(S)-3-Carboxy-4-hydroxyphenylglycine - CAS 55136-48-6
Category: Inhibitor
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Molecular Formula:
C9H9NO5
Molecular Weight:
211.17
COA:
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Targets:
mGluR
Description:
(S)-3-Carboxy-4-hydroxyphenylglycine has been found to be a mixed group II mGlu agonist as well as group I metabotropic glutamate receptor antagonist.
Purity:
≥98% by HPLC
Appearance:
White Solid
Synonyms:
(S)-5-(amino(carboxy)methyl)-2-hydroxybenzoic acid
MSDS:
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InChIKey:
CHZBCZTXSTWCIG-SSDOTTSWSA-N
InChI:
InChI=1S/C9H9NO5/c10-7(9(14)15)4-1-2-6(11)5(3-4)8(12)13/h1-3,7,11H,10H2,(H,12,13)(H,14,15)/t7-/m1/s1
Canonical SMILES:
C1=CC(=C(C=C1C(C(=O)O)N)C(=O)O)O
1.Stimulation of high-affinity GTPase activity through group II metabotropic glutamate receptors in rat hippocampal and striatal membranes.
Odagaki Y;Nishi N;Koyama T Jpn J Pharmacol. 2000 Dec;84(4):399-404.
The stimulation of high-affinity GTPase activity through metabotropic glutamate receptors (mGluRs) was pharmacologically characterized with the use of a series of agonists for mGluRs in rat hippocampal and striatal membranes. The pharmacological profile of the response was almost identical to each other between both brain regions. Thus, the high-affinity GTPase activities were stimulated by several mGluR-related compounds with the following rank order of potency: (2S,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (DCG-IV) = (2S,1'S,2'S)-2-(carboxycyclopropyl)glycine (L-CCG-I) > L-glutamate = 2R,4R-4-aminopyrrolidine-2,4-dicarboxylate [(2R,4R)-APDC] > (S)-4-carboxy-3-hydroxyphenylglycine [(S)-4C3HPG] = 1S,3R-1-aminocyclopentane-1,3-dicarboxylate [(1S,3R)-ACPD] > (S)-3-carboxy-4-hydroxyphenylglycine [(S)-3C4HPG] = ibotenate. The negative logarithmically transformed EC50 (pEC50) values of these compounds in both brain regions were significantly correlated with those reported previously in the cerebral cortical membranes (N. Nishi et al., Br. J. Pharmacol., 130, 1664-1670, 2000). On the contrary, other reagents including a selective group I mGluRs agonist, (RS)-3,5-dihydroxyphenylglycine [(RS)-3,5-DHPG], and selective group III mGluRs agonists such as L(+)-2-amino-4-phosphonobutylate (L-AP4) and L-serine-O-phosphate (L-SOP) had little or no effects even at the highest concentration examined.
2.Regional distribution and pharmacological characteristics of [3H]N-acetyl-aspartyl-glutamate (NAAG) binding sites in rat brain.
Shave E;Pliss L;Lawrance ML;FitzGibbon T;Stastny F;Balcar VJ Neurochem Int. 2001 Jan;38(1):53-62.
Autoradiographical studies revealed that 10 nM [3H]N-acetyl-aspartyl-glutamate (NAAG) labelled grey matter structures, particularly in the hippocamus, cerebral neocortex, striatum, septal nuclei and the cerebellar cortex. The binding was inhibited by (2S,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)-glycine (DCG IV), an agonist at group II metabotropic glutamate receptors (mGluR II). (RS)-alpha-Methyl-4-tetrazolylphenylglycine (MTPG), (RS)-alpha-cyclopropyl-4-phosphonoglycine (CPPG) and (RS)-alpha-methylserine-O-phosphate monophenyl ester (MSOPPE), all antagonists at mGluR II and mGluR III, also inhibited [3H]NAAG binding. Other inhibitors were (1S,3R)-1-aminocyclopentane-1,3-dicarboxylate (ACPD), a broad-spectrum mGluR agonist with preference for groups I and II and the mGluR I agonists/mGluR II antagonists (S)-3-carboxy-4-hydroxyphenylglycine (3,4-CHPG) and (S)-4-carboxy-3-hydroxyphenylglycine (4,3-CHPG). Neither the mGluR I specific agonist (S)-dihydroxyphenylglycine nor any of the ionotropic glutamate receptor ligands such as kainate, AMPA and MK-801 had strong effects (except for the competitive NMDA antagonist CGS 19755, which produced 20-40% inhibition at 100 microM) suggesting that, at low nM concentrations, [3H]NAAG binds predominantly to metabotropic glutamate receptors, particularly those of the mGluR II type.
3.The enhancement and the inhibition of noradrenaline-induced cyclic AMP accumulation in rat brain by stimulation of metabotropic glutamate receptors.
Pilc A;Legutko B;Czyrak A Prog Neuropsychopharmacol Biol Psychiatry. 1996 May;20(4):673-90.
1. The actions of several metabotropic glutamate receptor and antagonists on noradrenaline (NA)-stimulated [3H]-cyclic AMP accumulation were investigated in rat cerebral cortical slices. 2. Quisqualate (QUIS), L-2-amino-3-phosphonopropionic acid (L-AP3) and glutamate (GLU) elicited concentration-dependent inhibition of (NA)-stimulated [3H]-cyclic AMP accumulation, with IC50 values of 105 +/- 29, 275 +/- 36 and 944 +/- 150 microM respectively. In contrast (Rs)-alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) (0.5 mM) and N-methyl-D-aspartic acid (NMDA) (0.5 mM) had no effect. 3. (2S,3S,4S)-alpha-(Carboxycyclopropyl)glycine (L-CCGI), 1-Aminocyclo-pentane-1S,3R-dicarbo-xylate (1S,3R-ACPD), ibotenate (IBO) and (RS)-4-carboxy-3-hydroxy-phenylglycine (CHPG)elicited a concentration-dependent enhancement of NA-stimulated [3H]-cyclic AMP accumulation, with EC50 values of 2.5 +/- 0.11, 42 +/- 1.3, 97.8 +/- 2.1 and 157 +/- 13.4 microM, respectively. 4. (S)-3-carboxy-4-hydroxyphenylglycine (3C4HPG) and (S)-4-carboxy-3-hydroxyphenyl-glycine (4C3HPG) produced a biphasic effect, at concentrations up to 100 and 500 microM, respectively, they significantly enhanced the action of NA (100 microM), at 1mM concentration both compounds as well as alpha-methyl-4-carboxyphenylglycine (MCPG) produced a significant inhibition of NA-stimulated cyclic AMP accumulation.
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CAS 55136-48-6 (S)-3-Carboxy-4-hydroxyphenylglycine

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