3-MATIDA - CAS 518357-51-2
Category: Inhibitor
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Molecular Formula:
C8H9NO4S
Molecular Weight:
215.23
COA:
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Targets:
mGluR
Description:
3-MATIDA is a potent metabotropic glutamate (mGlu1) receptor antagonist with IC50 value of 6.3 μM at rat mGlu1a. It displays ≥ 40-fold selectivity over other receptors. It has neuroprotective activity in cultured murine cortical cells and rat hippocampal slice cultures in vitro. It reduces the volume of ischemia-induced brain infarcts in rats following systemic administration in vivo.
Purity:
≥99% by HPLC
Synonyms:
α-Amino-5-carboxy-3-methyl-2-thiopheneaceticacid; 5-[amino(carboxy)methyl]-4-methylthiophene-2-carboxylic acid; 3-Methyl-aminothiophene dicarboxylic acid
MSDS:
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InChIKey:
KOMWRBFEDDEWEP-UHFFFAOYSA-N
InChI:
InChI=1S/C8H9NO4S/c1-3-2-4(7(10)11)14-6(3)5(9)8(12)13/h2,5H,9H2,1H3,(H,10,11)(H,12,13)
Canonical SMILES:
CC1=C(SC(=C1)C(=O)O)C(C(=O)O)N
1.Enantioselective HPLC of potentially CNS-active acidic amino acids with a Cinchona carbamate based chiral stationary phase.
Sardella R;Lämmerhofer M;Natalini B;Lindner W Chirality. 2008 Mar;20(3-4):571-6. doi: 10.1002/chir.20529.
A tert-butylcarbamoylquinine-based chiral stationary phase (Chiralpak QN-AX) has been employed for the enantiomer separation of underivatized chiral acidic amino acids, viz. 4-carboxyphenylalanine (4-CPHE), 1-aminoindan-1,5-dicarboxylic acid (AIDA), 2-(5-carboxy-3-methyl-2-thienyl)glycine (3-MATIDA), 2-(4-carboxy-5-methyl-2-thienyl)glycine (5-MATIDA), and 2-(2'-carboxy-3'-phenylcyclopropyl)glycine (PCCG). Some of the acidic amino acids have potential activity on the central nervous system and are thus of great interest. A stereoselective HPLC method that allows the baseline resolution of all the five test solutes has been developed. For that purpose the mobile phase composition (pH, organic modifier, and type) and flow rate were optimized. The final method makes use of mild elution conditions, namely methanol - 0.8 M ammonium acetate buffer (97.5:2.5; v/v) pH 5.5 which are also compatible with mass spectrometric detection.
2.Metabotropic glutamate 1 (mGlu1) receptor antagonists enhance GABAergic neurotransmission: a mechanism for the attenuation of post-ischemic injury and epileptiform activity?
Cozzi A;Meli E;Carlà V;Pellicciari R;Moroni F;Pellegrini-Giampietro DE Neuropharmacology. 2002 Aug;43(2):119-30.
Selective antagonists of mGlu1 metabotropic glutamate receptors attenuate neuronal death in models of cerebral ischemia. Because GABAergic mechanisms have recently been proposed to contribute to these neuroprotective effects, we examined the effects of selective mGlu1 antagonists characterized in our laboratory on GABAergic transmission in three different models of neuropathology. In rat organotypic hippocampal slices exposed to oxygen-glucose deprivation, the mGlu1 antagonists AIDA, CBPG and 3-MATIDA reduced CA1 pyramidal cell loss when added to the medium during the insult and the subsequent recovery period. This effect was mimicked by the GABA(A) and GABA(B) agonists muscimol and baclofen and partially prevented by the antagonists bicuculline and CGP 55845. In gerbils subjected to global ischemia, protection of CA1 pyramidal cells by transdialytic perfusion of AIDA and CBPG was associated with a significant increase in the basal and ischemic output of GABA and minor changes in the output of glutamate. In a mouse cortical wedge model, both muscimol and 3-MATIDA reduced the frequency of spontaneous bursts induced by 4-aminopyridine and this reduction was prevented by co-perfusion with bicuculline.
3.Group I metabotropic glutamate receptors stimulate the activity of poly(ADP-ribose) polymerase in mammalian mGlu1-transfected cells and in cortical cell cultures.
Meli E;Baronti R;Pangallo M;Picca R;Moroni F;Pellegrini-Giampietro DE Neuropharmacology. 2005;49 Suppl 1:80-8.
Group I metabotropic glutamate (mGlu) receptors (i.e. mGlu1 and mGlu5) coupled to phospholipase C have been widely investigated for their possible role in excitotoxic and post-ischemic neuronal death. Recently, phospholipase C has been shown to directly stimulate the activity of poly(ADP-ribose) polymerase (PARP), a nuclear enzyme involved in DNA repair that has been proposed to play a key role in necrotic cell death. In this study, we investigated whether the stimulation of group I mGlu receptors leads to an increase in PARP activity, as detected by flow cytometry, immunodot blot and immunocytochemistry, both in baby hamster kidney cells transfected with mGlu1a or mGlu5a receptors and in cultured cortical cells. Our results show that the group I mGlu receptor agonist DHPG elicited a significant increase in PARP activity that was completely abolished by the administration of the mGlu1 antagonist 3-MATIDA and partially prevented, in cortical neurons, by the mGlu5 antagonist MPEP. To evaluate whether this pathway is involved in post-ischemic neuronal death, we used a sublethal model of oxygen-glucose deprivation in mixed cortical cell cultures. DHPG exacerbated neuronal death, and this effect was significantly prevented by the application of the PARP inhibitor DPQ.
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CAS 518357-51-2 3-MATIDA

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