ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Synthesis and Biological Evaluation of d-Amino Acid Oxidase Inhibitors

View Author Information
MGI Pharma, Inc., 6611 Tributary Street, Baltimore, Maryland 21224, and Division of Clinical Neuroscience, Chiba University Center for Forensic Mental Health, 1-8-1 Inohana, Chiba 260-8670, Japan
* To whom correspondence should be addressed. Phone: 410-631-6762 . Fax: 410-631-6804 . E-mail: [email protected]
†MGI Pharma, Inc.
‡Chiba University Center for Forensic Mental Health.
Cite this: J. Med. Chem. 2008, 51, 12, 3357–3359
Publication Date (Web):May 29, 2008
https://doi.org/10.1021/jm800200u
Copyright © 2008 American Chemical Society

    Article Views

    2834

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    d-Amino acid oxidase (DAAO) catalyzes the oxidation of d-amino acids including d-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them, 5-chloro-benzo[d]isoxazol-3-ol (CBIO) potently inhibited DAAO with an IC50 in the submicromolar range. Oral administration of CBIO in conjunction with d-serine enhanced the plasma and brain levels of d-serine in rats compared to the oral administration of d-serine alone.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    Synthetic procedures for CMBI and 3an, elemental analysis data, in vitro d-amino acid oxidase assay method, and in vivo experimental procedures. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 118 publications.

    1. Haifeng Tang, Kristian Jensen, Evelyne Houang, Fiona M. McRobb, Sathesh Bhat, Mats Svensson, Art Bochevarov, Tyler Day, Markus K. Dahlgren, Jeffery A. Bell, Leah Frye, Robert J. Skene, James H. Lewis, James D. Osborne, Jason P. Tierney, James A. Gordon, Maria A. Palomero, Caroline Gallati, Robert S. L. Chapman, Daniel R. Jones, Kim L. Hirst, Mark Sephton, Alka Chauhan, Andrew Sharpe, Piero Tardia, Elsa A. Dechaux, Andrea Taylor, Ross D. Waddell, Andrea Valentine, Holden B. Janssens, Omar Aziz, Dawn E. Bloomfield, Sandeep Ladha, Ian J. Fraser, John M. Ellard. Discovery of a Novel Class of d-Amino Acid Oxidase Inhibitors Using the Schrödinger Computational Platform. Journal of Medicinal Chemistry 2022, 65 (9) , 6775-6802. https://doi.org/10.1021/acs.jmedchem.2c00118
    2. Ji Shen, Juan Qiao, Li Qi. Thermoresponsive Porous Polymer Membrane as a Switchable Enzyme Reactor for d-Amino Acid Oxidase Kinetics Study. ACS Applied Bio Materials 2021, 4 (1) , 966-973. https://doi.org/10.1021/acsabm.0c01426
    3. Michael Popiolek, Brendan Tierney, Stefanus J. Steyn, Michael DeVivo. Lack of Effect of Sodium Benzoate at Reported Clinical Therapeutic Concentration on d-Alanine Metabolism in Dogs. ACS Chemical Neuroscience 2018, 9 (11) , 2832-2837. https://doi.org/10.1021/acschemneuro.8b00229
    4. Po-Hsin Eric Yao, Sunil Kumar, Yu-Li Liu, Chiu-Ping Fang, Chia-Chen Liu, and Chung-Ming Sun . Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization. ACS Combinatorial Science 2017, 19 (4) , 271-275. https://doi.org/10.1021/acscombsci.7b00004
    5. Daniel W. Widlicka, John C. Murray, Karen J. Coffman, Chunguang Xiao, Michael A. Brodney, Joseph P. Rainville, and Brian Samas . Two Routes to 4-Fluorobenzisoxazol-3-one in the Synthesis of a 5-HT4 Partial Agonist. Organic Process Research & Development 2016, 20 (2) , 233-241. https://doi.org/10.1021/acs.oprd.5b00389
    6. Niyada Hin, Bridget Duvall, Dana Ferraris, Jesse Alt, Ajit G. Thomas, Rana Rais, Camilo Rojas, Ying Wu, Krystyna M. Wozniak, Barbara S. Slusher, and Takashi Tsukamoto . 6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel d-Amino Acid Oxidase Inhibitors. Journal of Medicinal Chemistry 2015, 58 (18) , 7258-7272. https://doi.org/10.1021/acs.jmedchem.5b00482
    7. Sarah C. Zimmermann, Rana Rais, Jesse Alt, Caitlin Burzynski, Barbara S. Slusher, and Takashi Tsukamoto . Structure–Metabolism Relationships in the Glucuronidation of d-Amino Acid Oxidase Inhibitors. ACS Medicinal Chemistry Letters 2014, 5 (11) , 1251-1253. https://doi.org/10.1021/ml500335z
