D-Amino acid oxidase inhibitors as a novel class of drugs for schizophrenia therapy

Current Pharmaceutical Design

Volumn 19, Issue 14, 2013, Pages 2499-2511

  Sacchi, Silvia ^a,b   Rosini, Elena ^a,b   Pollegioni, Loredano ^a,b   Molla, Gianluca ^a,b  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b POLITECNICO DI MILANO   (Italy)

Author keywords

D serine; Inhibitor; NMDA receptor; Schizophrenia

Indexed keywords

3 HYDROXYQUINOLIN 2 (1H)ONE; 4H FURO[3,2 B]PYRROLE 5 CARBOXYLIC ACID; 4H THIENO[3,2 B]PYRROLE 5 CARBOXYLIC ACID; 5 CHLORO 3 HYDROXY 4A,5 DIHYDRO 1,8 NAPHTHYRIDIN 2(1H)ONE; 5 CHLORO 6 FLUORO 3 HYDROXY 4A,5 DIHYDRO 1,8 NAPHTHYRIDIN 2 (1H)ONE; 5 METHYL 3 PYRAZOLECARBOXYLIC ACID; 6 CHLORO BENZO[D]ISOXAZOL 3 OL; CARBOXYLIC ACID DERIVATIVE; CHLORPROMAZINE; CLOZAPINE; DEXTRO AMINO ACID OXIDASE; DEXTRO AMINO ACID OXIDASE INHIBITOR; DEXTRO SERINE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; NEUROLEPTIC AGENT; OXIDOREDUCTASE INHIBITOR; POMAGLUMETAD METHIONIL; RISPERIDONE; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; ARTICLE; BRAIN FUNCTION; DRUG BLOOD LEVEL; DRUG CEREBROSPINAL FLUID LEVEL; DRUG CLEARANCE; DRUG EFFICACY; DRUG HALF LIFE; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG RESEARCH; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SPECIFICITY; HUMAN; IC 50; LIGAND BINDING; MAXIMUM PLASMA CONCENTRATION; MENTAL PATIENT; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN LOCALIZATION; PSYCHOPHARMACOTHERAPY; SCHIZOPHRENIA; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION; TRANQUILIZING ACTIVITY;

BRAIN; D-AMINO-ACID OXIDASE; ENZYME INHIBITORS; HUMANS; LIGANDS; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; RECEPTORS, N-METHYL-D-ASPARTATE; SCHIZOPHRENIA; SERINE; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 84877723597     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612811319140002     Document Type: Article

References (112)

1. Insel TR. Rethinking schizophrenia. Nature 2010; 468: 187-93.
2. Fatemi SH, Folsom TD. The neurodevelopmental hypothesis of schizophrenia, revisited. Schizophr Bull 2009; 35: 528-48.
3. Harrison PJ, Owen MJ. Genes for schizophrenia? Recent findings and their pathophysiological implications. Lancet 2003; 361: 417-9.
4. McDonald C, Murray RM. Early and late environmental risk factors for schizophrenia. Brain Res Brain Res Rev 2000; 31: 130-7.
5. Carlsson A. The current status of the dopamine hypothesis of schizophrenia. Neuropsychopharmacology 1988; 1: 179-86.
6. Creese I, Burt DR, Snyder SH. Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs. Science 1976; 192: 481-3.
7. Abi-Dargham A, Moore H. Prefrontal DA transmission at D1 receptors and the pathology of schizophrenia. Neuroscientist 2003; 9: 404-16.
8. Andreasen NC. A unitary model of schizophrenia: Bleuler's "fragmented phrene" as schizencephaly. Arch Gen Psychiatry 1999; 56: 781-7.
9. Harrison PJ, Weinberger DR. Schizophrenia genes, gene expression, and neuropathology: on the matter of their convergence. Mol Psychiatry 2005; 10: 40-68.
10. Coyle JT. Glutamate and schizophrenia: beyond the dopamine hypothesis. Cell Mol Neurobiol 2006; 26: 363-382.
11. Malhotra AK, Pinals DA, Weingartner H, et al. NMDA receptor function and human cognition: the effects of ketamine in healthy volunteers. Neuropsychopharmacology 1996; 14: 301-7.
