Novel human D-amino acid oxidase inhibitors stabilize an active-site lid-open conformation

Terry‑Lorenzo, Ryan T.; Chun, Lawrence E.; Brown, Scott P.; Heffernan, Michele L. R.; Fang, Q.  Kevin; Orsini, Michael A.; Pollegioni, Loredano; Hardy, Larry W.; Spear, Kerry L.; Large, Thomas H.

doi:10.1042/BSR20140071

Title: Novel human D-amino acid oxidase inhibitors stabilize an active-site lid-open conformation

Journal Article · Fri Jul 04 00:00:00 EDT 2014 · Bioscience Reports

DOI:https://doi.org/10.1042/BSR20140071· OSTI ID:1497140

Terry‑Lorenzo, Ryan T.; Chun, Lawrence E.; Brown, Scott P.; Heffernan, Michele L. R.; Fang, Q. Kevin; Orsini, Michael A.; Pollegioni, Loredano; Hardy, Larry W.; Spear, Kerry L.; Large, Thomas H.

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Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: INDUSTRY

OSTI ID:: 1497140

Journal Information:: Bioscience Reports, Vol. 34, Issue 4; ISSN 0144-8463

Publisher:: Portland Press - Biochemical Society

Country of Publication:: United States

Language:: ENGLISH

References (51)