    8. Xiaoyu Mu, Juan Qiao, Li Qi, Ying Liu, and Huimin Ma . Construction of a d-Amino Acid Oxidase Reactor Based on Magnetic Nanoparticles Modified by a Reactive Polymer and Its Application in Screening Enzyme Inhibitors. ACS Applied Materials & Interfaces 2014, 6 (15) , 12979-12987. https://doi.org/10.1021/am502901b
    9. Masumi Katane, Satsuki Matsuda, Yasuaki Saitoh, Masae Sekine, Takemitsu Furuchi, Nobuhiro Koyama, Izumi Nakagome, Hiroshi Tomoda, Shuichi Hirono, and Hiroshi Homma . The Antiviral Drug Acyclovir Is a Slow-Binding Inhibitor of d-Amino Acid Oxidase. Biochemistry 2013, 52 (33) , 5665-5674. https://doi.org/10.1021/bi400478a
    10. Takeshi Hondo, Masaichi Warizaya, Tatsuya Niimi, Ichiji Namatame, Tomohiko Yamaguchi, Keita Nakanishi, Toshihiro Hamajima, Katsuya Harada, Hitoshi Sakashita, Yuzo Matsumoto, Masaya Orita, and Makoto Takeuchi . 4-Hydroxypyridazin-3(2H)-one Derivatives as Novel d-Amino Acid Oxidase Inhibitors. Journal of Medicinal Chemistry 2013, 56 (9) , 3582-3592. https://doi.org/10.1021/jm400095b
    11. Seth C. Hopkins, Michele L. R. Heffernan, Lakshmi D. Saraswat, Carrie A. Bowen, Laurence Melnick, Larry W. Hardy, Michael A. Orsini, Michael S. Allen, Patrick Koch, Kerry L. Spear, Robert J. Foglesong, Mustapha Soukri, Milan Chytil, Q. Kevin Fang, Steven W. Jones, Mark A. Varney, Aude Panatier, Stephane H. R. Oliet, Loredano Pollegioni, Luciano Piubelli, Gianluca Molla, Marco Nardini, and Thomas H. Large . Structural, Kinetic, and Pharmacodynamic Mechanisms of d-Amino Acid Oxidase Inhibition by Small Molecules. Journal of Medicinal Chemistry 2013, 56 (9) , 3710-3724. https://doi.org/10.1021/jm4002583
    12. Masumi Katane, Naoko Osaka, Satsuki Matsuda, Kazuhiro Maeda, Tomonori Kawata, Yasuaki Saitoh, Masae Sekine, Takemitsu Furuchi, Issei Doi, Shuichi Hirono, and Hiroshi Homma . Identification of Novel d-Amino Acid Oxidase Inhibitors by in Silico Screening and Their Functional Characterization in Vitro. Journal of Medicinal Chemistry 2013, 56 (5) , 1894-1907. https://doi.org/10.1021/jm3017865
    13. James F. Berry, Dana V. Ferraris, Bridget Duvall, Niyada Hin, Rana Rais, Jesse Alt, Ajit G. Thomas, Camilo Rojas, Kenji Hashimoto, Barbara S. Slusher, and Takashi Tsukamoto . Synthesis and SAR of 1-Hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of d-Amino Acid Oxidase. ACS Medicinal Chemistry Letters 2012, 3 (10) , 839-843. https://doi.org/10.1021/ml300212a
    14. Allen J. Duplantier, Stacey L. Becker, Michael J. Bohanon, Kris A. Borzilleri, Boris A. Chrunyk, James T. Downs, Lain-Yen Hu, Ayman El-Kattan, Larry C. James, Shenping Liu, Jiemin Lu, Noha Maklad, Mahmoud N. Mansour, Scot Mente, Mary A. Piotrowski, Subas M. Sakya, Susan Sheehan, Stefanus J. Steyn, Christine A. Strick, Victoria A. Williams and Lei Zhang. Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1H)-one Series of Potent d-Amino Acid Oxidase (DAAO) Inhibitors. Journal of Medicinal Chemistry 2009, 52 (11) , 3576-3585. https://doi.org/10.1021/jm900128w
    15. Chezélle Stear, Anél Petzer, Chantalle Crous, Jacobus P. Petzer. Indazole derivatives as novel inhibitors of monoamine oxidase and D-amino acid oxidase. Medicinal Chemistry Research 2024, 33 (1) , 164-176. https://doi.org/10.1007/s00044-023-03176-x
    16. Chih-Chia Huang, I-Hua Wei, Hui-Ting Yang, Hsien-Yuan Lane. Determination of D-serine and D-alanine Tissue Levels in the Prefrontal Cortex and Hippocampus of Rats After a Single Dose of Sodium Benzoate, a D-Amino Acid Oxidase Inhibitor, with Potential Antipsychotic and Antidepressant Properties. Neurochemical Research 2023, 48 (7) , 2066-2076. https://doi.org/10.1007/s11064-023-03884-1
    17. Giuseppe De Simone, Benedetta Mazza, Licia Vellucci, Annarita Barone, Mariateresa Ciccarelli, Andrea de Bartolomeis. Schizophrenia Synaptic Pathology and Antipsychotic Treatment in the Framework of Oxidative and Mitochondrial Dysfunction: Translational Highlights for the Clinics and Treatment. Antioxidants 2023, 12 (4) , 975. https://doi.org/10.3390/antiox12040975
    18. Zach V Redding, Karen E Sabol. Reduced attentional lapses in male rats following a combination treatment of low-dose D-serine and atomoxetine. Journal of Psychopharmacology 2023, 37 (2) , 204-215. https://doi.org/10.1177/02698811221149652