12. Adler CM, Malhotra AK, Elman I, et al. Comparison of ketamineinduced thought disorder in healthy volunteers and thought disorder in schizophrenia. Am J Psychiatry 1999; 156: 1646-9.
13. Ross CA, Margolis RL, Reading SA, Pletnikov M, Coyle JT. Neurobiology of schizophrenia Neuron 2006; 52: 139-53.
14. Olney JW, Farber NB. Glutamate receptor dysfunction and schizophrenia. Arch Gen Psychiatry 1995; 52: 998-1007.
15. Javitt DC. Glutamate and schizophrenia: phencyclidine, N-methyl-D-aspartate receptors, and dopamine-glutamate interactions. Int Rev Neurobiol 2007; 78: 69-108.
16. Mothet JP, Parent AT, Wolosker H, et al. D-serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor. Proc Natl Acad Sci USA 2000; 97: 4926-31.
17. Pollegioni L, Piubelli L, Sacchi S, Pilone MS, Molla G. Physiological functions of D-amino acid oxidases: from yeast to humans. Cell Mol Life Sci 2007; 64: 1373-94.
18. Sacchi S, Bernasconi M, Martineau M, et al. pLG72 modulates intracellular D-serine levels through its interaction with D-amino acid oxidase: effect on schizophrenia susceptibility. J Biol Chem 2008; 283: 22244-56.
19. Pollegioni L, Sacchi S. Metabolism of the neuromodulator Dserine. Cell Mol Life Sci 2010; 67: 2387-404.
20. Pollegioni L, Molla G, Sacchi S, Rosini E, Verga R, Pilone MS. Properties and applications of microbial D-amino acid oxidases: current state and perspectives. Appl Microbiol Biotechnol 2008; 78: 1-16.
21. Momoi K, Fukui K, Watanabe F, Miyake Y. Molecular cloning and sequence analysis of cDNA encoding human kidney D-amino acid oxidase. FEBS Lett 1988; 238: 180-4.
22. Konno R. Assignment of D-amino-acid oxidase gene to a human and a mouse chromosome. Amino Acids 2001; 20: 401-8.
23. Pollegioni L, Sacchi S, Caldinelli L, et al. Engineering the properties of D-amino acid oxidases by a rational and a directed evolution approach. Curr Protein Pept Sci 2007; 8: 600-18.
24. Hasegawa H, Matsukawa T, Shinohara Y, Konno R, Hashimoto T. Role of renal D-amino-acid oxidase in pharmacokinetics of Dleucine. Am J Physiol Endocrinol Metab 2004; 287: 160-5.
25. D'Aniello G, Tolino A, D'Aniello A, Errico F, Fisher GH, Di Fiore MM. The role of D-aspartic acid and N-methyl-D-aspartic acid in the regulation of prolactin release. Endocrinology 2000; 141: 3862-70.
26. Wang Q, Cwik M, Wright CJ, Cunningham F, Pelligrino DA. The in vivo unidirectional conversion of nitro-D-arginine to nitro-Larginine. J Pharmacol Exp Ther 1999; 288: 270-3.
27. Fisher G, Lorenzo N, Abe H, et al. Free D-and L-amino acids in ventricular cerebrospinal fluid from Alzheimer and normal subjects. Amino Acids 1998; 15: 263-9.
28. Schell MJ, Molliver ME, Snyder SH. D-Serine, an endogenous synaptic modulator: localization to astrocytes and glutamatestimulated release. Proc Natl Acad Sci USA 1995; 92: 3948-52.
29. Abbott A. The drug deadlock. Nature 2010; 468: 158-9.
30. Patil ST, Zhang L, Martenyi F, et al. Activation of mGlu2/3 receptors as a new approach to treat schizophrenia: a randomized Phase 2 clinical trial. Nat Med 2007; 13: 1102-7.
31. Neims AH, Zieverink WD, Smilack JD. Distribution of D-amino acid oxidase in bovine and human nervous tissues. J Neurochem 1966; 13: 163-8.
32. Arnold G, Liscum L, Holtzman E. Ultrastructural localization of Damino acid oxidase in microperoxisomes of the rat nervous system. J Histochem Cytochem 1979; 27: 735-45.
33. Fisher GH, D'Aniello A, Vetere A, Padula L, Cusano GP, Man EH. Free D-aspartate and D-alanine in normal and Alzheimer brain. Brain Res Bull 1991; 26: 983-5.
