Agonist responses of (R)- and (S)-3-fluoro-gamma-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA(C) receptors

Izumi Yamamoto; Gildas P. Deniau; Navnath Gavande; Mary Chebib; Graham A. R. Johnston; David O'Hagan

doi:10.1039/c1cc12141c

Agonist responses of (R)- and (S)-3-fluoro-gamma-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA(C) receptors

Izumi Yamamoto, Gildas P. Deniau, Navnath Gavande, Mary Chebib, Graham A. R. Johnston, David O'Hagan^*

^*Corresponding author for this work

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

Abstract

The enantiomers of 3F-GABA were evaluated on GABA(C) receptors. Both enantiomers were agonists, with the (R)-enantiomer being an order of magnitude more potent. This result is consistent with a folded binding mode for GABA, a conclusion which suggests a different binding mode to that found in the related but pharmacologically distinct GABA(A) receptors.

Original language	English
Pages (from-to)	7956-7958
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	28
DOIs	https://doi.org/10.1039/c1cc12141c
Publication status	Published - 2011

Keywords

ANTAGONISTS
PHARMACOLOGY
LIGAND
X-RAY-STRUCTURE
CYCLOPENTENE
CONFORMATION
ANALOGS
MEDICINAL CHEMISTRY
FLUORINE
GATED ION-CHANNEL

Access to Document

10.1039/c1cc12141c

Cite this

@article{6c44d6bd5d684dd3b94f26d6f85763f8,

title = "Agonist responses of (R)- and (S)-3-fluoro-gamma-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA(C) receptors",

abstract = "The enantiomers of 3F-GABA were evaluated on GABA(C) receptors. Both enantiomers were agonists, with the (R)-enantiomer being an order of magnitude more potent. This result is consistent with a folded binding mode for GABA, a conclusion which suggests a different binding mode to that found in the related but pharmacologically distinct GABA(A) receptors.",

keywords = "ANTAGONISTS, PHARMACOLOGY, LIGAND, X-RAY-STRUCTURE, CYCLOPENTENE, CONFORMATION, ANALOGS, MEDICINAL CHEMISTRY, FLUORINE, GATED ION-CHANNEL",

author = "Izumi Yamamoto and Deniau, {Gildas P.} and Navnath Gavande and Mary Chebib and Johnston, {Graham A. R.} and David O'Hagan",

year = "2011",

doi = "10.1039/c1cc12141c",

language = "English",

volume = "47",

pages = "7956--7958",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "28",

}

TY - JOUR

T1 - Agonist responses of (R)- and (S)-3-fluoro-gamma-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA(C) receptors

AU - Yamamoto, Izumi

AU - Deniau, Gildas P.

AU - Gavande, Navnath

AU - Chebib, Mary

AU - Johnston, Graham A. R.

AU - O'Hagan, David

PY - 2011

Y1 - 2011

N2 - The enantiomers of 3F-GABA were evaluated on GABA(C) receptors. Both enantiomers were agonists, with the (R)-enantiomer being an order of magnitude more potent. This result is consistent with a folded binding mode for GABA, a conclusion which suggests a different binding mode to that found in the related but pharmacologically distinct GABA(A) receptors.

AB - The enantiomers of 3F-GABA were evaluated on GABA(C) receptors. Both enantiomers were agonists, with the (R)-enantiomer being an order of magnitude more potent. This result is consistent with a folded binding mode for GABA, a conclusion which suggests a different binding mode to that found in the related but pharmacologically distinct GABA(A) receptors.

KW - ANTAGONISTS

KW - PHARMACOLOGY

KW - LIGAND

KW - X-RAY-STRUCTURE

KW - CYCLOPENTENE

KW - CONFORMATION

KW - ANALOGS

KW - MEDICINAL CHEMISTRY

KW - FLUORINE

KW - GATED ION-CHANNEL

U2 - 10.1039/c1cc12141c

DO - 10.1039/c1cc12141c

M3 - Article

SN - 1359-7345

VL - 47

SP - 7956

EP - 7958

JO - Chemical Communications

JF - Chemical Communications

IS - 28

ER -

Agonist responses of (R)- and (S)-3-fluoro-gamma-aminobutyric acids suggest an enantiomeric fold for GABA binding to GABA(C) receptors

Abstract

Keywords

Access to Document

Fingerprint

Cite this