    19. Chien-Yi Kuo, Chieh-Hsin Lin, Hsien-Yuan Lane. Targeting d-Amino Acid Oxidase (DAAO) for the Treatment of Schizophrenia: Rationale and Current Status of Research. CNS Drugs 2022, 36 (11) , 1143-1153. https://doi.org/10.1007/s40263-022-00959-5
    20. Sadakatali S. Gori, Ajit G. Thomas, Arindom Pal, Robyn Wiseman, Dana V. Ferraris, Run-duo Gao, Ying Wu, Jesse Alt, Takashi Tsukamoto, Barbara S. Slusher, Rana Rais. D-DOPA Is a Potent, Orally Bioavailable, Allosteric Inhibitor of Glutamate Carboxypeptidase II. Pharmaceutics 2022, 14 (10) , 2018. https://doi.org/10.3390/pharmaceutics14102018
    21. Andrea de Bartolomeis, Licia Vellucci, Mark C. Austin, Giuseppe De Simone, Annarita Barone. Rational and Translational Implications of D-Amino Acids for Treatment-Resistant Schizophrenia: From Neurobiology to the Clinics. Biomolecules 2022, 12 (7) , 909. https://doi.org/10.3390/biom12070909
    22. Elizabeth Bester, Anél Petzer, Jacobus P. Petzer. Coumarin derivatives as inhibitors of d-amino acid oxidase and monoamine oxidase. Bioorganic Chemistry 2022, 123 , 105791. https://doi.org/10.1016/j.bioorg.2022.105791
    23. Jyothsna Chinnapura Seetharam, Rituparna Maiti, Archana Mishra, Biswa Ranjan Mishra. Efficacy and safety of add-on sodium benzoate, a D-amino acid oxidase inhibitor, in treatment of schizophrenia: A systematic review and meta-analysis. Asian Journal of Psychiatry 2022, 68 , 102947. https://doi.org/10.1016/j.ajp.2021.102947
    24. Andrea Baker, Lachlan Clarke, Peter Donovan, Jacobus P. J. Ungerer, Gunter Hartel, George Bruxner, Luca Cocchi, Anne Gordon, Vikas Moudgil, Gail Robinson, Digant Roy, Ravinder Sohal, Emma Whittle, James G. Scott. Cadence discovery: study protocol for a dose-finding and mechanism of action clinical trial of sodium benzoate in people with treatment-refractory schizophrenia. Trials 2021, 22 (1) https://doi.org/10.1186/s13063-021-05890-6
    25. Ju-Chun Pei, Da-Zhong Luo, Shiang-Shin Gau, Chia-Yuan Chang, Wen-Sung Lai. Directly and Indirectly Targeting the Glycine Modulatory Site to Modulate NMDA Receptor Function to Address Unmet Medical Needs of Patients With Schizophrenia. Frontiers in Psychiatry 2021, 12 https://doi.org/10.3389/fpsyt.2021.742058
    26. Evan R. Semenza, Maged M. Harraz, Efrat Abramson, Adarsha P. Malla, Chirag Vasavda, Moataz M. Gadalla, Michael D. Kornberg, Solomon H. Snyder, Robin Roychaudhuri. D-cysteine is an endogenous regulator of neural progenitor cell dynamics in the mammalian brain. Proceedings of the National Academy of Sciences 2021, 118 (39) https://doi.org/10.1073/pnas.2110610118
    27. Amir Meftah, Hiroshi Hasegawa, Joshua T. Kantrowitz. D-Serine: A Cross Species Review of Safety. Frontiers in Psychiatry 2021, 12 https://doi.org/10.3389/fpsyt.2021.726365
    28. Loredano Pollegioni, Gianluca Molla, Silvia Sacchi, Giulia Murtas. Human D-aspartate Oxidase: A Key Player in D-aspartate Metabolism. Frontiers in Molecular Biosciences 2021, 8 https://doi.org/10.3389/fmolb.2021.689719
    29. Giulia Murtas, Silvia Sacchi, Gabriella Tedeschi, Elisa Maffioli, Eugenio Notomista, Valeria Cafaro, Monica Abbondi, Jean-Pierre Mothet, Loredano Pollegioni. Antimicrobial d-amino acid oxidase-derived peptides specify gut microbiota. Cellular and Molecular Life Sciences 2021, 78 (7) , 3607-3620. https://doi.org/10.1007/s00018-020-03755-w
    30. Agnese C. Pippione, Stefano Sainas, Donatella Boschi, Marco L. Lolli. Hydroxyazoles as acid isosteres and their drug design applications—Part 2: Bicyclic systems. 2021, 273-311. https://doi.org/10.1016/bs.aihch.2020.12.002
    31. Mingming Wei, Maodun Xie, Zhen Zhang, Yujiao Wei, Juan Zhang, Hongli Pan, Benlong Li, Jingjing Wang, Yang Song, Chuangke Chong, Rui Zhao, Jiefu Wang, Li Yu, Guang Yang, Cheng Yang. Design and synthesis of novel Flavone-based histone deacetylase inhibitors antagonizing activation of STAT3 in breast cancer. European Journal of Medicinal Chemistry 2020, 206 , 112677. https://doi.org/10.1016/j.ejmech.2020.112677
