Utilization of kynurenic acid produced from D-kynurenine in an in vitro assay of D-amino acid oxidase activity

Journal of Health Science

Volumn 56, Issue 3, 2010, Pages 341-346

  Song, Ziyu ^a   Ogaya, Tadahiro ^a   Ichiba, Kana Ishii Hideaki ^a   Iizuka, Hideaki ^a   Fukushima, Takeshi ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

D amino acid oxidase; D kynurenine; Enzymatic assay; Enzymatic inhibitor; Kynurenic acid

Indexed keywords

CHLORPROMAZINE; DEXTRO ALANINE; DEXTRO AMINO ACID OXIDASE; DEXTRO SERINE; KYNURENIC ACID; KYNURENINE; ZINC;

ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME SUBSTRATE COMPLEX; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; PH;

EID: 77953297892     PISSN: 13449702     EISSN: 13475207     Source Type: Journal    
DOI: 10.1248/jhs.56.341     Document Type: Article

References (28)

1. Khoronenkova, S. V. and Tishkov, V. I. (2008) D-Amino acid oxidase: physiological role and applications. Biochemistry (Mosc), 73, 1511-1518.
2. Kawazoe, T., Park, H. K., Iwana, S., Tsuge, H. and Fukui, K. (2007) Human D-amino acid oxidase: an update and review. Chem. Rec, 7, 305-315.
3. Pollegioni, L., Diederichs, K., Molla, G., Umhau, S., Welte, W., Ghisla, S. and Pilone, M. S. (2002) Yeast D-amino acid oxidase: structural basis of its catalytic properties. J. Mol. Biol, 324, 535-546.
4. Kapoor, R., Lim, K. S. Y, Cheng, A., Garrick, T. and Kapoor, V. (2006) 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., 1106, 205-210.
5. John, J. P. (2009) Fronto-temporal dysfunction in schizophrenia: a selective review. Indian J. Psychiatry, 51, 180-190.
6. Hashimoto, K., Fukushima, T., Shimizu, E., Komatsu, N., Watanabe, H., Shinoda, N., Nakazato, M., Kumakiri, C, Okada, S., Hasegawa, H., Imai, K. and Iyo, M. (2003) Decreased serum levels of D-serine in patients with schizophrenia: evidence in support of the Af-methyl-D-aspartate receptor hypofunction hypothesis of schizophrenia. Arch. Gen. Psychiatry, 60, 572-576.
7. Tsai, G., Yang, P., Chung, L. C, Lange, N. and Coyle, J. T. (1998) D-Serine added to antipsychotics for the treatment of schizophrenia. Biol. Psychiatry, 44, 1081-1089.
8. Swartz, K. J., During, M. J., Freese, A. and Beal, M. F. (1990) Cerebral synthesis and release of kynurenic acid: an endogenous antagonist of excitatory amino acid receptors. J. NeuroscL, 10, 2965-2973.
9. Hilmas, C, Pereira, E. F. R., Alkondon, M., Rassoulpour, A., Schwarcz, R. and Albuquerque, E. X. (2001) The brain metabolite kynurenic acid inhibits alpha-7 nicotinic receptor activity and increases non-alpha-7 nicotinic receptor expression: physiopathological implications. J. NeuroscL, 21,7463-7473.
10. Fukushima, T., Sone, Y, Mitsuhashi, S., Tomiya, M. and Toyo'oka, T. (2009) Alteration of kynurenic acid concentration in rat plasma following optically pure kynurenine administration: a comparative study between enantiomers. Chirality, 21,468-472.
11. Ogaya, T., Song, Z., Ishii, K. and Fukushima, T. (2010) Changes in extracellular kynurenic acid concentrations in rat prefrontal cortex after D-kynurenine infusion: an in vivo microdialysis study. Neurochem. Res., 35, 559-563.
12. Vanoni, M. A., Cosma, A., Mazzeo, D., Mattevi, A., Todone, F. and Curti, B. (1997) Limited proteolysis and X-ray crystallography reveal the origin of substrate specificity and of the rate-limiting product release during oxidation of D-amino acids catalyzed by mammalian D-amino acid oxidase. Biochemistry, 36, 5624-5632.
13. Adage, T., Trillat, A.-C, Quattropani, A., Perrin, D., Cavarec, L., Shaw, J., Guerassimenko, O., Giachetti, C, Greco, B., Chumakov, I., Halazy, S., Roach, A. and Zaratin, P. (2008) In vitro and in vivo pharmacological profile of AS057278, a selective D-amino acid oxidase inhibitor with potential anti-psychotic properties. Eur. Neuropsychopharmacol, 18, 200-214.
