(S)-4-Carboxyphenylglycine - CAS 134052-73-6
Category: Inhibitor
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Molecular Formula:
C9H9NO4
Molecular Weight:
195.17
COA:
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Targets:
mGluR
Description:
(S)-4-Carboxyphenylglycine has been found to be a competitive group I metabotropic glutamate receptor antagonist(S)-4-Carboxyphenylglycine has been found to be a competitive group I metabotropic glutamate receptor antagonist and selective for mGluR1.
Purity:
≥99% by HPLC
Appearance:
Off-white Solid
Synonyms:
(S)-4CPG; (S)-4C-PG; (S)-4-Carboxyphenylglycine; (S)-4C-PG; (αS)-α-Amino-4-carboxybenzeneacetic Acid
MSDS:
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InChIKey:
VTMJKPGFERYGJF-ZETCQYMHSA-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)/t7-/m0/s1
Canonical SMILES:
C1=CC(=CC=C1C(C(=O)O)N)C(=O)O
1.Functional expression of system x(c)- is upregulated by asbestos but not crystalline silica in murine macrophages.
Pfau JC;Seib T;Overocker JJ;Roe J;Ferro AS Inhal Toxicol. 2012 Jul;24(8):476-85. doi: 10.3109/08958378.2012.689782. Epub 2012 Jun 14.
CONTEXT: ;Inhalation of asbestos or silica is associated with chronic and progressive diseases, including fibrosis, cancer, and increased risk of systemic autoimmunity. Because there is a need for treatment options for these diseases, a better understanding of their mechanistic etiologies is essential. While oxidative stress in macrophages is an early consequence of these exposures, it may also serve as a signaling mechanism involved in downstream immune dysregulation. The system x(c)(-) exchange protein is induced by oxidative stress, and exchanges equimolor levels of extracellular cystine for intracellular glutamate. Cystine is subsequently reduced to cysteine, the rate-limiting precursor for glutathione synthesis.;OBJECTIVE: ;As the primary transporter responsible for cystine/glutamate exchange on macrophages, system x(c)- was hypothesized to be inducible in response to asbestos and silica, and to increase viability through protection from oxidative stress.;RESULTS: ;When challenged with amphibole asbestos, but not crystalline silica, RAW 264.7 macrophages increased expression of xCT and the rate of cystine/glutamate exchange in sodium-free conditions. This upregulation was prevented with N-acetylcysteine, implicating oxidative stress.
2.Dual modulation of excitatory synaptic transmission by agonists at group I metabotropic glutamate receptors in the rat spinal dorsal horn.
Zhong J;Gerber G;Kojić L;Randić M Brain Res. 2000 Dec 29;887(2):359-77.
The effects of group I metabotropic glutamate (mGlu) receptors on excitatory transmission in the rat dorsal horn, but mostly substantia gelatinosa, neurons were investigated using conventional intracellular recording in slices. The broad spectrum mGlu receptor agonist (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid (1S, 3R-ACPD), the group I mGlu receptor selective agonist (S)-3, 5-dihydroxyphenylglycine (DHPG), and the selective mGlu subtype 5 agonist (RS)-2-chloro-5-hydroxyphenylglycine (CHPG), all induce long-lasting depression of A primary afferent fibers-mediated monosynaptic excitatory postsynaptic potential (EPSP), and long-lasting potentiation of polysynaptic EPSP, and EPSP in cells receiving C-afferent fiber input. The DHPG potentiation of polysynaptic EPSP was partially or fully reversed by (S)-4-carboxyphenylglycine (S-4CPG), the mGlu subtype 1 preferring antagonist. 2-Methyl-6-(phenylethynyl)-pyridine, the potent and selective mGlu subtype 5 antagonist, partially reversed the CHPG potentiation of polysynaptic EPSP. The effects of DHPG on monosynaptic and polysynaptic EPSPs were reduced, or abolished, by the N-methyl-D-aspartate (NMDA) receptor antagonist D(-)-2-amino-5-phosphonopentanoic acid (AP5).
3.Induction of long-term potentiation of C fibre-evoked spinal field potentials requires recruitment of group I, but not group II/III metabotropic glutamate receptors.
Azkue JJ;Liu XG;Zimmermann M;Sandkühler J Pain. 2003 Dec;106(3):373-9.
In superficial layers of the lumbar spinal dorsal horn, N-methyl-D-aspartate-dependent long-term potentiation (LTP) of C fibre-evoked field potentials, a synaptic model of central sensitisation and hyperalgesia, ensues the application of electrical high-frequency, high-intensity conditioning stimulation to the sciatic nerve. In order to investigate the putative involvement of the G protein-coupled metabotropic glutamate receptors (mGluRs) in the induction of this form of LTP, we applied a series of mGluR antagonists exhibiting distinct group-specific activity profiles to the spinal lumbar enlargement, prior to conditioning stimulation. The group I (mGluR1/5) and group II (mGluR2/3) mGluR antagonist (S)-alpha-methyl-4-carboxyphenylglycine or the selective mGluR1/5 antagonist (S)-4-carboxyphenylglycine consistently impaired the development of spinal LTP. However, potentiation occurred in the presence of the inactive enantiomer (R)-alpha-methyl-4-carboxyphenylglycine. LTP proved insensitive to the selective mGluR2/3 antagonists (2S)-alpha-ethylglutamic acid and LY341495, either spinally or intravenously delivered. LTP could also be induced in the presence of the selective group III (mGluR4/mGluR6-mGluR8) mGluR antagonist (RS)-alpha-methylserine-O-phosphate.
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CAS 134052-73-6 (S)-4-Carboxyphenylglycine

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