    32. Xiaoyun Deng, Yiding Zhang, Zhen Chen, Katsushi Kumata, Richard Van, Jian Rong, Tuo Shao, Akiko Hatori, Wakana Mori, Qingzhen Yu, Kuan Hu, Masayuki Fujinaga, Hsiao-Ying Wey, Yihan Shao, Lee Josephson, Giulia Murtas, Loredano Pollegioni, Ming-Rong Zhang, Steven Liang. Synthesis and preliminary evaluation of 4-hydroxy-6-(3-[11C]methoxyphenethyl)pyridazin-3(2H)-one, a 11C-labeled -amino acid oxidase (DAAO) inhibitor for PET imaging. Bioorganic & Medicinal Chemistry Letters 2020, 30 (16) , 127326. https://doi.org/10.1016/j.bmcl.2020.127326
    33. Shuang-Xi Gu, Hai-Feng Wang, Yuan-Yuan Zhu, Fen-Er Chen. Natural Occurrence, Biological Functions, and Analysis of D-Amino Acids. Pharmaceutical Fronts 2020, 02 (02) , e79-e87. https://doi.org/10.1055/s-0040-1713820
    34. . Bibliography. 2020, 137-248. https://doi.org/10.1016/B978-0-12-812212-9.16001-4
    35. Gianluca Molla, Antonio Chaves‐Sanjuan, Antonio Savinelli, Marco Nardini, Loredano Pollegioni. Structure and kinetic properties of human d ‐aspartate oxidase, the enzyme‐controlling d ‐aspartate levels in brain. The FASEB Journal 2020, 34 (1) , 1182-1197. https://doi.org/10.1096/fj.201901703R
    36. Hao Liu, Meng‐Jing Zhao, Zi‐Ying Wang, Qiao‐Qiao Han, Hai‐Yun Wu, Xiao‐fang Mao, Yong‐Xiang Wang. Involvement of d ‐amino acid oxidase in cerebral ischaemia induced by transient occlusion of the middle cerebral artery in mice. British Journal of Pharmacology 2019, 176 (17) , 3336-3349. https://doi.org/10.1111/bph.14764
    37. Qing Wang, Yuemeng Lv, Jing Pang, Xue Li, Xi Lu, Xiukun Wang, Xinxin Hu, Tongying Nie, Xinyi Yang, Yan Q. Xiong, Jiandong Jiang, Congran Li, Xuefu You. In vitro and in vivo activity of d-serine in combination with β-lactam antibiotics against methicillin-resistant Staphylococcus aureus. Acta Pharmaceutica Sinica B 2019, 9 (3) , 496-504. https://doi.org/10.1016/j.apsb.2019.01.017
    38. Tie Ma, Yin Wu, Beibei Chen, Wenjuan Zhang, Lang Jin, Chenxi Shen, Yazhou Wang, Yonghong Liu. D-Serine Contributes to Seizure Development via ERK Signaling. Frontiers in Neuroscience 2019, 13 https://doi.org/10.3389/fnins.2019.00254
    39. Mary-Anne B. MacKay, Maryana Kravtsenyuk, Rejish Thomas, Nicholas D. Mitchell, Serdar M. Dursun, Glen B. Baker. D-Serine: Potential Therapeutic Agent and/or Biomarker in Schizophrenia and Depression?. Frontiers in Psychiatry 2019, 10 https://doi.org/10.3389/fpsyt.2019.00025
    40. Taiki Nagano, Shunsuke Yamao, Anju Terachi, Hidetora Yarimizu, Haruki Itoh, Ryoko Katasho, Kosuke Kawai, Akio Nakashima, Tetsushi Iwasaki, Ushio Kikkawa, Shinji Kamada. d-amino acid oxidase promotes cellular senescence via the production of reactive oxygen species. Life Science Alliance 2019, 2 (1) , e201800045. https://doi.org/10.26508/lsa.201800045
    41. Bence Szilágyi, Csilla Hargitai, Ádám A. Kelemen, Anita Rácz, György G. Ferenczy, Balázs Volk, György M. Keserű. Synthesis and Biochemical Evaluation of Lid-Open D-Amino Acid Oxidase Inhibitors. Molecules 2019, 24 (2) , 290. https://doi.org/10.3390/molecules24020290
    42. Anat Biegon, Sigal Liraz-Zaltsman, Esther Shohami. Stimulation of N-methyl-D-aspartate receptors by exogenous and endogenous ligands improves outcome of brain injury. Current Opinion in Neurology 2018, 31 (6) , 687-692. https://doi.org/10.1097/WCO.0000000000000612
    43. Loredano Pollegioni, Silvia Sacchi, Giulia Murtas. Human D-Amino Acid Oxidase: Structure, Function, and Regulation. Frontiers in Molecular Biosciences 2018, 5 https://doi.org/10.3389/fmolb.2018.00107
    44. Bence Szilágyi, György G. Ferenczy, György M. Keserű. Drug discovery strategies and the preclinical development of D-amino-acid oxidase inhibitors as antipsychotic therapies. Expert Opinion on Drug Discovery 2018, 13 (10) , 973-982. https://doi.org/10.1080/17460441.2018.1524459
    45. Sigal Liraz-Zaltsman, Barbara Slusher, Dana Atrakchi-Baranes, Kineret Rosenblatt, Yael Friedman Levi, Efrat Kesner, Alcino J. Silva, Anat Biegon, Esther Shohami. Enhancement of Brain d -Serine Mediates Recovery of Cognitive Function after Traumatic Brain Injury. Journal of Neurotrauma 2018, 35 (14) , 1667-1680. https://doi.org/10.1089/neu.2017.5561
    46. Giulia Murtas, Laura Caldinelli, Pamela Cappelletti, Silvia Sacchi, Loredano Pollegioni. Human d -amino acid oxidase: The inactive G183R variant. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 2018, 1866 (7) , 822-830. https://doi.org/10.1016/j.bbapap.2017.12.007