14. Hashimoto, K., Fujita, Y, Horio, M., Kunitachi, S., Iyo, M., Ferraris, D. and Tsukamoto, T. (2009) Co- administration of a D-amino acid oxidase inhibitor potentiates the efficacy of D-serine in attenuating prepulse inhibition deficits after administration of dizocilpine. Biol. Psychiatry, 65, 1103-1106.
15. Ferraris, D., Duvall, B., Ko, Y.-S., Thomas, A. G., Rojas, C, Majer, P., Hashimoto, K. and Tsukamoto, T. (2008) Synthesis and biological evaluation of D-amino acid oxidase inhibitors. J. Med. Chem., 51, 3357-3359.
16. Duplantier, A. J., Becker, S. L., Bohanon, M. J., Borzilleri, K. A., Chrunyk, B. A., Downs, J. T, Hu, L. Y, El-Kattan, A., James, L. C, Liu, S., Lu, J., Maklad, N., Mansour, M. N., Mente, S., Piotrowski, M. A., Sakya, S. M., Sheehan, S., Steyn, S. J., Stride, C. A., Williams, V. A. and Zhang, L. (2009) Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(lH)-one series of potent D-amino acid oxidase (DAAO) inhibitors. J. Med. Chem., 52, 3576-3585.
17. Sparey, T., Abeywickrema, P., Almond, S., Brandon, N., Byrne, N., Campbell, A., Hutson, P. H., Jacobson, M., Jones, B., Munshi, S., Pascarella, D., Pike, A., Prasad, G. S., Sachs, N., Sakatis, M., Sardana, V., Venkatraman, S. and Young, M. B. (2008) The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors. Bioorg. Med. Chem. Lett, 18, 3386-3391.
18. Molla, G., Sacchi, S., Bernasconi, M., Pilone, M. S., Fukui, K. and Pollegioni, L. (2006) Characterization of human D-amino acid oxidase. FEBS Lett, 580, 2358-2364.
19. Caligiuri, A., D'Arrigo, P., Rosini, E., Tessaro, D., Molla, G., Servi, S. and Pollegioni, L. (2006) Enzymatic conversion of unnatural amino acids by yeast D-amino acid oxidase. Advanced Synthesis and Catalysis, 348, 2183-2190.
20. Hamase, K., Nagayasu, R., Morikawa, A., Konno, R. and Zaitsu, K. (2006) Sensitive high-performance liquid chromatographic assay for D-amino-acid oxidase activity in mammalian tissues using a fluorescent non-natural substrate, 5-fluoro-D-tryptophan. J. Chromatogr. A, 1106, 159-164.
21. Zhao, W., Konno, R., Zhou, X. J., Yin, M. and Wang, Y. X. (2008) Inhibition of D Amino-acid oxidase activity induces pain relief in mice. Cell. Mol. Neurobiol, 28, 581-591.
22. Simonetta, M. P., Pollegioni, L., Casalin, P., Curti, B. and Ronchi, S. (1989) Properties of D-amino acid oxidase from Rhodotorula gracilis. Eur. J. Biochem., 180, 199-204.
23. Shibata, K. (1988) Fluorimetric micro-determination of kynurenic acid, an endogenous blocker of neurotoxity, by high-performance liquid chromatography. J. Chromatogr. Biomed. AppL, 430, 376-380.
24. Heyes, M. P. and Quearry, B. J. (1990) Quantification of kynurenic acid in cerebrospinal fluid: effects of systemic and central L-kynurenine administration. J. Chromatogr., 530, 108-115.
25. Mitsuhashi, S., Fukushima, T., Kawai, J., Tomiya, M., Santa, T., Imai, K. and Toyo'oka, T. (2006) Improved method for the determination of kynurenic acid in rat plasma by column-switching HPLC with post-column fluorescence detection. Anal. Chim. Ada, 562, 36-3.
26. 2+-containing mobile phase for simultaneous determination of kynurenine, kynurenic acid and tryptophan in human plasma by high performance liquid chromatography. J. Chromatogr. B Analyt. Technol. Biomed. Life Set, 878, 603-608.
27. Yagi, K., Ozawa, T. and Nagatsu, T. (1960) Mechanism of inhibition of D-amino acid oxidase. IV. Inhibitory action of chlorpromazine. Biochim. Bio-phys. Ada, 43, 310-317.
28. Iwana, S., Kawazoe, T., Park, H. K., Tsuchiya, K., Ono, K., Yorita, K., Sakai, T., Kusumi, T. and Fukui, K. (2008) Chlorpromazine oligomer is a potentially active substance that inhibits human D- amino acid oxidase, product of a susceptibility gene for schizophrenia. J. Enzyme Inhib. Med. Chem., 23, 901-911.