Structure-guided design, synthesis and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands

Yoko Beniyama; Kenji Matsuno; Hiroyuki Miyachi

doi:10.1016/j.bmcl.2013.01.054

Structure-guided design, synthesis and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands

Yoko Beniyama, Kenji Matsuno, Hiroyuki Miyachi

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

20 Citations (Scopus)

Abstract

We designed a series of pyrazole-based carboxylic acids as candidate ligands of heart fatty acid binding protein (H-FABP, or FABP3), based on a comparison of the X-ray crystallographic structures of adipocyte fatty acid binding protein (FABP4)-selective inhibitor (BMS309403) complex and FABP3-elaidic acid complex. Some of the synthesized compounds exhibited dual FABP3/4 ligand activity, and some exhibited selectivity for FABP3.

Original language	English
Pages (from-to)	1662-1666
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2013.01.054
Publication status	Published - Mar 15 2013
Externally published	Yes

Keywords

FABP3
Heart fatty acid binding protein
Pyrazole
Structural design

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.2013.01.054

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title = "Structure-guided design, synthesis and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands",

abstract = "We designed a series of pyrazole-based carboxylic acids as candidate ligands of heart fatty acid binding protein (H-FABP, or FABP3), based on a comparison of the X-ray crystallographic structures of adipocyte fatty acid binding protein (FABP4)-selective inhibitor (BMS309403) complex and FABP3-elaidic acid complex. Some of the synthesized compounds exhibited dual FABP3/4 ligand activity, and some exhibited selectivity for FABP3.",

keywords = "FABP3, Heart fatty acid binding protein, Pyrazole, Structural design",

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AU - Matsuno, Kenji

AU - Miyachi, Hiroyuki

N1 - Funding Information: This work was supported in part by the Drug Discovery for Intractable Infectious Diseases Project, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, the Uehara Memorial Foundation, the Tokyo Biochemical Research Foundation (TBRF), and the Okayama Foundation for Science and Technology (OFST).

PY - 2013/3/15

Y1 - 2013/3/15

N2 - We designed a series of pyrazole-based carboxylic acids as candidate ligands of heart fatty acid binding protein (H-FABP, or FABP3), based on a comparison of the X-ray crystallographic structures of adipocyte fatty acid binding protein (FABP4)-selective inhibitor (BMS309403) complex and FABP3-elaidic acid complex. Some of the synthesized compounds exhibited dual FABP3/4 ligand activity, and some exhibited selectivity for FABP3.

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KW - FABP3

KW - Heart fatty acid binding protein

KW - Pyrazole

KW - Structural design

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Structure-guided design, synthesis and in vitro evaluation of a series of pyrazole-based fatty acid binding protein (FABP) 3 ligands

Abstract

Keywords

ASJC Scopus subject areas

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