(RS)-3,5-DHPG - CAS 146255-66-5
Category: Inhibitor
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Molecular Formula:
C8H9NO4
Molecular Weight:
183.16
COA:
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Targets:
mGluR
Description:
(RS)-3,5-DHPG is a group I metabotropic glutamate receptor agonist with selectivity for both mGluR1 and mGluR5. S-enantiomer (S)-3,5-DHPG is the active form.
Brife Description:
mGluR1 and mGluR5 agonist
Purity:
99%
Synonyms:
3,5-Dihydroxyphenylglycine; 2-amino-2-(3,5-dihydroxyphenyl)acetic acid; Alpha-Amino-3,5-dihydroxybenzeneacetic acid
MSDS:
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InChIKey:
HOOWCUZPEFNHDT-UHFFFAOYSA-N
InChI:
InChI=1S/C8H9NO4/c9-7(8(12)13)4-1-5(10)3-6(11)2-4/h1-3,7,10-11H,9H2,(H,12,13)
Canonical SMILES:
C1=C(C=C(C=C1O)O)C(C(=O)O)N
1.Endogenous activation of metabotropic glutamate receptors modulates GABAergic transmission to gonadotropin-releasing hormone neurons and alters their firing rate: a possible local feedback circuit.
Chu Z;Moenter SM J Neurosci. 2005 Jun 15;25(24):5740-9.
Gonadotropin-releasing hormone (GnRH) neurons are the primary central regulators of fertility, receiving input from GABAergic afferents via GABA(A) receptors. We tested whether metabotropic glutamate receptors (mGluRs) regulate GABA transmission to GnRH neurons and GnRH neuronal firing pattern. Whole-cell recordings were performed under conditions isolating ionotropic GABA postsynaptic currents (PSCs) in brain slices. The broad-spectrum mGluR agonist 1-aminocyclopentane-1,3-dicarboxylic acid (ACPD) decreased the frequency of GABA(A)-mediated spontaneous PSCs in a reversible manner. Amplitude and kinetics were not altered, suggesting that afferent GABA neurons are the primary targets. TTX eliminated the effects of ACPD in most tested neurons. Group II [2-(2,3-dicarboxycyclopropyl) glycine] and III (L-AP-4) mGluR agonists mediated this response; a group I agonist (3,5-dihydroxyphenylglycine) was not effective. The broad-spectrum antagonist alpha-methyl-4-carboxyphenylglycine (MCPG) and/or (RS)-alpha-cyclopropyl-4-phosphonophenylglycine (CPPG) (group III antagonist) enhanced spontaneous PSC frequency, particularly when initial frequency was low, suggesting that endogenous activation of mGluRs regulates GABA transmission to GnRH neurons.
2.Substrate recognition and catalysis by the cofactor-independent dioxygenase DpgC.
Fielding EN;Widboom PF;Bruner SD Biochemistry. 2007 Dec 11;46(49):13994-4000. Epub 2007 Nov 16.
The enzyme DpgC belongs to a small class of oxygenases not dependent on accessory cofactors for activity. DpgC is in the biosynthetic pathway for the nonproteinogenic amino acid 3,5-dihydroxyphenylglycine in actinomycetes bacteria responsible for the production of the vancomycin/teicoplanin family of antibiotic natural products. The X-ray structure of DpgC [Widboom, P. W., Fielding, E. N., Liu, Y., and Bruner, S. D. (2007) Nature 447, 342-345] confirmed the absence of cofactors and defined a novel hydrophobic dioxygen binding pocket adjacent to a bound substrate analogue. In this paper, the role specific amino acids play in substrate recognition and catalysis is examined through biochemical and structural characterization of site-specific enzyme mutations and alternate substrates. The results establish the importance of three amino acids, Arg254, Glu299, and Glu189, in the chemistry of DpgC. Arg254 and Glu189 join to form a specific contact with one of the phenolic hydroxyls of the substrate, and this interaction plays a key role in both substrate recognition and catalysis. The X-ray crystal structure of Arg254Lys was determined to address the role this residue plays in the chemistry.
3.Anticonvulsant effect of (RS)-1-aminoindan-1,5-dicarboxylic acid on pentetrazol-induced kindled seizures in mice.
Watanabe Y;Kaida Y;Takechi K;Kamei C Biol Pharm Bull. 2010;33(4):647-52.
The present study was undertaken to clarify the effect of group I metabotropic glutamate receptor (mGluR) antagonist, (RS)-1-aminoindan-1,5-dicarboxylic acid (AIDA) on pentetrazol-induced kindled seizures. The mechanism of the anticonvulsant effect of AIDA was also studied. Mice were anesthetized with pentobarbital; the electrodes and guide cannula were chronically implanted into the cortex and lateral ventricle. In order to induce kindling, pentetrazol at a dose of 40 mg/kg was injected intraperitoneally once every 48 h. Behavioral and electroencephalographic (EEG) seizures were observed for 20 min following pentetrazol administration. Intracerebroventricular (i.c.v.) injection of AIDA (1000 nmol/site) resulted in a significant inhibitory effect on pentetrazol-induced kindled seizures, and this effect was antagonized by a group I mGluR agonist, (RS)-3,5-dihydroxyphenylglycine ((RS)-3,5-DHPG). The effect of AIDA (200 nmol/site) on pentetrazol-induced kindled seizures was augmented by the simultaneous use of gamma-aminobutyric acid (GABA) mimetic drugs, such as NNC-711 and diazepam. Moreover, the effect of AIDA (1000 nmol/site) on pentetrazol-induced kindled seizures was antagonized by a GABA(A) receptor antagonist, bicuculline and a GABA(C) receptor antagonist, (1,2,5,6-tetrahydropyridin-4-yl) methylphosphinic acid (TPMPA).
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CAS 146255-66-5 (RS)-3,5-DHPG

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