34. Nagata Y, Horiike K, Maeda T. Distribution of free D-serine in vertebrate brains. Brain Res 1994; 634: 291-5.
35. Hamase K, Homma H, Takigawa Y, Fukushima T, Santa T, Imai K. Regional distribution and postnatal changes of D-amino acids in rat brain. Biochim Biophys Acta 1997; 1334: 214-22.
36. Inoue T, Hamase K, Morikawa A, Zaitsu K. Determination of minute amounts of D-leucine in various brain regions of rat and mouse using column-switching high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl 2000; 744: 213-9.
37. Hamase K, Inoue T, Morikawa A, Konno R, Zaitsu K. Determination of free D-proline and D-leucine in the brains of mutant mice lacking D-amino acid oxidase activity. Anal Biochem 2001; 298: 253-8.
38. Snyder SH, Kim PM. D-amino acids as putative neurotransmitters: focus on D-serine. Neurochem Res 2000; 25: 553-60.
39. Martineau M, Baux G, Mothet JP. D-serine signalling in the brain: friend and foe. Trends Neurosci 2006; 29: 481-91.
40. Stevens ER, Esguerra M, Kim PM, et al. D-serine and serine racemase are present in the vertebrate retina and contribute to the physiological activation of NMDA receptors. Proc Natl Acad Sci USA 2003; 100: 6789-94.
41. Panatier A, Theodosis DT, Mothet JP, et al. Glia-derived D-serine controls NMDA receptor activity and synaptic memory. Cell 2006; 125: 775-84.
42. Verrall L, Burnet PW, Betts JF, Harrison PJ. The neurobiology of D-amino acid oxidase and its involvement in schizophrenia. Mol Psychiatry 2010; 15: 122-37.
43. Molla G, Sacchi S, Bernasconi M, Pilone MS, Fukui K, Pollegioni L. Characterization of human D-amino acid oxidase. FEBS Lett 2006; 580: 2358-64.
44. Sasaki M, Konno R, Nihio M, Niwa A, Yasumura Y, Enami J. A single-base-pair substitution abolishes D-amino acid oxidase activity in the mouse. Biochim Biophis Acta 1992; 1139: 315-8.
45. Hashimoto A, Nishikawa T, Konno R, et al. Free D-serine, Daspartate and D-alanine in central nervous system and serum in mutant mice lacking D-amino acid oxidase. Neurosci Lett 1993; 152: 33-6.
46. Morikawa A, Hamase K, Inoue T, Konno R, Niwa A, Zaitsu K. Determination of free D-aspartic acid, D-serine and D-alanine in the brain of mutant mice lacking D-amino acid oxidase activity. J Chromatogr B Biomed Sci Appl 2001; 757: 119-25.
47. Horiike K, Tojo H, Arai R, Nozaki M, Maeda T. D-amino-acid oxidase is confined to the lower brain stem and cerebellum in rat brain: regional differentiation of astrocytes. Brain Res 1994; 652: 297-303.
48. Hashimoto A, Oka T, Nishikawa T. Anatomical distribution and postnatal changes in endogenous free D-aspartate and D-serine in rat brain and periphery. Eur J Neurosci 1995; 7: 1657-63.
49. Hamase K, Nagayasu R, Morikawa A, Konno R, Zaitsu K. Sensitive high-performance liquid chromatographic assay for D-aminoacid oxidase activity in mammalian tissues using a fluorescent nonnatural substrate, 5-fluoro-D-tryptophan. J Chromatogr A 2006; 1106: 159-64.
50. Madeira C, Freitas ME, Vargas-Lopes C, Wolosker H, Panizzutti R. Increased brain D-amino acid oxidase (DAAO) activity in schizophrenia. Schizophr Res 2008; 101: 76-83.
51. Yoshikawa M, Oka T, Kawaguchi M, Hashimoto A. MK-801 upregulates the expression of D-amino acid oxidase mRNA in rat brain. Brain Res Mol Brain Res 2004; 131: 141-4.
52. Hashimoto A, Yoshikawa M, Andoh H, et al. Effects of MK-801 on the expression of serine racemase and D-amino acid oxidase mRNAs and on the D-serine levels in rat brain. Eur J Pharmacol 2007; 555: 17-22.