    47. Silvia Sacchi, Pamela Cappelletti, Giulia Murtas. Biochemical Properties of Human D-amino Acid Oxidase Variants and Their Potential Significance in Pathologies. Frontiers in Molecular Biosciences 2018, 5 https://doi.org/10.3389/fmolb.2018.00055
    48. Bence Szilágyi, Péter Kovács, György G. Ferenczy, Anita Rácz, Krisztina Németh, Júlia Visy, Pál Szabó, Janez Ilas, György T. Balogh, Katalin Monostory, István Vincze, Tamás Tábi, Éva Szökő, György M. Keserű. Discovery of isatin and 1H-indazol-3-ol derivatives as d-amino acid oxidase (DAAO) inhibitors. Bioorganic & Medicinal Chemistry 2018, 26 (8) , 1579-1587. https://doi.org/10.1016/j.bmc.2018.02.004
    49. Agnese Chiara Pippione, Irene Maria Carnovale, Davide Bonanni, Marcella Sini, Parveen Goyal, Elisabetta Marini, Klaus Pors, Salvatore Adinolfi, Daniele Zonari, Claudio Festuccia, Weixiao Yuan Wahlgren, Rosmarie Friemann, Renzo Bagnati, Donatella Boschi, Simonetta Oliaro-Bosso, Marco Lucio Lolli. Potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors based on the benzoisoxazole moiety: application of a bioisosteric scaffold hopping approach to flufenamic acid. European Journal of Medicinal Chemistry 2018, 150 , 930-945. https://doi.org/10.1016/j.ejmech.2018.03.040
    50. Zoltán Orgován, György G. Ferenczy, Thomas Steinbrecher, Bence Szilágyi, Dávid Bajusz, György M. Keserű. Validation of tautomeric and protomeric binding modes by free energy calculations. A case study for the structure based optimization of d-amino acid oxidase inhibitors. Journal of Computer-Aided Molecular Design 2018, 32 (2) , 331-345. https://doi.org/10.1007/s10822-018-0097-y
    51. Giulia Murtas, Silvia Sacchi, Mattia Valentino, Loredano Pollegioni. Biochemical Properties of Human D-Amino Acid Oxidase. Frontiers in Molecular Biosciences 2017, 4 https://doi.org/10.3389/fmolb.2017.00088
    52. Alex Ryan, Andrea Baker, Frances Dark, Sharon Foley, Anne Gordon, Sean Hatherill, Stephen Stathis, Sukanta Saha, George Bruxner, Martin Beckman, Drew Richardson, Michael Berk, Olivia Dean, John McGrath, Cadence Working Group, James Scott. The efficacy of sodium benzoate as an adjunctive treatment in early psychosis - CADENCE-BZ: study protocol for a randomized controlled trial. Trials 2017, 18 (1) https://doi.org/10.1186/s13063-017-1908-5
    53. Gianluca Molla. Competitive Inhibitors Unveil Structure/Function Relationships in Human D-Amino Acid Oxidase. Frontiers in Molecular Biosciences 2017, 4 https://doi.org/10.3389/fmolb.2017.00080
    54. Jun Fang Jiang, Juan Qiao, Xiao Yu Mu, Myeong Hee Moon, Li Qi. Fabrication of enzyme reactor utilizing magnetic porous polymer membrane for screening D-Amino acid oxidase inhibitors. Talanta 2017, 165 , 251-257. https://doi.org/10.1016/j.talanta.2016.12.055
    55. Camilo Rojas, Jesse Alt, Nancy A Ator, Heather Wilmoth, Rana Rais, Niyada Hin, Michael DeVivo, Michael Popiolek, Takashi Tsukamoto, Barbara S Slusher. Oral administration of D-alanine in monkeys robustly increases plasma and cerebrospinal fluid levels but experimental D-amino acid oxidase inhibitors had minimal effect. Journal of Psychopharmacology 2016, 30 (9) , 887-895. https://doi.org/10.1177/0269881116652586
    56. Mayu Onozato, Hiromi Nakazawa, Hitomi Hakariya, Miho Shishikura, Chihiro Nagashima, Katsuyuki Ishimaru, Tatsuya Sakamoto, Hideaki Iizuka, Hideaki Ichiba, Takeshi Fukushima. Effect of risperidone on plasma d-serine concentration in rats post-administered with d-serine. Life Sciences 2016, 158 , 98-103. https://doi.org/10.1016/j.lfs.2016.06.021
    57. Dongsheng Xie, Jun Lu, Jin Xie, Junjun Cui, Teng-Fei Li, Yan-Chao Wang, Yuan Chen, Nian Gong, Xin-Yan Li, Lei Fu, Yong-Xiang Wang. Discovery and analgesic evaluation of 8-chloro-1,4-dihydropyrido[2,3- b ]pyrazine-2,3-dione as a novel potent d -amino acid oxidase inhibitor. European Journal of Medicinal Chemistry 2016, 117 , 19-32. https://doi.org/10.1016/j.ejmech.2016.04.017
