SOD (both P < 0.0001, respectively) in the whole CKD group. The positive relationship existed between sICAM-1, sVCAM-1 and age, high-sensitivity C-reactive protein, creatinine, and the duration of dialysis therapy. Multivariable analysis showed that KYN was a strong independent correlate of sICAM-1, whereas Cu/Zn SOD and platelets independently and significantly predicted sVCAM-1 in patients with CKD.ConclusionsThis study demonstrated that KYN is independently and significantly associated with elevated sICAM-1, whereas oxidative status and platelets independently and significantly predicted increased sVCAM-1 levels in patients with CKD. | Drummond KJ, Yates EA, Turnbull JE (2001)
Electrophoretic sequencing of heparin/heparan sulfate oligosaccharides using a highly sensitive fluorescent end label.
Proteomics 1, 304-310 [PubMed:11680877]
[show Abstract]
The sequencing of heparan sulfate oligosaccharides has recently become possible using integral Glycan Sequencing, which utilizes a combination of chemical and enzymatic degradation steps followed by polyacrylamide gel electrophoresis. This technique has previously employed the fluorescent label, anthranilic acid, and has been used to sequence low nmol amounts of purified saccharides. Here, we present an improved method, which uses the alternative label, 7-aminonapthalene-1,3-disulfonic acid, the reducing agent sodium triacetoxyborohydride and optimizes the nitrous acid step in heparin/heparan sulfate degradation. These improvements increase the sensitivity at least ten-fold taking the amount of starting material required into the pmol range. We show that this label is compatible with the integral glycan sequencing methodology and demonstrate its application to the sequencing of chemically modified heparin derivatives. Advances in sequencing techniques for heparan sulfate saccharides will permit detailed structure-function studies and will in the future underpin novel proteomics-based approaches aimed at studying their diverse functional roles as protein regulators. | Fujigaki S, Saito K, Takemura M, Fujii H, Wada H, Noma A, Seishima M (1998)
Species differences in L-tryptophan-kynurenine pathway metabolism: quantification of anthranilic acid and its related enzymes.
Archives of biochemistry and biophysics 358, 329-335 [PubMed:9784247]
[show Abstract]
Anthranilic acid (AA) has attracted considerable attention as one of the L-tryptophan-kynurenine pathway metabolites in the central nervous system. In this study, a highly sensitive and accurate method for the quantification of AA has been developed using reversed-phase high-performance liquid chromatography with electrochemical detection. Serum and cerebrospinal fluid (CSF) AA concentrations in different animal species were measured. CSF AA concentrations in rabbits were 1.1 +/- 0.1 nmol/liter, which were 5. 7-33.0 times lower than those in other species studied. Serum AA concentrations, however, were slightly higher in rabbits than in other species. In contrast, the concentrations of L-kynurenine (L-KYN) in both serum and CSF were substantially higher in rabbits than in other species. Tissue kynurenine pathway enzymes, indoleamine 2,3-dioxygenase (IDO), tryptophan 2,3-dioxygenase, kynurenine 3-hydroxylase, and kynureninase were determined in rabbits, rats, gerbils, and mice. These enzymes varied among species, especially lung IDO activities in rabbits were 146-516 times higher than those found in other species, but rabbit liver kynurenine 3-hydroxylase activities were lower by one order of magnitude than those of the other species tested. Furthermore, brain kynurenine 3-hydroxylasae activities were 12.3-23.2 times higher in gerbils than those in the other species tested. In addition, AA concentrations in serum following intravenous administration of L-KYN (5 mg/kg) were also measured in rabbits. AA levels peaked sharply within 5 min after administration and decreased in a time-dependent manner. At 5 min after administration, CSF L-KYN and AA concentrations were also increased by 1.76- and 2.56-fold, respectively, compared with basal levels. Increased AA concentrations in CSF following L-KYN administration may reflect the entry of AA into the CSF after conversion to AA in systemic tissue and/or the local synthesis of AA from L-KYN in the CNS. |
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2021-08-04