53. Verrall L, Walker M, Rawlings N, et al. D-Amino acid oxidase and serine racemase in human brain: normal distribution and altered expression in schizophrenia. Eur J Neurosci 2007; 26: 1657-69.
54. Kapoor R, Lim KS, Cheng A, Garrick T, Kapoor V. Preliminary evidence for a link between schizophrenia and NMDA-glycine site receptor ligand metabolic enzymes, D-amino acid oxidase (DAAO) and kynurenine aminotransferase-1 (KAT-1). Brain Res 2006; 1106: 205-10.
55. Bendikov I, Nadri C, Amar S, et al. A CSF and postmortem brain study of D-serine metabolic parameters in schizophrenia. Schizophr Res 2007; 90: 41-51.
56. Ono K, Shishido Y, Park HK, et al. Potential pathophysiological role of D-amino acid oxidase in schizophrenia: immunohistochemical and in situ hybridization study of the expression in human and rat brain. J Neural Transm 2009; 116: 1335-47.
57. Horiike K, Tojo H, Arai R, et al. Localization of D-amino acid oxidase in Bergmann glial cells and astrocytes of rat cerebellum. Brain Res Bull 1987; 19: 587-96.
58. Moreno S, Nardacci R, Cimini A, Cerù MP. Immunocytochemical localization of D-amino acid oxidase in rat brain. J Neurocytol 1999; 28: 169-85.
59. Wolosker H. Serine racemase and the serine shuttle between neurons and astrocytes. Biochim Biophys Acta 2011; 1814: 1558-66.
60. Kartvelishvily E, Shleper M, Balan L, Dumin E, Wolosker H. Neuron-derived D-serine release provides a novel means to activate N-methyl-D-aspartate receptors. J Biol Chem 2006; 281: 14151-62.
61. Sacchi S, Cappelletti P, Giovannardi S, Pollegioni L. Evidence for the interaction of D-amino acid oxidase with pLG72 in a glial cell line. Mol Cell Neurosci 2011; 48: 20-8.
62. Popiolek M, Ross JF, Charych E, et al. D-amino acid oxidase activity is inhibited by an interaction with bassoon protein at the presynaptic active zone. J Biol Chem 2011; 286: 28867-75.
63. Tsai G, Yang P, Chung LC, Lange N, Coyle JT. D-serine added to antipsychotics for the treatment of schizophrenia. Biol Psychiatry 1998; 44: 1081-9.
64. Heresco-Levy U, Javitt DC, Ebstein R, et al. D-serine efficacy as add-on pharmacotherapy to risperidone and olanzapine for treatment-refractory schizophrenia. Biol Psychiatry 2005; 57: 577-85.
65. Danysz W, Parsons CG. Glycine and N-methyl-D-aspartate receptors: physiological significance and possible therapeutic applications. Pharmacol Rev 1998; 50: 597-664.
66. Yamada K, Ohnishi T, Hashimoto K, et al. Identification of multiple serine racemase (SRR) mRNA isoforms and genetic analyses of SRR and DAO in schizophrenia and D-serine levels. Biol Psychiatry 2005; 57: 1493-503.
67. Goltsov AY, Loseva JG, Andreeva TV, et al. Polymorphism in the 5'-promoter region of serine racemase gene in schizophrenia. Mol Psychiatry 2006; 11: 325-6.
68. Strohmaier J, Georgi A, Schirmbeck F, et al. No association between the serine racemase gene (SRR) and schizophrenia in a German case-control sample. Psychiatr Genet 2007; 17: 125.
69. Chumakov I, Blumenfeld M, Guerassimenko O, et al. Genetic and physiological data implicating the new human gene G72 and the gene for D-amino acid oxidase in schizophrenia. Proc Natl Acad Sci USA 2002; 99: 13675-80.
70. Caldinelli L, Molla G, Bracci L, et al. Effect of ligand binding on human D-amino acid oxidase: implications for the development of new drugs for schizophrenia treatment. Protein Sci 2010; 19: 1500-12.
71. Burnet PW, Eastwood SL, Bristow GC, et al. D-amino acid oxidase activity and expression are increased in schizophrenia. Mol Psychiatry 2008; 13: 658-60.
72. Redzic ZB, Segal MB. The structure of the choroid plexus and the physiology of the choroid plexus epithelium. Adv Drug Deliv Rev 2004; 56: 1695-716.