    58. Camilo Rojas, Jesse Alt, Nancy A Ator, Ajit G Thomas, Ying Wu, Niyada Hin, Krystyna Wozniak, Dana Ferraris, Rana Rais, Takashi Tsukamoto, Barbara S Slusher. D-Amino-Acid Oxidase Inhibition Increases D-Serine Plasma Levels in Mouse But not in Monkey or Dog. Neuropsychopharmacology 2016, 41 (6) , 1610-1619. https://doi.org/10.1038/npp.2015.319
    59. Niyada Hin, Bridget Duvall, James F. Berry, Dana V. Ferraris, Rana Rais, Jesse Alt, Camilo Rojas, Barbara S. Slusher, Takashi Tsukamoto. d-Amino acid oxidase inhibitors based on the 5-hydroxy-1,2,4-triazin-6(1H)-one scaffold. Bioorganic & Medicinal Chemistry Letters 2016, 26 (8) , 2088-2091. https://doi.org/10.1016/j.bmcl.2016.02.068
    60. Megumi Iwasaki, Yoshiyuki Kashiwaguma, Chihiro Nagashima, Mao Izumi, Ayano Uekusa, Sumiko Iwasa, Mayu Onozato, Hideaki Ichiba, Takeshi Fukushima. A high‐performance liquid chromatography assay with a triazole‐bonded column for evaluation of d ‐amino acid oxidase activity. Biomedical Chromatography 2016, 30 (3) , 384-389. https://doi.org/10.1002/bmc.3559
    61. Shuai Ma, Xin-Yan Li, Nian Gong, Yong-Xiang Wang. Contributions of spinal d-amino acid oxidase to chronic morphine-induced hyperalgesia. Journal of Pharmaceutical and Biomedical Analysis 2015, 116 , 131-138. https://doi.org/10.1016/j.jpba.2015.03.021
    62. Ryan T. Terry-Lorenzo, Keiki Masuda, Kohtaroh Sugao, Q. Kevin Fang, Michael A. Orsini, Silvia Sacchi, Loredano Pollegioni. High-Throughput Screening Strategy Identifies Allosteric, Covalent Human D-Amino Acid Oxidase Inhibitor. SLAS Discovery 2015, 20 (10) , 1218-1231. https://doi.org/10.1177/1087057115600413
    63. Pamela Cappelletti, Luciano Piubelli, Giulia Murtas, Laura Caldinelli, Mattia Valentino, Gianluca Molla, Loredano Pollegioni, Silvia Sacchi. Structure–function relationships in human d-amino acid oxidase variants corresponding to known SNPs. Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics 2015, 1854 (9) , 1150-1159. https://doi.org/10.1016/j.bbapap.2015.02.005
    64. Yoshikazu Uto. 1,2-Benzisoxazole compounds: a patent review (2009 – 2014). Expert Opinion on Therapeutic Patents 2015, 25 (6) , 643-662. https://doi.org/10.1517/13543776.2015.1027192
    65. Akiko Matsuura, Yuko Fujita, Masaomi Iyo, Kenji Hashimoto. Effects of sodium benzoate on pre-pulse inhibition deficits and hyperlocomotion in mice after administration of phencyclidine. Acta Neuropsychiatrica 2015, 27 (3) , 159-167. https://doi.org/10.1017/neu.2015.1
    66. M. S. Frasinyuk. Synthesis and Aminomethylation of 3-Substituted 6-Hydroxy-1,2-Benzisoxazoles. Chemistry of Heterocyclic Compounds 2015, 50 (11) , 1616-1623. https://doi.org/10.1007/s10593-014-1631-z
    67. Matildé Le Bail, Magalie Martineau, Silvia Sacchi, Natalia Yatsenko, Inna Radzishevsky, Sandrine Conrod, Karima Ait Ouares, Herman Wolosker, Loredano Pollegioni, Jean-Marie Billard, Jean-Pierre Mothet. Identity of the NMDA receptor coagonist is synapse specific and developmentally regulated in the hippocampus. Proceedings of the National Academy of Sciences 2015, 112 (2) https://doi.org/10.1073/pnas.1416668112
    68. Andreas P. Häring, Philipp Klahn, Martin Jübermann, Fabian Mohr, Stefan F. Kirsch. Gold(I)-catalyzed heterocyclization of β-alkynyl hydroxamic acids: synthesis of isoxazolidin-3-ones. Monatshefte für Chemie - Chemical Monthly 2015, 146 (1) , 119-134. https://doi.org/10.1007/s00706-014-1319-1
    69. Brian R. Tuinema, Sarah A. Reid-Yu, Brian K. Coombes, . Salmonella Evades d -Amino Acid Oxidase To Promote Infection in Neutrophils. mBio 2014, 5 (6) https://doi.org/10.1128/mBio.01886-14
    70. Kanin Wichapong, Arthit Nueangaudom, Somsak Pianwanit, Fumio Tanaka, Sirirat Kokpol. Molecular dynamics simulation, binding free energy calculation and molecular docking of human D-amino acid oxidase (DAAO) with its inhibitors. Molecular Simulation 2014, 40 (14) , 1167-1189. https://doi.org/10.1080/08927022.2013.854892
    71. Dongsheng Xie, Yanchao Wang, Jin Xie, Jun Lu, Junjun Cui, Man Zhang, Lei Fu, Yongxiang Wang. Quinoxaline-2,3-diones: potential d-amino acid oxidase (DAAO) inhibitors. Medicinal Chemistry Research 2014, 23 (11) , 4977-4989. https://doi.org/10.1007/s00044-014-1068-z
