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Literature DB >> 23683589

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

Mithun Raje¹, Niyada Hin, Bridget Duvall, Dana V Ferraris, James F Berry, Ajit G Thomas, Jesse Alt, Camilo Rojas, Barbara S Slusher, Takashi Tsukamoto.

Abstract

A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors.

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Year: 2013 PMID： 23683589 PMCID： PMC3678123 DOI： 10.1016/j.bmcl.2013.04.062

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

13 in total

1. D-AMINO ACID OXIDASE. I. DISSOCIATION AND RECOMBINATION OF THE HOLOENZYME.

Authors: M DIXON; K KLEPPE
Journal: Biochim Biophys Acta Date: 1965-03-22

2. D-Amino acid oxidase-mediated increase in spinal hydrogen peroxide is mainly responsible for formalin-induced tonic pain.

Authors: Jin-Miao Lu; Nian Gong; Yan-Chao Wang; Yong-Xiang Wang
Journal: Br J Pharmacol Date: 2012-03 Impact factor: 8.739

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. Structural basis of D-DOPA oxidation by D-amino acid oxidase: alternative pathway for dopamine biosynthesis.

Authors: Tomoya Kawazoe; Hideaki Tsuge; Takahito Imagawa; Kenji Aki; Seiki Kuramitsu; Kiyoshi Fukui
Journal: Biochem Biophys Res Commun Date: 2007-02-08 Impact factor: 3.575

5. 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.

Authors: Tomoya Kawazoe; Hideaki Tsuge; Mirella S Pilone; Kiyoshi Fukui
Journal: Protein Sci Date: 2006-11-06 Impact factor: 6.725

6. 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

7. 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

8. The Therapeutic Potential of D-Amino Acid Oxidase (DAAO) Inhibitors.

Authors: Sean M Smith; Jason M Uslaner; Peter H Hutson
Journal: Open Med Chem J Date: 2010-05-27

9. 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

10. 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

7 in total

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

1. D-AMINO ACID OXIDASE. I. DISSOCIATION AND RECOMBINATION OF THE HOLOENZYME.

2. D-Amino acid oxidase-mediated increase in spinal hydrogen peroxide is mainly responsible for formalin-induced tonic pain.

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

4. Structural basis of D-DOPA oxidation by D-amino acid oxidase: alternative pathway for dopamine biosynthesis.

5. 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.

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

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

8. The Therapeutic Potential of D-Amino Acid Oxidase (DAAO) Inhibitors.

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

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

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

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

Review 3. Competitive Inhibitors Unveil Structure/Function Relationships in Human D-Amino Acid Oxidase.

Review 4. Human D-Amino Acid Oxidase: Structure, Function, and Regulation.

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

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

7. Modulating D-amino acid oxidase (DAAO) substrate specificity through facilitated solvent access.