(S)-3-Hydroxyphenylglycine - CAS 71301-82-1
Category: Inhibitor
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Molecular Formula:
C8H9NO3
Molecular Weight:
167.16
COA:
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Targets:
mGluR
Description:
(S)-3-Hydroxyphenylglycine is an agonist at group I metabotropic glutamate receptors (mGlu1) with no effect at mGlu2 or mGlu4.
Brife Description:
mGlu1 receptor agonist
Purity:
≥99% by HPLC
Synonyms:
(2S)-2-Amino-2-(3-hydroxyphenyl)acetic acid
MSDS:
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InChIKey:
DQLYTFPAEVJTFM-ZETCQYMHSA-N
InChI:
InChI=1S/C8H9NO3/c9-7(8(11)12)5-2-1-3-6(10)4-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m0/s1
Canonical SMILES:
C1=CC(=CC(=C1)O)C(C(=O)O)N
1.Activation of group I metabotropic glutamate receptors elicits pH changes in cultured rat cortical glia and neurons.
Amos BJ;Mathie A;Richards CD Neuroscience. 1998 Oct;86(4):1109-20.
Activation of metabotropic glutamate receptors is known to elicit a rise in intracellular Ca2+ and the present study was undertaken to see whether they also modulate the intracellular pH (pHi) of neurons and glia. Measurements of the pHi of neurons and astrocytes were made with the ratiometric fluorescent dye 2',7'-biscarboxyethyl-5,6-carboxyfluorescein. In the absence of bicarbonate, stimulation with the specific metabotropic glutamate receptor agonist 1S,3R-1-aminocyclopentane-1,3-dicarboxylic acid caused a fall in pHi in both astrocytes and neurons. In the presence of bicarbonate, stimulation with 25 microM 1S,3R-1-aminocyclopentane-1,3-dicarboxylic acid elicited a rise in pHi in the astrocytes, while the neurons responded with a small acidification. The astrocytic alkalinization could also be elicited by the specific group I metabotropic glutamate receptor agonist (S)-3-hydroxyphenylglycine but not by the group II agonist (2S,1'S,2'S)-(2-carboxycyclopropyl)glycine or by the group III agonist L(+)-2-amino-4-phosphonobutyric acid. The alkalinization of glial cells could be reduced by preloading the cells with BAPTA, but not by removal of extracellular Ca2+. Depolarization of the astrocytes with potassium elicited a small alkalinization, but stimulation with 100 microM 1S,3R-1-aminocyclopentane-1,3-dicarboxylic acid in high potassium medium elicited a further alkalinization.
2.Metabotropic glutamate receptors coupled to IP3 production mediate inhibition of IAHP in rat dentate granule neurons.
Abdul-Ghani MA;Valiante TA;Carlen PL;Pennefather PS J Neurophysiol. 1996 Oct;76(4):2691-700.
1. Whole cell recordings from dentate granule neurons in the hippocampal slice preparation reveal that (1 S, 3R)-1-aminocyclopentane-1,3-dicarboxylic acid (ACPD), a selective agonist at metabotropic glutamate receptors (mGluRs), inhibits a calcium-activated potassium current (IAHP) responsible for the postspike after-hyperpolarization. Inclusion of 1 mM of the Ca2+ chelator ethylene glycol-bis (beta-aminoethyl ether)-N,N,N',N'-tetraacetic acid in the patch pipette reduced the inhibitory action of ACPD on IAHP while having no effect on a similar action of serotonin (5-HT). Thus the known action of ACPD of mobilizing intracellular Ca2+ may be involved in this inhibitor action of ACPD. 2. Inhibition of IAHP is not secondary to effects on Ca2+ currents, because 10 microM ACPD, which inhibits IAHP by 95 +/- 5% (mean +/- SE), reduced the Ca2+ current by only 8 +/- 4%. 3. Activation of mGluRs accelerates the irreversible inhibition of IAHP that develops when 88 microM GTP-gamma-S is included in the pipette filling solution, whereas inclusion of 1 mM GDP-beta-S attenuated the inhibitory action of ACPD. These results indicate that the response to mGluR activation is G protein mediated. 4. Group I mGluRs, which includes mGluR1 and mGluR5, are G-protein-coupled receptors that are known to stimulate phospholipase C (PLC)-mediated hydrolysis of phosphoinositides to produce 1,4,5-triphosphate (IP3), which in turn is known to mobilize the release of intracellular Ca2+.
3.Metabotropic glutamate group II receptors are responsible for the depression of synaptic transmission induced by ACPD in the dentate gyrus.
Ugolini A;Bordi F Eur J Pharmacol. 1995 Dec 29;294(2-3):403-10.
The functional role of metabotropic glutamate (mGlu) receptors in the rat dentate gyrus was investigated. By using extracellular recording techniques in slices, it was found that the depression induced by the mGlu receptor agonist (1S,3R)-1-amino-cyclopentane-1,3-dicarboxylate (ACPD) was mediated through the mGlu group II receptors. The mGlu receptor antagonist alpha-methyl-4-carboxyphenylglycine (MCPG) (500 mu M), active at group I and group II subtype receptors, was effective in antagonizing the ACPD (30 mu M) - induced depression of the excitatory field potentials. An antagonist selective for group I, (S)-4-carboxyphenylglycine (4CPG), did not block the effects induced by ACPD, but by itself produced a dose-dependent depression of the field potentials. This ACPD-like effect shown at high concentrations of 4CPG (300 mu M) is explained by its group II receptor agonistic properties and was blocked by bath application of MCPG (500 mu M). A selective agonist of group I, (S)-3-hydroxyphenylglycine (3-HPG), did not cause any depression of synaptic transmission. However, the selective mGlu group II receptor agonist, (2S,3S,4S)-alpha-(carboxycyclopropyl)glycine (L-CCG-I), induced a marked dose-dependent depression and its action was blocked by MCPG (500 mu M).
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CAS 71301-82-1 (S)-3-Hydroxyphenylglycine

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