Literature DB >> 25408840

Structure-Metabolism Relationships in the Glucuronidation of d-Amino Acid Oxidase Inhibitors.

Sarah C Zimmermann1, Rana Rais1, Jesse Alt1, Caitlin Burzynski2, Barbara S Slusher1, Takashi Tsukamoto1.   

Abstract

Representative d-amino acid oxidase (DAAO) inhibitors were subjected to in vitro liver microsomal stability tests in the absence or presence of uridine diphosphate glucuronic acid (UDPGA). While carboxylate-based DAAO inhibitors displayed little glucuronidation, most DAAO inhibitors containing α-hydroxycarbonyl moiety exhibited nearly complete glucuronidation within 30 min. The one exception was 6-[2-(3,5-difluorophenyl)ethyl]-4-hydroxypyridazin-3(2H)-one 10, which exhibited some degree of resistance to glucuronidation by liver microsomes from mice, rats, and humans.

Entities:  

Keywords:  d-amino acid oxidase (DAAO); drug metabolism; glucuronidation

Year:  2014        PMID： 25408840      PMCID： PMC4233358          DOI： 10.1021/ml500335z

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  15 in total

1.  Biophysical and physicochemical methods differentiate highly ligand-efficient human D-amino acid oxidase inhibitors.

Authors:  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
Journal:  Eur J Med Chem       Date:  2011-05-13       Impact factor: 6.514

2.  Strategies for the modulation of phase II metabolism in a series of PKCε inhibitors.

Authors:  Jeremy J Clemens; Timothy Coon; Brett B Busch; Juliana L Asgian; Sarah Hudson; Andreas Termin; Tina B Flores; Dao Tran; Peggy Chiang; Sam Sperry; Ray Gross; Jeffrey Abt; Roger Heim; Sandra Lechner; Heather Twin; John Studley; Guy Brenchley; Philip N Collier; Francoise Pierard; Andrew Miller; Chau Mak; Vadims Dvornikovs; Juan-Miguel Jimenez; Dean Stamos
Journal:  Bioorg Med Chem Lett       Date:  2014-06-05       Impact factor: 2.823

Review 3.  Recent advances in the discovery of D-amino acid oxidase inhibitors and their therapeutic utility in schizophrenia.

Authors:  Dana V Ferraris; Takashi Tsukamoto
Journal:  Curr Pharm Des       Date:  2011       Impact factor: 3.116

4.  The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors.

Authors:  Tim Sparey; Pravien Abeywickrema; Sarah Almond; Nick Brandon; Noel Byrne; Alister Campbell; Pete H Hutson; Marlene Jacobson; Brian Jones; Sanjeev Munshi; Danette Pascarella; Andrew Pike; G Sridhar Prasad; Nancy Sachs; Melanie Sakatis; Vinod Sardana; Shankar Venkatraman; Mary Beth Young
Journal:  Bioorg Med Chem Lett       Date:  2008-04-13       Impact factor: 2.823

5.  Synthesis and SAR of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones as Inhibitors of D-Amino Acid Oxidase.

Authors:  James F Berry; Dana V Ferraris; Bridget Duvall; Niyada Hin; Rana Rais; Jesse Alt; Ajit G Thomas; Camilo Rojas; Kenji Hashimoto; Barbara S Slusher; Takashi Tsukamoto
Journal:  ACS Med Chem Lett       Date:  2012-09-16       Impact factor: 4.345

6.  Synthesis of kojic acid derivatives as secondary binding site probes of D-amino acid oxidase.

Authors:  Mithun Raje; Niyada Hin; Bridget Duvall; Dana V Ferraris; James F Berry; Ajit G Thomas; Jesse Alt; Camilo Rojas; Barbara S Slusher; Takashi Tsukamoto
Journal:  Bioorg Med Chem Lett       Date:  2013-05-01       Impact factor: 2.823

7.  Pharmacokinetics of oral D-serine in D-amino acid oxidase knockout mice.

Authors:  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
Journal:  Drug Metab Dispos       Date:  2012-07-26       Impact factor: 3.922

8.  Identification of novel D-amino acid oxidase inhibitors by in silico screening and their functional characterization in vitro.

Authors:  Masumi Katane; Naoko Osaka; Satsuki Matsuda; Kazuhiro Maeda; Tomonori Kawata; Yasuaki Saitoh; Masae Sekine; Takemitsu Furuchi; Issei Doi; Shuichi Hirono; Hiroshi Homma
Journal:  J Med Chem       Date:  2013-02-22       Impact factor: 7.446

9.  Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors.

Authors:  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; Lei Zhang
Journal:  J Med Chem       Date:  2009-06-11       Impact factor: 7.446

10.  In vitro and in vivo pharmacological profile of AS057278, a selective d-amino acid oxidase inhibitor with potential anti-psychotic properties.

Authors:  Tiziana Adage; Anne-Cécile Trillat; Anna Quattropani; Dominique Perrin; Laurent Cavarec; Jeffrey Shaw; Oxana Guerassimenko; Claudio Giachetti; Béatrice Gréco; Ilya Chumakov; Serge Halazy; Arthur Roach; Paola Zaratin
Journal:  Eur Neuropsychopharmacol       Date:  2007-08-02       Impact factor: 4.600
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  3 in total

1.  D-Amino acid oxidase inhibitors based on the 5-hydroxy-1,2,4-triazin-6(1H)-one scaffold.

Authors:  Niyada Hin; Bridget Duvall; James F Berry; Dana V Ferraris; Rana Rais; Jesse Alt; Camilo Rojas; Barbara S Slusher; Takashi Tsukamoto
Journal:  Bioorg Med Chem Lett       Date:  2016-02-23       Impact factor: 2.823

2.  Molecular modeling studies of 1,2,4-triazine derivatives as novel h-DAAO inhibitors by 3D-QSAR, docking and dynamics simulations.

Authors:  Ping Ping Qian; Shuai Wang; Kai Rui Feng; Yu Jie Ren
Journal:  RSC Adv       Date:  2018-04-17       Impact factor: 4.036

3.  6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel D-Amino Acid Oxidase Inhibitors.

Authors:  Niyada Hin; Bridget Duvall; Dana Ferraris; Jesse Alt; Ajit G Thomas; Rana Rais; Camilo Rojas; Ying Wu; Krystyna M Wozniak; Barbara S Slusher; Takashi Tsukamoto
Journal:  J Med Chem       Date:  2015-09-03       Impact factor: 7.446
  3 in total

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