A Cell-Based Ultra-High-Throughput Screening Assay for Identifying Inhibitors of D-Amino Acid Oxidase Brandish, P. E. Journal of Biomolecular Screening, Vol. 11, Issue 5 https://doi.org/10.1177/1087057106288181	journal	April 2006
A fast method of molecular shape comparison: A simple application of a Gaussian description of molecular shape Grant, J. A.; Gallardo, M. A.; Pickup, B. T. Journal of Computational Chemistry, Vol. 17, Issue 14 https://doi.org/10.1002/(SICI)1096-987X(19961115)17:14<1653::AID-JCC7>3.0.CO;2-K	journal	November 1996
The presence of free D-serine in rat brain Hashimoto, Atsushi; Nishikawa, Toru; Hayashi, Tohiski FEBS Letters, Vol. 296, Issue 1 https://doi.org/10.1016/0014-5793(92)80397-Y	journal	January 1992
Active Site Plasticity in d -Amino Acid Oxidase: A Crystallographic Analysis ^† ^, ^‡ Todone, Flavia; Vanoni, Maria Antonietta; Mozzarelli, Andrea Biochemistry, Vol. 36, Issue 19 https://doi.org/10.1021/bi9630570	journal	May 1997
Serine racemase and the serine shuttle between neurons and astrocytes Wolosker, Herman Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1814, Issue 11 https://doi.org/10.1016/j.bbapap.2011.01.001	journal	November 2011
Extended-Connectivity Fingerprints Rogers, David; Hahn, Mathew Journal of Chemical Information and Modeling, Vol. 50, Issue 5 https://doi.org/10.1021/ci100050t	journal	April 2010
Is rat an appropriate animal model to study the involvement of d-serine catabolism in schizophrenia? insights from characterization of d-amino acid oxidase: Rat d-amino acid oxidase Frattini, Luca F.; Piubelli, Luciano; Sacchi, Silvia FEBS Journal, Vol. 278, Issue 22 https://doi.org/10.1111/j.1742-4658.2011.08354.x	journal	October 2011
Spinal d-Amino Acid Oxidase Contributes to Neuropathic Pain in Rats Zhao, Wen-Juan; Gao, Zhen-Yu; Wei, Hong Journal of Pharmacology and Experimental Therapeutics, Vol. 332, Issue 1 https://doi.org/10.1124/jpet.109.158816	journal	October 2009
Modulation of NMDA receptor function by inhibition of d-amino acid oxidase in rodent brain Strick, Christine A.; Li, Cheryl; Scott, Liam Neuropharmacology, Vol. 61, Issue 5-6 https://doi.org/10.1016/j.neuropharm.2011.06.029	journal	October 2011
Extracellular concentration of endogenous free d-serine in the rat brain as revealed by in vivo microdialysis Hashimoto, A.; Oka, T.; Nishikawa, T. Neuroscience, Vol. 66, Issue 3 https://doi.org/10.1016/0306-4522(94)00597-X	journal	June 1995
Intestinal bacterial origin of d-alanine in urine of mutant mice lacking d-amino-acid oxidase Konno, R.; Niwa, A.; Yasumura, Y. Biochemical Journal, Vol. 268, Issue 2 https://doi.org/10.1042/bj2680263	journal	June 1990
Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase Raje, Mithun; Hin, Niyada; Duvall, Bridget Bioorganic & Medicinal Chemistry Letters, Vol. 23, Issue 13 https://doi.org/10.1016/j.bmcl.2013.04.062	journal	July 2013
d-Amino-acid oxidase is not present in the mouse liver Konno, Ryuichi; Sasaki, Masato; Asakura, Setsuko Biochimica et Biophysica Acta (BBA) - General Subjects, Vol. 1335, Issue 1-2 https://doi.org/10.1016/S0304-4165(96)00136-5	journal	April 1997
The neurobiology of D-amino acid oxidase and its involvement in schizophrenia Verrall, L.; Burnet, P. W. J.; Betts, J. F. Molecular Psychiatry, Vol. 15, Issue 2 https://doi.org/10.1038/mp.2009.99	journal	September 2009
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 Kawazoe, Tomoya; Tsuge, Hideaki; Pilone, Mirella S. Protein Science, Vol. 15, Issue 12 https://doi.org/10.1110/ps.062421606	journal	December 2006
Glia-Derived d-Serine Controls NMDA Receptor Activity and Synaptic Memory Panatier, Aude; Theodosis, Dionysia T.; Mothet, Jean-Pierre Cell, Vol. 125, Issue 4 https://doi.org/10.1016/j.cell.2006.02.051	journal	May 2006
Pharmacodynamic Effects of a d-Amino Acid Oxidase Inhibitor Indicate a Spinal Site of Action in Rat Models of Neuropathic Pain Hopkins, Seth C.; Zhao, Fei-Yue; Bowen, Carrie A. Journal of Pharmacology and Experimental Therapeutics, Vol. 345, Issue 3 https://doi.org/10.1124/jpet.113.204016	journal	March 2013
Engineering the Substrate Specificity of Porcine Kidney d-Amino Acid Oxidase by Mutagenesis of the “Active-Site Lid” Setoyama, Chiaki; Nishina, Yasuzo; Mizutani, Hisashi The Journal of Biochemistry, Vol. 139, Issue 5 https://doi.org/10.1093/jb/mvj094	journal	May 2006