73. Hashimoto K, Fukushima T, Shimizu E, et al. Decreased serum levels of D-serine in patients with schizophrenia: evidence in support of the N-methyl-D-aspartate receptor hypofunction hypothesis of schizophrenia. Arch Gen Psychiatry 2003; 60: 572-6.
74. Labrie V, Wang W, Barger SW, Baker GB, Roder JC. Genetic loss of D-amino acid oxidase activity reverses schizophrenia-like phenotypes in mice. Genes Brain Behav 2010; 9: 11-25.
75. Maekawa M, Okamura T, Kasai N, Hori Y, Summer KH, Konno R. D-amino-acid oxidase is involved in D-serine-induced nephrotoxicity. Chem Res Toxicol 2005; 18: 1678-82.
76. Williams RE, Lock EA. Sodium benzoate attenuates D-serine induced nephrotoxicity in the rat. Toxicology 2005; 207: 35-48.
77. Williams RE, Major H, Lock EA, Lenz EM, Wilson ID. D-Serineinduced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach. Toxicology 2005; 207: 179-90.
78. Kawazoe T, Tsuge H, Pilone MS, Fukui K. Crystal structure of human D-amino acid oxidase: context-dependent variability of the backbone conformation of the VAAGL hydrophobic stretch located at the si-face of the flavin ring. Protein Sci 2006; 15: 2708-17.
79. Mattevi A, Vanoni MA, Todone F, et al. Crystal structure of Damino acid oxidase: a case of active site mirror-image convergent evolution with flavocytochrome b2. Proc Natl Acad Sci USA 1996; 93: 7496-501.
80. Kawazoe T, Tsuge H, Imagawa T, Aki K, Kuramitsu S, Fukui K. Structural basis of D-DOPA oxidation by D-amino acid oxidase: alternative pathway for dopamine biosynthesis. Biochem Biophys Res Commun 2007; 355: 385-91.
81. Duplantier AJ, Becker SL, Bohanon MJ, et al. Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors. J Med Chem 2009; 52: 3576-85.
82. Sparey T, Abeywickrema P, Almond S, et al. The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors. Bioorg Med Chem Lett 2008; 18: 3386-91.
83. Curti B, Ronchi S, Simonetta PM. In: Müller F, Ed. Chemistry and Biochemistry of Flavoenzyme. CRC Press 1992; pp. 69-94.
84. Frattini LF, Piubelli L, Sacchi S, Molla G, Pollegioni L. Is rat an appropriate animal model to study the involvement of D-serine catabolism in schizophrenia? insights from characterization of Damino acid oxidase. FEBS J 2011; 278: 4362-73.
85. Pilone MS. D-Amino acid oxidase: new findings. Cell Mol Life Sci 2000; 57: 1732-47.
86. Spector R. Riboflavin accumulation by rabbit brain slices in vitro. J Neurosci 1980; 34: 1768-71.
87. Caldinelli L, Molla G, Sacchi S, Pilone MS, Pollegioni L. Relevance of weak flavin binding in human D-amino acid oxidase. Protein Sci 2009; 18: 801-10.
88. Porter DJ, Voet JG, Bright HJ. Mechanistic features of the Damino acid oxidase reaction studied by double stopped flow spectrophotometry. J Biol Chem 1977; 252: 4464-73.
89. Todone F, Vanoni MA, Mozzarelli A, et al. Active site plasticity in D-amino acid oxidase: a crystallographic analysis. Biochemistry 1997; 36: 5853-60.
90. Umhau S, Pollegioni L, Molla G, et al. The x-ray structure of Damino acid oxidase at very high resolution identifies the chemical mechanism of flavin-dependent substrate dehydrogenation. Proc Natl Acad Sci USA 2000; 97: 12463-68.
91. Molla G, Porrini D, Job V, et al. Role of arginine 285 in the active site of Rhodotorula gracilis D-amino acid oxidase. A site-directed mutagenesis study. J Biol Chem 2000; 275: 24715-21.
92. Ferraris D, Duvall B, Ko YS, et al. Synthesis and biological evaluation of D-amino acid oxidase inhibitors. J Med Chem 2008; 51: 3357-9.
93. Sacchi S, Lorenzi S, Molla G, Pilone MS, Rossetti C, Pollegioni L. Engineering the substrate specificity of D-amino-acid oxidase. J Biol Chem 2002; 277: 27510-6.
