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

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

doi:10.1016/j.bmcl.2013.04.062

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

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

School of Medicine

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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.

Original language	English (US)
Pages (from-to)	3910-3913
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	13
DOIs	https://doi.org/10.1016/j.bmcl.2013.04.062
State	Published - Jul 1 2013

Keywords

Flavoenzyme
Kojic acid
Schizophrenia
d-Amino acid oxidase

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2013.04.062

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title = "Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase",

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.",

keywords = "Flavoenzyme, Kojic acid, Schizophrenia, d-Amino acid oxidase",

author = "Mithun Raje and Niyada Hin and Bridget Duvall and Ferraris, {Dana V.} and Berry, {James F.} and Thomas, {Ajit G.} and Jesse Alt and Camilo Rojas and Slusher, {Barbara S.} and Takashi Tsukamoto",

note = "Funding Information: This work was in part supported by National Institutes of Health ( R01MH091387 to T.T.) and the Johns Hopkins Brain Science Institute NeuroTranslational Drug Discovery program . ",

year = "2013",

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doi = "10.1016/j.bmcl.2013.04.062",

language = "English (US)",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase

AU - Raje, Mithun

AU - Hin, Niyada

AU - Duvall, Bridget

AU - Ferraris, Dana V.

AU - Berry, James F.

AU - Thomas, Ajit G.

AU - Alt, Jesse

AU - Rojas, Camilo

AU - Slusher, Barbara S.

AU - Tsukamoto, Takashi

N1 - Funding Information: This work was in part supported by National Institutes of Health ( R01MH091387 to T.T.) and the Johns Hopkins Brain Science Institute NeuroTranslational Drug Discovery program .

PY - 2013/7/1

Y1 - 2013/7/1

N2 - 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.

AB - 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.

KW - Flavoenzyme

KW - Kojic acid

KW - Schizophrenia

KW - d-Amino acid oxidase

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JF - Bioorganic and Medicinal Chemistry Letters

IS - 13

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

Abstract

Keywords

ASJC Scopus subject areas

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