Synthesis and Biological Evaluation of d -Amino Acid Oxidase Inhibitors Ferraris, Dana; Duvall, Bridget; Ko, Yao-Sen Journal of Medicinal Chemistry, Vol. 51, Issue 12 https://doi.org/10.1021/jm800200u	journal	June 2008
Spatial learning and long-term potentiation of mutant mice lacking d-amino-acid oxidase Maekawa, Masao; Watanabe, Masashi; Yamaguchi, Shigeki Neuroscience Research, Vol. 53, Issue 1 https://doi.org/10.1016/j.neures.2005.05.008	journal	September 2005
pLG72 Modulates Intracellular D-Serine Levels through Its Interaction with D-Amino Acid Oxidase Sacchi, Silvia; Bernasconi, Mariagrazia; Martineau, Magalie Journal of Biological Chemistry, Vol. 283, Issue 32 https://doi.org/10.1074/jbc.M709153200	journal	June 2008
A Unified, Probabilistic Framework for Structure- and Ligand-Based Virtual Screening Swann, Steven L.; Brown, Scott P.; Muchmore, Steven W. Journal of Medicinal Chemistry, Vol. 54, Issue 5 https://doi.org/10.1021/jm1013677	journal	March 2011
Long-term potentiation depends on release of d-serine from astrocytes Henneberger, Christian; Papouin, Thomas; Oliet, Stéphane H. R. Nature, Vol. 463, Issue 7278 https://doi.org/10.1038/nature08673	journal	January 2010
Structure–function relationships in human d-amino acid oxidase Sacchi, Silvia; Caldinelli, Laura; Cappelletti, Pamela Amino Acids, Vol. 43, Issue 5 https://doi.org/10.1007/s00726-012-1345-4	journal	August 2012
Circuit-based framework for understanding neurotransmitter and risk gene interactions in schizophrenia Lisman, John E.; Coyle, Joseph T.; Green, Robert W. Trends in Neurosciences, Vol. 31, Issue 5 https://doi.org/10.1016/j.tins.2008.02.005	journal	May 2008
Metabolism of the neuromodulator d-serine Pollegioni, Loredano; Sacchi, Silvia Cellular and Molecular Life Sciences, Vol. 67, Issue 14 https://doi.org/10.1007/s00018-010-0307-9	journal	March 2010
d -Amino acid oxidase-mediated increase in spinal hydrogen peroxide is mainly responsible for formalin-induced tonic pain : Spinal hydrogen peroxide mediates tonic pain Lu, Jin-Miao; Gong, Nian; Wang, Yan-Chao British Journal of Pharmacology, Vol. 165, Issue 6 https://doi.org/10.1111/j.1476-5381.2011.01680.x	journal	February 2012
Enzymatic Conversion of Unnatural Amino Acids by YeastD-Amino Acid Oxidase Caligiuri, Antonio; D'Arrigo, Paola; Rosini, Elena Advanced Synthesis & Catalysis, Vol. 348, Issue 15 https://doi.org/10.1002/adsc.200606188	journal	October 2006
4-Hydroxypyridazin-3(2 H )-one Derivatives as Novel d -Amino Acid Oxidase Inhibitors Hondo, Takeshi; Warizaya, Masaichi; Niimi, Tatsuya Journal of Medicinal Chemistry, Vol. 56, Issue 9 https://doi.org/10.1021/jm400095b	journal	April 2013
Impact of enzyme concentration and residence time on apparent activity recovery in jump dilution analysis Copeland, Robert A.; Basavapathruni, Aravind; Moyer, Mikel Analytical Biochemistry, Vol. 416, Issue 2 https://doi.org/10.1016/j.ab.2011.05.029	journal	September 2011
Application of Belief Theory to Similarity Data Fusion for Use in Analog Searching and Lead Hopping Muchmore, Steven W.; Debe, Derek A.; Metz, James T. Journal of Chemical Information and Modeling, Vol. 48, Issue 5 https://doi.org/10.1021/ci7004498	journal	April 2008
Multiple risk pathways for schizophrenia converge in serine racemase knockout mice, a mouse model of NMDA receptor hypofunction Balu, D. T.; Li, Y.; Puhl, M. D. Proceedings of the National Academy of Sciences, Vol. 110, Issue 26 https://doi.org/10.1073/pnas.1304308110	journal	May 2013
N-methyl-d-aspartate (NMDA) receptor dysfunction or dysregulation: The final common pathway on the road to schizophrenia? Kantrowitz, Joshua T.; Javitt, Daniel C. Brain Research Bulletin, Vol. 83, Issue 3-4 https://doi.org/10.1016/j.brainresbull.2010.04.006	journal	September 2010
Characterization of human d -amino acid oxidase Molla, Gianluca; Sacchi, Silvia; Bernasconi, Mariagrazia FEBS Letters, Vol. 580, Issue 9 https://doi.org/10.1016/j.febslet.2006.03.045	journal	March 2006
Assessing the performance of OMEGA with respect to retrieving bioactive conformations Boström, Jonas; Greenwood, Jeremy R.; Gottfries, Johan Journal of Molecular Graphics and Modelling, Vol. 21, Issue 5 https://doi.org/10.1016/S1093-3263(02)00204-8	journal	March 2003