94. Caligiuri A, Rosini E, D'Arrigo P, Tessaro D, Molla G, Pollegioni L. Enzymatic conversion of unnatural amino acids by yeast Damino acid oxidase. Adv Synth Catal 2006; 348: 2183-90.
95. Sinnokrot MO, Valeev EF, Sherrill CD. Estimates of the ab initio limit for pi-pi interactions: the benzene dimer. J Am Chem Soc 2002; 124: 10887-93.
96. Dixon M, Kleppe K. D-Amino acid oxidase. II. Specificity, competitive inhibition and reaction sequence. Biochim Biophys Acta 1965; 96: 368-82.
97. Adams CE, Rathbone J, Thornley B, et al. Chlorpromazine for schizophrenia: a Cochrane systematic review of 50 years of randomised controlled trials. BMC Med 2005; 3: 15.
98. Yagi K, Nagatsu T, Ozawa T. Inhibitory action of chlorpromazine on the oxidation of D-amino-acid in the diencephalon part of the brain. Nature 1956; 177: 891-2.
99. Gabay S, Harris SR. Studies of flavin-adenine dinucleotiderequiring enzymes and phenothiazines-III. Inhibition kinetics with highly purified D-amino acid oxidase. Biochem Pharmacol 1965; 16: 803-12.
100. Brandish PE, Chiu CS, Schneewers J, et al. A cell-based ultra-high throughput screening assay for identifying inhibitors of Daminoacid oxidase. J Biomol Screen 2006; 11: 480-5.
101. Adage T, Trillat AC, Quattropani A, Perrin D, et al. In vitro and in vivo pharmacological profile of AS057278, a selective D-amino acid oxidase inhibitor with potential anti-psychotic properties. Eur Neuropsychopharmacol 2008; 18: 200-14.
102. Lange JH, Venhorst J, van Dongen MJ, et al. Biophysical and physicochemical methods differentiate highly ligand-efficient human D-amino acid oxidase inhibitors. Eur J Med Chem 2011; 46: 4808-19.
103. Hashimoto K, Fujita Y, Horio M, et al. Co-administration of a Damino acid oxidase inhibitor potentiates the efficacy of D-serine in attenuating prepulse inhibition deficits after administration of dizocilpine. Biol Psychiatry 2009; 65: 1103-6.
104. Horio M, Fujita Y, Ishima T, et al. Effects of D-amino acid oxidase inhibitor on the extracellular D-alanine levels and the efficacy of D-alanine on dizocilpine-induced prepulse inhibition deficients in mice. Open Clin Chem J 2009; 2: 16-21.
105. Abou El-Magd RM, Park HK, Kawazoe T, et al. The effect of risperidone on D-amino acid oxidase activity as a hypothesis for a novel mechanism of action in the treatment of schizophrenia. J Psycopharmacol 2010; 24: 1055-67.
106. Smith SM, Uslaner JM, Yao L, et al. The behavioural and neurochemical effects of a novel D-amino acid oxidase inhibitor compound 8 [4H-thieno [3,2-b]pyrrole-5-carboxylic acid] and Dserine. J Pharmacol Exp Ther 2009; 328: 921-30.
107. Strick CA, Li C, Scott L, et al. Modulation of NMDA receptor function by inhibition of D-amino acid oxidase in rodent brain. Neuropharmacology 2011; 61: 1001-15.
108. Fang QK, Hopkins S, Jones S, inventors; Sepracor Inc., assignee. Benzo[d]isoxazol-3-ol DAAO inhibitors. United States patent US 20050143434. 2004 Dec.
109. Heffernan MLR, Foglesong RJ, Hopkins SC, et al., Inventors; Sepracor Inc., assignee. Fluoro-substituted inhibitors of D-amino acid oxidase. United States patent US 20080004327. 2007 Jul.
110. Dorsey JM, Heffernan MLR, Fang QK, et al., Inventors; Sepracor Inc., assignee. Fused heterocycles. United States patent US 20080004328. 2008 Jan.
111. Willis A, Bender HU, Steel G, Valle D. PRODH variants and risk for schizophrenia. Amino Acids 2008; 35: 673-9.
112. Gründer G, Hippius H, Carlsson A. The "atypicality" of antipsychotics: a concept re-examined and re-defined. Nat Rev Drug Discov 2009; 8: 197-202.