Bioorg Med Chem. 2010 Aug 15;18(16):6089-98. Epub 2010 Jun 25.

A new metabotropic glutamate receptor agonist with in vivo anti-allodynic activity.

Stanley NJ, Hutchinson MR, Kvist T, Nielsen B, Mathiesen JM, Bräuner-Osborne H, Avery TD, Tiekink ER, Pedersen DS, Irvine RJ, Abell AD, Taylor DK.

Source

Discipline of Chemistry, The University of Adelaide, Adelaide, Australia.

Abstract

As part of the vital search towards improved therapeutic agents for the treatment of neuropathic pain, the central nervous system glutamate receptors have become a major focus of research. Outlined herein are the syntheses of two new biologically active 3'-cycloalkyl-substituted carboxycyclopropylglycines, utilizing novel synthetic chemistry. The reaction between substituted 1,2-dioxines and an aminophosphonate furnished the cyclopropane core in a single step with all required stereochemistry of pendant groups. In vitro binding assays at metabotropic glutamate receptors revealed selective activity. In vivo testing in a rodent model of neuropathic pain indicated one amino acid significantly and dose-dependently decreased mechanical allodynia.

PMID:: 20638290; [PubMed - indexed for MEDLINE]

LinkOut - more resources

Full Text Sources

Supplemental Content

Save items

Related citations in PubMed

Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist. [J Med Chem. 1996]
Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist.
Pellicciari R, Marinozzi M, Natalini B, Costantino G, Luneia R, Giorgi G, Moroni F, Thomsen C. J Med Chem. 1996 May 24; 39(11):2259-69.
Group II and group III metabotropic glutamate receptor agonists depress synaptic transmission in the rat spinal cord dorsal horn. [Neuroscience. 2000]
Group II and group III metabotropic glutamate receptor agonists depress synaptic transmission in the rat spinal cord dorsal horn.
Gerber G, Zhong J, Youn D, Randic M. Neuroscience. 2000; 100(2):393-406.
Group III metabotropic glutamate receptors inhibit hyperalgesia in animal models of inflammation and neuropathic pain. [Pain. 2008]
Group III metabotropic glutamate receptors inhibit hyperalgesia in animal models of inflammation and neuropathic pain.
Goudet C, Chapuy E, Alloui A, Acher F, Pin JP, Eschalier A. Pain. 2008 Jul; 137(1):112-24. Epub 2007 Sep 27.
Analgesic effects of the selective group II (mGlu2/3) metabotropic glutamate receptor agonists LY379268 and LY389795 in persistent and inflammatory pain models after acute and repeated dosing. [Neuropharmacology. 2005]
Analgesic effects of the selective group II (mGlu2/3) metabotropic glutamate receptor agonists LY379268 and LY389795 in persistent and inflammatory pain models after acute and repeated dosing.
Jones CK, Eberle EL, Peters SC, Monn JA, Shannon HE. Neuropharmacology. 2005; 49 Suppl 1:206-18.
Review Phenylglycine derivatives as antagonists of metabotropic glutamate receptors. [Trends Pharmacol Sci. 1994]
Review Phenylglycine derivatives as antagonists of metabotropic glutamate receptors.
Watkins J, Collingridge G. Trends Pharmacol Sci. 1994 Sep; 15(9):333-42.

See reviews... See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
BioAssay
PubChem BioAssay experiments on the biological activities of small molecules that cite the current articles. The depositors of BioAssay data provide these references.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.

Recent activity

Clear Turn Off Turn On

A new metabotropic glutamate receptor agonist with in vivo anti-allodynic activi...
A new metabotropic glutamate receptor agonist with in vivo anti-allodynic activity.
Bioorg Med Chem. 2010 Aug 15 ;18(16):6089-98. Epub 2010 Jun 25 .

PubMed
Protein-driven membrane stresses in fusion and fission.
Protein-driven membrane stresses in fusion and fission.
Trends Biochem Sci. 2010 Dec ;35(12):699-706. Epub 2010 Jul 16 .

PubMed
Assessing risk factors for transmission of infection.
Assessing risk factors for transmission of infection.
Am J Epidemiol. 1991 Jun 15 ;133(12):1199-209.

PubMed
An orally bioavailable positive allosteric modulator of the mGlu4 receptor with ...
An orally bioavailable positive allosteric modulator of the mGlu4 receptor with efficacy in an animal model of motor dysfunction.
Bioorg Med Chem Lett. 2010 Aug 15 ;20(16):4901-5. Epub 2010 Jun 25 .

PubMed
Autoerotic death. A definition.
Autoerotic death. A definition.
Am J Forensic Med Pathol. 1991 Mar ;12(1):74-6.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to:

A new metabotropic glutamate receptor agonist with in vivo anti-allodynic activity.

Source

Abstract

Publication Types, MeSH Terms, Substances

Publication Types

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Other Literature Sources

Chemical Information

Education

Medical

Molecular Biology Databases

Supplemental Content

Save items

Related citations in PubMed

Related information

Recent activity

Simple NCBI Directory

Getting Started

Resources

Popular

Featured

NCBI Information