    72. Kenji Hashimoto. Targeting of NMDA receptors in new treatments for schizophrenia. Expert Opinion on Therapeutic Targets 2014, 18 (9) , 1049-1063. https://doi.org/10.1517/14728222.2014.934225
    73. Ryan T. Terry-Lorenzo, Lawrence E. Chun, Scott P. Brown, Michele L. R. Heffernan, Q. Kevin Fang, Michael A. Orsini, Loredano Pollegioni, Larry W. Hardy, Kerry L. Spear, Thomas H. Large. Novel human D -amino acid oxidase inhibitors stabilize an active-site lid-open conformation. Bioscience Reports 2014, 34 (4) https://doi.org/10.1042/BSR20140071
    74. Marcello D’Ascenzo, Maria Vittoria Podda, Claudio Grassi. The role of D-serine as co-agonist of NMDA receptors in the nucleus accumbens: relevance to cocaine addiction. Frontiers in Synaptic Neuroscience 2014, 6 https://doi.org/10.3389/fnsyn.2014.00016
    75. Andrea R. Durrant, Uriel Heresco-Levy. D-Serine in Neuropsychiatric Disorders: New Advances. Advances in Psychiatry 2014, 2014 , 1-16. https://doi.org/10.1155/2014/859735
    76. Esther Jortzik, Lihui Wang, Jipeng Ma, Katja Becker. Flavins and Flavoproteins: Applications in Medicine. 2014, 113-157. https://doi.org/10.1007/978-1-4939-0452-5_7
    77. Miho Shishikura, Hitomi Hakariya, Sumiko Iwasa, Takashi Yoshio, Hideaki Ichiba, Kazuko Yorita, Kiyoshi Fukui, Takeshi Fukushima. Evaluation of human D-amino acid oxidase inhibition by anti-psychotic drugs in vitro. BioScience Trends 2014, 8 (3) , 149-154. https://doi.org/10.5582/bst.2014.01034
    78. Silvia Sacchi. D -Serine metabolism: new insights into the modulation of D -amino acid oxidase activity. Biochemical Society Transactions 2013, 41 (6) , 1551-1556. https://doi.org/10.1042/BST20130184
    79. W. Dieb, A. Hafidi. Astrocytes are Involved in Trigeminal Dynamic Mechanical Allodynia. Journal of Dental Research 2013, 92 (9) , 808-813. https://doi.org/10.1177/0022034513498898
    80. Kenji Hashimoto, Berend Malchow, Peter Falkai, Andrea Schmitt. Glutamate modulators as potential therapeutic drugs in schizophrenia and affective disorders. European Archives of Psychiatry and Clinical Neuroscience 2013, 263 (5) , 367-377. https://doi.org/10.1007/s00406-013-0399-y
    81. Mithun Raje, Niyada Hin, Bridget Duvall, Dana V. Ferraris, James F. Berry, Ajit G. Thomas, Jesse Alt, Camilo Rojas, Barbara S. Slusher, Takashi Tsukamoto. Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase. Bioorganic & Medicinal Chemistry Letters 2013, 23 (13) , 3910-3913. https://doi.org/10.1016/j.bmcl.2013.04.062
    82. Mao Horio, Hisashi Mori, Kenji Hashimoto. Is D-Cycloserine a Prodrug for D-Serine in the Brain?. Biological Psychiatry 2013, 73 (12) , e33-e34. https://doi.org/10.1016/j.biopsych.2012.07.013
    83. J.‐M. Billard. Serine racemase as a prime target for age‐related memory deficits. European Journal of Neuroscience 2013, 37 (12) , 1931-1938. https://doi.org/10.1111/ejn.12226
    84. Hongbo He, Amanda H. Mahnke, Sukhjeevan Doyle, Ni Fan, Chih-Chieh Wang, Benjamin J. Hall, Ya-Ping Tang, Fiona M. Inglis, Chu Chen, Jeffrey D. Erickson. Neurodevelopmental Role for VGLUT2 in Pyramidal Neuron Plasticity, Dendritic Refinement, and in Spatial Learning. The Journal of Neuroscience 2012, 32 (45) , 15886-15901. https://doi.org/10.1523/JNEUROSCI.4505-11.2012
    85. John A. Morrow, Robert Gilfillan, Stuart A. Neale. Glutamatergic Approaches for the Treatment of Schizophrenia. 2012, 56-98. https://doi.org/10.1039/9781849734943-00056
    86. Silvia Sacchi, Laura Caldinelli, Pamela Cappelletti, Loredano Pollegioni, Gianluca Molla. Structure–function relationships in human d-amino acid oxidase. Amino Acids 2012, 43 (5) , 1833-1850. https://doi.org/10.1007/s00726-012-1345-4
    87. Masahiro Yamanaka, Yurika Miyoshi, Hiroko Ohide, Kenji Hamase, Ryuichi Konno. d-Amino acids in the brain and mutant rodents lacking d-amino-acid oxidase activity. Amino Acids 2012, 43 (5) , 1811-1821. https://doi.org/10.1007/s00726-012-1384-x
    88. Jin-Lu Huang, Xiao-Ling Chen, Cheng Guo, Yong-Xiang Wang. Contributions of spinal d-amino acid oxidase to bone cancer pain. Amino Acids 2012, 43 (5) , 1905-1918. https://doi.org/10.1007/s00726-012-1390-z
