(RS)-4-Carboxyphenylglycine - CAS 7292-81-1
Category: Inhibitor
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Molecular Formula:
C9H9NO4
Molecular Weight:
195.17
COA:
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Targets:
Others
Description:
(RS)-4-Carboxyphenylglycine has been found to be a broad spectrum EAA ligand.
Purity:
≥99% by HPLC
Appearance:
White Solid
Synonyms:
α-Amino-4-carboxybenzeneacetic Acid; (±)-α-Amino-4-carboxy-benzeneacetic Acid
MSDS:
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InChIKey:
VTMJKPGFERYGJF-UHFFFAOYSA-N
InChI:
InChI=1S/C9H9NO4/c10-7(9(13)14)5-1-3-6(4-2-5)8(11)12/h1-4,7H,10H2,(H,11,12)(H,13,14)
Canonical SMILES:
C1=CC(=CC=C1C(C(=O)O)N)C(=O)O
1.The function of metabotropic excitatory amino acid receptors in synaptic transmission in the thalamus: studies with novel phenylglycine antagonists.
Salt TE;Eaton SA Neurochem Int. 1994 May;24(5):451-8.
The phenylglycines 3-hydroxyphenylglycine, 4-carboxy-3-hydroxy-phenylglycine (4C3HPG), 4-carboxyphenylglycine (4CPG) and alpha-methyl-4-carboxyphenylglycine (MCPG) were evaluated as putative selective antagonists of metabotropic glutamate receptors on single neurones of the ventrobasal thalamus of rats, with a view to using these compounds as tools to elucidate synaptic mechanisms in this brain area. The S-isomers of the latter three compounds were found to reduce excitations evoked by iontophoretically applied 1S,3R-ACPD, but not those evoked by ionotropic excitatory amino receptor agonists. When the antagonists were tested against sensory synaptic responses of ventrobasal neurones, it was found that responses evoked by noxious thermal stimulation of the peripheral receptive field were reduced in parallel with responses to 1S,3R-ACPD. In contrast, responses of neurones evoked by non-noxious (air-jet) stimuli were not reduced by the phenylglycine antagonists and 4C3HPG was found to enhance such responses, possibly by a presynaptic action mediated via mGluR2 receptors. The reductions of nociceptive responses are discussed in the context of antagonism of mGluR1 receptors, which are known to be numerous in the thalamus and located on post-synaptic dendrites.
2.Group I metabotropic glutamate receptors mediate phospholipase D stimulation in rat cultured astrocytes.
Servitja JM;Masgrau R;Sarri E;Picatoste F J Neurochem. 1999 Apr;72(4):1441-7.
We have studied the activation of phospholipase D (PLD) by glutamate in rat cultured astrocytes by measuring the PLD-catalyzed formation of [32P]phosphatidylbutanol in [32P]Pi-prelabeled cells, stimulated in the presence of butanol. Glutamate elicited the activation of PLD in cortical astrocytes but not in cortical neurons, whereas similar glutamate activation of phosphoinositide phospholipase C was found in both astrocytes and neurons. The extent of PLD stimulation by glutamate was similar in astrocytes from brain cortex and hippocampus, but no effect was found in cerebellar astrocytes. In cortical astrocytes, the glutamate response was insensitive to antagonists of ionotropic glutamate receptors and was reproduced by agonists of metabotropic glutamate receptors (mGluRs) with a rank order of agonist potency similar to that reported for group I mGluR-mediated phosphoinositide phospholipase activation [quisqualate > (S)-3,5-dihydroxyphenylglycine > (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid]. The response to (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid was inhibited by the mGluR antagonist (S)-alpha-methyl-4-carboxyphenylglycine and, less potently, by 1-aminoindan-1,5-dicarboxylic acid and 4-carboxyphenylglycine, two antagonists of group I mGluRs that display higher potency on mGluR1 than on mGluR5.
3.Intrathecal metabotropic glutamate receptor antagonists do not decrease mechanical hyperalgesia in a rat model of postoperative pain.
Zahn PK;Brennan TJ Anesth Analg. 1998 Dec;87(6):1354-9.
Spinal metabotropic glutamate receptors (mGluR) have been implicated in hyperalgesia after injury. The purpose of this study was to examine the effects of intrathecal (IT) mGluR antagonists on mechanical hyperalgesia in a rat model of human postoperative pain. The hindpaw withdrawal threshold to punctate stimulation using von Frey filaments and the response frequency to a nonpunctate stimulus applied directly to the wound were also measured. The effects of 1T (+)-alpha-methyl-carboxyphenylglycine ([+]-MCPG), (S)-carboxyphenylglycine ([S]-4-CPG), (RS)-alphacyclopropyl-4-phosphonophenylglycine ([RS]-CPPG) and L-2-amino-3-phosphonopropionic acid (L-AP3) on incision-induced mechanical hyperalgesia were examined. The withdrawal thresholds to punctate stimuli were not different from vehicle treatment after the IT administration of (+)-MCPG (100, 500 nmol), (S)4CPG (30, 100 nmol), (RS)-CPPG (100, 500 nmol), or L-AP3 (1, 30, 100 nmol). None of the IT mGluR antagonists decreased the response frequency to the nonpunctate stimulus. The largest dose of (+)-MCPG produced sufficient receptor antagonism because spontaneous nociceptive behaviors caused by the IT administration of a mGluR agonist were reduced.
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CAS 7292-81-1 (RS)-4-Carboxyphenylglycine

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