Behavioral and biochemical characterization of a mutant mouse strain lacking d-amino acid oxidase activity and its implications for schizophrenia Almond, S. L.; Fradley, R. L.; Armstrong, E. J. Molecular and Cellular Neuroscience, Vol. 32, Issue 4 https://doi.org/10.1016/j.mcn.2006.05.003	journal	August 2006
The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors Sparey, Tim; Abeywickrema, Pravien; Almond, Sarah Bioorganic & Medicinal Chemistry Letters, Vol. 18, Issue 11 https://doi.org/10.1016/j.bmcl.2008.04.020	journal	June 2008
Structural, Kinetic, and Pharmacodynamic Mechanisms of d -Amino Acid Oxidase Inhibition by Small Molecules Hopkins, Seth C.; Heffernan, Michele L. R.; Saraswat, Lakshmi D. Journal of Medicinal Chemistry, Vol. 56, Issue 9 https://doi.org/10.1021/jm4002583	journal	April 2013
Structural basis of d-DOPA oxidation by d-amino acid oxidase: Alternative pathway for dopamine biosynthesis Kawazoe, Tomoya; Tsuge, Hideaki; Imagawa, Takahito Biochemical and Biophysical Research Communications, Vol. 355, Issue 2 https://doi.org/10.1016/j.bbrc.2007.01.181	journal	April 2007
Demystifying Brain Penetration in Central Nervous System Drug Discovery: Miniperspective Di, Li; Rong, Haojing; Feng, Bo Journal of Medicinal Chemistry, Vol. 56, Issue 1 https://doi.org/10.1021/jm301297f	journal	November 2012
D-Amino Acid Oxidase Inhibitors as a Novel Class of Drugs for Schizophrenia Therapy Sacchi, Silvia; Rosini, Elena; Pollegioni, Loredano Current Pharmaceutical Design, Vol. 19, Issue 14 https://doi.org/10.2174/1381612811319140002	journal	March 2013
Crystal structure of D-amino acid oxidase: a case of active site mirror-image convergent evolution with flavocytochrome b2. Mattevi, A.; Vanoni, M. A.; Todone, F. Proceedings of the National Academy of Sciences, Vol. 93, Issue 15 https://doi.org/10.1073/pnas.93.15.7496	journal	July 1996
NMDA receptors in nervous system diseases Zhou, Qiang; Sheng, Morgan Neuropharmacology, Vol. 74 https://doi.org/10.1016/j.neuropharm.2013.03.030	journal	November 2013
A Simple Statistical Parameter for Use in Evaluation and Validation of High Throughput Screening Assays Zhang, J. -H. Journal of Biomolecular Screening, Vol. 4, Issue 2 https://doi.org/10.1177/108705719900400206	journal	April 1999
Targeted disruption of serine racemase affects glutamatergic neurotransmission and behavior Basu, A. C.; Tsai, G. E.; Ma, C-L Molecular Psychiatry, Vol. 14, Issue 7 https://doi.org/10.1038/mp.2008.130	journal	December 2008
Catalytic Properties of d-Amino Acid Oxidase in Cephalosporin C Bioconversion: A Comparison between Proteins from Different Sources Pollegioni, Loredano; Caldinelli, Laura; Molla, Gianluca Biotechnology Progress, Vol. 20, Issue 2 https://doi.org/10.1021/bp034206q	journal	January 2004
Synaptic and Extrasynaptic NMDA Receptors Are Gated by Different Endogenous Coagonists Papouin, Thomas; Ladépêche, Laurent; Ruel, Jérôme Cell, Vol. 150, Issue 3 https://doi.org/10.1016/j.cell.2012.06.029	journal	August 2012
Synthesis and SAR of 1-Hydroxy-1 H -benzo[ d ]imidazol-2(3 H )-ones as Inhibitors of d -Amino Acid Oxidase Berry, James F.; Ferraris, Dana V.; Duvall, Bridget ACS Medicinal Chemistry Letters, Vol. 3, Issue 10 https://doi.org/10.1021/ml300212a	journal	August 2012
Mechanism of inhibition of D-amino acid oxidase IV. Inhibitory action of chlorpromazine Yagi, Kunio; Ozawa, Takayuki; Nagatsu, Toshiharu Biochimica et Biophysica Acta, Vol. 43 https://doi.org/10.1016/0006-3002(60)90441-8	journal	January 1960
Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1 H )-one Series of Potent d -Amino Acid Oxidase (DAAO) Inhibitors ^† Duplantier, Allen J.; Becker, Stacey L.; Bohanon, Michael J. Journal of Medicinal Chemistry, Vol. 52, Issue 11 https://doi.org/10.1021/jm900128w	journal	June 2009
FRED Pose Prediction and Virtual Screening Accuracy McGann, Mark Journal of Chemical Information and Modeling, Vol. 51, Issue 3 https://doi.org/10.1021/ci100436p	journal	February 2011

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Title: Novel human D-amino acid oxidase inhibitors stabilize an active-site lid-open conformation

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