    89. Rana Rais, Ajit G. Thomas, Krystyna Wozniak, Ying Wu, Hanna Jaaro-Peled, Akira Sawa, Christine A. Strick, Sandra J. Engle, Nicholas J. Brandon, Camilo Rojas, Barbara S. Slusher, Takashi Tsukamoto. Pharmacokinetics of Oral d-Serine in d-Amino Acid Oxidase Knockout Mice. Drug Metabolism and Disposition 2012, 40 (11) , 2067-2073. https://doi.org/10.1124/dmd.112.046482
    90. Nian Gong, Yan-Chao Wang, Hui-Li Wang, Ai-Niu Ma, Kenji Hashimoto, Yong-Xiang Wang. Interactions of the potent d-amino acid oxidase inhibitor CBIO with morphine in pain and tolerance to analgesia. Neuropharmacology 2012, 63 (3) , 460-468. https://doi.org/10.1016/j.neuropharm.2012.04.030
    91. Emerson A Nunes, Erin M MacKenzie, David Rossolatos, Jorge Perez-Parada, Glen B Baker, Serdar M Dursun. d -serine and schizophrenia: an update. Expert Review of Neurotherapeutics 2012, 12 (7) , 801-812. https://doi.org/10.1586/ern.12.65
    92. Pierre Pernot, Caroline Maucler, Yannick Tholance, Natalia Vasylieva, Gabriel Debilly, Loredano Pollegioni, Raymond Cespuglio, Stéphane Marinesco. d-Serine diffusion through the blood–brain barrier: Effect on d-serine compartmentalization and storage. Neurochemistry International 2012, 60 (8) , 837-845. https://doi.org/10.1016/j.neuint.2012.03.008
    93. Yoshikazu Uto. Benzisoxazole analogs as glycogen synthase activators, a patent evaluation (WO2011057956). Expert Opinion on Therapeutic Patents 2012, 22 (6) , 701-707. https://doi.org/10.1517/13543776.2012.681303
    94. Jin‐Miao Lu, Nian Gong, Yan‐Chao Wang, Yong‐Xiang Wang. d ‐Amino acid oxidase‐mediated increase in spinal hydrogen peroxide is mainly responsible for formalin‐induced tonic pain. British Journal of Pharmacology 2012, 165 (6) , 1941-1955. https://doi.org/10.1111/j.1476-5381.2011.01680.x
    95. Taku Nagai, Jinghua Yu, Yuko Kitahara, Toshitaka Nabeshima, Kiyofumi Yamada. D-Serine Ameliorates Neonatal PolyI:C Treatment^|^ndash;Induced Emotional and Cognitive Impairments in Adult Mice. Journal of Pharmacological Sciences 2012, 120 (3) , 213-227. https://doi.org/10.1254/jphs.12142FP
    96. Jesse Alt, Camilo Rojas, Krystyna Wozniak, Ying Wu, Dana Ferraris, Takashi Tsukamoto, Barbara Slusher. Development of a high-throughput method for the determination of pharmacological levels of plasma d-serine. Analytical Biochemistry 2011, 419 (2) , 106-109. https://doi.org/10.1016/j.ab.2011.08.018
    97. Luca F. Frattini, Luciano Piubelli, Silvia Sacchi, Gianluca Molla, Loredano Pollegioni. Is rat an appropriate animal model to study the involvement of d ‐serine catabolism in schizophrenia? insights from characterization of d ‐amino acid oxidase. The FEBS Journal 2011, 278 (22) , 4362-4373. https://doi.org/10.1111/j.1742-4658.2011.08354.x
    98. Jos H.M. Lange, Jennifer Venhorst, Maria J.P. van Dongen, Jurjen Frankena, Firas Bassissi, Natasja M.W.J. de Bruin, Cathaline den Besten, Stephanie B.A. de Beer, Chris Oostenbrink, Natalia Markova, Chris G. Kruse. Biophysical and physicochemical methods differentiate highly ligand-efficient human D-amino acid oxidase inhibitors. European Journal of Medicinal Chemistry 2011, 46 (10) , 4808-4819. https://doi.org/10.1016/j.ejmech.2011.04.023
    99. Christine A. Strick, Cheryl Li, Liam Scott, Brian Harvey, Mihály Hajós, Stefanus J. Steyn, Mary A. Piotrowski, Larry C. James, James T. Downs, Brian Rago, Stacey L. Becker, Ayman El-Kattan, Youfen Xu, Alan H. Ganong, F. David Tingley, Andres D. Ramirez, Patricia A. Seymour, Victor Guanowsky, Mark J. Majchrzak, Carol B. Fox, Christopher J. Schmidt, Allen J. Duplantier. Modulation of NMDA receptor function by inhibition of d-amino acid oxidase in rodent brain. Neuropharmacology 2011, 61 (5-6) , 1001-1015. https://doi.org/10.1016/j.neuropharm.2011.06.029
    100. Stanisław Ryng, Michał Zimecki, Aneta Jezierska-Mazzarello, Jarosław J. Panek, Marcin Mączyński, Tadeusz Głowiak, Wanda Sawka-Dobrowolska, Aleksander Koll. A complex study of 5-amino-3-methyl-4-[2-(5-amino-1,3,4-oxadiazolo)]-isoxazole monohydrate: A new low-molecular-weight immune response modifier. Journal of Molecular Structure 2011, 999 (1-3) , 60-67. https://doi.org/10.1016/j.molstruc.2011.05.031
    Load all citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect