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

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

doi:10.1039/C1CC12141C

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

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

Author affiliations

* Corresponding authors

^a Faculty of Pharmacy, University of Sydney, NSW, Australia

^b University of St Andrews, EASTChem School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, UK
E-mail: do1@st-andrews.ac.uk
Fax: (+44)1334 463800
Tel: (+44)1334 467171

^c Adrien Albert Laboratory of Medicinal Chemistry, Department of Pharmacology DO6, University of Sydney, NSW, Australia

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.

This article is part of the themed collection: RACI100: Celebrating Australian Chemistry

Download options Please wait...

Supplementary files

Supplementary information PDF (243K)

Article information

DOI: https://doi.org/10.1039/C1CC12141C
Article type: Communication
Submitted: 14 apr 2011
Accepted: 25 may 2011
First published: 13 iyn 2011

Download Citation

Chem. Commun., 2011,47, 7956-7958

Permissions

Request permissions

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

I. Yamamoto, G. P. Deniau, N. Gavande, M. Chebib, G. A. R. Johnston and D. O'Hagan, Chem. Commun., 2011, 47, 7956 DOI: 10.1039/C1CC12141C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications